Find hotels near Oak Street, Chicago from $169

Top reasons to visit Oak Street

• Upscale Shopping: Oak Street features a variety of boutique stores offering high-end fashion and unique items.
• Vibrant Atmosphere: Experience a lively environment filled with bustling streets, trendy cafes, and friendly locals.
• Proximity to Oak Street Beach: Just a short walk away, enjoy the sun and sand at this beautiful urban beach.
• Recreational Activities: Engage in fun nights with billiards and other entertainment options available nearby.
• Diverse Accommodation: Choose from a range of comfortable hotels and stylish apartments to suit your needs.

Find great hotels near Oak Street

Discover a range of accommodation options along Oak Street in Chicago, where comfort meets convenience. From pet-friendly hotels to stylish apartments, you'll find the perfect place to unwind after a day of exploring. Enjoy easy access to Oak Street Beach and indulge in a vibrant shopping experience. Whether you're on a business trip or a leisurely vacation, Oak Street offers a variety of hotels tailored to suit every traveler's needs.

• Hyatt Regency Chicago: A premier 4-star property with a guest rating of 9.4, Hyatt Regency Chicago offers a refreshing nature-themed experience just 0.9 miles from Oak Street. This hotel is perfect for business travelers seeking a blend of productivity and relaxation. Guests can enjoy outdoor amenities like a tranquil terrace, ideal for unwinding while soaking in the natural surroundings. With a focus on wellness and an atmosphere that promotes connection with nature, this hotel ensures a balanced stay for both leisure and business.
• LondonHouse Chicago, Curio Collection by Hilton: With a luxurious 4.5-star rating and a guest score of 9.4, LondonHouse Chicago offers an upscale getaway only 0.9 miles from Oak Street. This hotel is perfect for those seeking a spa-themed experience combined with a vibrant shopping atmosphere. Indulge in the full-service spa featuring aromatherapy treatments and massage therapy, ensuring relaxation after a day of shopping at nearby boutiques. Its prime location in the shopping district adds to its allure, making it a wonderful choice for luxury travelers.
• The Whitehall Hotel, BW Premier Collection: A charming 4-star hotel with a guest rating of 8.4, The Whitehall Hotel is located a mere 0.1 miles from Oak Street. This boutique-style hotel caters to pet-friendly travelers and business guests alike. The property features uniquely designed decor and artwork that enhances its character. With its thoughtful pet policy, including amenities for furry companions, The Whitehall Hotel ensures a warm and welcoming atmosphere for all guests, making it an excellent choice for a memorable stay.

Where to stay near Oak Street

Oak Street, located near the vibrant downtown Chicago, offers a unique blend of romantic and family-friendly vibes. Just a short distance from Oak Street Beach, visitors can explore picturesque locations and enjoy the urban oasis atmosphere. Nearby attractions include trendy boutiques and delightful cafes, providing an unforgettable experience filled with friendly people and scenic views. Whether you're here for business or leisure, Oak Street is the perfect starting point to discover all that Chicago has to offer.

• Chicago: As a vibrant metropolis, Chicago serves as the backdrop for your Oak Street adventure. Known for its blend of cultural attractions and outdoor spaces, the city welcomes travelers year-round, with peak visits from July to September. Explore an array of family-friendly activities, including shopping in iconic districts, attending thrilling sports events, or enjoying a show at one of its renowned theaters. Local landmarks like the historic stadiums and expansive urban parks enhance the city's appeal, making Chicago a must-visit destination.
• Downtown Chicago: Nestled within the heart of the city, Downtown Chicago is the bustling neighborhood where Oak Street resides. This area also enjoys a steady influx of visitors, particularly during the warmer months of July to September. Downtown offers a rich tapestry of experiences, from shopping at high-end boutiques to enjoying the vibrant arena entertainment scene. The neighborhood is adorned with attractions such as the famous tourist precinct and lush urban parks, making it a perfect spot for family outings and city exploration.
• Magnificent Mile: Located just 0.4 miles from Oak Street, the Magnificent Mile is a renowned shopping and dining destination that attracts visitors throughout the year, especially in the spring and summer months. Families and outdoor enthusiasts alike flock to this lively area for its array of shops, educational venues, and entertainment options. The proximity to major attractions, including tourist precincts and sports facilities, ensures that there’s no shortage of activities. A stroll along the Magnificent Mile promises a delightful blend of excitement and leisure.

Things to do near Oak Street

Oak Street in Chicago is a vibrant destination known for its upscale shopping and unique wildlife experiences. Visitors can enjoy a lively atmosphere while exploring boutique stores and dining options. For some recreation, you can also find places featuring billiards tables, perfect for a fun night out with friends. Whether you're shopping or unwinding, Oak Street offers an exciting mix of activities to make your vacation memorable.

Shopping

On Oak Street, you can explore luxury boutiques and designer shops perfect for gifts and souvenirs. If you're up for a drive, check out the Water Tower Place, where you’ll find an array of stores and dining options to enhance your shopping experience.

Recreation

Experience luxury at Chevy Chase Country Club, where you can enjoy golf and unwind in a serene environment. Ravinia Green Country Club offers relaxation and recreational activities amidst beautiful landscapes. For a unique experience, visit Broken Arrow Golf Club, known for its elegant setting and excellent golfing opportunities.

Adventure

Explore Oak Street Beach for sunbathing, swimming, and beach volleyball, offering stunning views of Lake Michigan. Visit nearby Oak Street's upscale shops and restaurants, providing a vibrant atmosphere for food and fashion enthusiasts. For a thrill, rent a bike and cruise along the scenic lakefront trail.

Nightlife

Explore the vibrant nightlife at Oak Street Beach with its lively beach bars, perfect for enjoying cocktails by the shore. For a more upscale experience, visit the nearby lounges offering craft cocktails and stunning city views. Don't miss the local music scene at intimate venues that showcase emerging talent.

Booking tips and Expedia advantages for Oak Street

• 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: Expedia's search tool makes it easy to choose your budget, desired location, and other preferences. You can arrange your results to display prices from lowest to highest, highlighting the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type. For instance, if you select the Eco-certified filter, you'll find a range of sustainable and environmentally friendly hotels ready for booking.
• Consider bundling your trip: You can save money by combining your Oak Street hotel reservations with your flights and activities through an Expedia package.

Find the best attractions near Oak Street

When visiting Oak Street, Chicago, immerse yourself in the vibrant city life by exploring iconic skyscrapers and enjoying a leisurely stroll through urban parks. This area offers a blend of cultural experiences and family-friendly activities, ensuring there's something for everyone. Don't miss the chance to explore the lively streets filled with shops and eateries that reflect the city's dynamic spirit.

• Michigan Avenue: Experience the vibrant energy of Michigan Avenue, a bustling thoroughfare known for its shopping, dining, and iconic skyline. This street is a hub of activity and offers a mix of modern and historic architecture, making it a perfect spot for both shopping enthusiasts and architecture lovers.
• Navy Pier: Discover the charm of Navy Pier, a lively jetty featuring stunning views of Lake Michigan. With attractions like the Ferris wheel and various restaurants, it’s a friendly atmosphere perfect for families and friends to enjoy scenic walks and entertainment.
• Millennium Park: Explore Millennium Park, a beautiful urban oasis featuring lush gardens, public art, and outdoor performances. It’s a family-friendly destination where you can relax, enjoy cultural events, and take in the stunning city skyline.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Average	Slightly 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 15 miles away, with nearby hotels like the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both 2 miles from the airport. Chicago Midway International Airport (MDW) is closer at 10 miles, featuring luxurious options such as the 5-star Langham and Trump International Hotel, both 9 miles away. For those considering Milwaukee's General Mitchell International Airport (MKE), it is 74 miles from Oak Street, with notable hotels like the 4.5-star Pfister Hotel just 6 miles from MKE.