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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 13 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 13 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 13 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 146 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 26 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 14 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 9 activities

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

Free cancellation available

Popular places to visit

Kathy Osterman Beach

Spend a day swimming and paddling on Lake Michigan or soaking up the sun on a peaceful beach located at the northern tip of Lincoln Park.

Loyola Beach

Why not spend a lazy afternoon at Loyola Beach during your trip to Chicago? Stroll along this family-friendly area's beaches or simply enjoy its restaurants.

Swedish American Museum Center

You can spend an afternoon exploring the galleries in Swedish American Museum Center during your travels in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Rosemont Avenue Beach

Why not spend a lazy afternoon at Rosemont Avenue Beach during your trip to Chicago? Stroll along the lakeside or experience the area's theatre scene.

Joseph J. Gentile Center

Catch an event at Joseph J. Gentile Center during your trip to Chicago. Stroll along this family-friendly area's beaches or simply enjoy its restaurants.

Loyola University Chicago

Enjoy the student vibe at Loyola University Chicago during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.