Price found within the past 48 hours. Click for updated prices.

Pendry Chicago

Downtown Chicago

S$6,183

per person

3 Feb - 8 Feb

found 23 hours ago

Return direct flight included

Singapore (SIN) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Excellent location to stay in the heart of the city.

Reviewed on 17 Dec, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

S$6,782

per person

3 Feb - 8 Feb

found 23 hours ago

Return direct flight included

Singapore (SIN) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on 14 Dec, 2025

Nobu Hotel Chicago

Downtown Chicago

S$7,046

per person

3 Feb - 8 Feb

found 23 hours ago

Return direct flight included

Singapore (SIN) to Chicago (ORD)

9.4/10 Exceptional! (748 reviews)

It was fine. I expected more for $1000/ night

Reviewed on 16 Dec, 2025

Tours & day trips

See all 144 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 49 activities

Zen Route - Private & Exclusive Full Day Tour with Lunch Included

Free cancellation available

Food, drink & nightlife

See all 21 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 12 activities

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Free cancellation available

Popular places to visit

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.

Chicago Theatre

See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.

Carbide and Carbon Building

After visiting Carbide and Carbon Building, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

James M. Nederlander Theatre

You can make plans for a show at James M. Nederlander Theatre on your trip to Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Michigan Avenue Bridge

Learn about the local history of Chicago when you take a trip to Michigan Avenue Bridge. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Wrigley Building

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the fascinating museums and notable monuments in this vibrant area.