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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! (5,054 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Room was clean more outdated that pictures show but it was fine for a one night stay I would considered it again.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)

This is a great hotel. Excellent staff, cleanliness is superior and the location is perfect. I will be staying there again!

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

See all 20 activities

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

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.

Willis Tower

4.5/5(81 reviews)

The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.

Skydeck Ledge

4.5/5(71 reviews)

You can find out about the history of Chicago when you stop by Skydeck Ledge. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Richard J. Daley Center

Richard J. Daley Center 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 visit the notable monuments in this vibrant area.

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.