Oak Street

Photo by Eleonora Bertacchi
Photo by Eleonora Bertacchi

Plan a trip to see Oak Street

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago/Midway Airport

Hilton Garden Inn Chicago/Midway Airport

3 out of 5
Bedford Park
per person
4 Sept - 8 Sept
found 23 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.4/10 Very Good! (1,001 reviews)
This hotel is alway is 5 star

Reviewed on 19 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Sept - 8 Sept
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Trump International Hotel is an amazing hotel. Fabulous staff, immaculately clean. I look forward to staying there again

Reviewed on 22 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
4 Sept - 8 Sept
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,763 reviews)
Friendly bartender made the whole trip amazing, the beds and bathroom were really nice!

Reviewed on 22 Jun 2025

Tours & day trips

See all 174 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.4 out of 10 with 1393 reviews
Free cancellation available
Price is £36 per adult
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Food, drink & nightlife

See all 34 activities
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
9.6 out of 10 with 7 reviews
Free cancellation available
Price is £31 per adult
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Private & custom tours

See all 33 activities
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
Price is £9 per adult*
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Attractions

See all 19 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 628 reviews
Free cancellation available
Price is £22 per adult
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Adventure & outdoor

See all 14 activities
Chicago White Sox Baseball Game at Guaranteed Rate Field

Chicago White Sox Baseball Game at Guaranteed Rate Field

Activity duration is 2 hours and 30 minutes
Price is £30 per adult
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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 riverfront or experience the acclaimed theatre scene 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 acclaimed art galleries.

John Hancock Center
Washington Square

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

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 fascinating museums 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 Hotel Deals

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
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
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
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
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 Wade
The Wade
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
The Wade
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
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
citizenM Chicago Downtown
Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
Freehand Chicago
See all 3,953 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.