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Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

€455

per person

20 Nov - 27 Nov

found 22 hours ago

Return flight included

Boston (BOS) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

Food price was high but everything was fine

Reviewed on 4 Oct 2025

Pendry Chicago

Downtown Chicago

€522

per person

20 Nov - 27 Nov

found 22 hours ago

Return flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

Excellent location, great restaurants nearby. Nice, spacious rooms.

Reviewed on 3 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,029

per person

20 Nov - 25 Nov

found 10 hours ago

Return flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Clean room. Great staff

Reviewed on 2 Oct 2025

Tours & day trips

See all 156 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

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.

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Northerly Island Park which includes views, a city and a river or creek

Northerly Island Natural Area

Bird life, paved paths and a built-in music venue give one of Chicago’s newest green spaces much to offer to nature lovers, exercisers and music fans.

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.

Lake Meadows Park

Lake Meadows Park 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 fascinating museums.

Monument to the Great Northern Migration

You can find out about the history of Chicago with a visit to Monument to the Great Northern Migration. Experience the acclaimed art galleries and fascinating museums in this vibrant area.