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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

€654

per person

1 Feb - 6 Feb

found 7 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 8 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 16 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 24 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

State Street

During your visit to Chicago, you can find the perfect gifts to bring home at State Street. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Chicago Cultural Center

4/5(6 reviews)

You can enjoy a show at Chicago Cultural Center during your trip to Chicago. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Crown Fountain

Innovative and certainly unique, this art installation in Millennium Park features the faces of 1,000 Chicagoans blown up five stories tall.

CIBC Theatre

You can enjoy a show at CIBC Theatre on your trip to Chicago. Discover the entertainment choices and notable monuments in this vibrant area.

Cloud Gate

4.5/5(3 reviews)

You can learn about the history of Chicago with a visit to Cloud Gate. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Marshall Field Building

You can learn about the history of Chicago with a trip to Marshall Field Building. Stroll along the riverfront or experience the entertainment choices in this vibrant area.