Chicago Oak Street Hotels

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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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, (1003)
"Our stay "
United States
Tashauannea
The price is HK$3,694
HK$4,336 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Peninsula Chicago
Premium bedding, down duvets, pillow-top 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 HK$3,007
HK$3,530 total
includes taxes & fees
5 Jan - 6 Jan 2026
Park Hyatt 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 HK$3,213
HK$3,772 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Langham, 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 HK$1,081
HK$1,269 total
includes taxes & fees
2 Jan - 3 Jan 2026
Residence Inn Chicago Downtown Magnificent Mile
Business centre
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
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 HK$1,249
HK$1,695 total
includes taxes & fees
1 Jan - 2 Jan 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 HK$1,672
HK$2,191 total
includes taxes & fees
19 Jan - 20 Jan 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 HK$2,887
HK$3,389 total
includes taxes & fees
4 Jan - 5 Jan 2026
Waldorf Astoria 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, (3434)
"Amazing place to stay and super accommodating "
United States
Carson
The price is HK$1,078
HK$1,265 total
includes taxes & fees
28 Dec - 29 Dec
L7 Chicago by LOTTE
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 HK$956
HK$1,123 total
includes taxes & fees
2 Jan - 3 Jan 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 HK$3,266
HK$3,834 total
includes taxes & fees
11 Jan - 12 Jan 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, (3051)
"Excellent stay great location and great rooms"
United States
Joseph
The price is HK$775
HK$1,129 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel Riu Plaza Chicago
Restaurant
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 0.2 km from Oak Street
9.2 out of 10, Wonderful, (1302)
"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "
United States
Yoshio
The price is HK$1,050
HK$1,462 total
includes taxes & fees
9 Jan - 10 Jan 2026
Thompson Chicago, by Hyatt
In-room safe, desk, laptop workspace, blackout curtains
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 HK$894
HK$1,050 total
includes taxes & fees
4 Jan - 5 Jan 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 HK$840
HK$986 total
includes taxes & fees
4 Jan - 5 Jan 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, (3464)
"Great hotel! "
United States
Kianna
The price is HK$1,078
HK$1,265 total
includes taxes & fees
4 Jan - 5 Jan 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 HK$832
HK$977 total
includes taxes & fees
2 Jan - 3 Jan 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 HK$894
HK$1,050 total
includes taxes & fees
19 Jan - 20 Jan 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 HK$1,120
HK$1,543 total
includes taxes & fees
20 Jan - 21 Jan 2026
Hyatt Regency Chicago
Front of property
The Talbott, Autograph Collection

The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
0.2 km from Oak Street
9.2 out of 10, Wonderful, (62)
"The location is great, always outstanding service."
United States
Yazmin
The price is HK$927
HK$1,316 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Talbott, Autograph Collection
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

The Peninsula Chicago

The Peninsula Chicago

10/10 Excellent
"Love my stay"
ana 4-night trip
Posted 14 hours ago
The Peninsula 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 trip to Chicago. Stroll along the riverfront or experience the acclaimed art galleries 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 when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
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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, take a look at the 732 hotels and other accommodation options 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 traveller data, and this hotel offers a fitness centre and valet parking. Other good choices close by include The Whitehall Hotel, BW Premier Collection and Eurostars Magnificent Mile.
How many hotels will I be able to find close to Oak Street?
Expedia has 732 hotels and other accommodation options 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! Most hotel reservations are refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to view the best deals available near Oak Street.
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 theatre.
How can I get to Oak Street?
With so many transport options, seeing the area around Oak Street is simple. Take advantage of metro transport 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.

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