Oak Street Tours and Activities
Visit Oak Street
Plan a trip to see Oak Street
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,178, price is now CA $800 per person
CA $800
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
I wish the space was bigger. It was too tight for me and my young girls but the staff was so extra nice and welcoming.
Reviewed on Jul 14, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 2026
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was CA $1,458, price is now CA $1,029 per person
CA $1,029
per person
Aug 24 - Aug 28
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I enjoyed my stay here. Clean room, well maintained property and great location just 3 miles from Chicago. The best part was the friendly staff. The breakfast was a 4.5 out 5, just adequate foe the day's need, nothing super special. I would definitely return.
Reviewed on Jul 13, 2026
Tours & day trips
See all 271 activities
Architecture River Tour
Activity duration is 1 hour
9.6 out of 10 with 1572 reviews
Free cancellation available
Private & custom tours
See all 66 activities
Chamarel 7 Colours and Waterfalls - Exclusive South West Tour
Activity duration is 9 hours
9.8 out of 10 with 44 reviews
Free cancellation available
![City centre Chicago City Tour In a Lamborghini[60 Minute Experience]](https://mediaim.expedia.com/localexpert/50806683/b6324a0b-7fb0-4936-8b5f-2fdebe79ae59.jpg?impolicy=resizecrop&rw=500&rh=280)
Food, drink & nightlife
See all 42 activities
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan
Activity duration is 2 hours
6.8 out of 10 with 22 reviews
Classes & workshops
See all 28 activities
Chicago: BYOB Spray Paint and Sip Workshop
Activity duration is 1 hour and 30 minutes
10.0 out of 10 with 15 reviews
Free cancellation available
Attractions
See all 22 activities
360 CHICAGO Observation Deck
Activity duration is 2 hours
8.6 out of 10 with 731 reviews
Free cancellation available
Stay near popular Oak Street attractions
Best Lodging Options Near Oak Street
Check availability on hotels close to Oak Street
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place Chicago IL
River Hotel
75 East Wacker Drive Chicago IL
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.