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theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

S$461

per person

6 Jan - 11 Jan

found 1 day ago

Return direct flight included

Hartford (BDL) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

great staff...loved our stay.

Reviewed on 22 Nov, 2025

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

S$728

per person

6 Jan - 11 Jan

found 1 day ago

Return direct flight included

Hartford (BDL) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on 25 Nov, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

S$505

per person

6 Jan - 11 Jan

found 1 day ago

Return direct flight included

Hartford (BDL) to Chicago (ORD)

9.2/10 Wonderful! (317 reviews)

The room was beautiful and clean and a good city view of the city

Reviewed on 26 Nov, 2025

Tours & day trips

See all 151 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 50 activities

Experience Chicago Cocktail Adventure Part 2

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 11 activities

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

Free cancellation available

Popular places to visit

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Chicago Children's Museum

You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Ohio Street Beach

Why not spend a care-free afternoon at Ohio Street Beach during your travels in Chicago? Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Milton Lee Olive Park

Explore the great outdoors at Milton Lee Olive Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Chicago Harbor Lighthouse

Learn about the local history of Chicago with a stop at Chicago Harbor Lighthouse. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Smith Museum of Stained Glass Windows

You can spend an afternoon studying the exhibits at Smith Museum of Stained Glass Windows in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.