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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 150 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 25 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

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Milton Lee Olive Park

Explore the great outdoors at Milton Lee Olive Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

875 North Michigan Avenue

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.

Ohio Street Beach

Why not spend a care-free afternoon at Ohio Street Beach during your travels in Chicago? Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Chicago Water Tower

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.