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

theWit Chicago, a Hilton Hotel

Downtown Chicago

€779

per person

2 Nov - 7 Nov

found 15 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9/10 Wonderful! (1,008 reviews)

The service was excellent, they made my birthday very special!

Reviewed on 19 Aug 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,160

per person

2 Nov - 7 Nov

found 15 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,679 reviews)

This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Langham, Chicago

Downtown Chicago

€1,218

per person

2 Nov - 7 Nov

found 15 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

Tours & day trips

See all 174 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 35 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 32 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 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Fourth Presbyterian Church

Find out about the history of Chicago when you take a trip to Fourth Presbyterian Church. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

John Hancock Center

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

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 art galleries in this vibrant area.

Chicago Water Tower

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.