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Pendry Chicago

Downtown Chicago

€456

per person

20 Nov - 25 Nov

found 1 day ago

Return flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

This place would’ve been great if it wasn’t for the elevators. They took forever during the day to arrive to the floor we were staying in. At one point we waited 20min for an elevator, got on and got stuck on the 14th floor. Once it opened after a couple of minutes of being stuck. We took the stairs all the way down. Other than that, very clean and nice hotel but not worth the price.

Reviewed on 11 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,050

per person

20 Nov - 25 Nov

found 1 day ago

Return flight included

Boston (BOS) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

The best hotel in chicago

Reviewed on 11 Oct 2025

The Emily Hotel

Downtown Chicago

€608

per person

20 Nov - 25 Nov

found 1 day ago

Return flight included

Boston (BOS) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant.

Reviewed on 10 Oct 2025

Tours & day trips

See all 155 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 25 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 12 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Gen. John Logan Memorial

Set on a grassy mound in a quiet corner of Grant Park, this equestrian statue celebrates an American Civil War hero and faithful servant of Abraham Lincoln.

Lollapalooza

After visiting Lollapalooza, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Grant Park

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Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Auditorium Building and Theatre

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Roosevelt University

Explore the campus of Roosevelt University during your visit to Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.