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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 21 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 21 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 155 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 25 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

Illinois Institute of Technology

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

State Street Village

You can find out about the history of Chicago with a stop at State Street Village. Stroll along the lakeside or visit the notable monuments in this vibrant area.

SR Crown Hall

Find out about the history of Chicago with a stop at SR Crown Hall. Experience the acclaimed art galleries and fascinating museums 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.

Near South Health Center

If Near South Health Center is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Captain Ernest A Griffin Place

You can learn about the history of Chicago with a visit to Captain Ernest A Griffin Place. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.