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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

€654

per person

1 Feb - 6 Feb

found 1 day 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 1 day 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

Chicago luxury home suites

Downtown Chicago

€2,364

per person

29 Dec - 2 Jan

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

10/10 Exceptional! (1 review)

Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on 26 Nov 2025

Tours & day trips

See all 146 activities

Wendella's 90-min Chicago River Architecture Tour

Private & custom tours

See all 47 activities

Experience Chicago Cocktail Adventure Part 2

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 14 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 10 activities

Chicago Perfume Making Classes on Magnificent Mile

Free cancellation available

Popular places to visit

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4944 S Woodlawn Ave

Find out about the history of Chicago with a stop at 4944 S Woodlawn Ave. Stroll along the lakeside or visit the notable monuments in this vibrant area.