Tours in Chicago

Top Tours in Chicago, IL

Chicago Tours

  • Traveller favourites
    Tours, activities and experiences bookable on Tripadvisor, ranked according to revenue made by Tripadvisor on those bookings, plus the number of page views by Tripadvisor users, and the quantity and quality of reviews
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S$0 - S$800 +
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353 places sorted by traveller favourites
City Tours
1–2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 97% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$68.66
per adult
City Tours
1–2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 91% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$61.53
per adult
City Tours
2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 93% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$51.27
per adult
City Tours
3 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 95% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$109.86
per adult
Bus Tours
90–120 minutes
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 90% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$67.39
per adult
City Tours
5 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 95% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$152.36
per adult
City Tours
4 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 98% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$131.83
per adult
City Tours
45 minutes
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 92% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$33.69
per adult
Helicopter Tours
45 minutes
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 100% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$1,243.78
per group
Bus Tours
4 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 100% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$306.18
per adult
Day Cruises
1–2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 95% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$61.53
per adult
Attractions & Museums
4 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 94% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$39.55
per adult
City Tours
2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 100% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$625.96
per group
Bus Tours
3–4 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 95% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$145.91
per adult
Segway Tours
2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 99% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$112.04
per adult
Bus Tours
4 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 92% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$256.37
per adult
Walking Tours
2–3 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 100% of travellers
This number is based on the percentage of all Tripadvisor reviews for this product that have a bubble rating of 4 or higher
from
S$169.27
per adult
Showing results 1-30 of 353
*Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.

What travellers are saying

  • dobe N
    Melbourne, Australia5 contributions
    This was the fourth time we've taken the cruise. Never tire of the spectacular views which are greatly informed by knowledgable and friendly staff.
    On the basis of guide Ashley's knowledge, we visited a number of the iconic buildings we viewed from the river.
    Our favourite Chicago thing.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Tracy M
    2 contributions
    Absolutely fabulous and exceeded our expectations. The guide made us laugh and made it such a fun experience. Don’t miss this tour if you travel to Chicago. Breathtaking views and immense history.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • bbnlady2020
    17 contributions
    We had a perfect day and weather for our lake and river cruise the boat was comfortable we got lots of great pictures and the tour person was very thorough and explaining all about architectural details and pointing out things that we would not have noticed had she not been there. I highly recommend it
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Holly W
    1 contribution
    Connor was amazing! He kept the entire group engaged. His story telling skills were second to none. He was able to interweave the mafia connections with the tragedies in the Chicago area seamlessly. I did not expect the experience to be as educational and entertaining as it was. Even if you were born in Chicago, you will learn fascinating facts about the city on this tour. Highly recommended.
    Written 25 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Judith L
    2 contributions
    View of the skyline was beautiful and we loved the host pointing out various buildings designed by famous architects.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Roberta K
    1 contribution
    Exceeded expectations. So informative and fun. Stephanie, our guide was so funny and really got us excited about the buildings.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Laura J
    London, UK12 contributions
    the Chicago big bus tour showed you around the main attractions of Chicago, had a very nice day - if your easily cold definitely bring a hoodie and glasses as it gets very windy near the great lakes! i had one day in Chicago so I did the big bus tour and had a meal at the famous restaurant and hopped back on
    Written 15 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • JCMC9
    Texas34 contributions
    Great food tour with James! Lots of fun food-best was the hot dog. Also saw Chicago sites like the Bean and the Palmer Hotel. Had elderly father with us and the pace worked out well-with frequent stops and smooth sidewalks and ramps it was just fine.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Kathy B
    Ellicott City, MD23 contributions
    We truly enjoyed this tour. The tour guide was very informative and entertaining as she told the stories of the infamous crime bosses of the north and south gangs. She also threw in some other if it’s about the city as we traveled. We got off the bus a few times to see and experience some of the history. Very nice addition to our experience while visiting Chicago.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Stephanie B
    5 contributions
    this was a nice history lesson. Although I wish it was a little longer for the price. We still enjoed it
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • avasquez810
    Honolulu, HI2 contributions
    My experience was extremely entertaining and informative. Thank you very very much Hillary “with two Al’s” ! I think we got the best tour guide possible. Hillary was very funny while giving us architecture 101 course.
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • hqvtraveler
    Mount Vernon, WA24 contributions
    Guide Tall Dave did a fantastic job of showing some key architectural sites and telling us about their history. Chicago has some amazing gems that you wouldn’t find unless you go on a tour like this. Your culminated in enjoying three classic foods famous to the area. Tour well managed and guide was great at keeping our group together. Highly recommend. Be prepared to walk about 3 miles or so!
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Connector245500
    1 contribution
    Our tour guide, Josie was fabulous. She made the trip by her enthusiasm, building a sense of comradary within our group and fun sense of humor. She was a pure delight! Go hungry-- you eat a lot!! You also drink a fair amount. It was really fun!
    Written 24 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Nique B
    2 contributions
    It was a very beautiful experience. Staff was nice, ride was smooth, & the city’s view was just beautiful!
    Written 21 July 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Yuliya L
    Oakville, Canada4 contributions
    We took this tour at the end of our stay, so it was kind of repetitive to a walking tour, as expected. The tour guide was very knowledgable, and was moving fast through the descriptions and facts. I would prefer longer stories about some buildings vs short facts about everything. Kids 6 and 10 didn't like it much.
    Written 6 September 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Frequently Asked Questions about Chicago