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 36 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

Merchandise Mart

4/5(4 reviews)

You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Cadillac Palace Theatre

You can get tickets for a performance at Cadillac Palace Theatre on your trip to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

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 fascinating museums in this vibrant area.

Daley Plaza

You can learn about the history of Chicago when you stop by Daley Plaza. Experience the acclaimed theatre scene and fascinating museums 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 theatre scene and notable monuments in this vibrant area.