Second City Tours and Activities

Plan a trip to see Second City

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $959, price is now CA $673 per person
CA $673
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,237, price is now CA $873 per person
CA $873
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on Feb 9, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,396, price is now CA $1,002 per person
CA $1,002
per person
Apr 25 - Apr 29
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Love the room! Very ritzy!!

Reviewed on Feb 8, 2026

Tours & day trips

See all 154 activities
Flyover in Chicago

Flyover in Chicago

Activity duration is 30 minutes
9.8 out of 10 with 13 reviews
Free cancellation available
Price is CA $52 per adult
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Private & custom tours

See all 58 activities
Chicago Cocktail Adventure Part 1

Chicago Cocktail Adventure Part 1

Activity duration is 3 hours
Free cancellation available
Price is CA $7 per adult
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Food, drink & nightlife

See all 24 activities
Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

Activity duration is 3 hours
10.0 out of 10 with 263 reviews
Free cancellation available
Price is CA $109 per adult
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Attractions

See all 19 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.6 out of 10 with 699 reviews
Free cancellation available
Price is CA $40 per adult
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Classes & workshops

See all 13 activities
BYOB Spray Paint and Sip at Studio W.I.P.

BYOB Spray Paint and Sip at Studio W.I.P.

Activity duration is 1 hour and 30 minutes
9.8 out of 10 with 235 reviews
Free cancellation available
Price is CA $62 per adult
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Popular places to visit

Chicago History Museum featuring interior views

Chicago History Museum

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

Chicago History Museum
Chicago cityscape at twilight, featuring a mix of residential and commercial buildings, including a church and modern apartment complex. River West, Chicago, Illinois, United States

Park West

You can make plans for a show at Park West during your stay in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

Park West
Chicago, lake shore drive, lake michigan, North Avenue Beach, aerial view,

North Avenue Beach

Why not spend a carefree afternoon at North Avenue Beach during your travels in Chicago? Experience the acclaimed art scene and entertainment choices in this vibrant area.

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

Lincoln Park Zoo

This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!

Lincoln Park Zoo

Henry Gerber House

Learn about the local history of Chicago with a stop at Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.

Henry Gerber House

Lighthouse ArtSpace Chicago

You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your trip to Chicago. Discover the entertainment choices and notable monuments in this vibrant area.

Lighthouse ArtSpace Chicago

Best Lodging Options Near Second City

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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Hotel Riu Plaza Chicago
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
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Eurostars Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Aloft Chicago Mag Mile
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
165 East Ontario Street Chicago IL
Courtyard by Marriott Chicago Magnificent Mile
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
See all 4,336 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.