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Our top choices for Oak Street hotels

1. 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)
"Welcoming and attentive staff throughout the hotel made my stay an enjoyable and memorable experience."
United States
Charles
The price is NT$20,191
NT$24,005 total
includes taxes & fees
Aug 9 - Aug 10
The Peninsula Chicago

2. The Langham, Chicago

The Langham, Chicago
5.0 star property
River North, 1.4 km from Oak Street
9.8 out of 10, Exceptional, (1,000 reviews)
"Wonderful hotel stay"
United States
Robert
The price is NT$17,532
NT$20,844 total
includes taxes & fees
Aug 16 - Aug 17
The Langham, Chicago

3. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
River North, 1.3 km from Oak Street
9.6 out of 10, Exceptional, (1,957 reviews)
"Great location and wonderful staff."
United States
Ryan
The price is NT$15,143
NT$18,004 total
includes taxes & fees
Aug 9 - Aug 10
Trump International Hotel & Tower Chicago

4. 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
9.6 out of 10, Exceptional, (1,001 reviews)
"The location was great, the staff was friendly and attentive."
United States
Karla
The price is NT$12,330
NT$15,619 total
includes taxes & fees
Aug 23 - Aug 24
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

5. 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)
"Our room was wonderful"
United States
Jennifer
The price is NT$17,881
NT$21,259 total
includes taxes & fees
Aug 9 - Aug 10
Park Hyatt Chicago

6. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 1.6 km from Oak Street
9.6 out of 10, Exceptional, (4,477 reviews)
"Great stay"
United States
Julie Ann
The price is NT$8,348
NT$9,924 total
includes taxes & fees
Aug 24 - Aug 25
L7 Chicago by LOTTE

7. The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
Rush and Division, 0.2 km from Oak Street
9.6 out of 10, Exceptional, (147 reviews)
"Great property and staff! Loved the size and location"
United States
Angela
The price is NT$6,083
NT$8,385 total
includes taxes & fees
Aug 30 - Aug 31
The Talbott, Autograph Collection

8. 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, (584 reviews)
"Fantastic hotel, large room, double sinks, lovely kitchen area with everything you need. Beds really comfy and amazing views. Breakfast great addition!"
United Kingdom
Sarah
The price is NT$9,498
NT$11,292 total
includes taxes & fees
Aug 31 - Sep 1
Residence Inn Chicago Downtown Magnificent Mile

9. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (4,324 reviews)
"Great place to stay!"
United States
lakadria
The price is NT$5,783
NT$6,875 total
includes taxes & fees
Aug 31 - Sep 1
citizenM Chicago Downtown

10. Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 1.1 km from Oak Street
9.4 out of 10, Exceptional, (1,002 reviews)
"Great place to stay, We always have fun here and the bartenders are the best!"
United States
Patrick
The price is NT$6,784
NT$8,066 total
includes taxes & fees
Aug 9 - Aug 10
Moxy Chicago Downtown

11. Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
4.0 star property
The Loop, 2.6 km from Oak Street
9.4 out of 10, Exceptional, (1,460 reviews)
"Restaurant was great and front desk staff were very kind!"
United States
Amber
The price is NT$6,838
NT$8,129 total
includes taxes & fees
Aug 23 - Aug 24
Canopy by Hilton Chicago Central Loop

12. Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Rush and Division, 0.2 km from Oak Street
9.4 out of 10, Exceptional, (2,564 reviews)
"Great hotel, centrally located to a lot of great things!"
United States
Steven
The price is NT$8,694
NT$11,296 total
includes taxes & fees
Aug 30 - Aug 31
Sofitel Chicago Magnificent Mile

13. Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
2.6 km from Oak Street
9.4 out of 10, Exceptional, (895 reviews)
"The breakfast is a must try there."
United States
Yidong
The price is NT$14,150
NT$17,631 total
includes taxes & fees
Aug 20 - Aug 21
Nobu Hotel Chicago

14. Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop
3.5 star property
Theatre District, 2.2 km from Oak Street
9.4 out of 10, Exceptional, (1,000 reviews)
"Loved my stay here! Great location and comfy living for an extended stay!"
United States
Emma
The price is NT$7,398
NT$8,796 total
includes taxes & fees
Aug 23 - Aug 24
Residence Inn Chicago Downtown/Loop

15. 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)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
United States
August
The price is NT$17,122
NT$20,357 total
includes taxes & fees
Aug 9 - Aug 10
Four Seasons Hotel Chicago

16. The St. Regis Chicago

The St. Regis Chicago
5.0 star property
1.6 km from Oak Street
9.4 out of 10, Exceptional, (128 reviews)
"We had a great stay and will come back again in the near future!"
United States
Princess
The price is NT$18,188
NT$21,624 total
includes taxes & fees
Aug 23 - Aug 24
The St. Regis Chicago

17. The LaSalle Chicago, Autograph Collection by Marriott

The LaSalle Chicago, Autograph Collection by Marriott
4.5 star property
Theatre District, 2.5 km from Oak Street
9.4 out of 10, Exceptional, (380 reviews)
"Good location, easy to access, restaurants and bar convenient."
United States
Elizabeth
The price is NT$8,400
NT$9,986 total
includes taxes & fees
Aug 30 - Aug 31
The LaSalle Chicago, Autograph Collection by Marriott

18. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 2.1 km from Oak Street
9.4 out of 10, Exceptional, (2,626 reviews)
"Nice Stay"
United States
Morgan
The price is NT$6,481
NT$8,819 total
includes taxes & fees
Aug 31 - Sep 1
Sable at Navy Pier Chicago, Curio Collection by Hilton

19. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (3,534 reviews)
"Great stay"
United States
Alexis
The price is NT$7,398
NT$9,829 total
includes taxes & fees
Sep 1 - Sep 2
The Royal Sonesta Chicago Downtown

20. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 2.6 km from Oak Street
9.2 out of 10, Wonderful, (1,395 reviews)
"Very nice would stay again"
United States
Dawn
The price is NT$6,838
NT$8,130 total
includes taxes & fees
Aug 23 - Aug 24
Hilton Garden Inn Chicago Central Loop
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
Front of property - evening/night
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
1,000 reviews
View
Terrace/patio
Trump International Hotel & Tower Chicago
5.0 star property
9.6
Exceptional
1,957 reviews
View
Frette Italian sheets, premium bedding, in-room safe, desk
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 star property
9.6
Exceptional
1,001 reviews
View
Breakfast, lunch, dinner and brunch served
Park Hyatt Chicago
5.0 star property
9.6
Exceptional
1,000 reviews
View

Top Oak Street Hotel Reviews

Other attractions near Oak Street

Find out more about Oak Street

Top reasons to visit Oak Street

  • Upscale Shopping: Oak Street features a variety of high-end boutiques, perfect for indulging in retail therapy.
  • Oak Street Beach: Enjoy sunbathing, leisurely walks, and stunning views at the picturesque beach.
  • Cultural Attractions: Explore nearby art museums and skyscrapers that showcase Chicago's vibrant cultural scene.
  • Family-Friendly Parks: Relax in scenic parks like Lincoln Park, offering lush greenery and playgrounds.
  • Diverse Dining Options: Savor delicious meals at various dining establishments, catering to all tastes.

Find great hotels near Oak Street

Discover the ideal hotel accommodations along Oak Street in Chicago, where you can enjoy a delightful blend of luxury and convenience. From pet-friendly options to business travel amenities, this vibrant area offers a variety of lodging types, including hotels and apartments. With easy access to the stunning Oak Street Beach and a range of shopping experiences, you're sure to find the perfect spot to make your stay memorable.

  • Hyatt Regency Chicago: Located in the heart of the city, Hyatt Regency Chicago is a 4-star eco-certified hotel that merges urban sophistication with a commitment to sustainability. Just 1.4km from Oak Street, this property is perfect for eco-friendly travelers looking for a vibrant city-themed experience. Guests can enjoy spacious rooms equipped with modern amenities, a fitness center, and on-site dining options that emphasize fresh, locally sourced ingredients. The hotel's central location allows easy access to Chicago’s top attractions, making it a great base for exploring the city.
  • The Whitehall Hotel, BW Premier Collection: With a prime location just 161m from Oak Street, The Whitehall Hotel is a charming 4-star property that welcomes everyone, including pets. Designed for business travelers and LGBTQIA-friendly, this hotel features cozy accommodations and a welcoming atmosphere. Amenities include complimentary Wi-Fi, a business center, and a fitness room. The hotel’s pet policy allows for dogs and service animals, ensuring that no family member is left behind. Its close proximity to shopping and dining makes it ideal for both leisure and business stays.
  • LondonHouse Chicago, Curio Collection by Hilton: Elevate your vacation at LondonHouse Chicago, a luxurious 4.5-star hotel located 1.4km from Oak Street. This spa-themed property offers a full-service spa and luxurious accommodations for travelers seeking relaxation and indulgence. The hotel is LGBTQIA welcoming and features stunning views of the city skyline. Guests can enjoy a rooftop bar, an upscale restaurant, and various wellness treatments, including deep tissue massages and body wraps. With its sophisticated ambiance and attentive service, LondonHouse guarantees an unforgettable stay in the Windy City.

Where to stay near Oak Street

Discover the charm of Oak Street, Chicago, where romance meets urban excitement. Stroll along the picturesque Oak Street Beach, perfect for sunbathing or a leisurely walk. Enjoy shopping at nearby boutiques and savor delightful dining options. For a family-friendly vibe, visit the scenic parks like Lincoln Park, offering lush greenery and playgrounds. With its friendly atmosphere and stunning views, Oak Street is an ideal spot to unwind and explore the best of Chicago.

  • Chicago: As a vibrant metropolis, Chicago is an exciting destination full of cultural experiences and urban landscapes. Oak Street, located right in the heart of the city, offers visitors a mix of family-friendly attractions, outdoor activities, and city-themed experiences. The city is known for its impressive shopping districts, thrilling arena events, and captivating theater productions. Notable nearby landmarks include iconic sports stadiums, bustling tourist precincts, and beautiful urban parks that provide a perfect escape from the city's hustle and bustle. With year-round appeal, Chicago sees the most visitors during the summer months, making it a lively place to explore.
  • Downtown Chicago: Nestled within the larger city, Downtown Chicago serves as the bustling core that attracts travelers from around the globe. Like Oak Street, Downtown boasts an array of family-oriented activities, outdoor spaces, and city-themed attractions. Visitors can enjoy shopping at high-end boutiques, catch a game at local sports facilities, or indulge in the vibrant theater scene. With its proximity to urban parks and tourist precincts, Downtown Chicago offers a perfect blend of leisure and entertainment. The neighborhood remains popular throughout the year, with peak travel occurring in the warm summer months.
  • Magnificent Mile: Located a mere 644m from Oak Street, Magnificent Mile is a shopper's paradise and a cultural hotspot. This iconic stretch is renowned for its upscale shopping, diverse dining options, and educational attractions. Visitors flock to the area year-round for family-friendly experiences and outdoor adventures. Highlights include stunning views of the city skyline, access to the famous jetty pier, and a host of cultural landmarks. The peak travel seasons from March to April and July ensure a vibrant atmosphere, making it the perfect spot for tourists looking to immerse themselves in the heart of Chicago.

Things to do near Oak Street

Oak Street in Chicago offers a vibrant mix of shopping and wildlife experiences, making it a fantastic destination for tourists. You can explore the upscale boutiques, enjoy city attractions, and participate in exciting water sports nearby. Whether you're looking to indulge in retail therapy or discover the natural beauty of the area, Oak Street has something for everyone to enjoy during their visit.

Shopping

Experience shopping on Oak Street with the 900 North Michigan Shops, just 161m away, offering a mix of entertainment and luxury. Chicago Place Mall, 644m away, is perfect for family outings. For a local vibe, visit City Market, located 1.6km from Oak Street.

Recreation

Experience the vibrant energy at Wrigley Field, just 6.4km away, where you can catch a game and soak in the sports atmosphere. For music lovers, the House of Blues Chicago, only 1.4km from Oak Street, offers live performances in a lively setting. Enjoy nature at Northerly Island, 4.8km away, perfect for relaxation and outdoor activities.

Adventure

Explore the Salt Creek Trail, a scenic hiking path 19.3km from Oak Street, where you can immerse yourself in nature's beauty and enjoy outdoor adventure. For a splash of fun, visit Rainbow Falls Waterpark, located 32.2km away, offering thrilling water rides perfect for family entertainment.

Nightlife

Experience the vibrant nightlife on Oak Street. Catch a show at the Chicago Theatre, just 1.6km away, for a taste of culture. For a fun night out, visit Dave & Buster's, only 483m away, for games and drinks, or explore the Amazing Chicago's Funhouse Maze for family-friendly adventure.

*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 between December and February when hotel prices are lower. Booking your stay on a Monday rather than a Saturday will also help you save. Use Expedia's search tool to filter for budget-friendly options and eco-certified hotels. Look for package deals that combine flights, hotels, and activities to maximize savings. Additionally, take advantage of free activities and explore the area on foot or via public transport to keep costs down.

  • 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 customize your travel 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 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 some money by combining your Oak Street hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Oak Street

Oak Street in Chicago offers a vibrant mix of attractions, including stunning skyscrapers, serene urban parks, and captivating art museums. Visitors can immerse themselves in the cultural scene while enjoying family-friendly activities. For a perfect day, consider relaxing at Oak Street Beach, and for convenience, there are motels nearby to enhance your stay. Experience the best of city life and leisure all in one place.

  • Michigan Avenue: This iconic street, located 966m from Oak Street, is known for its bustling city vibes. Stroll along the Magnificent Mile, where you'll find upscale shopping, vibrant architecture, and a variety of dining options, making it a perfect destination for urban explorers.
  • Navy Pier: Situated 1.6km from Oak Street, Navy Pier offers a unique blend of urban scenery and friendly atmosphere. Enjoy stunning views of Lake Michigan, explore attractions like the Ferris wheel, and indulge in diverse culinary experiences along the waterfront.
  • Millennium Park: Just 1.6km away from Oak Street, this urban park is a family-friendly oasis in the city. Relax in beautiful green spaces, marvel at the famous Cloud Gate sculpture, and enjoy outdoor concerts and events throughout the year.

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

To visit Oak Street in Chicago, you can fly into three major airports. Chicago O'Hare International Airport (ORD) is 24.1km away, with nearby hotels like the 4.5-star Loews Chicago O'Hare and the 4-star Hyatt Regency O'Hare, both just 3.2km from the airport. Chicago Midway International Airport (MDW) is 16.1km away, with luxurious options such as The Langham, Chicago and Nobu Hotel Chicago, both about 8-14.5km from MDW. Lastly, Chicago Executive Airport (PWK) is 32.2km from Oak Street, with the 4.5-star Deer Path Inn 16.1km away and Hilton Chicago/Northbrook just 1.6km from PWK. Each airport offers convenient access to these hotels.

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 696 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 The Chicago Hotel Collection Ambassador Gold Coast and Omni Chicago Hotel.
How many hotels should I expect to find close to Oak Street?
Expedia has 696 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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