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Hotel Riu Plaza Chicago

Downtown Chicago

S$2,412

per person

29 May - 31 May

found 10 hours ago

Return flight included

Singapore (SIN) to Chicago (ORD)

9.4/10 Exceptional! (3,438 reviews)

Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel

Reviewed on 10 Mar, 2026

Arlo Chicago

Downtown Chicago

S$2,593

per person

29 May - 31 May

found 10 hours 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

Downtown Chicago

S$2,583

per person

29 May - 31 May

found 10 hours 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

Free cancellation available

Private & custom tours

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Chicago Cocktail Adventure Part 1

Free cancellation available

Food, drink & nightlife

See all 24 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Classes & workshops

See all 21 activities

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

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Popular places to visit

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 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.

North Avenue Beach

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.

Lincoln Park Zoo

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.

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.

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.