Chicago Oak Street Hotels: 2026 Limited-Time Hotel Deals @Expedia

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Our top choices for Oak Street hotels

1. The Peninsula Chicago

Streeterville, 0.5 km from Oak Street

Justin

HK$4,902

HK$5,828 total

includes taxes & fees

30 Aug - 31 Aug

2. The Langham, Chicago

River North, 1.4 km from Oak Street

Christopher

HK$4,416

HK$5,250 total

includes taxes & fees

7 Sept - 8 Sept

3. L7 Chicago by LOTTE

Theatre District, 1.6 km from Oak Street

Nicole

HK$1,687

HK$2,006 total

includes taxes & fees

30 Aug - 31 Aug

4. Trump International Hotel & Tower Chicago

River North, 1.3 km from Oak Street

Jorge

HK$3,677

HK$4,371 total

includes taxes & fees

30 Aug - 31 Aug

5. Residence Inn Chicago Downtown Magnificent Mile

Streeterville, 0.8 km from Oak Street

Claudia

HK$1,726

HK$2,052 total

includes taxes & fees

7 Sept - 8 Sept

6. Park Hyatt Chicago

Streeterville, 0.4 km from Oak Street

Jennifer

HK$4,341

HK$5,161 total

includes taxes & fees

30 Aug - 31 Aug

7. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Streeterville, 1 km from Oak Street

Jennifer

HK$2,973

HK$3,767 total

includes taxes & fees

20 Aug - 21 Aug

8. Hotel Riu Plaza Chicago

Streeterville, 0.8 km from Oak Street

Peter

HK$1,463

HK$1,963 total

includes taxes & fees

1 Sept - 2 Sept

9. Hyatt Regency Chicago

The Loop, 1.5 km from Oak Street

Tameka

HK$1,853

HK$2,483 total

includes taxes & fees

30 Aug - 31 Aug

10. citizenM Chicago Downtown

Theatre District, 1.5 km from Oak Street

lakadria

HK$1,333

HK$1,585 total

includes taxes & fees

7 Sept - 8 Sept

11. The Royal Sonesta Chicago Downtown

The Loop, 1.5 km from Oak Street

Brandon

HK$1,522

HK$2,060 total

includes taxes & fees

1 Sept - 2 Sept

12. Arlo Chicago

Theatre District, 1.7 km from Oak Street

Robert

HK$1,193

HK$1,664 total

includes taxes & fees

8 Sept - 9 Sept

13. Moxy Chicago Downtown

River North, 1.1 km from Oak Street

Julia

HK$1,412

HK$1,679 total

includes taxes & fees

7 Sept - 8 Sept

14. Sofitel Chicago Magnificent Mile

0.2 km from Oak Street

Anton

HK$2,031

HK$2,648 total

includes taxes & fees

7 Sept - 8 Sept

15. Aloft by Marriott Chicago Downtown River North

River North, 1.1 km from Oak Street

Ronald

HK$1,333

HK$1,585 total

includes taxes & fees

7 Sept - 8 Sept

16. Residence Inn by Marriott Chicago Downtown / River North

River North, 1.3 km from Oak Street

Josephine L

HK$1,490

HK$1,772 total

includes taxes & fees

7 Sept - 8 Sept

17. Springhill Suites by Marriott Chicago Downtown/ River North

River North, 1.3 km from Oak Street

Coreena K

HK$1,451

HK$1,725 total

includes taxes & fees

7 Sept - 8 Sept

18. Loews Chicago Hotel

Streeterville, 1.3 km from Oak Street

Frank

HK$1,875

HK$2,509 total

includes taxes & fees

7 Sept - 8 Sept

19. The Talbott, Autograph Collection

0.2 km from Oak Street

Angela

HK$1,562

HK$2,137 total

includes taxes & fees

23 Aug - 24 Aug

20. Viceroy Chicago

0.3 km from Oak Street

David Michael

HK$2,073

HK$2,724 total

includes taxes & fees

7 Sept - 8 Sept

View all properties

Compare popular hotels close to Oak Street

Property	Property class	Guest rating
The Peninsula Chicago	9.8 Exceptional 1,007 reviews	View
The Langham, Chicago	9.8 Exceptional 1,008 reviews	View
L7 Chicago by LOTTE	9.6 Exceptional 4,591 reviews	View
Trump International Hotel & Tower Chicago	9.6 Exceptional 1,990 reviews	View
Residence Inn Chicago Downtown Magnificent Mile	9.6 Exceptional 602 reviews	View

Top Oak Street Hotel Reviews

Congress Plaza Hotel

8/10 Good

"Quick check in. Accessible to CTA- Redline and great thai resto for lunch and breakfast corner right across hotel"

Warwick Allerton - Chicago

10/10 Excellent

"Great location and friendly staff."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"We loved it! Absolutely amazing location and hotel"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Good location very clean"

Kasa Magnificent Mile Chicago

8/10 Good

"Loved the check-in and check-out process. Very easy and excellent communication through texts, emails and the Kasa desk in the lobby. The security via the fobs and designated elevators was excellent. The water pressure was good in the shower, and the towels were fluffy. The view in this corner unit is phenomenal, and that was the clear highlight of the rental, along with the location as long as you don’t mind the street noise. The rental unit was adequate for our needs, but we expected more modern furnishings and a usable fold-out couch. The coils are coming through the mattress. We realize it’s been a hot summer, but the couch smelled of stale perspiration. Not fresh at all. Same with the refrigerator. Ice cube trays for the freezer would be helpful. We had to run to the store for ice. The bathroom is sad. It needs an update badly. There was a big chunk of the tub chipped off of the floor of the bathtub. The toliet was very slow in flushing."

Thompson Chicago, by Hyatt

8/10 Good

"Nice hotel in a great location. Room was clean and quiet but like a lot of things it’s the small things that make a hotel great. Here’s what I found: 1. The coffee in the room is just a small cup of espresso for 2. 2. No coffee bar in the lobby or any place at all to grab a large cup and take back to the room. 3. The lobby and public areas are so over air conditioned one has to wear a jacket in the heat of summer. This goes for the casual restaurant on the ground floor. When we could we ate outside. 4. The gym is nice but has minimal equipment even though there is room for a few machines. When I return to Chicago I’ll probably try a different hotel but I wouldn’t be opposed to staying at the Thompson again."

Four Seasons Hotel Chicago

10/10 Excellent

"Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around"

Other attractions near Oak Street

A large indoor Christmas tree in a shopping mall.

900 North Michigan Shops

8.6/10 (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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A tall skyscraper with a spire, a flagpole with an American flag, and a stone building with arched windows.

875 North Michigan Avenue

9.2/10 (2,926 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 fascinating museums.

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Topgolf Swing Suite

You can take time to visit Topgolf Swing Suite during your travels to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

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Mariano Plaza

After visiting Mariano Plaza, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

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The Drake

The Drake is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.

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Fourth Presbyterian Church

10.0/10 (2 reviews)

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

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360 CHICAGO

You can learn about the history of Chicago with a visit to 360 CHICAGO. Amble around this vibrant area's riverfront or experience its fascinating museums.

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Bronzeville Black Chamber of Commerce

Find out about the history of Chicago when you take a trip to Bronzeville Black Chamber of Commerce. Discover the entertainment choices and notable monuments 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 693 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, Four Seasons Hotel Chicago is one of the top choices for your stay based on our traveller data, and this hotel offers a full-service spa and a restaurant. Other good choices close by include The Chicago Hotel Collection Ambassador Gold Coast and Kasa Magnificent Mile Chicago.

How many hotels will I be able to find close to Oak Street?

Expedia has 693 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 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.

Chicago Oak Street Hotels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Oak Street hotels

1. The Peninsula Chicago

2. The Langham, Chicago

3. L7 Chicago by LOTTE

4. Trump International Hotel & Tower Chicago

5. Residence Inn Chicago Downtown Magnificent Mile

6. Park Hyatt Chicago

7. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

8. Hotel Riu Plaza Chicago

9. Hyatt Regency Chicago

10. citizenM Chicago Downtown

11. The Royal Sonesta Chicago Downtown

12. Arlo Chicago

13. Moxy Chicago Downtown

14. Sofitel Chicago Magnificent Mile

15. Aloft by Marriott Chicago Downtown River North

16. Residence Inn by Marriott Chicago Downtown / River North

17. Springhill Suites by Marriott Chicago Downtown/ River North

18. Loews Chicago Hotel

19. The Talbott, Autograph Collection

20. Viceroy Chicago

Compare popular hotels close to Oak Street

Top Oak Street Hotel Reviews

Congress Plaza Hotel

Warwick Allerton - Chicago

InterContinental Chicago Magnificent Mile by IHG

The Chicago Hotel Collection - Magnificent Mile

Kasa Magnificent Mile Chicago

Thompson Chicago, by Hyatt

Four Seasons Hotel Chicago

Other attractions near Oak Street

900 North Michigan Shops

875 North Michigan Avenue

Topgolf Swing Suite

Mariano Plaza

The Drake

Fourth Presbyterian Church

360 CHICAGO

Bronzeville Black Chamber of Commerce

Frequently asked questions

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