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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

€654

per person

1 Feb - 6 Feb

found 17 hours ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,003 reviews)

Our room was very clean, beautiful view, and extremely friendly staff. I would especially like to thank and acknowledge the outstanding customer service from Beth Ann. Her help and kindness were greatly appreciated.

Reviewed on 25 Nov 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,215

per person

1 Feb - 6 Feb

found 19 hours ago

Return flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Everything perfect , comfortable room , nice staff make out stay unforgettable.

Reviewed on 27 Nov 2025

Level Chicago – Old Town

Downtown Chicago

€1,195

per person

29 Dec - 2 Jan

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on 25 Nov 2025

Tours & day trips

See all 152 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 49 activities

Experience Chicago Cocktail Adventure Part 2

Free cancellation available

Food, drink & nightlife

See all 26 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 11 activities

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Free cancellation available

Popular places to visit

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Oak Street

During your trip to Chicago, you can find the perfect gifts to bring home at Oak Street. Experience the entertainment choices and fascinating museums in this vibrant area.

Chicago History Museum

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

900 North Michigan Shops

5/5(1 review)

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

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Annunciation Greek Orthodox Cathedral

After visiting Annunciation Greek Orthodox Cathedral, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.