Chicago Highlights Bike Tour with Classic Foods and Craft Beer
4.9
(766)
🕑 4h 30m
Free cancellation
Combine a bike tour of downtown Chicago with the Windy City’s most popular culinary pleasures on this excursion. Make your way to the bike shop for a safety briefing, then slip on your helmet and hop on your bicycle. You’ll undoubtedly work up an appetite while you pedal along the streets of iconic neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and the Gold Coast. On the night tour, visit the Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront Trail. Along the way, stop to enjoy the tastes of Chicago at two breweries, a pizza shop, a hot dog stand and a bakery. Gain culinary and cultural insight from your local guide who shares neighborhood history and food traditions. Learn about the origin of Chicago’s famed deep-dish pizza, find out what makes craft beer a local specialty, and discover the difference between a Chicago-style and regular hot dog. This tour covers approximately 13 miles (21 kilometers) and requires a moderate fitness level.
Languages:
English
📍540 N Lake Shore Dr., Chicago, IL 60611, USA
🏢Operated by Bobby's Bike Hike - Chicago
Highlights
- ✓Taste Chicago's most well-known foods and drinks
- ✓Ride through the city's most popular neighborhoods
- ✓Your guide will provide historical and cultural insights as you go
- ✓Enjoy enough samples to add up to a generous meal, plus beer
What you'll see & do
- ✓AM Day & PM Night Route: Few foods define a city like deep-dish does Chicago. On both our Day Route to Wrigley and our Night Route Downtown, you’ll sink your fork into layers of cheese, rich tomato sauce, and buttery crust — one of the most iconic Chicago Classic Dishes ever created. Whether enjoyed under bright afternoon skies or after the skyline begins to glow, it’s bold, indulgent, and unforgettable. Insider tip: don’t rush it — true Chicagoans know deep-dish is meant to be savored slowly. On our Chicago Food & Bike Tour, you’ll ride by Bicycle between tastings and discover the stories behind this legendary pie. It’s a centerpiece of the ultimate Food & Bike Tour in Chicago, blending flavor, history, and city energy into one epic experience.
- ✓AM Day Route: A stop at The Wiener’s Circle on our Day Route to Wrigley is pure Chicago attitude served on a poppy seed bun. Bite into a true Chicago Style Hot Dog — piled high with mustard, neon relish, onions, tomato, sport peppers, a pickle spear, and absolutely no ketchup — one of the most beloved Chicago Classic Dishes in the city. By day, this iconic stand is a neighborhood staple, known for its history, humor, and no-nonsense authenticity. Insider tip: order it “with everything” like a local and step aside to dress it properly before that first snap of the all-beef bite. On our Chicago Food & Bike Tour, you’ll ride by Bicycle through vibrant North Side streets before savoring this legendary stop. It’s a flavorful highlight of the ultimate Food & Bike Tour in Chicago, blending personality, tradition, and bold taste into one unforgettable daytime experience.
- ✓PM Night Route: There’s something unforgettable about enjoying a Chicago Style Hot Dog after dark. On our Night Route Downtown, bite into this fully loaded favorite — mustard, neon relish, onions, tomato, sport peppers, pickle spear, and never ketchup — one of the most iconic Chicago Classic Dishes in the city. As the skyline glows and city lights reflect off the streets, the flavors somehow hit even harder. Insider tip: order it “with everything” and embrace the no-ketchup rule — locals take that seriously. On our Chicago Food & Bike Tour, you’ll roll up by Bicycle, experience downtown’s electric nighttime energy, and savor authentic Chicago tradition. It’s a bold highlight of the ultimate Food & Bike Tour in Chicago, blending city lights, flavor, and local pride into one unforgettable ride.
- ✓AM Day Route: A stop at Billy Goat Tavern in Wrigleyville on our Day Route to Wrigley is a bite into pure Chicago lore. Famous for its no-frills charm and decades of local character, this legendary spot serves up a juicy Italian beef — thin-sliced, seasoned to perfection, and dipped just the way locals like it — one of the city’s boldest Chicago Classic Dishes. By day, the energy around Wrigleyville makes it even better. Insider tip: order it “dipped” for the full authentic experience, and grab extra napkins — you’ll need them. On our Chicago Food & Bike Tour, you’ll roll up by Bicycle, explore vibrant neighborhood streets, and savor flavors rooted in Chicago tradition. It’s a savory highlight of the ultimate Food & Bike Tour in Chicago, blending sports history, local legend, and unforgettable taste into one dynamic daytime ride.
- ✓AM Day & PM Night Routes: Sampling Garretts Popcorn on both our Day Route to Wrigley and our Night Route Downtown is a true taste of Chicago tradition. Since 1949, Garretts has been crafting its famous caramel and cheese blend — sweet, savory, and completely addictive — making it one of the most beloved Chicago Classic Dishes in the city. By day, enjoy it as you cruise sunny lakefront paths. By night, savor it with the skyline glowing around you — the perfect handheld treat between iconic stops. Insider tip: locals swear by mixing the caramel and cheese together for the ultimate Chicago-style combo. On our Chicago Food & Bike Tour, you’ll ride by Bicycle between tastings and discover the stories behind the flavors. It’s a delicious highlight of the ultimate Food & Bike Tour in Chicago, blending nostalgia, city views, and bold local taste into one unforgettable ride.
- ✓AM Day Route: Bittersweet Pastry Shop on our Day Route to Wrigley is where elegance meets indulgence. This beloved Lincoln Park bakery is known for handcrafted European-style pastries, rich chocolate creations, and desserts that feel like edible art — a sweet finale featuring one of our favorite Chicago Classic Dishes. By day, it’s a cozy neighborhood gem where locals linger over coffee and flawless confections. Insider tip: look for seasonal specialties — regulars know that’s where the pastry chefs truly shine. On our Chicago Food & Bike Tour, you’ll ride by Bicycle through charming streets before rewarding yourself with a decadent treat. It’s a delicious highlight of the ultimate Food & Bike Tour in Chicago, blending neighborhood charm, culinary craftsmanship, and a perfectly sweet finish to your daytime adventure.
- ✓AM Day Route. Pedal into the heart of Chicago baseball on our Day Route to Wrigley. There’s nothing like rolling up to iconic Wrigley Field by Bicycle, feeling the buzz of Wrigleyville, and soaking in over a century of sports history under the afternoon sun. The neighborhood energy is contagious — packed patios, local fans, and that unmistakable ivy-covered charm. On our Chicago Food & Bike Tour, you don’t just see Wrigley Field — you experience the culture that surrounds it. Along the way, you’ll savor legendary Chicago Classic Dishes, hear the stories that shaped the city, and explore vibrant North Side neighborhoods most visitors never discover. This unforgettable Food & Bike Tour in Chicago blends sunshine, flavor, and authentic local character into one dynamic ride — the perfect daytime adventure for food lovers and culture seekers alike.
- ✓AM Day Route and PM Night Route. Ride the stunning Lake Michigan Lakefront Trail on both our Day Route to Wrigley and our Night Route Downtown, where open skies by day and glowing skylines by night create two completely different but equally unforgettable experiences. Cruise by Bicycle along the water’s edge, feel the breeze off the lake, and take in panoramic views that define Chicago’s natural beauty. On our Chicago Food & Bike Tour, this iconic stretch connects vibrant neighborhoods, historic landmarks, and stops featuring unforgettable Chicago Classic Dishes. It’s more than a scenic ride — it’s the heartbeat of the city. This immersive Food & Bike Tour in Chicago blends waterfront freedom, rich culture, and bold flavor into one extraordinary adventure, whether you choose sunshine or city lights.
- ✓AM Day Route and PM Night Route. Glide past the elegant Gold Coast mansions on both our Day Route to Wrigley and our Night Route Downtown, where historic wealth, architectural grandeur, and timeless design tell the story of Chicago’s rise to prominence. By day, you’ll admire ornate façades and tree-lined streets by Bicycle under bright blue skies. By night, those same streets glow with sophistication, adding a dramatic edge to the experience. On our Chicago Food & Bike Tour, these stunning homes are more than photo ops — they’re windows into the city’s powerful past. Between stops featuring unforgettable Chicago Classic Dishes, our guides reveal the families, fortunes, and fascinating stories behind the gates. This immersive Food & Bike Tour in Chicago blends luxury, history, and flavor into one unforgettable ride — whether you choose sunshine or skyline lights.
- ✓AM Day Route.Cruise through the tree-lined streets of Lincoln Park on our Day Route to Wrigley, where historic brownstones, vibrant cafés, and lakefront paths create one of the city’s most charming neighborhoods. Rolling by Bicycle, you’ll feel the relaxed, local rhythm that makes this area a favorite for both longtime residents and first-time visitors. On our Chicago Food & Bike Tour, Lincoln Park isn’t just scenery — it’s part of the story. Between bites of iconic Chicago Classic Dishes, our guides share the rich history, architectural gems, and cultural moments that shaped this beloved community. This immersive Food & Bike Tour in Chicago blends neighborhood character, culinary flavor, and fresh air into an unforgettable daytime experience that goes far beyond the typical tourist route.
- ✓AM Day Route and PM Night Route: North Avenue Beach is where Chicago’s bold personality meets the open water. On our Day Route to Wrigley, cruise by Bicycle past volleyball courts, the iconic boat-shaped beach house, and sweeping skyline views that feel straight out of a postcard. By day, it’s the ultimate expression of Chicago’s lakefront culture — active, social, and full of summer energy. On our Night Route Downtown, the beach transforms into a dramatic vantage point where the skyline glows against Lake Michigan, offering one of the most breathtaking nighttime views in the city. On our Chicago Food & Bike Tour, North Avenue Beach showcases how nature and architecture coexist in perfect balance. Between stops featuring unforgettable Chicago Classic Dishes, you’ll experience the lakefront as locals do. This immersive Food & Bike Tour in Chicago blends culture, scenery, and flavor into one unforgettable ride.
- ✓AM Day Route. Ride through vibrant Northalsted on our Day Route to Wrigley, one of Chicago’s most colorful and inclusive neighborhoods. Cruise by Bicycle past bold murals, lively patios, and iconic landmarks that celebrate decades of culture, community, and pride. The energy here is welcoming, creative, and unmistakably Chicago. On our Chicago Food & Bike Tour, Northalsted isn’t just a pass-through — it’s part of the story. As you savor unforgettable Chicago Classic Dishes, our guides share the history that shaped this dynamic district and its impact on the city’s cultural landscape. This immersive Food & Bike Tour in Chicago blends flavor, neighborhood character, and authentic local spirit into a daytime experience that goes far beyond the typical tourist route.
- ✓AM Day Tour: Lincoln Park Zoo on our Day Route to Wrigley is a refreshing surprise in the heart of the city. Ride by Bicycle past one of the only free zoos in the country, where historic architecture, open green space, and skyline views blend seamlessly. Since 1868, this beloved landmark has reflected Chicago’s commitment to accessible culture, conservation, and community. Insider tip: glance south along the Nature Boardwalk for one of the most underrated daytime skyline views — locals quietly love this angle. On our Chicago Food & Bike Tour, Lincoln Park Zoo adds a family-friendly cultural touch between stops featuring unforgettable Chicago Classic Dishes. It’s a defining highlight of the ultimate Food & Bike Tour in Chicago, blending history, nature, and neighborhood charm into one unforgettable daytime ride.
- ✓PM Night Route: The Chicago Riverwalk at night is pure urban theater. On our Night Route Downtown, glide by Bicycle as the river mirrors glowing skyscrapers and historic bridges light up overhead. Once the city’s industrial lifeline, the Riverwalk has transformed into a vibrant corridor of architecture, nightlife, and waterfront culture — a powerful symbol of Chicago’s reinvention. Insider tip: watch the reflections just after dusk, when the sky is deep blue but not fully dark — locals know that’s when the skyline pops brightest in photos. On our Chicago Food & Bike Tour, this stop connects story and scenery between tastings of unforgettable Chicago Classic Dishes. It’s a defining highlight of the ultimate Food & Bike Tour in Chicago, blending history, flavor, and illuminated city energy into one unforgettable ride.
- ✓PM Night Route: Buckingham Fountain is one of Chicago’s most iconic landmarks — and on our Night Route Downtown, it becomes pure magic. Ride by Bicycle as the fountain comes alive with choreographed lights set against the glowing skyline. By day, on our Chicago Food & Bike Tour, you’ll see its grand Beaux-Arts design up close and learn how it symbolizes the city’s connection to Lake Michigan. Insider tip: time your visit for the top-of-the-hour water show — and stand slightly southeast of the fountain for the best skyline backdrop in your photos. Between stops featuring unforgettable Chicago Classic Dishes, this landmark adds grandeur and story to your journey. It’s a highlight of the ultimate Food & Bike Tour in Chicago, blending architecture, history, and unforgettable city views into one extraordinary ride.
- ✓PM Night Route: The Loop at night is Chicago at full throttle. On our Night Route Downtown, ride by Bicycle beneath glowing skyscrapers, historic theaters, and the rumble of the elevated “L” tracks overhead. This is the city’s financial and cultural core — where architecture, commerce, and creativity collide in dramatic fashion after dark. Insider tip: look up as you pass under the illuminated “L” tracks — the steel structure framed against lit buildings creates a classic Chicago photo locals love. On our Chicago Food & Bike Tour, The Loop delivers big-city energy between tastings of unforgettable Chicago Classic Dishes. It’s a powerful highlight of the ultimate Food & Bike Tour in Chicago, blending history, skyline spectacle, and nighttime momentum into one unforgettable ride.
- ✓AM Day Route and PM Night Route: Oak Street Beach isn’t just a scenic stop — it’s where Chicago comes alive. On our Day Route to Wrigley, cruise by Bicycle past sunbathers, volleyball courts, and the iconic skyline rising behind golden sand. By day, it captures the city’s lakefront lifestyle — active, social, and proudly outdoors. On our Night Route Downtown, the same shoreline transforms into a dramatic stage where the skyline sparkles and Lake Michigan reflects the lights of the city. It’s romantic, cinematic, and unmistakably Chicago. On our Chicago Food & Bike Tour, Oak Street Beach represents the cultural heartbeat of summer in the Midwest — a place where urban energy meets natural beauty. Between stops featuring unforgettable Chicago Classic Dishes, you’ll experience how the lakefront shapes the city’s identity. This unforgettable Food & Bike Tour in Chicago blends skyline, shoreline, and story into one powerful ride.
- ✓PM Night Route: Millennium Park at night is Chicago on full display. On our Night Route Downtown, ride by Bicycle as the park glows beneath the skyline, with Cloud Gate reflecting city lights and the surrounding architecture shimmering in the dark. What was once rail yards is now one of the most celebrated public spaces in America — a symbol of Chicago’s creativity and civic pride. Insider tip: stand slightly off-center at Cloud Gate for a reflection that captures both you and the skyline in one epic shot. On our Chicago Food & Bike Tour, this stop adds culture and spectacle between tastings of unforgettable Chicago Classic Dishes. It’s a highlight of the ultimate Food & Bike Tour in Chicago, blending art, architecture, and nighttime magic into one unforgettable ride.
- ✓PM Night Route: Museum Campus at night is one of Chicago’s most breathtaking hidden gems. On our Night Route Downtown, ride by Bicycle as the Field Museum, Shedd Aquarium, and Adler Planetarium glow against the dark lakefront, with the full skyline rising brilliantly behind them. The calm of Lake Michigan paired with the illuminated city creates a cinematic moment few visitors experience. Insider tip: pause near the Adler Planetarium and look back toward downtown — locals know this is one of the absolute best skyline photo angles in the city. On our Chicago Food & Bike Tour, this stop adds depth and drama between tastings of unforgettable Chicago Classic Dishes. It’s a highlight of the ultimate Food & Bike Tour in Chicago, blending culture, architecture, and nighttime magic into one unforgettable ride.
- ✓PM Night Route: Navy Pier at night is pure Chicago energy. On our Night Route Downtown, ride by Bicycle as the Centennial Wheel lights up the lakefront and the skyline sparkles behind you. Originally built in 1916 as a shipping and recreation pier, it has evolved into one of the city’s most vibrant gathering places — blending history, entertainment, and waterfront charm. Insider tip: pause near the east end of the pier for sweeping lake views back toward downtown — locals know this is one of the best nighttime skyline angles in the city. On our Chicago Food & Bike Tour, Navy Pier adds excitement and spectacle between tastings of unforgettable Chicago Classic Dishes. It’s a standout moment on the ultimate Food & Bike Tour in Chicago, combining lake breeze, bright lights, and bold city flavor into one unforgettable ride.
- ✓PM Night Route. Experience River North after dark on our Night Route Downtown, where city lights reflect off glass towers and the energy is unmistakably electric. Glide by Bicycle through one of Chicago’s most vibrant districts, home to world-class dining, iconic architecture, and a nightlife scene that defines the modern city. On our Chicago Food & Bike Tour, River North transforms into a glowing playground of culture and cuisine. Between bites of unforgettable Chicago Classic Dishes, our guides share the stories behind the skyline and the evolution of this once-industrial neighborhood into a creative powerhouse. This unforgettable Food & Bike Tour in Chicago blends illuminated views, bold flavors, and big-city excitement into a nighttime adventure you won’t want to miss.
- ✓AM Day & PM Night Route: Take in incredible views along the lakefront on our Day Route to Wrigley or our Night Route Downtown, where Chicago’s skyline meets the open waters of Lake Michigan. By day, cruise by Bicycle under bright skies with sweeping panoramic views. By night, watch the city glow against the dark water for a completely different kind of magic. On our Chicago Food & Bike Tour, the lakefront isn’t just a backdrop — it’s a defining part of the journey. Between stops featuring unforgettable Chicago Classic Dishes, you’ll experience the balance of nature, architecture, and culture that makes this city extraordinary. This unforgettable Food & Bike Tour in Chicago delivers fresh air, iconic scenery, and bold flavor in one dynamic ride.
What's included
- ✓Named a Top 20 Food Tour in the World by TripAdvisor—experience why guests rave about Bobby’s tours!
- ✓Water Bottle is provided on this Chicago Classics Bike & Food Tour
- ✓Fun, local guides share insider tips, history, food, & hidden gems for an unforgettable experience.
- ✓Two Different Routes to Choose. Day Route to Wrigley or Night Route of Downtown Attractions.
- ✓Meals
- ✓Bicycle use
What's not included
- ✓$15 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
- ✓Local craft beer samples can be added for a fee (Three 9oz pours)you can purchase this option upon arrival for $19.99/person
Good to know
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
If you have dietary restrictions, please add a note in the special requirements section when booking, and email us after booking to confirm they can accommodate. You will see our email at your tickets or vouchers.
Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Minimum age is 16 years
Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
This Tour was rated Top 20 Food Tours in the World by TripAdvisor
VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
Cancellation policy
- •A full refund will apply if you cancel more than 24 hours before the activity start time.
- •No refund is possible if you cancel less than 24 hours before the activity start time.
Free cancellation
🔒 Secure checkout
from
US$ 85.00
Chicago Highlights Bike Tour with Classic Foods and Craft Beer
4.9
(766)
🕑 4h 30m
Free cancellation
Combine a bike tour of downtown Chicago with the Windy City’s most popular culinary pleasures on this excursion. Make your way to the bike shop for a safety briefing, then slip on your helmet and hop on your bicycle. You’ll undoubtedly work up an appetite while you pedal along the streets of iconic neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and the Gold Coast. On the night tour, visit the Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront Trail. Along the way, stop to enjoy the tastes of Chicago at two breweries, a pizza shop, a hot dog stand and a bakery. Gain culinary and cultural insight from your local guide who shares neighborhood history and food traditions. Learn about the origin of Chicago’s famed deep-dish pizza, find out what makes craft beer a local specialty, and discover the difference between a Chicago-style and regular hot dog. This tour covers approximately 13 miles (21 kilometers) and requires a moderate fitness level.
Languages:
English
📍540 N Lake Shore Dr., Chicago, IL 60611, USA
🏢Operated by Bobby's Bike Hike - Chicago
Highlights
- ✓Taste Chicago's most well-known foods and drinks
- ✓Ride through the city's most popular neighborhoods
- ✓Your guide will provide historical and cultural insights as you go
- ✓Enjoy enough samples to add up to a generous meal, plus beer
What you'll see & do
- ✓AM Day & PM Night Route: Few foods define a city like deep-dish does Chicago. On both our Day Route to Wrigley and our Night Route Downtown, you’ll sink your fork into layers of cheese, rich tomato sauce, and buttery crust — one of the most iconic Chicago Classic Dishes ever created. Whether enjoyed under bright afternoon skies or after the skyline begins to glow, it’s bold, indulgent, and unforgettable. Insider tip: don’t rush it — true Chicagoans know deep-dish is meant to be savored slowly. On our Chicago Food & Bike Tour, you’ll ride by Bicycle between tastings and discover the stories behind this legendary pie. It’s a centerpiece of the ultimate Food & Bike Tour in Chicago, blending flavor, history, and city energy into one epic experience.
- ✓AM Day Route: A stop at The Wiener’s Circle on our Day Route to Wrigley is pure Chicago attitude served on a poppy seed bun. Bite into a true Chicago Style Hot Dog — piled high with mustard, neon relish, onions, tomato, sport peppers, a pickle spear, and absolutely no ketchup — one of the most beloved Chicago Classic Dishes in the city. By day, this iconic stand is a neighborhood staple, known for its history, humor, and no-nonsense authenticity. Insider tip: order it “with everything” like a local and step aside to dress it properly before that first snap of the all-beef bite. On our Chicago Food & Bike Tour, you’ll ride by Bicycle through vibrant North Side streets before savoring this legendary stop. It’s a flavorful highlight of the ultimate Food & Bike Tour in Chicago, blending personality, tradition, and bold taste into one unforgettable daytime experience.
- ✓PM Night Route: There’s something unforgettable about enjoying a Chicago Style Hot Dog after dark. On our Night Route Downtown, bite into this fully loaded favorite — mustard, neon relish, onions, tomato, sport peppers, pickle spear, and never ketchup — one of the most iconic Chicago Classic Dishes in the city. As the skyline glows and city lights reflect off the streets, the flavors somehow hit even harder. Insider tip: order it “with everything” and embrace the no-ketchup rule — locals take that seriously. On our Chicago Food & Bike Tour, you’ll roll up by Bicycle, experience downtown’s electric nighttime energy, and savor authentic Chicago tradition. It’s a bold highlight of the ultimate Food & Bike Tour in Chicago, blending city lights, flavor, and local pride into one unforgettable ride.
- ✓AM Day Route: A stop at Billy Goat Tavern in Wrigleyville on our Day Route to Wrigley is a bite into pure Chicago lore. Famous for its no-frills charm and decades of local character, this legendary spot serves up a juicy Italian beef — thin-sliced, seasoned to perfection, and dipped just the way locals like it — one of the city’s boldest Chicago Classic Dishes. By day, the energy around Wrigleyville makes it even better. Insider tip: order it “dipped” for the full authentic experience, and grab extra napkins — you’ll need them. On our Chicago Food & Bike Tour, you’ll roll up by Bicycle, explore vibrant neighborhood streets, and savor flavors rooted in Chicago tradition. It’s a savory highlight of the ultimate Food & Bike Tour in Chicago, blending sports history, local legend, and unforgettable taste into one dynamic daytime ride.
- ✓AM Day & PM Night Routes: Sampling Garretts Popcorn on both our Day Route to Wrigley and our Night Route Downtown is a true taste of Chicago tradition. Since 1949, Garretts has been crafting its famous caramel and cheese blend — sweet, savory, and completely addictive — making it one of the most beloved Chicago Classic Dishes in the city. By day, enjoy it as you cruise sunny lakefront paths. By night, savor it with the skyline glowing around you — the perfect handheld treat between iconic stops. Insider tip: locals swear by mixing the caramel and cheese together for the ultimate Chicago-style combo. On our Chicago Food & Bike Tour, you’ll ride by Bicycle between tastings and discover the stories behind the flavors. It’s a delicious highlight of the ultimate Food & Bike Tour in Chicago, blending nostalgia, city views, and bold local taste into one unforgettable ride.
- ✓AM Day Route: Bittersweet Pastry Shop on our Day Route to Wrigley is where elegance meets indulgence. This beloved Lincoln Park bakery is known for handcrafted European-style pastries, rich chocolate creations, and desserts that feel like edible art — a sweet finale featuring one of our favorite Chicago Classic Dishes. By day, it’s a cozy neighborhood gem where locals linger over coffee and flawless confections. Insider tip: look for seasonal specialties — regulars know that’s where the pastry chefs truly shine. On our Chicago Food & Bike Tour, you’ll ride by Bicycle through charming streets before rewarding yourself with a decadent treat. It’s a delicious highlight of the ultimate Food & Bike Tour in Chicago, blending neighborhood charm, culinary craftsmanship, and a perfectly sweet finish to your daytime adventure.
- ✓AM Day Route. Pedal into the heart of Chicago baseball on our Day Route to Wrigley. There’s nothing like rolling up to iconic Wrigley Field by Bicycle, feeling the buzz of Wrigleyville, and soaking in over a century of sports history under the afternoon sun. The neighborhood energy is contagious — packed patios, local fans, and that unmistakable ivy-covered charm. On our Chicago Food & Bike Tour, you don’t just see Wrigley Field — you experience the culture that surrounds it. Along the way, you’ll savor legendary Chicago Classic Dishes, hear the stories that shaped the city, and explore vibrant North Side neighborhoods most visitors never discover. This unforgettable Food & Bike Tour in Chicago blends sunshine, flavor, and authentic local character into one dynamic ride — the perfect daytime adventure for food lovers and culture seekers alike.
- ✓AM Day Route and PM Night Route. Ride the stunning Lake Michigan Lakefront Trail on both our Day Route to Wrigley and our Night Route Downtown, where open skies by day and glowing skylines by night create two completely different but equally unforgettable experiences. Cruise by Bicycle along the water’s edge, feel the breeze off the lake, and take in panoramic views that define Chicago’s natural beauty. On our Chicago Food & Bike Tour, this iconic stretch connects vibrant neighborhoods, historic landmarks, and stops featuring unforgettable Chicago Classic Dishes. It’s more than a scenic ride — it’s the heartbeat of the city. This immersive Food & Bike Tour in Chicago blends waterfront freedom, rich culture, and bold flavor into one extraordinary adventure, whether you choose sunshine or city lights.
- ✓AM Day Route and PM Night Route. Glide past the elegant Gold Coast mansions on both our Day Route to Wrigley and our Night Route Downtown, where historic wealth, architectural grandeur, and timeless design tell the story of Chicago’s rise to prominence. By day, you’ll admire ornate façades and tree-lined streets by Bicycle under bright blue skies. By night, those same streets glow with sophistication, adding a dramatic edge to the experience. On our Chicago Food & Bike Tour, these stunning homes are more than photo ops — they’re windows into the city’s powerful past. Between stops featuring unforgettable Chicago Classic Dishes, our guides reveal the families, fortunes, and fascinating stories behind the gates. This immersive Food & Bike Tour in Chicago blends luxury, history, and flavor into one unforgettable ride — whether you choose sunshine or skyline lights.
- ✓AM Day Route.Cruise through the tree-lined streets of Lincoln Park on our Day Route to Wrigley, where historic brownstones, vibrant cafés, and lakefront paths create one of the city’s most charming neighborhoods. Rolling by Bicycle, you’ll feel the relaxed, local rhythm that makes this area a favorite for both longtime residents and first-time visitors. On our Chicago Food & Bike Tour, Lincoln Park isn’t just scenery — it’s part of the story. Between bites of iconic Chicago Classic Dishes, our guides share the rich history, architectural gems, and cultural moments that shaped this beloved community. This immersive Food & Bike Tour in Chicago blends neighborhood character, culinary flavor, and fresh air into an unforgettable daytime experience that goes far beyond the typical tourist route.
- ✓AM Day Route and PM Night Route: North Avenue Beach is where Chicago’s bold personality meets the open water. On our Day Route to Wrigley, cruise by Bicycle past volleyball courts, the iconic boat-shaped beach house, and sweeping skyline views that feel straight out of a postcard. By day, it’s the ultimate expression of Chicago’s lakefront culture — active, social, and full of summer energy. On our Night Route Downtown, the beach transforms into a dramatic vantage point where the skyline glows against Lake Michigan, offering one of the most breathtaking nighttime views in the city. On our Chicago Food & Bike Tour, North Avenue Beach showcases how nature and architecture coexist in perfect balance. Between stops featuring unforgettable Chicago Classic Dishes, you’ll experience the lakefront as locals do. This immersive Food & Bike Tour in Chicago blends culture, scenery, and flavor into one unforgettable ride.
- ✓AM Day Route. Ride through vibrant Northalsted on our Day Route to Wrigley, one of Chicago’s most colorful and inclusive neighborhoods. Cruise by Bicycle past bold murals, lively patios, and iconic landmarks that celebrate decades of culture, community, and pride. The energy here is welcoming, creative, and unmistakably Chicago. On our Chicago Food & Bike Tour, Northalsted isn’t just a pass-through — it’s part of the story. As you savor unforgettable Chicago Classic Dishes, our guides share the history that shaped this dynamic district and its impact on the city’s cultural landscape. This immersive Food & Bike Tour in Chicago blends flavor, neighborhood character, and authentic local spirit into a daytime experience that goes far beyond the typical tourist route.
- ✓AM Day Tour: Lincoln Park Zoo on our Day Route to Wrigley is a refreshing surprise in the heart of the city. Ride by Bicycle past one of the only free zoos in the country, where historic architecture, open green space, and skyline views blend seamlessly. Since 1868, this beloved landmark has reflected Chicago’s commitment to accessible culture, conservation, and community. Insider tip: glance south along the Nature Boardwalk for one of the most underrated daytime skyline views — locals quietly love this angle. On our Chicago Food & Bike Tour, Lincoln Park Zoo adds a family-friendly cultural touch between stops featuring unforgettable Chicago Classic Dishes. It’s a defining highlight of the ultimate Food & Bike Tour in Chicago, blending history, nature, and neighborhood charm into one unforgettable daytime ride.
- ✓PM Night Route: The Chicago Riverwalk at night is pure urban theater. On our Night Route Downtown, glide by Bicycle as the river mirrors glowing skyscrapers and historic bridges light up overhead. Once the city’s industrial lifeline, the Riverwalk has transformed into a vibrant corridor of architecture, nightlife, and waterfront culture — a powerful symbol of Chicago’s reinvention. Insider tip: watch the reflections just after dusk, when the sky is deep blue but not fully dark — locals know that’s when the skyline pops brightest in photos. On our Chicago Food & Bike Tour, this stop connects story and scenery between tastings of unforgettable Chicago Classic Dishes. It’s a defining highlight of the ultimate Food & Bike Tour in Chicago, blending history, flavor, and illuminated city energy into one unforgettable ride.
- ✓PM Night Route: Buckingham Fountain is one of Chicago’s most iconic landmarks — and on our Night Route Downtown, it becomes pure magic. Ride by Bicycle as the fountain comes alive with choreographed lights set against the glowing skyline. By day, on our Chicago Food & Bike Tour, you’ll see its grand Beaux-Arts design up close and learn how it symbolizes the city’s connection to Lake Michigan. Insider tip: time your visit for the top-of-the-hour water show — and stand slightly southeast of the fountain for the best skyline backdrop in your photos. Between stops featuring unforgettable Chicago Classic Dishes, this landmark adds grandeur and story to your journey. It’s a highlight of the ultimate Food & Bike Tour in Chicago, blending architecture, history, and unforgettable city views into one extraordinary ride.
- ✓PM Night Route: The Loop at night is Chicago at full throttle. On our Night Route Downtown, ride by Bicycle beneath glowing skyscrapers, historic theaters, and the rumble of the elevated “L” tracks overhead. This is the city’s financial and cultural core — where architecture, commerce, and creativity collide in dramatic fashion after dark. Insider tip: look up as you pass under the illuminated “L” tracks — the steel structure framed against lit buildings creates a classic Chicago photo locals love. On our Chicago Food & Bike Tour, The Loop delivers big-city energy between tastings of unforgettable Chicago Classic Dishes. It’s a powerful highlight of the ultimate Food & Bike Tour in Chicago, blending history, skyline spectacle, and nighttime momentum into one unforgettable ride.
- ✓AM Day Route and PM Night Route: Oak Street Beach isn’t just a scenic stop — it’s where Chicago comes alive. On our Day Route to Wrigley, cruise by Bicycle past sunbathers, volleyball courts, and the iconic skyline rising behind golden sand. By day, it captures the city’s lakefront lifestyle — active, social, and proudly outdoors. On our Night Route Downtown, the same shoreline transforms into a dramatic stage where the skyline sparkles and Lake Michigan reflects the lights of the city. It’s romantic, cinematic, and unmistakably Chicago. On our Chicago Food & Bike Tour, Oak Street Beach represents the cultural heartbeat of summer in the Midwest — a place where urban energy meets natural beauty. Between stops featuring unforgettable Chicago Classic Dishes, you’ll experience how the lakefront shapes the city’s identity. This unforgettable Food & Bike Tour in Chicago blends skyline, shoreline, and story into one powerful ride.
- ✓PM Night Route: Millennium Park at night is Chicago on full display. On our Night Route Downtown, ride by Bicycle as the park glows beneath the skyline, with Cloud Gate reflecting city lights and the surrounding architecture shimmering in the dark. What was once rail yards is now one of the most celebrated public spaces in America — a symbol of Chicago’s creativity and civic pride. Insider tip: stand slightly off-center at Cloud Gate for a reflection that captures both you and the skyline in one epic shot. On our Chicago Food & Bike Tour, this stop adds culture and spectacle between tastings of unforgettable Chicago Classic Dishes. It’s a highlight of the ultimate Food & Bike Tour in Chicago, blending art, architecture, and nighttime magic into one unforgettable ride.
- ✓PM Night Route: Museum Campus at night is one of Chicago’s most breathtaking hidden gems. On our Night Route Downtown, ride by Bicycle as the Field Museum, Shedd Aquarium, and Adler Planetarium glow against the dark lakefront, with the full skyline rising brilliantly behind them. The calm of Lake Michigan paired with the illuminated city creates a cinematic moment few visitors experience. Insider tip: pause near the Adler Planetarium and look back toward downtown — locals know this is one of the absolute best skyline photo angles in the city. On our Chicago Food & Bike Tour, this stop adds depth and drama between tastings of unforgettable Chicago Classic Dishes. It’s a highlight of the ultimate Food & Bike Tour in Chicago, blending culture, architecture, and nighttime magic into one unforgettable ride.
- ✓PM Night Route: Navy Pier at night is pure Chicago energy. On our Night Route Downtown, ride by Bicycle as the Centennial Wheel lights up the lakefront and the skyline sparkles behind you. Originally built in 1916 as a shipping and recreation pier, it has evolved into one of the city’s most vibrant gathering places — blending history, entertainment, and waterfront charm. Insider tip: pause near the east end of the pier for sweeping lake views back toward downtown — locals know this is one of the best nighttime skyline angles in the city. On our Chicago Food & Bike Tour, Navy Pier adds excitement and spectacle between tastings of unforgettable Chicago Classic Dishes. It’s a standout moment on the ultimate Food & Bike Tour in Chicago, combining lake breeze, bright lights, and bold city flavor into one unforgettable ride.
- ✓PM Night Route. Experience River North after dark on our Night Route Downtown, where city lights reflect off glass towers and the energy is unmistakably electric. Glide by Bicycle through one of Chicago’s most vibrant districts, home to world-class dining, iconic architecture, and a nightlife scene that defines the modern city. On our Chicago Food & Bike Tour, River North transforms into a glowing playground of culture and cuisine. Between bites of unforgettable Chicago Classic Dishes, our guides share the stories behind the skyline and the evolution of this once-industrial neighborhood into a creative powerhouse. This unforgettable Food & Bike Tour in Chicago blends illuminated views, bold flavors, and big-city excitement into a nighttime adventure you won’t want to miss.
- ✓AM Day & PM Night Route: Take in incredible views along the lakefront on our Day Route to Wrigley or our Night Route Downtown, where Chicago’s skyline meets the open waters of Lake Michigan. By day, cruise by Bicycle under bright skies with sweeping panoramic views. By night, watch the city glow against the dark water for a completely different kind of magic. On our Chicago Food & Bike Tour, the lakefront isn’t just a backdrop — it’s a defining part of the journey. Between stops featuring unforgettable Chicago Classic Dishes, you’ll experience the balance of nature, architecture, and culture that makes this city extraordinary. This unforgettable Food & Bike Tour in Chicago delivers fresh air, iconic scenery, and bold flavor in one dynamic ride.
What's included
- ✓Named a Top 20 Food Tour in the World by TripAdvisor—experience why guests rave about Bobby’s tours!
- ✓Water Bottle is provided on this Chicago Classics Bike & Food Tour
- ✓Fun, local guides share insider tips, history, food, & hidden gems for an unforgettable experience.
- ✓Two Different Routes to Choose. Day Route to Wrigley or Night Route of Downtown Attractions.
- ✓Meals
- ✓Bicycle use
What's not included
- ✓$15 per person suggested guide gratuity. (via Cash, Venmo and PayPal)
- ✓Local craft beer samples can be added for a fee (Three 9oz pours)you can purchase this option upon arrival for $19.99/person
Good to know
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
If you have dietary restrictions, please add a note in the special requirements section when booking, and email us after booking to confirm they can accommodate. You will see our email at your tickets or vouchers.
Tour Operator can accommodate vegetarians or those who don’t eat beef or pork but can’t cater for gluten-free (limited options) or vegan (extremely limited options) diets.
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Minimum age is 16 years
Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
This Tour was rated Top 20 Food Tours in the World by TripAdvisor
VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21+)
Cancellation policy
- •A full refund will apply if you cancel more than 24 hours before the activity start time.
- •No refund is possible if you cancel less than 24 hours before the activity start time.
Free cancellation
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US$ 85.00