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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

€654

per person

1 Feb - 6 Feb

found 6 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 7 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 14 hours 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 151 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 25 activities

Odyssey Chicago River Premier Dinner Cruise

Attractions

See all 16 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.

Holy Name Cathedral

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Aldo Castillo Gallery

You can spend time browsing the exhibits at Aldo Castillo Gallery during your travels in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Project Room

You can spend time studying the exhibits at Project Room in Chicago. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Cooking & Hospitality Institute of Chicago

Walk around the campus at Cooking & Hospitality Institute of Chicago during your visit to Chicago. Amble around this vibrant area's riverfront or experience its fascinating museums.

Ohio Place Dog Park

Ohio Place Dog Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed art galleries and fascinating museums in this vibrant area.