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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)

Excellent stay. Loved everything about this hotel. Definitely coming back.

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 143 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 16 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

The 606

The 606 is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music and sunsets in the area.

Humboldt Park Beach

Why not spend a lazy afternoon at Humboldt Park Beach during your trip to Chicago? Experience the live music and theatre scene in this vibrant area.

National Museum of Puerto Rican Arts & Culture

You can spend time browsing the exhibits at National Museum of Puerto Rican Arts & Culture during your travels in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Norwegian - American Hospital

If Norwegian - American Hospital is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Busy Beaver Button Museum

You can spend time studying the exhibits at Busy Beaver Button Museum during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Paseo Boricua

Learn about the local history of Chicago when you take a trip to Paseo Boricua. Stroll along the lakeside or experience the fascinating museums in this vibrant area.