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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

per person

30 Oct - 3 Nov

found 6 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 6 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (2,270 reviews)

Great hotel and great service! Would definitely recommend to anyone staying in the Mag mile area. The breakfast buffet was really good and convenient. The room was very comfortable and spacious.

Reviewed on 11 Aug 2025

Pendry Chicago

Downtown Chicago

per person

30 Oct - 3 Nov

found 6 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 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 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

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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.

Bridgeport Art Center

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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.

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 theatre scene in this vibrant area.

Stephen A. Douglas Tomb and Memorial

Find out about the history of Chicago when you spend time at Stephen A. Douglas Tomb and Memorial. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.