Plan a trip to see Chicago Defender Original Site

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Virgin Hotels Chicago

Downtown Chicago

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per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,334 reviews)

I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Pendry Chicago

Downtown Chicago

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per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,006 reviews)

Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,635 reviews)

Great views, great service, great location

Reviewed on Jul. 13, 2025

Tours & day trips

See all 177 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 34 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 30 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

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