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 1 day 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 1 day ago

Return direct flight included

Singapore (SIN) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

From staff to room it was a amazing experience.

Reviewed on 18 Dec, 2025

Nobu Hotel Chicago

Downtown Chicago

S$7,046

per person

3 Feb - 8 Feb

found 1 day 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 Loop Synagogue

Chicago Loop Synagogue 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.

CIBC Theatre

You can enjoy a show at CIBC Theatre on your trip to Chicago. Discover the entertainment choices 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.

State Street

During your visit to Chicago, you can find the perfect gifts to bring home at State Street. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Picasso Statue

Learn about the local history of Chicago when you take a trip to Picasso Statue. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Daley Plaza

You can learn about the history of Chicago when you stop by Daley Plaza. Experience the acclaimed art galleries and fascinating museums in this vibrant area.