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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $620 per person
$620
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,043, price is now $1,151 per person
$1,151
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,477, price is now $862 per person
$862
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)
We really enjoyed our stay. clean rooms and staff was very friendly

Reviewed on Jul 22, 2026

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 267 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour
9.6 out of 10 with 1584 reviews
Free cancellation available
Price is $39 per adult
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Private & custom tours

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Chamarel 7 Colours and Waterfalls - Exclusive South West Tour

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
Price is $125 per traveler*
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Food, drink & nightlife

See all 41 activities
City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Activity duration is 2 hours
6.8 out of 10 with 22 reviews
Price is $63 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 $40 per adult
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Attractions

See all 22 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 2 hours
8.6 out of 10 with 731 reviews
Free cancellation available
Price is $30 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 entertainment choices and acclaimed theater scene 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
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Omni Chicago Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
The Wade
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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Hotel Riu Plaza Chicago
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 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
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
InterContinental Chicago Magnificent Mile by IHG
See all 3,982 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.