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Hotel Riu Plaza Chicago

Downtown Chicago

S$2,412

per person

29 May - 31 May

found 13 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 13 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 13 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 190 activities

Flyover in Chicago

Free cancellation available

Private & custom tours

See all 60 activities

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

Kingston Mines

You can enjoy a show at Kingston Mines on your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Victory Gardens Theater

You can get tickets for a performance at Victory Gardens Theater on your trip to Chicago. Experience the fascinating museums and entertainment choices in this vibrant area.

Lincoln Hall

You can get tickets for a performance at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

St. Clements Church

After visiting St. Clements Church, make a plan to see the other sights and activities in Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

Children's Memorial Hospital

If Children's Memorial Hospital is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Apollo Theater Chicago

You can make plans for a show at Apollo Theater Chicago during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.