Plan a trip to see Picasso Statue

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Pendry Chicago

Downtown Chicago

CA $820

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,064 reviews)

Very impressive, 5 star quality for 4 star prices. Highly recommend.

Reviewed on Aug. 30, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,229

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,694 reviews)

5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

The Emily Hotel

Downtown Chicago

CA $1,400

per person

Oct 3 - Oct 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,192 reviews)

The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug. 22, 2025

Tours & day trips

See all 171 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 36 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

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