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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $866, price is now $534 per person
$534
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
The staff is super nice and great amenities

Reviewed on Oct 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,252, price is now $720 per person
$720
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on Oct 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $943, price is now $566 per person
$566
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Súper cerca a todas las atracciones de Chicago

Reviewed on Oct 12, 2026

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 255 activities
Architecture River Tour from Navy Pier

Architecture River Tour from Navy Pier

Activity duration is 1 hour
9.6 out of 10 with 1657 reviews
Free cancellation available
Price is $39 per adult
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Private & custom tours

See all 72 activities
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 38 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 23 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 17 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 747 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
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
Congress Plaza Hotel

Congress Plaza Hotel

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

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
River Hotel
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Eurostars Magnificent Mile
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
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 Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
The Wade
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
Warwick Allerton - Chicago
See all 4,075 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.