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Sep 12 - Sep 13
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Our top choices for Oak Street hotels

1. The Sono Chicago

The Sono Chicago
Old Town Chicago, 1.5 km from Oak Street
United States
Bronwyn
NT$6,993
NT$8,210 total
includes taxes & fees
Sep 20 - Sep 21
The Sono Chicago

2. The Langham, Chicago

The Langham, Chicago
River North, 1.4 km from Oak Street
United States
Leslie
NT$23,631
NT$28,095 total
includes taxes & fees
Oct 4 - Oct 5
The Langham, Chicago

3. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
River North, 1.3 km from Oak Street
United States
Jorge
NT$15,972
NT$18,989 total
includes taxes & fees
Sep 20 - Sep 21
Trump International Hotel & Tower Chicago

4. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Theatre District, 1.6 km from Oak Street
United States
christina
NT$8,152
NT$9,692 total
includes taxes & fees
Oct 1 - Oct 2
L7 Chicago by LOTTE

5. Park Hyatt Chicago

Park Hyatt Chicago
Streeterville, 0.4 km from Oak Street
United States
Catherine
NT$21,154
NT$25,150 total
includes taxes & fees
Sep 20 - Sep 21
Park Hyatt Chicago

6. Hyatt Regency Chicago

Hyatt Regency Chicago
The Loop, 1.5 km from Oak Street
United States
Steve
NT$8,860
NT$11,663 total
includes taxes & fees
Sep 26 - Sep 27
Hyatt Regency Chicago

7. 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
NT$22,298
NT$27,451 total
includes taxes & fees
Oct 8 - Oct 9
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

8. citizenM Chicago Downtown

citizenM Chicago Downtown
Theatre District, 1.5 km from Oak Street
United States
Germaine
NT$6,107
NT$7,261 total
includes taxes & fees
Sep 20 - Sep 21
citizenM Chicago Downtown

9. Moxy Chicago Downtown

Moxy Chicago Downtown
River North, 1.1 km from Oak Street
United States
Justin
NT$6,302
NT$7,493 total
includes taxes & fees
Sep 20 - Sep 21
Moxy Chicago Downtown

10. Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop
Theatre District, 2.2 km from Oak Street
United States
Karla
NT$9,082
NT$10,797 total
includes taxes & fees
Sep 26 - Sep 27
Residence Inn Chicago Downtown/Loop

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 2.1 km from Oak Street
United States
Ashraf
NT$9,011
NT$11,804 total
includes taxes & fees
Oct 1 - Oct 2
Sable at Navy Pier Chicago, Curio Collection by Hilton

12. Loews Chicago Hotel

Loews Chicago Hotel
Streeterville, 1.3 km from Oak Street
United States
Elisa
NT$8,386
NT$11,099 total
includes taxes & fees
Sep 20 - Sep 21
Loews Chicago Hotel

13. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
The Loop, 1.5 km from Oak Street
United States
ShaRona
NT$7,563
NT$10,004 total
includes taxes & fees
Sep 20 - Sep 21
The Royal Sonesta Chicago Downtown

14. Aloft by Marriott Chicago Downtown River North

Aloft by Marriott Chicago Downtown River North
River North, 1.1 km from Oak Street
United States
Michelle
NT$6,962
NT$8,277 total
includes taxes & fees
Sep 20 - Sep 21
Aloft by Marriott Chicago Downtown River North

15. 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
Claudia
NT$6,957
NT$8,271 total
includes taxes & fees
Sep 27 - Sep 28
Springhill Suites by Marriott Chicago Downtown/ River North

16. Arlo Chicago

Arlo Chicago
Theatre District, 1.7 km from Oak Street
United States
Juana
NT$7,669
NT$10,112 total
includes taxes & fees
Sep 20 - Sep 21
Arlo Chicago

17. Viceroy Chicago

Viceroy Chicago
0.3 km from Oak Street
United States
Margaret
NT$13,550
NT$17,157 total
includes taxes & fees
Oct 8 - Oct 9
Viceroy Chicago

18. Hotel EMC2, Autograph Collection

Hotel EMC2, Autograph Collection
Streeterville, 0.9 km from Oak Street
United States
Abey
NT$11,329
NT$13,469 total
includes taxes & fees
Sep 27 - Sep 28
Hotel EMC2, Autograph Collection

19. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Theatre District, 2 km from Oak Street
Canada
Jennifer
NT$7,726
NT$10,124 total
includes taxes & fees
Sep 27 - Sep 28
Staypineapple, An Iconic Hotel, The Loop

20. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Streeterville, 0.2 km from Oak Street
United States
Teresa
NT$20,885
NT$24,830 total
includes taxes & fees
Oct 4 - Oct 5
Four Seasons Hotel 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 spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.
The Sono Chicago
10.0
Exceptional
550 reviews
View
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
The Langham, Chicago
9.8
Exceptional
1,004 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
2,019 reviews
View
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.
L7 Chicago by LOTTE
9.6
Exceptional
4,785 reviews
View
A couple dining at a table with a view of a cityscape and a sunset.
Park Hyatt Chicago
9.6
Exceptional
1,000 reviews
View

Top Oak Street Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Amazing location, very clean, and the air conditioner was phenomenal!"
Daniel Rae 3-night trip
Posted 1 hour ago
Hilton Chicago/Magnificent Mile Suites
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"As"
Juliet 1-night trip
Posted 4 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"I had an absolutely wonderful stay at the Congress Plaza Hotel! From the moment you walk into the grand, historic lobby, you feel the incredible history and architectural beauty of the building. I wish I had a Lake front view."
Steven 1-night trip
Posted 4 hours ago
Congress Plaza Hotel
River Hotel

River Hotel

10/10 Excellent
"Stayed at the River hotel for a concert in Chicago. The property itself is in a perfect location for downtown scenery. The room was clean and offered great amenities. The staff was helpful and even explained some tips and tricks to get the uber faster and how to get to the stadium. Overall a great stay"
Derek Aaron 1-night trip
Posted 5 hours ago
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"The hotel was clean and beautiful! Great staff at check in and check out."
Janine 1-night trip
Posted 5 hours ago
Hyatt Regency Chicago
Warwick Allerton - Chicago

Warwick Allerton - Chicago

10/10 Excellent
"It was our first time in Chicago, and we would definitely stay here again. The hotel is clean, quiet, and so pretty. (with an art deco vibe) It’s also located in a great area, very easily walkable to most shops/attractions/etc that were already on our list. The staff was so friendly. I wish I got the name of the lovely lady who was so generous to my friends and I. Overall such a nice comfy place to stay at!"
Angelica 2-night trip
Posted 1 day ago
Warwick Allerton - Chicago
The Wade

The Wade

8/10 Good
"Staff was friendly, bar was nice, but don’t go to Timmy’s for food or good drinks. And don’t drink the water in the room"
Perrico 1-night trip
Posted 1 day ago
The Wade

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.
See properties

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 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, Four Seasons Hotel Chicago is one of the top choices for your stay based on our traveler 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 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 Tribune Tower 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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