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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 22 hours 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 22 hours 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 22 hours 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 149 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 49 activities

Experience Chicago Cocktail Adventure Part 2

Free cancellation available

Food, drink & nightlife

See all 24 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 10 activities

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

Free cancellation available

Popular places to visit

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Clarke House Museum

You can spend time studying the exhibits at Clarke House Museum during your travels in Chicago. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Burnham Park

After visiting Burnham Park, make a plan to see the other sights and activities in Chicago. Stroll along the area's beautiful beaches or simply savour its top-notch restaurants.

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Field Museum of Natural History

A great destination for all the family, home to over 2 million artefacts on archaeology, history and science, from dinosaur bones to Egyptian mummies.