Chicago Hotel Guide - Oak Street hotels in Chicago, United States of America.

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Oak Street hotels

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Streeterville, 0.5 km from Oak Street
9.8 out of 10, Exceptional, (1,000 reviews)
"The best hotel ! Always pleasant to stay ! "
United States
Maysa
The price is €501
includes taxes & fees
5 Mar - 6 Mar
The Peninsula 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, (1,003 reviews)
"Gorgeous property, facilities, and location."
United States
Hussein
The price is €454
includes taxes & fees
23 Mar - 24 Mar
The Langham, Chicago

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Streeterville, 0.4 km from Oak Street
9.6 out of 10, Exceptional, (1,001 reviews)
"Everything was great… but the staff was absolutely amazing! Thank you for taking such great care of us. "
United States
Gaybrielle
The price is €410
includes taxes & fees
29 Mar - 30 Mar
Park Hyatt Chicago

Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 0.8 km from Oak Street
9.6 out of 10, Exceptional, (466 reviews)
"Cozy, Friendly, Good place to stay"
United States
Donghyeon
The price is €154
includes taxes & fees
29 Mar - 30 Mar
Residence Inn Chicago Downtown Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (2,314 reviews)
"Staff was friendly and helpful! Great stay!"
United States
Kristin
The price is €218
includes taxes & fees
2 Mar - 3 Mar
Sofitel Chicago Magnificent Mile

Viceroy Chicago

Viceroy Chicago
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (1,177 reviews)
"Great stay "
United States
Allyson
The price is €243
includes taxes & fees
5 Mar - 6 Mar
Viceroy Chicago

The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (80 reviews)
"Great location! just the right size and tucked away "
United States
andy
The price is €143
includes taxes & fees
23 Mar - 24 Mar
The Talbott, Autograph Collection

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, (1,001 reviews)
"Beautiful hotel"
United States
Sean
The price is €398
includes taxes & fees
8 Mar - 9 Mar
Four Seasons Hotel Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (1,001 reviews)
"Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. "
United States
Glenn
The price is €407
includes taxes & fees
29 Mar - 30 Mar
Waldorf Astoria Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 star property
Streeterville, 1 km from Oak Street
9.4 out of 10, Exceptional, (1,000 reviews)
"Great location, quiet and clean. "
United States
Laurette
The price is €235
includes taxes & fees
20 Mar - 21 Mar
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 1.1 km from Oak Street
9.4 out of 10, Exceptional, (901 reviews)
"Clean, friendly staff, and excellent location "
United States
Paulina
The price is €106
includes taxes & fees
8 Mar - 9 Mar
Moxy Chicago Downtown

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, (1,839 reviews)
"Exceptional service, great location, beautiful hotel"
United States
Julie
The price is €369
includes taxes & fees
8 Mar - 9 Mar
Trump International Hotel & Tower Chicago

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, (1,215 reviews)
"Great stay! "
United States
Megan
The price is €114
includes taxes & fees
8 Mar - 9 Mar
Aloft Chicago Downtown River North

Loews Chicago Hotel

Loews Chicago Hotel
4.5 star property
Streeterville, 1.3 km from Oak Street
9.4 out of 10, Exceptional, (1,575 reviews)
"Outstanding location great stay!"
United States
Michael
The price is €237
includes taxes & fees
10 Mar - 11 Mar
Loews Chicago Hotel

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
River North, 1.3 km from Oak Street
9.4 out of 10, Exceptional, (1,081 reviews)
"Great hotel, good food and great service ! "
United States
Fernando
The price is €114
includes taxes & fees
8 Mar - 9 Mar
Springhill Suites by Marriott Chicago Downtown/ River North

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Streeterville, 0.5 km from Oak Street
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location, service, and gym "
United States
Maxim
The price is €394
includes taxes & fees
8 Mar - 9 Mar
The Ritz-Carlton, Chicago

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, (1,000 reviews)
"Excellent hotel"
United States
Denise
The price is €168
includes taxes & fees
1 Mar - 2 Mar
Hotel EMC2, Autograph Collection

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 0.1 km from Oak Street
9.2 out of 10, Wonderful, (1,323 reviews)
"great stay"
United States
Loan
The price is €163
includes taxes & fees
16 Mar - 17 Mar
Thompson Chicago, by Hyatt

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, (1,030 reviews)
"Everyone was attentive beautiful place will definitely book again"
United States
Paola
The price is €129
includes taxes & fees
22 Mar - 23 Mar
Residence Inn by Marriott Chicago Downtown / River North

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Near North Side, 0.8 km from Oak Street
9.4 out of 10, Exceptional, (184 reviews)
"Awesome stay "
United States
Sally
Kasa River North 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.

Compare popular hotels close to Oak Street

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Bar (on property)
The Peninsula Chicago
5.0 star property
9.8
Exceptional
1,000 reviews
View
Lobby
The Langham, Chicago
5.0 star property
9.8
Exceptional
1,003 reviews
View
Breakfast, lunch, dinner served; American cuisine, al fresco dining
Park Hyatt Chicago
5.0 star property
9.6
Exceptional
1,001 reviews
View
Lobby lounge
Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
9.6
Exceptional
466 reviews
View
Exterior
Sofitel Chicago Magnificent Mile
4.5 star property
9.4
Exceptional
2,314 reviews
View

Top Oak Street Hotel Reviews

Hotels near other Oak Street attractions

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 756 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 an indoor pool and a fitness centre. Other good choices close by include Hotel Riu Plaza Chicago and Embassy Suites by Hilton Chicago Downtown River North.
How many hotels will I be able to find close to Oak Street?
Expedia has 756 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 Historic Michael Jordan Restaurant are some of the local landmarks to explore. You can watch performances at Second City, House of Blues Chicago and Chicago Theatre 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.