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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, (1,017 reviews)
"The best hotel ! Always pleasant to stay ! "
United States
Maysa
The price is SAR 1,947
SAR 2,285 total
includes taxes & fees
16 Feb - 17 Feb
The Peninsula Chicago

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Streeterville, 0.4 km from Oak Street
9.6 out of 10, Exceptional, (1,000 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 SAR 1,482
SAR 1,740 total
includes taxes & fees
16 Feb - 17 Feb
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, (457 reviews)
"Cozy, Friendly, Good place to stay"
United States
Donghyeon
The price is SAR 521
SAR 612 total
includes taxes & fees
22 Feb - 23 Feb
Residence Inn Chicago Downtown Magnificent Mile

The Langham, Chicago

The Langham, Chicago
5.0 star property
River North, 1.4 km from Oak Street
9.8 out of 10, Exceptional, (1,002 reviews)
"Gorgeous property, facilities, and location."
United States
Hussein
The price is SAR 1,632
SAR 1,915 total
includes taxes & fees
8 Mar - 9 Mar
The Langham, Chicago

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (2,327 reviews)
"Staff was friendly and helpful! Great stay!"
United States
Kristin
The price is SAR 634
SAR 855 total
includes taxes & fees
16 Feb - 17 Feb
Sofitel Chicago Magnificent Mile

The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (77 reviews)
"Great location! just the right size and tucked away "
United States
andy
The price is SAR 537
SAR 741 total
includes taxes & fees
26 Feb - 27 Feb
The Talbott, Autograph Collection

Viceroy Chicago

Viceroy Chicago
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (1,168 reviews)
"Great stay "
United States
Allyson
The price is SAR 784
SAR 1,030 total
includes taxes & fees
24 Feb - 25 Feb
Viceroy Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (1,000 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 SAR 1,584
SAR 1,859 total
includes taxes & fees
1 Mar - 2 Mar
Waldorf Astoria 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, (3,322 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is SAR 445
SAR 628 total
includes taxes & fees
16 Feb - 17 Feb
Hotel Riu Plaza 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, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North 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 reviews)
"Beautiful hotel"
United States
Sean
The price is SAR 1,500
SAR 1,761 total
includes taxes & fees
1 Mar - 2 Mar
Four Seasons Hotel Chicago

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, (1,312 reviews)
"great stay"
United States
Loan
The price is SAR 506
SAR 705 total
includes taxes & fees
1 Mar - 2 Mar
Thompson Chicago, by Hyatt

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, (1,211 reviews)
"Great stay! "
United States
Megan
The price is SAR 414
SAR 487 total
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Downtown River North

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 1.1 km from Oak Street
9.4 out of 10, Exceptional, (886 reviews)
"Clean, friendly staff, and excellent location "
United States
Paulina
The price is SAR 422
SAR 495 total
includes taxes & fees
22 Feb - 23 Feb
Moxy Chicago Downtown

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, (1,046 reviews)
"Great hotel, good food and great service ! "
United States
Fernando
The price is SAR 431
SAR 506 total
includes taxes & fees
16 Feb - 17 Feb
Springhill Suites by Marriott Chicago Downtown/ River North

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 SAR 566
SAR 665 total
includes taxes & fees
16 Feb - 17 Feb
Hotel EMC2, Autograph Collection

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, (1,022 reviews)
"Friendly staff, clean & comfortable room, and great location!"
United States
Unja
The price is SAR 450
SAR 528 total
includes taxes & fees
22 Feb - 23 Feb
Residence Inn by Marriott Chicago Downtown / River North

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (4,225 reviews)
"Friendly staff, cozy room, good location. "
United States
Andrew
The price is SAR 401
SAR 471 total
includes taxes & fees
16 Feb - 17 Feb
citizenM 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, (1,840 reviews)
"Exceptional service, great location, beautiful hotel"
United States
Julie
The price is SAR 1,195
SAR 1,403 total
includes taxes & fees
22 Feb - 23 Feb
Trump International Hotel & Tower 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, (1,005 reviews)
"Great location, quiet and clean. "
United States
Laurette
The price is SAR 859
SAR 1,118 total
includes taxes & fees
27 Feb - 28 Feb
The Gwen, a Luxury Collection Hotel, Michigan Avenue 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
1,017 reviews
View
Breakfast, lunch, dinner served; American cuisine, alfresco dining
Park Hyatt Chicago
5.0 star property
9.6
Exceptional
1,000 reviews
View
Lobby lounge
Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
9.6
Exceptional
457 reviews
View
Lobby
The Langham, Chicago
5.0 star property
9.8
Exceptional
1,002 reviews
View
Exterior
Sofitel Chicago Magnificent Mile
4.5 star property
9.4
Exceptional
2,327 reviews
View

Top Oak Street Hotel Reviews

Hotels near other Oak Street attractions

Find out more about Oak Street

Top reasons to visit Oak Street

  • Iconic Beaches: Oak Street Beach offers a beautiful spot for relaxation and water sports, perfect for enjoying the sun.
  • Vibrant Shopping: Explore luxury boutiques and charming cafes, making it an ideal destination for shopping enthusiasts.
  • Cultural Attractions: Nearby art museums and historic sites provide rich cultural experiences for visitors.
  • Urban Parks: Lush parks in the area offer scenic views and peaceful retreats from city life.
  • Diverse Accommodations: A variety of hotels and apartments cater to different vacation needs, ensuring a comfortable stay.

Find great hotels near Oak Street

Discover a variety of accommodation options on Oak Street, Chicago, perfect for your vacation needs. From pet-friendly hotels to comfortable apartments, you’ll find everything you need for a memorable stay. Enjoy the convenience of being close to Oak Street Beach and explore nearby shopping and dining experiences. Whether you're traveling for leisure or business, there's a perfect place for you to unwind in this vibrant area.

  • Hyatt Regency Chicago: Experience the perfect blend of comfort and convenience at Hyatt Regency Chicago, a 4-star hotel located 1.4km from Oak Street. Ideal for business travelers and those seeking an LGBTQIA-friendly environment, this hotel offers modern amenities including a state-of-the-art fitness center, spacious meeting rooms, and high-speed internet access. Guests rave about the attentive staff and vibrant atmosphere, making it a great choice for both business and leisure. With its central location, you’ll have easy access to Chicago’s iconic attractions.
  • The Whitehall Hotel, BW Premier Collection: Nestled just 161m from Oak Street, The Whitehall Hotel is a charming 4-star property that welcomes both guests and their furry friends. This LGBTQIA-friendly hotel is located in a bustling shopping district and features pet-friendly accommodations, ensuring a comfortable stay for all. Guests can enjoy stylishly decorated rooms, complimentary Wi-Fi, and a delightful on-site dining experience. With its close proximity to shopping and attractions, The Whitehall is perfect for travelers seeking both convenience and comfort.
  • LondonHouse Chicago, Curio Collection by Hilton: For a luxurious getaway, look no further than LondonHouse Chicago, a 4.5-star hotel located 1.4km from Oak Street. This upscale property is perfect for those wanting to indulge in a shopping and LGBTQIA-friendly vacation. With exquisite dining options featuring stunning views of the city, a rooftop lounge, and elegantly designed rooms, guests are immersed in a world of elegance. LondonHouse offers a unique blend of historic charm and modern comfort, making it an exceptional choice for discerning travelers.

Where to stay near Oak Street

Oak Street offers an enchanting blend of romance and family-friendly vibes, perfect for any traveler. Just a short stroll away, you’ll find picturesque parks and scenic beaches, providing a tranquil escape from the urban hustle. The nearby shopping areas boast luxury boutiques and charming cafes, making it an ideal spot to unwind and indulge. Experience the welcoming atmosphere of friendly locals while soaking in the beauty of this vibrant Chicago destination.

  • Chicago: As a vibrant metropolis, Chicago is a hub of activity and culture, with Oak Street nestled within its dynamic atmosphere. Travelers can enjoy a variety of experiences throughout the year, though peak tourist seasons are from June to August. Chicago offers a rich tapestry of family-friendly activities, outdoor adventures, and urban exploration. Visitors can indulge in shopping at diverse retail outlets, catch a thrilling game at local sports stadiums, or unwind in one of the city's many urban parks, making it a well-rounded destination for all types of travelers.
  • Downtown Chicago: Situated in the heart of the city, Downtown Chicago is a bustling neighborhood that complements the Oak Street experience. With visitor numbers peaking from July to September, this area is perfect for those seeking family activities, outdoor fun, and a quintessential city experience. Downtown is known for its vibrant shopping areas, entertainment venues, and theaters. The proximity to major landmarks, including sports facilities and urban parks, ensures a lively atmosphere where visitors can immerse themselves in the local culture and enjoy the city's energetic vibe.
  • Magnificent Mile: Just 644m from Oak Street, the Magnificent Mile is a renowned shopping district that attracts visitors year-round. With peak travel periods in March to April and July, this neighborhood is perfect for families and urban explorers alike. The Magnificent Mile boasts a myriad of shopping opportunities, educational attractions, and entertainment venues. Visitors can take leisurely strolls along the picturesque streets, explore historic sites, or enjoy a day at the nearby jetty pier. Its vibrant atmosphere makes it a must-visit destination during your Chicago vacation.

Things to do near Oak Street

Oak Street in Chicago is a vibrant destination offering a mix of shopping and outdoor activities. Visitors can enjoy water sports along the nearby shores or explore city attractions that showcase the rich culture and history of the area. With its lively atmosphere and beautiful surroundings, Oak Street provides a perfect blend of excitement and relaxation for tourists looking to experience the best of Chicago.

Shopping

For a delightful shopping experience, visit the 900 North Michigan Shops, just 161m from Oak Street, offering vibrant city vibes. The Chicago Place Mall, located 644m away, is perfect for family outings. If you're up for a drive, explore other shopping areas further out.

Recreation

At Wrigley Field, immerse yourself in the energetic atmosphere of a live sports event, just 6.4km from Oak Street. Enjoy soulful music and vibrant performances at the House of Blues Chicago, located 1.4km away. For a serene escape, visit Northerly Island Natural Area, 4.8km away, embracing nature's tranquility.

Adventure

Explore the scenic Salt Creek Trail, a great hiking destination located 19.3km from Oak Street, where adventure meets breathtaking views. For family fun, visit Rainbow Falls Waterpark, situated 32.2km away, offering thrilling water attractions and entertainment for all ages.

Nightlife

Experience the vibrant nightlife on Oak Street with a visit to the Chicago Theatre for captivating performances, or enjoy drinks and games at Dave & Buster's. For a unique adventure, explore Amazing Chicago's Funhouse Maze, offering thrilling experiences just a short distance 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 on your trip to Oak Street, consider visiting between December and February when hotel prices are lower. Mondays typically offer the cheapest rates, while Saturdays are the most expensive. Use Expedia to refine your hotel search based on budget and preferences, and consider the Eco-certified filter for sustainable options. Additionally, bundling your hotel, flights, and activities can lead to significant savings. Don't forget to explore free activities in the area and utilize public transport, which is both affordable and convenient for getting around.

  • 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: Utilize Expedia's search tool to refine your options based on your budget, preferred location, and desired 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 arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Oak Street hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Oak Street

Oak Street in Chicago offers a vibrant mix of attractions, including iconic skyscrapers, lush urban parks, and fascinating art museums. Ideal for travelers seeking cultural experiences or family fun, visitors can enjoy the nearby Oak Street Beach, perfect for relaxation and recreation. Additionally, there are various motels conveniently located near the beach for a comfortable stay.

  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue offers a vibrant city atmosphere filled with upscale shopping, dining, and iconic architecture. A stroll along this bustling street provides a taste of Chicago's urban energy.
  • Navy Pier: This popular destination features stunning waterfront views, entertainment options, and scenic gardens. With a lively atmosphere and friendly locals, Navy Pier is perfect for leisurely strolls, dining, and enjoying various attractions.
  • Millennium Park: A beautiful urban park that showcases art installations, gardens, and outdoor concerts. Millennium Park is an ideal spot for families to relax and enjoy the city's cultural offerings amidst lush greenery.

Best time to go to Oak Street

The best time to visit Oak Street can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Oak Street falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Oak Street falls in January, 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 SunnyAverageSlightly 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 SunnySlightly HighSlightly 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 in Chicago is convenient with access to three major airports. Chicago O'Hare International Airport (ORD) is approximately 24.1km away, with nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel, 3.2km from the airport, and the 4-star Hilton Chicago O'Hare Airport, just 161m away. Midway International Airport (MDW) is about 16.1km from Oak Street, featuring luxurious options such as the 5-star Nobu Hotel Chicago, 12.9km away. Additionally, Chicago Executive Airport (PWK) is located 32.2km from Oak Street, with hotels like the 4.5-star Deer Path Inn, 16.1km from the airport, providing easy access for travelers.

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 757 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, Hilton Chicago/Magnificent Mile Suites is one of the top choices for your stay based on our traveler data, and this hotel offers an indoor pool and a fitness center. Other good choices close by include Embassy Suites by Hilton Chicago Downtown River North and Hotel Riu Plaza Chicago.
How many hotels should I expect to find close to Oak Street?
Expedia has 757 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 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 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.

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