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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

Food, drink & nightlife

See all 26 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 26 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

Chicago History Museum

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

Lincoln Park Zoo

4/5(27 reviews)

This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!

Park West

You can enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

South Pond

Commune with nature and explore the great outdoors at South Pond during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Lincoln Park Conservatory

This glass structure filled with exotic plants is the perfect place to spend a quiet afternoon.

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.