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theWit Chicago, a Hilton Hotel

Downtown Chicago

€495

per person

1 Feb - 6 Feb

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on 10 Nov 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

€896

per person

1 Feb - 6 Feb

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,761 reviews)

Room exceptional well kept, staff extremely nice Ms Diana in the front desk and Luis in the concierge were superb

Reviewed on 10 Nov 2025

Pendry Chicago

Downtown Chicago

€595

per person

1 Feb - 6 Feb

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Rooms are lovely, bar / restaurant is top notch. Love staying at the pendry!

Reviewed on 10 Nov 2025

Tours & day trips

See all 160 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 50 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 12 activities

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Free cancellation available

Popular places to visit

Armitage Avenue

During your trip to Chicago, you can enjoy retail therapy at Armitage Avenue. Stroll along the lakeside in this vibrant area or visit its lively bars.

Royal George Theater

You can make plans for a show at Royal George Theater during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Steppenwolf Theatre

You can enjoy a show at Steppenwolf Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

The Salt Shed

You can get tickets for a performance at The Salt Shed on your trip to Chicago. Experience the live music and theatre scene in this vibrant area.

Kendall College

Explore the campus of Kendall College as part of your travels around Chicago. Experience the entertainment choices and fascinating museums in this vibrant area.

St. Stanislaus Kostka Church

After visiting St. Stanislaus Kostka Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.