Second City Tours and Activities

Plan a trip to see Second City

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,263, price is now AU$971 per person
AU$971
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,361, price is now AU$1,027 per person
AU$1,027
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on 11 Oct 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was AU$1,295, price is now AU$977 per person
AU$977
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on 4 Oct 2025

Tours & day trips

See all 166 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1485 reviews
Free cancellation available
Price is AU$75 per adult
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Private & custom tours

See all 30 activities
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
Price is AU$14 per adult*
Eastside Chicago The Heist Exploration Game and TourOpens in new tab

Food, drink & nightlife

See all 27 activities
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
9.0 out of 10 with 20 reviews
Free cancellation available
Price is AU$65 per adult
Chicago: Architecture Boat Tour with DrinksOpens in new tab

Attractions

See all 17 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 671 reviews
Free cancellation available
Price is AU$45 per adult
360 CHICAGO Observation DeckOpens in new tab

Adventure & outdoor

See all 14 activities
Chicago: Two Flight Indoor Skydiving Experience

Chicago: Two Flight Indoor Skydiving Experience

Activity duration is 1 hour
10.0 out of 10 with 1 review
Free cancellation available
Price is AU$158 per traveller
Chicago: Two Flight Indoor Skydiving ExperienceOpens in new tab

Popular places to visit

Chicago History Museum which includes interior views

Chicago History Museum

4.5/5(2 reviews)

Explore the rich and exciting history of this great, iconic all-American city through an array of artefacts, hands-on exhibits and multi-media presentations.

Chicago History Museum
Park West

Park West

You can enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Park West
North Avenue Beach

North Avenue Beach

Why not spend a care-free afternoon at North Avenue Beach during your travels in Chicago? Experience the fascinating museums and acclaimed art galleries in this vibrant area.

North Avenue Beach
Lincoln Park Zoo showing zoo animals and land animals as well as a couple

Lincoln Park Zoo

4.5/5(7 reviews)

This small zoo right in the heart of Chicago, Lincoln Park is an ideal family destination, popular with small children eager to see the many different animals.

Lincoln Park Zoo
South Pond

South Pond

Commune with nature and explore the great outdoors at South Pond during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

South Pond

Henry Gerber House

Learn about the local history of Chicago when you take a trip to Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.

Henry Gerber House

Top Second City Hotel & Accommodation Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy, Chicago, IL
The Chicago Hotel Collection Ambassador Gold Coast
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Freehand Chicago
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
The Whitehall Hotel, BW Premier Collection
Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Claridge House
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street, Chicago, IL
Hotel Lincoln
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,008 properties in Second City
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.