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River Hotel

Downtown Chicago

S$2,097

per person

2 May - 8 May

found 1 day ago

Return flight included

Singapore (SIN) to Chicago (ORD)

8.8/10 Excellent! (5,034 reviews)

Room was clean more outdated that pictures show but it was fine for a one night stay I would considered it again. Check in and out was simple

Reviewed on 17 Mar, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

S$2,369

per person

2 May - 8 May

found 1 day ago

Return flight included

Singapore (SIN) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Staff was extremely accommodating. The breakfast was extraordinary. Hotel cleanliness was superb. Thanks for a wonderful stay.

Reviewed on 18 Mar, 2026

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

S$2,396

per person

2 May - 8 May

found 1 day ago

Return flight included

Singapore (SIN) to Chicago (ORD)

8.6/10 Excellent! (4,398 reviews)

We stay at this hotel each time we travel to downtown Chicago and the price, cleanliness, location and overall experience is always wonderful.

Reviewed on 17 Mar, 2026

Tours & day trips

See all 198 activities

Flyover in Chicago

Free cancellation available

Private & custom tours

See all 57 activities

Chamarel 7 Colours and Waterfalls - Exclusive South West Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

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Chicago CityPASS®: Experience 5 must-see attractions

Free cancellation available

Classes & workshops

See all 18 activities

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

Free cancellation available

Popular places to visit

Merchandise Mart

You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

House of Blues Chicago

You can get tickets for a performance at House of Blues Chicago during your trip to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Ceiling of the Cadillac palace ...great place to see a show.

Cadillac Palace Theatre

You can get tickets for a performance at Cadillac Palace Theatre on your trip to Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Chicago City Hall

Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Chicago Riverwalk

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Daley Plaza

You can learn about the history of Chicago when you stop by Daley Plaza. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.