Oak Street

Photo by Eleonora Bertacchi
Photo by Eleonora Bertacchi
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
It’s super convenient bc it’s on the pier but beware it’s connected so it’s not its own building. Still we felt safe and it was very clean

Reviewed on 16 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Tours & day trips

See all 178 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1419 reviews
Free cancellation available
Price is S$63 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
8.6 out of 10 with 14 reviews
Free cancellation available
Price is S$54 per adult
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Private & custom tours

See all 31 activities
Chicago's Dark Side Self-Guided Smartphone Walking Tour

Chicago's Dark Side Self-Guided Smartphone Walking Tour

Activity duration is 1 hour and 15 minutes
9.8 out of 10 with 6 reviews
Free cancellation available
Price is S$13 per adult
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Attractions

See all 17 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 644 reviews
Free cancellation available
Price is S$38 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 S$45 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 lakeside 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 theatre scene.

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

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the lakeside or experience the fascinating museums 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 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 fascinating museums.

Chicago Water Tower

Top Oak Street Hotel Deals

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
Congress Plaza Hotel

Congress Plaza Hotel

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

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Freehand 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 4,042 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.