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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

€654

per person

1 Feb - 6 Feb

just found

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 2 hours ago

Return flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Great stay. Excellent location.

Reviewed on 23 Nov 2025

Level Chicago – Old Town

Downtown Chicago

€1,195

per person

29 Dec - 2 Jan

found 9 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

Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Tribune Tower

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

Wrigley Building

4.5/5(3 reviews)

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Shops at Northbridge

You can find the perfect gifts to bring home at Shops at Northbridge during your trip to Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

Shops at North Bridge

Spend a day exploring the department store, luxury fashion outlets and food court at this mall on the glitzy Magnificent Mile shopping district.

Michigan Avenue Bridge

4.5/5(8 reviews)

Learn about the local history of Chicago when you take a trip to Michigan Avenue Bridge. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.