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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

per person

30 Oct - 3 Nov

found 11 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,007 reviews)

Restaurant had good breakfast

Reviewed on 9 Aug 2025

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

30 Oct - 3 Nov

found 11 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (2,270 reviews)

i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on 11 Aug 2025

Pendry Chicago

Downtown Chicago

per person

30 Oct - 3 Nov

found 11 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,033 reviews)

Gorgeous hotel. Hotel staff in all areas were extremely professional and helpful to include front desk, concierge, bar tenders, hostess and cleaning crew.

Reviewed on 10 Aug 2025

Tours & day trips

See all 176 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 31 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

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Zhou B Art Center

You can spend time browsing the exhibits at Zhou B Art Center during your trip to Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Bridgeport Art Center

You can spend time browsing the exhibits at Bridgeport Art Center during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Bubbly Creek

Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Theatre on the Lake

You can make plans for a show at Theatre on the Lake on your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.