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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)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 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)

I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on 6 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 154 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 11 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Printer\'s Row which includes a city and heritage architecture

Harold Washington Library Center

Harold Washington Library Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Discover the acclaimed art galleries and notable monuments in this vibrant area.

Auditorium Building and Theatre

4.5/5(2 reviews)

You can make plans for a show at Auditorium Building and Theatre on your trip to Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.

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.

DePaul University-Loop Campus

Explore the campus of DePaul University-Loop Campus during your visit to Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Afrocentric Bookstore

Enjoy a stop at Afrocentric Bookstore, an entertaining place to visit in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Jazz Institute of Chicago

You can enjoy some culture when you stop by Jazz Institute of Chicago in Chicago. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.