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Pendry Chicago

Downtown Chicago

per person

18 Sept - 22 Sept

found 14 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,033 reviews)

We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 11 Aug 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

18 Sept - 22 Sept

found 14 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,679 reviews)

Amazing property well worth the money

Reviewed on 11 Aug 2025

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

18 Sept - 22 Sept

found 14 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Tours & day trips

See all 175 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 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 14 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Swedish American Museum Center

You can spend an afternoon exploring the galleries in Swedish American Museum Center during your travels in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Hutchinson Street Historic District

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

About Face Theater

You can enjoy a show at About Face Theater on your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Methodist Hospital of Chicago

If Methodist Hospital of Chicago is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Riviera Theatre

You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Pegasus Players

You can get tickets for a performance at Pegasus Players on your trip to Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.