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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 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 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 12 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Michigan Avenue Bridge

Learn about the local history of Chicago when you take a trip to Michigan Avenue Bridge. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Wrigley Building

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Tribune Tower

You can learn about the history of Chicago with a visit to Tribune Tower. Discover the fascinating museums and notable monuments in this vibrant area.

Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Carbide and Carbon Building

You can find out about the history of Chicago with a stop at Carbide and Carbon Building. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Shops at Northbridge

You can find the perfect gifts to bring home at Shops at Northbridge during your trip to Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.