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Pendry Chicago

Downtown Chicago

per person

18 Sept - 22 Sept

found 20 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 20 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 20 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 177 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 15 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

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Chicago Water Tower

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

John Hancock Center

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Fourth Presbyterian Church

Find out about the history of Chicago when you take a trip to Fourth Presbyterian Church. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Museum of Contemporary Art Chicago

You can spend an afternoon studying the exhibits at Museum of Contemporary Art Chicago during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.