Find hotels near Oak Street, Chicago from ₩181,380

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Dec 26 - Dec 27
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Dec 27 - Dec 28
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Dec 26 - Dec 28
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Jan 2 - Jan 4

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Our top choices for Oak Street hotels

Front of property - evening/night
The Peninsula Chicago

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Streeterville, 0.6 km from Oak Street
9.8 out of 10, Exceptional, (1004)
"Our stay "
United States
Tashauannea
The price is ₩687,995
₩807,637 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Peninsula Chicago
Lobby
The Langham, Chicago

The Langham, Chicago

The Langham, Chicago
5.0 star property
River North, 1.4 km from Oak Street
9.8 out of 10, Exceptional, (1002)
"Great ex"
United States
Maricela
The price is ₩596,745
₩700,519 total
includes taxes & fees
Jan 18 - Jan 19, 2026
The Langham, Chicago
Suite, Terrace (Water Tower) | Premium bedding, down comforters, pillowtop beds, minibar
Park Hyatt Chicago

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Magnificent Mile, 0.5 km from Oak Street
9.6 out of 10, Exceptional, (1000)
"beautiful room and hotel great bar!"
United States
ravi
The price is ₩558,479
₩655,598 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Park Hyatt Chicago
Aerial view
Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
River North, 0.7 km from Oak Street
9.6 out of 10, Exceptional, (417)
"Great stay"
United States
John E
The price is ₩200,720
₩235,625 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Residence Inn Chicago Downtown Magnificent Mile
Business center
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Near North Side, 0.8 km from Oak Street
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 1.6 km from Oak Street
9.6 out of 10, Exceptional, (3435)
"Amazing place to stay and super accommodating "
United States
Carson
The price is ₩200,143
₩234,947 total
includes taxes & fees
Dec 29 - Dec 30
L7 Chicago by LOTTE
Exterior
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (2273)
"Great hotel "
United States
Shantasha
The price is ₩231,983
₩314,726 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Sofitel Chicago Magnificent Mile
Interior
Viceroy Chicago

Viceroy Chicago

Viceroy Chicago
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (1146)
"Clean, well designed rooms and great staff"
United States
Austin
The price is ₩310,466
₩406,853 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Viceroy Chicago
Exterior
Waldorf Astoria Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (1002)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is ₩537,722
₩631,231 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Waldorf Astoria Chicago
Daily full breakfast for a fee
Hotel EMC2, Autograph Collection

Hotel EMC2, Autograph Collection

Hotel EMC2, Autograph Collection
4.0 star property
Streeterville, 0.9 km from Oak Street
9.4 out of 10, Exceptional, (1001)
"Clean room, great location "
United States
Ashley
The price is ₩177,616
₩208,504 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hotel EMC2, Autograph Collection
Reception
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Streeterville, 0.2 km from Oak Street
9.4 out of 10, Exceptional, (1001)
"Amazing place! Our family of 6 had a fantastic time here for a night. "
United States
Brooke
The price is ₩608,332
₩714,120 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Four Seasons Hotel Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 0.8 km from Oak Street
9.4 out of 10, Exceptional, (3054)
"Excellent stay great location and great rooms"
United States
Joseph
The price is ₩143,925
₩209,648 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Hotel Riu Plaza Chicago
Room, 2 Queen Beds, Corner (View) | In-room safe, desk, laptop workspace, blackout drapes
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North
3.5 star property
River North, 1.1 km from Oak Street
9.4 out of 10, Exceptional, (1160)
"Great stay!"
United States
Tea
The price is ₩166,567
₩195,533 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aloft Chicago Downtown River North
Exterior
Moxy Chicago Downtown

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 1.1 km from Oak Street
9.4 out of 10, Exceptional, (857)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is ₩156,428
₩183,632 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Moxy Chicago Downtown
Lobby
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 1.4 km from Oak Street
9.4 out of 10, Exceptional, (3465)
"Great hotel! "
United States
Kianna
The price is ₩200,114
₩234,913 total
includes taxes & fees
Jan 7 - Jan 8, 2026
LondonHouse Chicago, Curio Collection by Hilton
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (4116)
"Great hotel"
United States
Richard
The price is ₩154,511
₩181,380 total
includes taxes & fees
Jan 14 - Jan 15, 2026
citizenM Chicago Downtown
Exterior
Residence Inn by Marriott Chicago Downtown / River North

Residence Inn by Marriott Chicago Downtown / River North

Residence Inn by Marriott Chicago Downtown / River North
3.5 star property
River North, 1.3 km from Oak Street
9.4 out of 10, Exceptional, (1002)
"Clean hotel, clean room, easy check in, great central location"
United States
Steven J
The price is ₩166,567
₩195,533 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Residence Inn by Marriott Chicago Downtown / River North
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (3394)
"The Hotel was amazing great location "
United States
Donnisha
The price is ₩208,571
₩287,351 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Hyatt Regency Chicago
Property amenity
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 star property
River North, 1 km from Oak Street
9.4 out of 10, Exceptional, (1000)
"One of my favorite hotels in Chicago. Always an excellent stay. "
United States
Liane
The price is ₩294,244
₩387,922 total
includes taxes & fees
Jan 23 - Jan 24, 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
River North, 1.3 km from Oak Street
9.4 out of 10, Exceptional, (1805)
"Amazing hotel, location, staff, and food!!"
United States
Wendy
The price is ₩429,599
₩504,307 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Trump International Hotel & Tower Chicago
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.
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Top Oak Street Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great hotel on the riverwalk with great amenities. "
Morgan 1-night trip
Posted 10 hours ago
Hyatt Regency Chicago

Hotels near other Oak Street attractions

At Bloomingdales, great place to shop and eat. 🎄
Photo by Rita Irvine
Open Photo by Rita Irvine

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
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Chicago_JohnHancockCenter_6065131_02

875 North Michigan Avenue

4.5/5 (2,896 reviews)
You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
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Frequently asked questions

What's the area like around Oak Street?
Oak Street is located in Chicago. This metropolitan area is known for its stunning architecture and top museums. If you're looking for a convenient place to stay, check out the 732 hotels and other accommodations you'll find within a mile.
What's the best place to stay close to Oak Street?
Adjacent to Oak Street, Hilton Chicago/Magnificent Mile Suites is one of the top choices for your stay based on our traveler data, and this hotel offers a fitness center and valet parking. Other good choices close by include The Whitehall Hotel, BW Premier Collection and Eurostars Magnificent Mile.
How many hotels should I expect to find close to Oak Street?
Expedia has 732 hotels and other accommodations within a mile from Oak Street.
If I need to cancel the hotel reservation for my stay near Oak Street, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within a 24-hour period of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to review the top deals on offer near Oak Street.
Where can I learn more about changing or cancelling my trip in the area near Oak Street?
To access more information about picking new dates or cancelling your stay near Oak Street, click here.
What can I see and do near Oak Street?
You might want to spend some time browsing the exhibits at Museum of Contemporary Art Chicago, Chicago History Museum, or Art Institute of Chicago. Chicago Water Tower, Holy Name Cathedral, and Tribune Tower are some of the local landmarks to explore. You can watch performances at Broadway Playhouse, Second City, and House of Blues Chicago if you're interested in local theater.
How can I get to Oak Street?
With so many transportation options, seeing the area around Oak Street is a breeze. Take advantage of metro transit at State Station, Clark-Lake Station, and Lake Station. If you want to journey outside of the area, jump aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.