Second City

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Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on 9 Mar, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.

Reviewed on 9 Mar, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar, 2026

Tours & day trips

See all 192 activities
Flyover in Chicago

Flyover in Chicago

Activity duration is 30 minutes
9.8 out of 10 with 14 reviews
Free cancellation available
Price is S$48 per adult
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Private & custom tours

See all 60 activities
Chicago Cocktail Adventure Part 1

Chicago Cocktail Adventure Part 1

Activity duration is 3 hours
Free cancellation available
Price is S$6 per adult
Chicago Cocktail Adventure Part 1Opens in new tab

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 S$102 per adult
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Classes & workshops

See all 21 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 S$57 per adult
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Attractions

See all 20 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 700 reviews
Free cancellation available
Price is S$38 per adult
360 CHICAGO Observation DeckOpens in new tab

Popular places to visit

Chicago History Museum featuring interior views

Chicago History Museum

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
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 enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

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

North Avenue Beach

5/5(1 review)

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

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

Lincoln Park Zoo

4/5(27 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

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

Lighthouse ArtSpace Chicago

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

Lighthouse ArtSpace Chicago

Top Second City Hotel 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
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
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
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
Eurostars Magnificent Mile

Eurostars Magnificent Mile

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

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
Hotel Lincoln
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street Chicago IL
Level Chicago – Old Town
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Aloft Chicago Mag Mile
See all 4,232 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.

The Annual Holiday Sale

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.