Oak Street

Photo by Eleonora Bertacchi
Photo by Eleonora Bertacchi

Tours & day trips

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Flyover in Chicago

Flyover in Chicago

Activity duration is 30 minutes
9.4 out of 10 with 12 reviews
Free cancellation available
Price is S$51 per adult
Flyover in Chicago

Private & custom tours

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Chicago Quest Experience: The Heist

Chicago Quest Experience: The Heist

Activity duration is 1 hour and 35 minutes
Free cancellation available
Price is S$14 per adult*
Chicago Quest Experience: The Heist

Food, drink & nightlife

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Chicago Favourites Ultimate Food and Walking Tour

Chicago Favourites Ultimate Food and Walking Tour

Activity duration is 3 hours
9.8 out of 10 with 34 reviews
Free cancellation available
Price is S$114 per adult
Chicago Favourites Ultimate Food and Walking Tour

Attractions

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360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.6 out of 10 with 608 reviews
Free cancellation available
Price is S$40 per adult
360 CHICAGO Observation Deck

Classes & workshops

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BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Activity duration is 1 hour and 30 minutes
10.0 out of 10 with 11 reviews
Price is S$60 per adult
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Popular places to visit

900 North Michigan Shops

900 North Michigan Shops

5/5(1 review)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

900 North Michigan Shops
Fourth Presbyterian Church

Fourth Presbyterian Church

Find out about the history of Chicago when you take a trip to Fourth Presbyterian Church. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Fourth Presbyterian Church
John Hancock Center

John Hancock Center

4.5/5(84 reviews)

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.

John Hancock Center
Washington Square

Washington Square

Explore the great outdoors at Washington Square, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Washington Square
Oak Street Beach

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Oak Street Beach
Chicago Water Tower

Chicago Water Tower

4.5/5(33 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Chicago Water Tower

Top Oak Street Hotel Deals

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
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
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
Hotel Felix River North/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
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Embassy Suites by Hilton Chicago Downtown River North
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Warwick Allerton - Chicago
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 3,663 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.