Chicago Oak Street Hotels

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Check prices for these dates

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
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, (1005)
"Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing "
United States
christie
The price is HK$3,696
HK$4,339 total
includes taxes & fees
4 Jan - 5 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, (1002)
"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 HK$3,009
HK$3,533 total
includes taxes & fees
7 Jan - 8 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, (1000)
"Langham is always a superior stay"
United States
THADDEUS LAMONT
The price is HK$3,148
HK$3,695 total
includes taxes & fees
11 Jan - 12 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, (412)
"Great stay"
United States
John E
The price is HK$1,050
HK$1,233 total
includes taxes & fees
26 Dec - 27 Dec
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
Bar (on property)
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, (2267)
"Great location, nice bar."
United States
Erik
The price is HK$1,254
HK$1,700 total
includes taxes & fees
22 Dec - 23 Dec
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, (1143)
"Very nice hotel, great rooms, comfy bed and the staff were all very friendly."
United States
Randall
The price is HK$1,673
HK$2,192 total
includes taxes & fees
7 Jan - 8 Jan 2026
Viceroy 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, (3398)
"Enjoyed my stay"
United States
Karen
The price is HK$903
HK$1,060 total
includes taxes & fees
22 Dec - 23 Dec
L7 Chicago by LOTTE
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, (1001)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is HK$2,957
HK$3,471 total
includes taxes & fees
18 Jan - 19 Jan 2026
Waldorf Astoria Chicago
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, (999)
"Amazing place! Our family of 6 had a fantastic time here for a night. "
United States
Brooke
The price is HK$3,268
HK$3,836 total
includes taxes & fees
11 Jan - 12 Jan 2026
Four Seasons Hotel 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, (1000)
"Great stay!"
United States
Bethany
The price is HK$957
HK$1,124 total
includes taxes & fees
25 Dec - 26 Dec
Hotel EMC2, Autograph Collection
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, (3015)
"Excellent stay great location and great rooms"
United States
Joseph
The price is HK$772
HK$1,125 total
includes taxes & fees
12 Jan - 13 Jan 2026
Hotel Riu Plaza Chicago
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, (1164)
"Great stay!"
United States
Tea
The price is HK$856
HK$1,005 total
includes taxes & fees
28 Dec - 29 Dec
Aloft Chicago Downtown River North
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, (1300)
"Great hotel!"
United States
Julie
The price is HK$1,050
HK$1,463 total
includes taxes & fees
7 Jan - 8 Jan 2026
Thompson Chicago, by Hyatt
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, (856)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is HK$840
HK$987 total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (4105)
"Great stay"
United States
Ericka
The price is HK$754
HK$885 total
includes taxes & fees
25 Dec - 26 Dec
citizenM 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, (3448)
"Great hotel! "
United States
Kianna
The price is HK$1,015
HK$1,191 total
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
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, (3403)
"The Hotel was amazing great location "
United States
Donnisha
The price is HK$1,082
HK$1,498 total
includes taxes & fees
5 Jan - 6 Jan 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, (1002)
"One of my favorite hotels in Chicago. Always an excellent stay. "
United States
Liane
The price is HK$1,647
HK$2,162 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Exterior
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (3167)
"Staff, location, views and rooms were amazing!!"
United States
Gabriela Michelle Riveiro
The price is HK$887
HK$1,290 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Royal Sonesta Chicago Downtown
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean room, few dust spots, warm and cozy stay "
Terrica 4-night trip
Posted 14 hours ago
Hilton Chicago/Magnificent Mile Suites

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 720 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 Embassy Suites by Hilton Chicago Downtown River North and The Whitehall Hotel, BW Premier Collection.
How many hotels will I be able to find close to Oak Street?
Expedia has 720 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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