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10 Dec - 11 Dec
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11 Dec - 12 Dec
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12 Dec - 14 Dec
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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)
"Excellent service throughout the hotel"
United States
Karen
The price is 11.972.244 ₫
14.054.156 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Peninsula Chicago
Breakfast, lunch, dinner served; American cuisine, al fresco dining
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, (1001)
"Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!! "
United States
Larissa
The price is 11.465.295 ₫
13.459.111 ₫ total
includes taxes & fees
2 Jan - 3 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, (1003)
"Langham is always a superior stay"
United States
THADDEUS LAMONT
The price is 10.897.403 ₫
12.792.462 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Langham, Chicago
Lobby
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, (407)
"Great stay"
United States
John E
The price is 3.348.990 ₫
3.931.380 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Residence Inn Chicago Downtown Magnificent Mile
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, (2255)
"The staff, food, and service were great. "
United States
Randy
The price is 4.483.326 ₫
6.036.555 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Sofitel Chicago Magnificent Mile
Lounge
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
Penthouse (Suite) | Egyptian cotton sheets, premium bedding, down duvets, minibar
Viceroy Chicago

Viceroy Chicago

Viceroy Chicago
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (1138)
" Great trip, hotel and location was very nice. Lots of stores and restaurants near by, walkable. "
United States
Julyana
The price is 5.666.755 ₫
7.426.047 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Viceroy Chicago
Front of property
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, (1000)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is 10.020.600 ₫
11.763.182 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Waldorf Astoria Chicago
Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view
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, (999)
"Amazing hotel"
United States
David
The price is 11.075.400 ₫
13.001.411 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Four Seasons Hotel Chicago
55-inch LCD TV with cable channels, TV, pay films
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, (3351)
"I loved the location."
United States
Laura
The price is 3.714.755 ₫
4.360.751 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
L7 Chicago by LOTTE
Exterior
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)
"Great stay!"
United States
Bethany
The price is 3.241.911 ₫
3.805.680 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hotel EMC2, Autograph Collection
Traditional Room, 2 Queen Beds | Property entrance
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, (1163)
"Clean room, friendly staff, perfect location"
United States
Matt
The price is 2.767.485 ₫
3.248.753 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Aloft Chicago Downtown River North
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, (2964)
"Excellent stay great location and great rooms"
United States
Joseph
The price is 2.478.174 ₫
3.652.235 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Hotel Riu Plaza Chicago
Meeting facility
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, (1293)
"Really enjoyed the hotel, bar and area"
United States
Angela
The price is 3.562.149 ₫
4.959.138 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Thompson Chicago, by Hyatt
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, (3398)
"I always love staying at this place when I visit"
Canada
William
The price is 3.586.320 ₫
4.983.941 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hyatt Regency Chicago
Serves breakfast, lunch and dinner
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, (851)
"Great place to stay"
United States
Mason
The price is 2.965.163 ₫
3.480.804 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Moxy Chicago Downtown
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, (4107)
"Great stay"
United States
Ericka
The price is 2.820.199 ₫
3.310.632 ₫ total
includes taxes & fees
21 Dec - 22 Dec
citizenM Chicago Downtown
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (3420)
"Great Hotel!"
United States
Siranush
The price is 3.438.121 ₫
4.036.011 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Frette Italian sheets, premium bedding, in-room safe, desk
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)
"Perfect stay. Highly recommend "
United States
David
The price is 5.354.425 ₫
7.059.138 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Terrace/patio
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, (1780)
"Amazing hotel, location, staff, and food!!"
United States
Wendy
The price is 7.291.305 ₫
8.559.263 ₫ total
includes taxes & fees
4 Jan - 5 Jan 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

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.
See properties
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 742 hotels and other accommodation options you'll find within a mile.
How many hotels will I be able to find close to Oak Street?
Expedia has 742 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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