The Best Hotels Closest to Oak Street in Chicago - 2026 Updated Prices

Our top choices for Oak Street hotels

The Sono Chicago

Old Town Chicago, 1.5 km from Oak Street

Susan

5.159.577 ₫ total

includes taxes & fees

6 Jul - 7 Jul

The Peninsula Chicago

Streeterville, 0.5 km from Oak Street

Dennis

18.774.395 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Breakfast, lunch, dinner and brunch served

Park Hyatt Chicago

Streeterville, 0.4 km from Oak Street

Claire

15.348.066 ₫ total

includes taxes & fees

30 Jun - 1 Jul

The Langham, Chicago

River North, 1.4 km from Oak Street

Sanjay

18.511.554 ₫ total

includes taxes & fees

19 Jul - 20 Jul

Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.8 km from Oak Street

Niranjan

6.132.970 ₫ total

includes taxes & fees

1 Jul - 2 Jul

Sofitel Chicago Magnificent Mile

0.2 km from Oak Street

Karolina

8.076.316 ₫ total

includes taxes & fees

5 Jul - 6 Jul

The Talbott, Autograph Collection

0.2 km from Oak Street

Hayley

6.611.797 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Waldorf Astoria Chicago

0.2 km from Oak Street

Jorge

16.036.465 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Hotel Riu Plaza Chicago

Streeterville, 0.8 km from Oak Street

Kyle

6.351.302 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Viceroy Chicago

0.3 km from Oak Street

Graham

10.515.873 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view

Four Seasons Hotel Chicago

Streeterville, 0.2 km from Oak Street

lora

16.584.048 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Frette Italian sheets, premium bedding, in-room safe, desk

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Streeterville, 1 km from Oak Street

Karla

10.452.064 ₫ total

includes taxes & fees

1 Jul - 2 Jul

Trump International Hotel & Tower Chicago

River North, 1.3 km from Oak Street

Tammy Lynn

14.667.315 ₫ total

includes taxes & fees

5 Jul - 6 Jul

55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

Theatre District, 1.6 km from Oak Street

Joel

9.352.464 ₫ total

includes taxes & fees

7 Jul - 8 Jul

Thompson Chicago, by Hyatt

Gold Coast, 0.1 km from Oak Street

Carla

6.601.169 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Hilton Grand Vacations Club Chicago Magnificent Mile

Streeterville, 1 km from Oak Street

Bjorn Holger

7.425.380 ₫ total

includes taxes & fees

6 Jul - 7 Jul

Hotel EMC2, Autograph Collection

Streeterville, 0.9 km from Oak Street

Sheetal

6.226.840 ₫ total

includes taxes & fees

1 Jul - 2 Jul

Traditional Room, 2 Queen Beds | Property entrance

Aloft by Marriott Chicago Downtown River North

River North, 1.1 km from Oak Street

Chloe

5.186.426 ₫ total

includes taxes & fees

5 Jul - 6 Jul

Moxy Chicago Downtown

River North, 1.1 km from Oak Street

Kelly

4.505.813 ₫ total

includes taxes & fees

1 Jul - 2 Jul

citizenM Chicago Downtown

Theatre District, 1.5 km from Oak Street

Jennifer

5.288.120 ₫ total

includes taxes & fees

1 Jul - 2 Jul

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Compare popular hotels close to Oak Street

Property	Property class	Guest rating
The Sono Chicago	3.5 star property	10.0 Exceptional 526 reviews	View
The Peninsula Chicago	5.0 star property	9.8 Exceptional 1,003 reviews	View
Park Hyatt Chicago	5.0 star property	9.6 Exceptional 1,001 reviews	View
The Langham, Chicago	5.0 star property	9.8 Exceptional 1,008 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	4.0 star property	9.6 Exceptional 557 reviews	View

Top Oak Street Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The positives are definitely the location, the affordability and the breakfast was fantastic! We stayed overnight with friends and their room was updated with new floors but our room had dated old stained carpet and one of the chairs was stained. We also only had one outlet that worked in the room but the bathroom was very clean and the bed was comfortable."

The Drake

8/10 Good

"Our room was spacious and clean. The only thing I'd point out is that on the lake side, it was kind of noisy in the evening-- lots of cars going by and revving their engines. That being said, when the park closes at about 11:00, it went silent. This definitely did not keep me up at night, but it might bother another person. The staff was very helpful. It was a nice touch that they offered us water to take on our adventures."

Freehand Chicago

10/10 Excellent

"Loved this place. I was traveling for work and needed a hotel that was centrally located, safe, and within walking distance of restaurants, attractions, and the areas where I’d be working. Freehand checked all the boxes. The rooms were clean, the hotel was well maintained, and it had a character that’s hard to find in chain hotels. I especially loved the eclectic vibe, Art Deco details, and the way they’ve preserved many of the building’s original features; from the beautiful woodwork and fixtures to the old mail chute. This is definitely a place for travelers who enjoy experiences that are a little off the beaten path. It’s unique, stylish, and full of personality while still being comfortable and practical. A great spot to explore Chicago during the day and rest your head comfortably at night."

Hotels near other Oak Street attractions

900 North Michigan Shops

8.6/5 (55 reviews)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

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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 702 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 702 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.

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Our top choices for Oak Street hotels

The Sono Chicago

The Peninsula Chicago

Park Hyatt Chicago

The Langham, Chicago

Residence Inn Chicago Downtown Magnificent Mile

Sofitel Chicago Magnificent Mile

The Talbott, Autograph Collection

Waldorf Astoria Chicago

Hotel Riu Plaza Chicago

Viceroy Chicago

Four Seasons Hotel Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Trump International Hotel & Tower Chicago

L7 Chicago by LOTTE

Thompson Chicago, by Hyatt

Hilton Grand Vacations Club Chicago Magnificent Mile

Hotel EMC2, Autograph Collection

Aloft by Marriott Chicago Downtown River North

Moxy Chicago Downtown

citizenM Chicago Downtown

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Hotels near other Oak Street attractions

900 North Michigan Shops

Frequently asked questions

Explore a world of travel with Expedia