See (and taste) the best of Chicago in just half a day on this bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along the Lakefront Trail, admire views of Millennium Park, and discover the Chicago Riverwalk. As you go, stop to sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, and a tasty dessert for good measure.
- See many of Chicago’s top sights and neighborhoods, all in one tour
- Traveling by bike lets you see more of the city in less time
- Enjoy enough generous samples to add up to a hearty lunch
- This two-in-one biking and tasting tour is ideal for first-time visitors
What To Expect
Lakefront Trail
The 18-mile Lakefront Trail has been contributing to Chicago’s cycle success since 1963. The paved path provides walkers, runners, and bicyclists with a safe and fun way to travel along the Lake Michigan, for both recreation and commuting.
15 minutes • Admission Ticket Free
Oak Street Beach
On a busy Saturday in July, Oak Street Beach is packed with the blankets and swim gear of up to 300,000 Chicagoans. Pop-up bars, volleyball nets, and easy-access to downtown make this one of Chicago’s finest sandy spots.
15 minutes • Admission Ticket Free
North Avenue Beach
Chicago’s most popular beach
10 minutes • Admission Ticket Free
Gold Coast
Opulent Mansions
• Admission Ticket Free
Chicago Riverwalk
Gorgeous at night
10 minutes • Admission Ticket Included
The Chicago Theatre
Iconic Chicago Marquee sign
• Admission Ticket Included
Millennium Park
Located at the northwest corner of larger Grant Park, Millennium Park is home to Chicago’s most beloved works of public art, including Cloud Gate, The Crown Fountain, and the Pritzker Pavilion.
15 minutes • Admission Ticket Free
Buckingham Fountain
When the Buckingham Fountain was built in 1927, it was the largest fountain in the world. Now the centerpiece of Chicago’s famous Grant Park, the fountain attracts crowds from all over the world to see its stunning light and water shows.
15 minutes • Admission Ticket Free
Soldier Field
Built in 1924, Soldier Field is the oldest NFL stadium in the United States. During the American football season, it’s the home of our roaring Chicago Bears, but the park also hosts some of the city’s biggest concerts in the spring and summer.
15 minutes • Admission Ticket Not Included
Navy Pier
If you happen to choose a Wednesday or Saturday night for this incredible journey, you’ll get a bonus spectacle on the way back to headquarters: a Navy Pier fireworks show! Throughout WWI and WWII, Navy Pier was one of America’s largest pilot-training bases. Now a popular visitor destination, the pier is home to countless restaurants, boutiques, theatres, and amusement park rides.
15 minutes • Admission Ticket Free
Lou Malnati’s Pizzeria
Try Chicago’s famous deep dish pizza
15 minutes • Admission Ticket Included
Bongiorno’s Cucina Italiana & Pizzeria
Try the delicious Italian beef sandwich with a view of the Riverwalk.
15 minutes • Admission Ticket Included
Museum Campus
Experience Museum Campus and it’s great views of downtown Chicago.
5 minutes • Admission Ticket Free
Adler Planetarium
The best viewing spot in Chicago.
5 minutes • Admission Ticket Free
Northerly Island
A former Airstrip turned municipal park and sanctuary.
5 minutes • Admission Ticket Free
Millennium Hall
Cooking up excellent Chicago style hot dogs and Italian Beef.
10 minutes • Admission Ticket Included
Billy Goat Tavern (Millennium Park)
Authentic Chicago-style Hot Dogs
10 minutes • Admission Ticket Included
The Art Institute of Chicago
Ride by the world famous lions
• Admission Ticket Included
Grant Park
Chicago’s Front Lawn, home to Buckingham Fountain
10 minutes • Admission Ticket Free
Lincoln Park
Travel through one of Chicago’s largest parks, along the lakefront
10 minutes • Admission Ticket Free
Highlight
Confirmation will be received at time of booking
If you have dietary restrictions, please add a note in the special requirements section when booking, and email to [email protected] after booking to confirm they can accommodate.
Not wheelchair accessible
Near public transportation
Infant seats available
Travelers should have a moderate physical fitness level
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.
VIP Adult Beverage upgrade (3 samples) available upon arrival for $19.99 per person extra (Ages 21 )
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Our groups have exclusive VIP access to locations we visit.
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.
Please note: children must be strong, capable riders and be able to bike for 9 miles
This tour/activity will have a maximum of 16 travelers
Max group – 15
