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Top Picks for Chicago Experiences

Q: How many Experiences are available in Chicago on Trip.com?

Trip.com offers 42 Experiences in Chicago

Q: What are the top-rated Experiences in Chicago?

Chicago: Prohibition-Era Culture & Architectural Treasures Skyline lake boat tour from Navy Pier Chicago: City Minibus Tour with Optional Architecture Cruise

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Discover 42 Experiences in Chicago on Trip.com, updated September 14, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From BHD 5.28 per person, with an average total of BHD 26.22. Choose the option that suits your plan.

With 5.046k verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.45k reviews and a 4.7 rating.

Now on Trip.com: "Chicago: City Minibus Tour with Optional Architecture Cruise", a 4-hour adventure in Chicago!

The next available day tour departs on September 15, 2025. Book now to secure your spot!

Chicago Experiences usually take about 4 hours — perfect for a relaxed, immersive experience!

42% of Chicago Experiences now offer English-speaking guides

September is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Chicago Crime and Mob Bus Tour .

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

Search attractions or local attractions & tours

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42 Results for Chicago Experiences

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Recommended

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Duration: 45 mins

4.7/5

Great· 1.4k reviews· 160 booked

FromBHD 10.550

Lake Michigan Sunset Cruise in Chicago

Duration: 90 mins

4.6/5

Satisfactory· 362 reviews

FromBHD 16.960

Chicago: City Minibus Tour with Optional Architecture Cruise

Duration: 2–4 hrs

4.9/5

Excellent· 14 reviews

FromBHD 18.460

Chicago: Westside Food Tasting Bike Tour with Guide

Duration: 4 hrs

FromBHD 37.690

Chicago in a Day: Explore Food, History, and Iconic Architecture

Duration: 5 hrs

4.9/5

Excellent· 1.1k reviews

FromBHD 38.030

City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise

Duration: 2 hrs

FromBHD 51.010

Chicago Crime and Mob Bus Tour

Duration: 90–120 mins

4.7/5

Great· 1.4k reviews

FromBHD 18.460

Chicago City Tour with Architecture River Cruise Option

Duration: 2–4 hrs

4.8/5

Great· 655 reviews

FromBHD 18.440

Chicago: 2-Hour Kayak Rental from North Rockwell

Duration: 2 hrs

FromBHD 19.520

Chicago: Sunset Kayak Tour on the Chicago River

Duration: 1.5 hrs

FromBHD 21.680

Chicago: Prohibition-Era Culture & Architectural Treasures

Duration: 2.5 hrs

5.0/5

Excellent· 1 review

FromBHD 18.510

Chicago River 45-min architecture cruise

Duration: 45–60 mins

English

FromBHD 5.280

Big Bus Chicago Hop-on Hop-off Bus Tour

English

27 booked

FromBHD 13.670

The Chicago Theatre Tour Experience

Duration: 1 hr

English

FromBHD 11.310

Chicago Seadog: Lakefront Speedboat Tour

Duration: 30 mins

FromBHD 16.130

Skyline lake boat tour from Navy Pier

Duration: 45 mins

English

5.0/5

Excellent· 1 review

FromBHD 6.860

Spirit of Chicago dinner cruise

English

FromBHD 43.990

Chicago Premier Lake Michigan brunch cruise

Duration: 120 mins

English

FromBHD 39.050

All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

FromBHD 5.880

Bite into Chicago: Discover the City’s Most Iconic Food

Duration: 2 hrs

4.7/5

Great· 79 reviews

FromBHD 28.810

Architecture cruise on the Chicago River from Navy Pier

Duration: 75 mins

English

FromBHD 10.920

Big Bus Chicago: Hop-on Hop-off Bus Tour

Duration: 2 hrs

English

FromBHD 16.960

Chicago Odyssey dinner cruise

English

FromBHD 73.650

Chicago: Guided Food Tour + Bike or Kayak Rental

Duration: 150 mins

English

FromBHD 32.030

Chicago: Premier Dinner Cruise on Lake Michigan

Duration: 150 mins

FromBHD 66.440

Chicago: Food and Prohibition Architecture Guided Tour

Duration: 5 hrs

English

FromBHD 37.310

Chicago: Canine Cruise

Duration: 90 mins

English

FromBHD 15.830

Lake Michigan: Premier Brunch or Lunch Cruise

Duration: 2 hrs

FromBHD 40.690

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Frequently asked questions about Chicago Experiences

How many Experiences are available in Chicago on Trip.com?

What are the best Experiences in Chicago?

What are the top-rated Experiences in Chicago?

How can I contact Trip.com customer support?

Reviews/Trip Moments

★

Product reviews: Chicago River 45-Minute Architecture Tour from Magnificent Mile

Guest User2024-10-07

Beautiful views! Very informative. So many fun facts you will learn. We definitely recommend when you’re in Chicago. Staff did a great job. Thank you!

★

Product reviews: Lake Michigan Sunset Cruise in Chicago

Guest User2025-08-21

Kenny was the best tour guide!!! I’d do it all over again!!! Great vibes, music, views,!! Best time of our trip

★

Product reviews: Chicago: City Minibus Tour with Optional Architecture Cruise

Guest User2025-09-01

Enjoyed touring many different areas and receiving lots of educational information on Chicago (with a great sense of humor, thanks to Rick).

★

Product reviews: Chicago in a Day: Explore Food, History, and Iconic Architecture

Guest User2025-08-17

Rich was very welcoming and friendly from the beginning! He was very knowledgeable about the history and architecture of many of the beautiful buildings in the city. Millennium Park was a great stop too. The food choices were excellent and he provided history of the restaurants and the Chicago food. Wonderful day in the city. We learned a lot and really enjoyed the entire group. Rich was fantastic!! I would definitely recommend this tour.

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