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

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)

A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.

Reviewed on 12 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

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.

Daley Plaza

You can learn about the history of Chicago when you stop by Daley Plaza. Experience the fascinating museums and entertainment choices in this vibrant area.

Richard J. Daley Center

Richard J. Daley Center 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 visit the notable monuments in this vibrant area.

Picasso Statue

Learn about the local history of Chicago when you take a trip to Picasso Statue. Discover the acclaimed art galleries and notable monuments in this vibrant area.

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.

Chicago Loop Synagogue

Chicago Loop Synagogue 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 art galleries in this vibrant area.