Chicago Lakefront Trail Tours (Updated July 2026)

Chicago, USA
Chicago Lakefront Trail

If you are looking for things to do in Chicago we have 8 Tours and Activities to Experience Chicago Lakefront Trail. Check out our verified traveler reviews and photos of Chicago Lakefront Trail tours and other things to do in Chicago, and book securely when you find the perfect one. Learn the best ways to see famous Chicago Lakefront Trail and explore the most popular things to do in Chicago.

Chicago Lakefront Trail
Lake Shore Drive, Chicago, Illinois

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Bike Tour of Chicago's Lakefront Neighborhoods
Likely to Sell Out
Likely to Sell Out

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (230)
$59
$58

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
Special Offer
Special Offer

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike,...

4 hours 30 minutesFree Cancellation
4 hours 30 minutesFree Cancellation
4 hours 30 minutes • Free Cancellation
5.0 (739)
$89
$88

Chicago's Ultimate City Bike Tour of Top Downtown Attractions
Likely to Sell Out
Likely to Sell Out

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (245)
$59
$58

Chicago Family Food and Bike Tour with Top Attractions
Special Offer
Special Offer

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
4.9 (97)
$79
$78

Lakefront Segway Tour in Chicago
Special Offer
Special Offer

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
4.7 (141)
$70
$69

Chicago's West Side Foodie Ride Bike Tour
Special Offer
Special Offer

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (112)
$99
$98

Private Chicago Guided Tour with Hotel Pickup
Special Offer
Special Offer

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour...

4 hoursHotel pickup offeredFree Cancellation
4 hoursHotel pickup offeredFree Cancellation
4 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
$819.60
$818.60

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer
Special Offer
Special Offer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (1)
$179
$178

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