Sightseeing Cruises
1 hour
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 97% of travellers
97% of reviewers gave this product a bubble rating of 4 or higher.
from
$86
per adult
THE 10 BEST Chicago City Tours
City Tours in Chicago
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$0 - $900 +
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Experiences you don’t want to miss
Products in this shelf are the top products picked from the current list and based on the existing sort
101 results sorted by featured
- Our Featured sort order ranks tours, activities, and experiences by several factors including the revenue generated by Tripadvisor from these bookings, your individual user browsing history and preferences while using Tripadvisor, the frequency of user clicks generally, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.
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Sightseeing Cruises
45 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
90% of reviewers gave this product a bubble rating of 4 or higher.
from
$49
per adult
Ghost Tours
2 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
94% of reviewers gave this product a bubble rating of 4 or higher.
from
$62
per adult
Beer & Brewery Tours
3 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 96% of travellers
96% of reviewers gave this product a bubble rating of 4 or higher.
from
$149
per adult
Sightseeing 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 91% of travellers
91% of reviewers gave this product a bubble rating of 4 or higher.
from
$77
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 99% of travellers
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$62
per adult
Beer & Brewery 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 97% of travellers
97% of reviewers gave this product a bubble rating of 4 or higher.
from
$175
per adult
Christmas
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
100% of reviewers gave this product a bubble rating of 4 or higher.
from
$149
per adult
Ghost 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
100% of reviewers gave this product a bubble rating of 4 or higher.
from
$114
per adult
Car Tours
2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
from
$551
per group
Historical Tours
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
97% of reviewers gave this product a bubble rating of 4 or higher.
from
$114
per adult
Culinary Tours
3 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
98% of reviewers gave this product a bubble rating of 4 or higher.
from
$156
$141
per adult
Historical 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
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$84
per adult
Pastry 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 99% of travellers
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$119
per adult
Sightseeing Cruises
30 minutes
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
from
$57
per adult
Culinary Tours
3 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
97% of reviewers gave this product a bubble rating of 4 or higher.
from
$140
per adult
Likely To Sell Out
3–4 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
from
$174
per adult
Likely To Sell Out
1–2 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
100% of reviewers gave this product a bubble rating of 4 or higher.
from
$53
per adult
Bus Tours
2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
from
$167
per adult
Bike Tours
3 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
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$97
per adult
Architecture Tours
2 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
98% of reviewers gave this product a bubble rating of 4 or higher.
from
$62
per adult
Beer & Brewery Tours
4–5 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
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$156
per adult
Historical Tours
45 minutes
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
Recommended by 97% of travellers
97% of reviewers gave this product a bubble rating of 4 or higher.
from
$1,485
per group
Likely To Sell Out
1–2 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
from
$114
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 98% of travellers
98% of reviewers gave this product a bubble rating of 4 or higher.
from
$112
per adult
Private and Luxury
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
99% of reviewers gave this product a bubble rating of 4 or higher.
from
$114
per adult
Culinary 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 98% of travellers
98% of reviewers gave this product a bubble rating of 4 or higher.
from
$156
per adult
Rail Tours
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
95% of reviewers gave this product a bubble rating of 4 or higher.
from
$63
per adult
Ghost Tours
3 hours
Free cancellation
Not sure? You can cancel this booking up to 24 hours in advance for a full refund.
from
$174
per adult
Historical 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
91% of reviewers gave this product a bubble rating of 4 or higher.
from
$114
per adult
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Showing results 1-30 of 101
*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
- MalcolmChristchurch, New Zealand6 contributionsGreat introduction to the Chicago architectural styles and particularly spectacular examples within a short distance of the river. Fun and informative commentary.Written 6 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Veronica M19 contributionsNice cruise down the river. We did the 3:30 cruise and it was great. Your guide was funny and informative. Would definitely recommend if you’re in the area. It’s a nice view of the skyline. Worth the price for us.Written 25 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Flyer5982281 contributionWe had a great time on this tour! Sophia’s warmth, enthusiasm and knowledge made for a wonderful experience. Would highly recommend this tourWritten 4 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- B VPittsburgh, PA18 contributionsMickey Jordan was a great tour guide, with good information and stops. The food was great and provided our group with the best of Chicago, including pizza, hot dog and Italian beef. We ended at a Christmas Market for apple cider and a brownie. It ended up being around 3.5 hours of walking, eating and talking in the cold but it was worth it.Written 30 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- teamsnardyVincennes, IN558 contributionsEnjoy a relaxing, historic and current event tour of Chicago’s ‘other shoreline’. Boats are clean, safe, punctual and very informative. Recommended on a warm summer evening. See the hidden side of the windy city.Written 23 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- craig sBloomington, IN5 contributionsThis was a fantastic tour, made that way largely by our wonderful tour guide Kylie. The selection of buildings was wonderful and very intentionally covered a variety of styles. The tour notably included the The Chicago Board of Trade Building, the Marquette Building, the Palmer House Hotel, and the Chicago Cultural Center. Kylie was amazingly knowledgeable about architecture and the history of Chicago. We went on this tour with our 16-year-old niece from Germany, who wants to be an architect. and our niece's best friend (also from Germany). It is a testament to Kylie's tour leading that both young ladies had a great time. I know a little bit about design and at the end of the tour I was surprised at how much I had learned. We booked this tour through TripAdvisor and then at the last minute found out it is actually a Viator-organized tour. I have had tours from Viator that were good in spite of the tour guide. I think this is the first time ever I have been on a Viator-organized tour that was great because of it's tour guide. I cannot say enough about how this two-hour walking tour will enhance your understanding of and love for Chicago.Written 1 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- GrandTour1744711 contributionSuch a great time. Excellent beer. We met so many amazing people on the tour. The tour guide told us interesting facts about Chicago. The barrel bus was so unique.Written 25 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Kym11 contributionsJeanine wea a great guide! Lots of good food from deep dish pizza, beef sandwich, Garrett’s popcorn, Chicago dog, and the Palmer brownie. Every stop was well organize, and we stayed on track for the 3 hour time limit. Our guide was very entertaining.Written 1 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Dreamer4664291 contributionThe Gangster mini bus tour was great! Matthew, our tour guide had amazing stories and was so entertaining! We took the 6 pm ride. So glad we did the bus. Would have been quite cold to walk. He allowed for a few stops off the bus with a great photo spot for the city lights. Was the perfect night activity for teens and adults! Lots of Chicago history included.Written 1 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- amy g10 contributionsWe are huge Chicago Fire, PD and Med fans and this private tour was perfect for a birthday gift. Two hours was just the right length and the best part was talking to actual CFD firemen and getting a tour of the working firehouse. We got to sit in the engine and take all the photos we wanted. Deen was a great guide and made sure we got to visit lots of additional Chicago landmarks during the tour. Worth every penny for tv show fans!Written 18 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Cristy V8 contributionsThis tour was amazing! Our tour guide, Mike, was phenomenal. We were first-timers riding a Segway, but thanks to our excellent tour guide, we felt extremely comfortable and safe. He was funny and knowledgeable. We had a great time and recommend this tour with Captain Segway 500%!Written 29 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- aniaTaplow, UK5 contributionsDanny was a fantastic tour guide. Lots of history of both Chicago and the Food. The tour was well paced with lots of stops for rests (while enjoying delicious food) and meant that despite the cold weather we were quite comfortable the entire time. Consider skipping breakfast (we didn't and are consequently planning on skipping dinner). There is a lot of food, all of it very tasty. The only Chicago specific food that I was aware of before this tour was the Deep Dish Pizza...I learned that Chicago has a very rich culinary history. Make sure you wear comfortable walking shoes.Written 3 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Traci DSmyrna, TN17 contributionsThis was a wonderful experience. The tour guide Rick was funny, very informative and accommodating. With a smaller group it was easy to hear and navigate. We were able to see places we didn’t know about and learn some neat facts. We highly recommend!Written 4 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- Steve R9 contributionsWe thoroughly enjoyed our Underground Donut tour. The donuts from the shops we went to were absolutely delicious. Our tour guide Jackson was very knowledgeable not only about the history of the donut shops but also Chicago. He made the tour fun with his great sense of humor. We'd highly recommend this donut tour!Written 5 December 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
- jangT5327TP23 contributionsThey sold hats, gloves and blankets on the boat I had told my family of adults not to worry about the cold because every boat I’ve been on had blankets that they give you that’s This is the first place that sold them and that’s why they get a four instead of a fiveWritten 10 November 2024This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
