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Pendry Chicago

Downtown Chicago

€456

per person

20 Nov - 25 Nov

just found

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

just found

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

Swissotel - Chicago

Downtown Chicago

€694

per person

10 Nov - 16 Nov

found 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Tours & day trips

See all 158 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 29 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 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

National Museum of Mexican Art

You can spend time exploring the galleries in National Museum of Mexican Art during your travels in Chicago. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.

Cooper Dual Language Academy

You can spend time studying the exhibits at Cooper Dual Language Academy during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

St Adalbert Church

St Adalbert Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed theatre scene in this vibrant area.

St Pius Church

After visiting St Pius Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Addams/Medill Park

After visiting Addams/Medill Park, make a plan to see the other sights and activities in Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Canalport Riverwalk Park

After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.