Oak Street Tours

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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,364, price is now $352 per person
$352
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $810, price is now $459 per person
$459
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $690, price is now $406 per person
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 252 activities
Architecture River Tour from Navy Pier

Architecture River Tour from Navy Pier

Activity duration is 1 hour
9.6 out of 10 with 1668 reviews
Free cancellation available
Price is $39 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 $114 per adult
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Food, drink & nightlife

See all 33 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 44 reviews
Price is $158 per adult
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Classes & workshops

See all 28 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 $40 per adult
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Attractions

See all 19 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 748 reviews
Free cancellation available
Price is $27 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 theater scene and fascinating museums 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
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Congress Plaza Hotel
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
River Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
The Wade
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
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Eurostars Magnificent Mile
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
127 West Huron, at LaSalle Chicago IL
The Godfrey Hotel Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
See all 4,155 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.