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Hotel Riu Plaza Chicago

Downtown Chicago

S$2,412

per person

29 May - 31 May

found 18 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 18 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 18 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 191 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 25 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Classes & workshops

See all 22 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

Humboldt Park

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Illinois Centennial Memorial Column

Learn about the local history of Chicago with a stop at Illinois Centennial Memorial Column. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.

Kimball Arts Center

Enjoy an outing to Kimball Arts Center during your stay in Chicago.

Busy Beaver Button Museum

You can spend time studying the exhibits at Busy Beaver Button Museum during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Humboldt Park Beach

Why not spend a lazy afternoon at Humboldt Park Beach during your trip to Chicago? Experience the live music and theatre scene in this vibrant area.

National Museum of Puerto Rican Arts & Culture

You can spend time browsing the exhibits at National Museum of Puerto Rican Arts & Culture during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.