Chicago Trip

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Things to do in Chicago

Shopping

Woodfield Mall offers a vibrant shopping experience with a mix of business and family-friendly entertainment. For a unique visit, explore LEGOLAND® Discovery Center, perfect for kids and adults alike. Chicago Place Mall combines city vibes with shopping, making it a great spot for souvenirs and gifts.

Recreation

Experience the vibrant atmosphere at Wrigley Field, where you can enjoy a thrilling baseball game. For a cultural evening, the Rosemont Theatre offers captivating performances that celebrate family and romance. Unwind at House of Blues Chicago, where live music creates an electrifying backdrop for relaxation and entertainment.

Adventure

At Galloping Ghost, you can immerse yourself in a vast array of arcade games, perfect for family fun and adventure. Rainbow Falls Waterpark offers thrilling water slides and wave pools for an exciting day out. Pirates Cove Children's Theme Park provides a delightful experience with various attractions for young adventurers.

Nightlife

Chicago's nightlife offers vibrant experiences with venues like Blues on Halstead, where you can enjoy romantic city vibes and live music. For a fun night out, visit Dave & Buster's for drinks and entertainment. Kingston Mines promises an energetic atmosphere with fantastic blues performances and a lively crowd.

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

Find the best attractions in Chicago

Chicago is ideal for family, outdoor, and city-themed holidays, offering a diverse range of attractions such as urban parks, modern universities, and event venues. Visitors can immerse themselves in the city's rich culture while exploring family-friendly experiences. Don't miss the vibrant downtown Chicago, where you can discover a variety of activities and sights to enhance your trip.

  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a vibrant street lined with upscale shops, dining, and iconic architecture. Stroll along this bustling thoroughfare to experience the pulse of Chicago, with its blend of modern skyscrapers and historic landmarks, making it perfect for shopping and people-watching.
  • Navy Pier: A lively destination, Navy Pier offers stunning views of Lake Michigan and the city skyline. Enjoy a variety of attractions, including amusement rides, gardens, and dining options. The friendly atmosphere and scenic spots make it ideal for leisurely walks and family outings.
  • Millennium Park: This urban oasis features beautiful gardens, art installations, and the famous Cloud Gate sculpture. Perfect for families, Millennium Park provides a space for outdoor activities, concerts, and cultural events, all set against the backdrop of the city's stunning architecture.

Best time to go to Chicago

The best time to visit Chicago can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chicago falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chicago 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 SunnyAverageSlightly 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 SunnySlightly HighSlightly 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

Tips to save on your trip to Chicago

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chicago.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Chicago.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.