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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 129 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 43 activities

Experience Chicago Cocktail Adventure Part 2

Free cancellation available

Food, drink & nightlife

See all 23 activities

Odyssey Chicago River Premier Dinner Cruise

Attractions

See all 13 activities

Chicago CityPASS®: Experience 5 must-see attractions

Free cancellation available

Classes & workshops

See all 10 activities

Chicago Perfume Making Classes on Magnificent Mile

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.

Madison Street Theatre

You can get tickets for a performance at Madison Street Theatre during your trip to Oak Park. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Mills Park

Mills Park is just one of the places to see in Oak Park, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Pleasant Home

You can spend an afternoon studying the exhibits at Pleasant Home in Oak Park. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.