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Check prices for these dates

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16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
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23 Oct - 25 Oct

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Our top choices for Oak Street hotels

1. The Peninsula Chicago

The Peninsula Chicago
Streeterville, 0.5 km from Oak Street
United States
Melinda
AED 2,296
AED 2,729 total
includes taxes & fees
15 Nov - 16 Nov
The Peninsula Chicago

2. The Langham, Chicago

The Langham, Chicago
River North, 1.4 km from Oak Street
United States
Saramae
AED 1,998
AED 2,376 total
includes taxes & fees
15 Nov - 16 Nov
The Langham, Chicago

3. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Theatre District, 1.6 km from Oak Street
United States
Jeffrey Thomas
AED 565
AED 672 total
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE

4. Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
Streeterville, 0.8 km from Oak Street
United States
Kaitlyn
AED 808
AED 961 total
includes taxes & fees
1 Nov - 2 Nov
Residence Inn Chicago Downtown Magnificent Mile

5. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
River North, 1.3 km from Oak Street
United States
Cecille
AED 1,694
AED 2,014 total
includes taxes & fees
1 Nov - 2 Nov
Trump International Hotel & Tower Chicago

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

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Streeterville, 1 km from Oak Street
United States
Jessica
AED 1,319
AED 1,677 total
includes taxes & fees
30 Oct - 31 Oct
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

7. Park Hyatt Chicago

Park Hyatt Chicago
Streeterville, 0.4 km from Oak Street
United States
Tom
AED 1,957
AED 2,327 total
includes taxes & fees
15 Nov - 16 Nov
Park Hyatt Chicago

8. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
The Loop, 1.4 km from Oak Street
United States
Keeven
AED 821
AED 1,085 total
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton

9. citizenM Chicago Downtown

citizenM Chicago Downtown
Theatre District, 1.5 km from Oak Street
United States
Katarina
AED 624
AED 742 total
includes taxes & fees
1 Nov - 2 Nov
citizenM Chicago Downtown

10. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Streeterville, 0.8 km from Oak Street
United States
Aaron
AED 607
AED 827 total
includes taxes & fees
11 Nov - 12 Nov
Hotel Riu Plaza Chicago

11. Loews Chicago Hotel

Loews Chicago Hotel
Streeterville, 1.3 km from Oak Street
Canada
Daniel
AED 900
AED 1,201 total
includes taxes & fees
15 Nov - 16 Nov
Loews Chicago Hotel

12. Viceroy Chicago

Viceroy Chicago
0.3 km from Oak Street
United States
Emily
AED 1,132
AED 1,468 total
includes taxes & fees
1 Nov - 2 Nov
Viceroy Chicago

13. Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
0.2 km from Oak Street
United States
Mariellen
AED 1,172
AED 1,502 total
includes taxes & fees
1 Nov - 2 Nov
Sofitel Chicago Magnificent Mile

14. Hyatt Regency Chicago

Hyatt Regency Chicago
The Loop, 1.5 km from Oak Street
United States
Addison
AED 874
AED 1,170 total
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago

15. Moxy Chicago Downtown

Moxy Chicago Downtown
River North, 1.1 km from Oak Street
United States
Justin
AED 595
AED 707 total
includes taxes & fees
1 Nov - 2 Nov
Moxy Chicago Downtown

16. The Talbott, Autograph Collection

The Talbott, Autograph Collection
0.2 km from Oak Street
United States
Karina
AED 820
AED 1,106 total
includes taxes & fees
1 Nov - 2 Nov
The Talbott, Autograph Collection

17. Arlo Chicago

Arlo Chicago
Theatre District, 1.7 km from Oak Street
United States
Pam
AED 656
AED 896 total
includes taxes & fees
2 Nov - 3 Nov
Arlo Chicago

18. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
The Loop, 1.5 km from Oak Street
United States
Jordyn
AED 621
AED 856 total
includes taxes & fees
1 Nov - 2 Nov
The Royal Sonesta Chicago Downtown

19. Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
River North, 1.3 km from Oak Street
United States
Keith
AED 624
AED 742 total
includes taxes & fees
1 Nov - 2 Nov
Springhill Suites by Marriott Chicago Downtown/ River North

20. The St. Regis Chicago

The St. Regis Chicago
1.6 km from Oak Street
United States
Xiomara
AED 2,035
AED 2,419 total
includes taxes & fees
12 Nov - 13 Nov
The St. Regis Chicago
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Compare popular hotels close to Oak Street

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
The Peninsula Chicago
9.8
Exceptional
1,000 reviews
View
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
The Langham, Chicago
9.8
Exceptional
1,000 reviews
View
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
L7 Chicago by LOTTE
9.6
Exceptional
5,044 reviews
View
A modern hotel lobby with a spiral staircase, seating areas, and large windows offering city views.
Residence Inn Chicago Downtown Magnificent Mile
9.6
Exceptional
657 reviews
View
A cityscape with a river, a bridge, and a dining area with tables and chairs.
Trump International Hotel & Tower Chicago
9.6
Exceptional
2,051 reviews
View

Top Oak Street Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"The historic hotel is unique and lovely in a 1927-ish way. The rooms are not large and lush; they are efficient yet very clean and comfortable - perfect for a 2-day stay. The elevator holds 5 people at a time, and I respect and support that housekeeping is by request. Nora, an outstanding restaurant, is accessible from the lobby. No meals are included in the stay. However, there is plenty of restaurants nearby. Along with Nora is The Capital Grille, the upscale steakhouse chain across the street. The location of St. Clair is close to Michigan Avenue shopping, Navy Pier, downtown, and Northwestern hospital. I will stay there again."
Andrianna 2-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"This is an old hotel built for the 1893 Worlds fair. But it was cheap and available at the last minute."
Bruce 4-night trip
Posted less than an hour ago
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"The hotel is in a great location. The room was decent and so was the breakfast. We were entitled to vouchers for breakfast, cocktails and dinner as well as water bottles. At check-in, it would have been nice to be told that and get those vouchers. We had to ask for them the next day after reading a message received from the hotel. It would be nice also at check-in to let us know that housekeeping is every other day. Overall we still had a good stay."
Carlos 4-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Great place"
Aaron 6-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great stay.."
Codie 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Property is closing on 11/16/2026."
Lynn 3-night trip
Posted 5 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Wade

The Wade

10/10 Excellent
"Loved this trendy hotel. Great location, amenities, and service."
Sheilaann 3-night trip
Posted 21 hours ago
The Wade
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

10/10 Excellent
"Godfrey is a beautiful hotel in a great location. I had the deluxe King room that was very spacious and it had an amazing view. Staff was friendly and attentive. I will definitely be staying here when I am back in Chicago."
Makenzie 1-night trip
Posted 1 day ago
The Godfrey Hotel Chicago
Freehand Chicago

Freehand Chicago

10/10 Excellent
"It was comfortable"
Ece 4-night trip
Posted 1 day ago
Freehand Chicago

Other attractions near Oak Street

A large indoor Christmas tree in a shopping mall.
Photo by Rita Irvine

900 North Michigan Shops

8.6/10 (55 reviews)
You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
See properties
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 with a visit to 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 entertainment choices 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 riverfront or experience the acclaimed theater scene 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 acclaimed art scene 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 theater scene.
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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 entertainment choices.
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Loyola University Museum of Art

9.0/10 (2 reviews)
You can spend time exploring the galleries in Loyola University Museum of Art during your trip to Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.
See properties

Find out more about Oak Street

Top reasons to visit Oak Street

  • Upscale Shopping: Oak Street is renowned for its luxury boutiques and designer stores, offering a premier shopping experience.
  • Beautiful Oak Street Beach: Enjoy relaxation and recreational activities at the stunning beach along Lake Michigan.
  • Cultural Enrichment: Explore nearby art museums and urban parks that showcase Chicago's rich culture and vibrant atmosphere.
  • Wildlife Encounters: Experience opportunities to connect with local wildlife in the surrounding parks and natural areas.
  • Diverse Accommodations: Choose from a variety of lodging options, including pet-friendly hotels and cozy apartments.

Find great hotels near Oak Street

Discover a variety of accommodation options along Oak Street, Chicago, designed to meet your every need. Whether you're seeking a pet-friendly hotel, a cozy apartment, or a business-friendly stay, the area offers diverse choices. With convenient access to Oak Street Beach and vibrant shopping experiences, you'll find the perfect place to relax and unwind during your visit to this iconic city.

  • Hyatt Regency Chicago: This 4-star hotel offers a vibrant city-themed experience located in the heart of the shopping district, only 1.4km from Oak Street. Ideal for travelers seeking a blend of urban excitement and nature, the Hyatt Regency Chicago features spacious rooms with stunning city views. Guests can indulge in various amenities, including a fitness center, on-site dining options, and access to nearby shopping venues. Its central location makes it perfect for those looking to explore the city while enjoying modern comforts.
  • The Whitehall Hotel, BW Premier Collection: Situated a mere 161m from Oak Street, this charming 4-star boutique hotel is perfect for pet-friendly travelers and business visitors alike. The Whitehall Hotel boasts uniquely designed rooms adorned with distinctive decor and artworks, creating a cozy yet sophisticated atmosphere. With a pet-friendly policy allowing pets onsite, guests can enjoy their stay worry-free. Additional amenities include business services and a welcoming ambiance, making it a great choice for those looking for a home away from home in the city.
  • LondonHouse Chicago, Curio Collection by Hilton: This luxurious 4.5-star hotel is located 1.4km from Oak Street and offers an exceptional spa-themed experience. LondonHouse Chicago welcomes LGBTQIA travelers and features a full-service spa with various relaxation options, including massages and hydrotherapy treatments. The hotel's rooftop bar provides breathtaking views of the city skyline, perfect for unwinding after a day of shopping in the nearby district. With modern design and a commitment to inclusivity, this hotel is a standout choice for discerning visitors.

Where to stay near Oak Street

Oak Street offers a delightful blend of experiences, from romantic strolls along its scenic beach to family-friendly parks nearby. Explore upscale shopping along the iconic Oak Street boutiques and enjoy the vibrant atmosphere of the surrounding neighborhoods. With picturesque locations and friendly locals, you'll find both relaxation and adventure just steps away from the beach, making it the perfect destination for any traveler seeking a unique urban experience.

  • Chicago: As a vibrant metropolis, Chicago is the heart of the Midwest, with Oak Street nestled within its bustling core. Known for its rich cultural scene, Chicago attracts travelers year-round, with peak visitor numbers from June to August. This city offers an ideal blend of family-friendly attractions, outdoor activities, and urban experiences. Don't miss the chance to explore its famous shopping districts, iconic theaters, and state-of-the-art sports facilities, all within easy reach. The local landmarks, including Millennium Park and Navy Pier, make Chicago a must-visit destination for any traveler.
  • Downtown Chicago: Situated in the very center of the city, Downtown Chicago is a lively neighborhood that encompasses Oak Street. With consistent visitor numbers throughout the year, it also sees peaks during the summer months. Families and outdoor enthusiasts flock to this area for its array of attractions, including renowned shopping spots, entertainment arenas, and theaters. Notable landmarks such as Grant Park and the Art Institute of Chicago are just a stone's throw away, providing ample opportunities for exploration and enjoyment in this vibrant urban landscape.
  • Magnificent Mile: Located a mere 644m from Oak Street, the Magnificent Mile is renowned for its upscale shopping and vibrant atmosphere. This neighborhood draws visitors year-round, particularly during the spring and summer seasons. Travelers come here for family activities and urban adventures, with easy access to shopping areas, educational venues, and entertainment facilities. Highlights include the iconic John Hancock Center and the scenic waterfront at the jetty pier, making the Magnificent Mile a perfect blend of leisure and excitement for any visitor.

Things to do near Oak Street

When visiting Oak Street in Chicago, you'll find a vibrant mix of activities, including shopping at upscale boutiques and exploring nearby city attractions. Don't miss the chance to enjoy water sports along the shores of Lake Michigan, where you can engage in various recreational activities. Additionally, the area offers opportunities for wildlife encounters, making it a well-rounded destination for any tourist.

Shopping

On Oak Street, you can explore the 900 North Michigan Shops, just 161m away, offering a vibrant mix of entertainment and family-friendly vibes. Also nearby is the Chicago Place Mall, 644m away, perfect for a family outing. Don’t miss the Harry Potter Shop Chicago, also 644m away, for some magical souvenirs.

Recreation

At Wrigley Field, immerse yourself in the energetic atmosphere of a live baseball game, just 6.4km from Oak Street. Enjoy soulful music at the House of Blues Chicago, only 1.4km away. For tranquility, visit Northerly Island Natural Area, a serene escape 4.8km from Oak Street.

Adventure

Embark on an adventure at Salt Creek Trail, a scenic hiking destination located 19.3km from Oak Street, offering beautiful outdoor vibes. For a splash of fun, visit Rainbow Falls Waterpark, situated 32.2km away, where you can enjoy thrilling water slides and family-friendly entertainment.

Nightlife

Experience the vibrant nightlife on Oak Street with a visit to the Chicago Theatre, offering romance and culture just 1.6km away. For a fun pub atmosphere, check out Dave & Buster's, only 483m away, or embark on an adventure at Amazing Chicago's Funhouse Maze, also 1.6km away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Oak Street

To save money during your visit to Oak Street, consider traveling in the off-peak months of December to February, when hotel prices are lower. Aim to book your stay on a Monday, as it’s the least expensive day. Utilize Expedia's search tools to find eco-friendly hotels and sort results by price for the best deals. Additionally, combine your hotel stay with flights and activities to secure package discounts. For budget-friendly transportation, explore public transit options, and take advantage of free local attractions to enhance your experience without overspending.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Oak Street are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Oak Street is Monday. The most expensive day to stay around Oak Street is Saturday.
  • Find cheap hotels on Expedia: Certainly. Here's a paraphrased version of your text in a trusted and attentive tone:Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. For instance, selecting the “Eco-certified” filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay on Oak Street with your flights and activities through an Expedia package deal.

Find the best attractions near Oak Street

Oak Street, Chicago offers a vibrant experience with its iconic skyscrapers, lush urban parks, and captivating art museums. This area is perfect for those seeking cultural enrichment and family-friendly activities. Don't miss the beautiful Oak Street Beach, ideal for relaxation and recreation. For convenience, consider staying at nearby motels to fully enjoy your visit to this lively neighborhood.

  • Michigan Avenue: Experience the vibrant energy of Michigan Avenue, also known as the Magnificent Mile. This bustling street features a mix of high-end shopping, dining, and iconic architecture, making it a must-visit for those looking to immerse themselves in the city's urban vibe.
  • Navy Pier: Enjoy the scenic views and friendly atmosphere at Navy Pier, a lively destination offering entertainment, dining, and attractions. Stroll along the waterfront, take a ride on the Ferris wheel, or relax at one of the many parks while soaking in the stunning skyline.
  • Millennium Park: Discover the beauty of Millennium Park, an urban oasis featuring public art, gardens, and performance spaces. It's a great spot for families to enjoy outdoor activities, concerts, and the famous Cloud Gate sculpture, all while surrounded by the city's skyline.

Best time to go to Oak Street

The best time to visit Oak Street is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

The nearest major airports for your trip to Oak Street

Traveling to Oak Street, Chicago, can be conveniently done via its major airports. Chicago O'Hare International Airport (ORD) is approximately 24.1km away, with notable hotels nearby, including the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both just 3.2km from the airport. Chicago Midway International Airport (MDW) is about 16.1km from Oak Street, featuring luxurious options like the 5-star Langham, Chicago and Nobu Hotel Chicago, located 8 and 14.5km away, respectively. For those considering Chicago Executive Airport (PWK), located 32.2km away, the 4.5-star Deer Path Inn is a comfortable choice just 16.1km away.

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, check out the 685 hotels and other accommodations you'll find within a mile.
What's the best place to stay close to Oak Street?
Adjacent to Oak Street, Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and in-room kitchens. Other good choices close by include The Chicago Hotel Collection Ambassador Gold Coast and River Hotel.
How many hotels should I expect to find close to Oak Street?
Expedia has 685 hotels and other accommodations 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! You'll find that most hotel reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within a 24-hour period of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to review the top deals on offer near Oak Street.
Where can I learn more about changing or cancelling my trip in the area near Oak Street?
To access more information about picking new dates or cancelling your stay near Oak Street, click here.
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 Former Medinah Temple 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 theater.
How can I get to Oak Street?
With so many transportation options, seeing the area around Oak Street is a breeze. Take advantage of metro transit 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.