Second City Tours and Activities
Visit Second City
Plan a trip to see Second City
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.
Reviewed on Jun 16, 2026
Tours & day trips
See all 253 activities
Architecture River Tour
Activity duration is 1 hour
9.6 out of 10 with 1534 reviews
Free cancellation available
Private & custom tours
See all 64 activities
Chamarel 7 Colours and Waterfalls - Exclusive South West Tour
Activity duration is 9 hours
9.8 out of 10 with 32 reviews
Free cancellation available
![City centre Chicago City Tour In a Lamborghini[60 Minute Experience]](https://mediaim.expedia.com/localexpert/50806683/b6324a0b-7fb0-4936-8b5f-2fdebe79ae59.jpg?impolicy=resizecrop&rw=500&rh=280)
Food, drink & nightlife
See all 38 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
Activity duration is 2 hours and 30 minutes
8.0 out of 10 with 41 reviews
Classes & workshops
See all 22 activities
Chicago: BYOB Spray Paint and Sip Workshop
Activity duration is 1 hour and 30 minutes
10.0 out of 10 with 14 reviews
Free cancellation available
Attractions
See all 22 activities
360 CHICAGO Observation Deck
Activity duration is 2 hours
8.6 out of 10 with 717 reviews
Free cancellation available
Stay near popular Second City attractions
Best Lodging Options Near Second City
Check availability on hotels close to Second City
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place Chicago IL
Eurostars Magnificent Mile
660 North State Street Chicago IL
Freehand Chicago
19 East Ohio Street Chicago IL
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.