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 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

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 art galleries in this vibrant area.

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.

Willis Tower

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.

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.

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.