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 19 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 19 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 19 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 22 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

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 fascinating museums.

333 West Wacker Drive

After visiting 333 West Wacker Drive, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

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.

Marina City

You can learn about the history of Chicago when you stop by Marina City. Amble around this vibrant area's riverfront or experience its entertainment choices.

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 art galleries 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.