Plan a trip to see Oak Street

Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $543

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,007 reviews)

This was by far the BEST Hotel!!!

Reviewed on Sep. 1, 2025

Park Hyatt Chicago

Downtown Chicago

CA $2,089

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug. 31, 2025

Art Villa

West Town

CA $2,538

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

Tours & day trips

See all 167 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 32 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

Popular places to visit

900 North Michigan Shops

4/5(5 reviews)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

John Hancock Center

4.5/5(194 reviews)

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

Oak Street Beach

Why not spend a carefree afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.

Chicago Water Tower

4/5(82 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art scene.