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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 12 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 12 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 12 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 147 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 47 activities

Experience Chicago Cocktail Adventure Part 2

Free cancellation available

Food, drink & nightlife

See all 26 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 16 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

Unity Temple

Frank Lloyd Wright’s magnum opus, Unity Temple is a revolutionary design over a hundred years old – a remarkable example of religious architecture.

Ernest Hemingway Museum and House

A captivating insight into the life and work of the Nobel Prize-winning author and one of the true giants of American literature.

Frank Lloyd Wright Historic District

4/5(1 review)

Visit the birthplace of modern architecture to explore the world's largest collections of homes and buildings designed by Frank Lloyd Wright.

Garfield Park

After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed theatre scene in this vibrant area.

Garfield Park Conservatory

This striking conservatory – home to rare tropical plants and decorated with art and water features – provides a beautiful hiatus from the hectic pace of Chicago.

Oak Park Conservatory

Enjoy a stop at Oak Park Conservatory, an entertaining place to visit in Oak Park. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.