Price found within the past 48 hours. Click for updated prices.

Pendry Chicago

Downtown Chicago

€998

per person

29 Dec - 2 Jan

found 2 hours ago

Return flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

We loved the Pendry!

Reviewed on 27 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,698

per person

19 Dec - 24 Dec

found 22 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.4/10 Exceptional! (1,761 reviews)

The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.

Reviewed on 3 Nov 2025

The Emily Hotel

Downtown Chicago

€1,268

per person

19 Dec - 24 Dec

found 22 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.2/10 Wonderful! (1,248 reviews)

Always a great stay! Staff are great and rooms present great value.

Reviewed on 1 Nov 2025

Tours & day trips

See all 152 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 49 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 26 activities

Odyssey Lake Michigan Premier Dinner Cruise

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

Merchandise Mart

You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its fascinating museums.

333 West Wacker Drive

After visiting 333 West Wacker Drive, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Cadillac Palace Theatre

You can get tickets for a performance at Cadillac Palace Theatre on your trip to Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Chicago City Hall

Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Marina City

You can learn about the history of Chicago when you stop by Marina City. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Assumption Church

Assumption Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.