Find hotels near Oak Street, Chicago from NT$3,748

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Our top choices for Oak Street hotels

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Streeterville, 0.6 km from Oak Street
9.8 out of 10, Exceptional, (1011)
"Best hotel in Chicago"
United States
Michael
The price is NT$14,992
NT$17,599 total
includes taxes & fees
Jan 4 - 2026/1/5
The Peninsula Chicago

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Magnificent Mile, 0.5 km from Oak Street
9.6 out of 10, Exceptional, (1002)
"beautiful room and hotel great bar!"
United States
ravi
The price is NT$12,207
NT$14,329 total
includes taxes & fees
Jan 4 - 2026/1/5
Park Hyatt Chicago

The Langham, Chicago

The Langham, Chicago
5.0 star property
River North, 1.4 km from Oak Street
9.8 out of 10, Exceptional, (1000)
"Langham is always a superior stay"
United States
THADDEUS LAMONT
The price is NT$12,768
NT$14,989 total
includes taxes & fees
Jan 18 - 2026/1/19
The Langham, Chicago

Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
River North, 0.7 km from Oak Street
9.6 out of 10, Exceptional, (414)
"Great stay"
United States
John E
The price is NT$4,261
NT$5,002 total
includes taxes & fees
Jan 1 - 2026/1/2
Residence Inn Chicago Downtown Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (2270)
"Great location, nice bar."
United States
Erik
The price is NT$5,085
NT$6,895 total
includes taxes & fees
Dec 24 - Dec 25
Sofitel Chicago Magnificent Mile

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, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Viceroy Chicago

Viceroy Chicago
4.5 star property
0.3 km from Oak Street
9.4 out of 10, Exceptional, (1143)
"Very nice hotel, great rooms, comfy bed and the staff were all very friendly."
United States
Randall
The price is NT$6,786
NT$8,893 total
includes taxes & fees
Jan 4 - 2026/1/5
Viceroy Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
0.2 km from Oak Street
9.4 out of 10, Exceptional, (1003)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is NT$11,994
NT$14,079 total
includes taxes & fees
Jan 18 - 2026/1/19
Waldorf Astoria Chicago

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, (3414)
"Enjoyed my stay"
United States
Karen
The price is NT$3,664
NT$4,302 total
includes taxes & fees
Dec 24 - Dec 25
L7 Chicago by LOTTE

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, (1001)
"Amazing place! Our family of 6 had a fantastic time here for a night. "
United States
Brooke
The price is NT$13,256
NT$15,561 total
includes taxes & fees
Jan 11 - 2026/1/12
Four Seasons Hotel Chicago

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, (1000)
"Great stay!"
United States
Bethany
The price is NT$3,882
NT$4,557 total
includes taxes & fees
Dec 28 - Dec 29
Hotel EMC2, Autograph Collection

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, (3021)
"Excellent stay great location and great rooms"
United States
Joseph
The price is NT$3,130
NT$4,564 total
includes taxes & fees
Jan 4 - 2026/1/5
Hotel Riu Plaza Chicago

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 0.2 km from Oak Street
9.2 out of 10, Wonderful, (1303)
"Great hotel!"
United States
Julie
The price is NT$4,261
NT$5,933 total
includes taxes & fees
Jan 4 - 2026/1/5
Thompson Chicago, by Hyatt

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (4112)
"Great stay"
United States
Ericka
The price is NT$3,193
NT$3,748 total
includes taxes & fees
Dec 28 - Dec 29
citizenM Chicago Downtown

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 1.4 km from Oak Street
9.4 out of 10, Exceptional, (3460)
"Great hotel! "
United States
Kianna
The price is NT$4,115
NT$4,831 total
includes taxes & fees
Jan 4 - 2026/1/5
LondonHouse Chicago, Curio Collection by Hilton

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, (1166)
"Great stay!"
United States
Tea
The price is NT$3,472
NT$4,076 total
includes taxes & fees
Jan 1 - 2026/1/2
Aloft Chicago Downtown River North

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 1.5 km from Oak Street
9.4 out of 10, Exceptional, (3409)
"The Hotel was amazing great location "
United States
Donnisha
The price is NT$4,387
NT$6,076 total
includes taxes & fees
Jan 5 - 2026/1/6
Hyatt Regency Chicago

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 1.1 km from Oak Street
9.4 out of 10, Exceptional, (856)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is NT$3,409
NT$4,001 total
includes taxes & fees
Jan 4 - 2026/1/5
Moxy Chicago Downtown

Loews Chicago Hotel

Loews Chicago Hotel
4.5 star property
Streeterville, 1.3 km from Oak Street
9.4 out of 10, Exceptional, (1589)
"Easy to get around and great staff on-site. "
United States
Marilyn
The price is NT$5,650
NT$7,633 total
includes taxes & fees
Jan 5 - 2026/1/6
Loews Chicago Hotel

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, (1797)
"Amazing hotel, location, staff, and food!!"
United States
Wendy
The price is NT$9,390
NT$11,023 total
includes taxes & fees
Jan 4 - 2026/1/5
Trump International Hotel & Tower 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.

Top Oak Street Hotel Reviews

Hotels near other Oak Street attractions

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 732 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 a fitness center and valet parking. Other good choices close by include The Whitehall Hotel, BW Premier Collection and Embassy Suites by Hilton Chicago Downtown River North.
How many hotels should I expect to find close to Oak Street?
Expedia has 732 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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