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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 1 day 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 1 day 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 19 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 28 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 27 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 15 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

Lincoln Park

4.5/5(13 reviews)

This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley View Rooftop

Catch an event at Wrigley View Rooftop during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Hutchinson Street Historic District

You can learn about the history of Chicago with a visit to Hutchinson Street Historic District. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

Temple Sholom

Temple Sholom 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.

Our Lady of Mount Carmel Church

Our Lady of Mount Carmel Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.