Oak Street Tours and Activities

A coastal cityscape with high-rise buildings, a beach, and a river.

Plan a trip to see Oak Street

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,184, price is now CA $1,361 per person
CA $1,361
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (556 reviews)
Great! But parking was bad.

Reviewed on Aug 26, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,263, price is now CA $1,464 per person
CA $1,464
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,456, price is now CA $1,613 per person
CA $1,613
per person
Nov 17 - Nov 21
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)

Tours & day trips

See all 257 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour
9.6 out of 10 with 1622 reviews
Free cancellation available
Price is CA $54 per adult
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Private & custom tours

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Chicago: Shooting & Spinning Art Experience (Neon Lights)

Chicago: Shooting & Spinning Art Experience (Neon Lights)

Activity duration is 45 minutes
Free cancellation available
Price is CA $159 per adult
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Food, drink & nightlife

See all 40 activities
City Cruises Chicago: Lake Michigan Premier Dinner Cruise

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Activity duration is 2 hours and 30 minutes
8.0 out of 10 with 43 reviews
Price is CA $220 per adult
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Classes & workshops

See all 30 activities
Chicago: BYOB Spray Paint and Sip Workshop

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
Price is CA $56 per adult
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Attractions

See all 21 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 737 reviews
Free cancellation available
Price is CA $42 per adult
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Stay near popular Oak Street attractions

Oak Street

9.4/10 (3 reviews)
During your trip to Chicago, you can do some window-shopping at Oak Street. Experience the acclaimed art scene and entertainment choices in this vibrant area.
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Best Lodging Options Near Oak Street

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Kasa Magnificent Mile Chicago
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
120 East Delaware Place Chicago IL
Four Seasons Hotel Chicago
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
The Whitehall Hotel, BW Premier Collection
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The Chicago Hotel Collection - Magnificent Mile
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave Chicago IL
The Westin Michigan Avenue Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
20 E Chestnut St Chicago IL
Sofitel Chicago Magnificent Mile
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Hilton Chicago/Magnificent Mile Suites
See all 3,946 properties in Oak Street
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.