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

Pendry Chicago

Downtown Chicago

€880

per person

1 Feb - 6 Feb

found 16 hours ago

Return flight included

Dublin (DUB) to Chicago (ORD)

18.8/10 Exceptional! (1,130 reviews)

Staff was our favorite part! Very very professional and friendly

Reviewed on 14 Nov 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,756

per person

19 Dec - 24 Dec

found 16 hours ago

Return flight included

Manchester (MAN) to Chicago (ORD)

18.8/10 Exceptional! (1,773 reviews)

Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

€888

per person

1 Feb - 6 Feb

found 16 hours ago

Return flight included

Dublin (DUB) to Chicago (ORD)

18.4/10 Exceptional! (317 reviews)

I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on 28 Oct 2025

Tours & day trips

See all 151 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 48 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago Craft Brewery Barrel Bus Tour

Free cancellation available

Attractions

See all 15 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

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Hutchinson Street Historic District

You can learn about the history of Chicago with a visit to Hutchinson Street Historic District. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Lucky Strike at Wrigleyville

You can take time to visit Lucky Strike at Wrigleyville during your travels to Chicago. Experience the entertainment choices and acclaimed theatre scene in this walkable area.

Chicago's Mercury Theater

You can enjoy a show at Chicago's Mercury Theater during your trip to Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

Defiant Theatre

You can enjoy a show at Defiant Theatre during your stay in Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.