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Pendry Chicago

Downtown Chicago

per person

18 Sept - 22 Sept

found 12 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 12 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 12 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

Merchandise Mart

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 theatre scene.

333 West Wacker Drive

After visiting 333 West Wacker Drive, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

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.

Marina City

You can learn about the history of Chicago when you stop by Marina City. Amble around this vibrant area's riverfront or experience its entertainment choices.

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 acclaimed art galleries in this vibrant area.

James M. Nederlander Theatre

You can make plans for a show at James M. Nederlander Theatre on your trip to Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.