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

Pendry Chicago

Downtown Chicago

per person

19 Aug - 24 Aug

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,006 reviews)

Staff was very friendly and helpful. We had a great stay in every way possible!

Reviewed on 30 Jun 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

19 Aug - 24 Aug

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,623 reviews)

Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.

Reviewed on 27 Jun 2025

Level Chicago – Old Town

Downtown Chicago

per person

19 Aug - 24 Aug

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9/10 Wonderful! (320 reviews)

This was a wonderful location. It wasn't a type of stay that I am familiar with, in that, there isn't really a lot of people to reach out to ask for assistance. But, all in all, I would definitely stay there again.

Reviewed on 29 Jun 2025

Tours & day trips

See all 179 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 18 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

311 S Wacker Dr

You can learn about the history of Chicago with a trip to 311 S Wacker Dr. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Willis Tower

4.5/5(81 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Chicago Board of Trade Building

You can learn about the history of Chicago when you stop by Chicago Board of Trade Building. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.

Printer\'s Row which includes a city and heritage architecture

Harold Washington Library Center

Harold Washington Library Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Discover the fascinating museums and notable monuments in this vibrant area.

The Old Post Office

You can find out about the history of Chicago with a visit to The Old Post Office. Discover the entertainment choices and notable monuments in this vibrant area.