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Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

HK$4,889

per person

6 Nov - 9 Nov

found 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,427 reviews)

Cleaning staff amazing! Great proximity to everything on Michigan Ave! Starbucks across the street along with Garrett’s popcorn !

Reviewed on 6 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

HK$7,488

per person

6 Nov - 9 Nov

found 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on 6 Oct 2025

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

HK$5,140

per person

6 Nov - 9 Nov

found 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

Front desk clerk was great. Made us feel like VIPs.

Reviewed on 5 Oct 2025

Tours & day trips

See all 25 activities

Chicago: Moonlight Paddle Tour on the Chicago River

Free cancellation available

Food, drink & nightlife

See all 5 activities

Vito's Vault Chicago finest dinner theatre speakeasy

Free cancellation available

Adventure & outdoor

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Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Private & custom tours

See all 4 activities

Chicago Helicopter 25-Mile Tour for up to Three Passengers

Free cancellation available

Shows & concerts

See all 3 activities

Chicago Blackhawks Ice Hockey Game at United Centre

Popular places to visit

Unity Temple

This was Frank Lloyd Wright’s first major public building and is still considered one of his greatest achievements.

Ernest Hemingway Museum and House

Peek into the early life of one America’s best-loved writers.

Frank Lloyd Wright Historic District

Visit the birthplace of modern architecture to explore the world's largest collections of homes and buildings designed by Frank Lloyd Wright.

Rush Oak Park Hospital

If Rush Oak Park Hospital is what brings you to town, hopefully you'll have a chance to explore more of Oak Park.

Madison Street Theatre

You can get tickets for a performance at Madison Street Theatre during your trip to Oak Park. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.