Oak Street Tours

Photo by Eleonora Bertacchi


Plan a trip to see Oak Street

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
The Westin Michigan Avenue Chicago
The French Country Inn Lake Geneva

Browse tours and tickets to explore Oak Street

Tours & day trips

See all 195 activities

Private & custom tours

See all 42 activities

Food, drink & nightlife

See all 31 activities

Adventure & outdoor

See all 17 activities

Popular places to visit


Best Lodging Options Near Oak Street

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Congress Plaza Hotel
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
The Whitehall Hotel, BW Premier Collection
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Embassy Suites by Hilton Chicago Downtown River North
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Warwick Allerton - Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Hilton Garden Inn Chicago Downtown/Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
InterContinental Chicago Magnificent Mile by IHG
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Aloft Chicago Mag Mile
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.

Things to do near Oak Street

Oak Street in Chicago is a vibrant destination offering a mix of shopping and outdoor activities. Visitors can explore upscale boutiques and local shops, while also enjoying nearby wildlife attractions. Additionally, the area provides opportunities for water sports, making it perfect for those seeking adventure. With its blend of urban charm and recreational options, Oak Street promises an exciting experience for tourists.

Shopping

Experience shopping on Oak Street with the nearby 900 North Michigan Shops, just 0.1 miles away, offering a blend of entertainment and family-friendly vibes. The Chicago Place Mall, located 0.4 miles away, provides a vibrant city atmosphere. For a local flavor, visit City Market, 1 mile away.

Recreation

Experience the vibrant energy of Wrigley Field, just 4 miles from Oak Street, where you can catch a thrilling game. Enjoy live music at House of Blues Chicago, only 0.9 miles away, or laugh out loud at Second City, also 0.9 miles away, perfect for family fun.

Adventure

Explore the Salt Creek Trail, a scenic hiking path located 12 miles from Oak Street, where you can immerse yourself in nature and enjoy breathtaking views. For a fun-filled day, visit Rainbow Falls Waterpark, 20 miles away, offering thrilling water slides and family-friendly entertainment.

Nightlife

In Oak Street, Chicago, enjoy a vibrant nightlife with the Chicago Theatre, showcasing culture and romance just 1 mile away. For a fun twist, head to Dave & Buster's, only 0.3 miles away, where drinks and entertainment await. Don’t miss the adventure at Amazing Chicago's Funhouse Maze, also 1 mile away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Oak Street

Oak Street in Chicago offers a vibrant mix of attractions, including stunning skyscrapers, urban parks, and art museums, perfect for culture enthusiasts and families alike. Don't miss the nearby Oak Street Beach for a relaxing day by the water. For accommodations, consider motels close to the beach to enhance your stay and explore the city's rich offerings.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with upscale shops, restaurants, and iconic architecture. Experience the vibrant city atmosphere as you stroll along and take in the sights of historic buildings and modern skyscrapers, making it a haven for shopping and dining enthusiasts.
  • Navy Pier: A popular entertainment destination, Navy Pier offers stunning views of Lake Michigan and a variety of attractions including rides, restaurants, and gardens. Enjoy a leisurely walk along the pier, take a boat tour, or relax with friends in a lively, friendly environment.
  • Millennium Park: A beautiful urban park, Millennium Park features stunning art installations such as the Cloud Gate sculpture. Perfect for families, it offers outdoor activities, concerts, and green spaces to enjoy a day out in the heart of the city.

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 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

Booking tips and Expedia advantages for Oak Street

To save money on your visit to Oak Street, plan your trip between December and February for the lowest lodging rates. Booking a stay on a Monday can also reduce costs compared to Saturdays. Use Expedia to find budget-friendly hotels by filtering for eco-certified options and sorting by price. Consider booking a package deal that includes flights and activities for additional savings. Joining Expedia's One Key membership offers exclusive discounts and the chance to earn OneKeyCash for future stays. Don't forget to explore free activities in the area to keep your 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 refine your preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will show you sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, simply sort the price filter from low to high.
  • Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel stay on Oak Street with your flights and activities.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.