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Hilton Chicago

Downtown Chicago

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per person

Aug 29 - Sep 1

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (1,986 reviews)

For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on Jul. 16, 2025

Virgin Hotels Chicago

Downtown Chicago

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per person

Sep 4 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (1,334 reviews)

I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul. 15, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

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per person

Sep 4 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,635 reviews)

Beautiful and upscale property

Reviewed on Jul. 17, 2025

Tours & day trips

See all 176 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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Chicago's Dark Side Self-Guided Smartphone Walking Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

The 606

After visiting The 606, make a plan to see the other sights and activities in Chicago.

Illinois Centennial Memorial Column

Learn about the local history of Chicago when you spend time at Illinois Centennial Memorial Column. Stroll along the lakeside in this vibrant area, or check out its top-notch restaurants.

Humboldt Park

Humboldt 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 scene and entertainment choices in this vibrant area.

Garfield Park Conservatory

While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.

Kosciuszko Dog Park

Kosciuszko Dog Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music and sunsets in the area.

Busy Beaver Button Museum

You can spend time studying the exhibits at Busy Beaver Button Museum in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.