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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 148 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 48 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 10 activities

Chicago Perfume Making Classes on Magnificent Mile

Free cancellation available

Popular places to visit

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Margaret Burroughs Beach

Why not spend a lazy afternoon at Margaret Burroughs Beach during your trip to Chicago? Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Copernicus Statue showing a statue or sculpture

Lakefront Trail

5/5(1 review)

Lakefront Trail is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Wander the lakeside and beautiful beaches in the area.

Robert W Roloson Houses

You can find out about the history of Chicago with a visit to Robert W Roloson Houses. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Pilgrim Baptist Church

After visiting Pilgrim Baptist Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.