Chicago Holidays from £670

Things to do in Chicago

Chicago is perfect for family, outdoor, and city-themed holidays, offering a vibrant mix of activities. Visitors can enjoy shopping areas, arena entertainment, and theatre performances. Key attractions include fascinating city tours, a Cubs game, outdoor activities, and live music events, ensuring a memorable experience in the Windy City.

Shopping

Experience shopping in Chicago at Woodfield Mall, a vibrant centre with entertainment and family-friendly options. Visit LEGOLAND® Discovery Center for unique gifts and enjoy the Arboretum of South Barrington, another lively mall offering a mix of shopping and entertainment for all ages.

Recreation

Wrigley Field offers a vibrant atmosphere for sports enthusiasts, where you can enjoy a game and soak in the lively energy. The Chicago Theatre provides a cultural experience with its stunning performances and romantic ambiance, perfect for a family night out. Cog Hill Golf & Country Club invites you to unwind amidst scenic outdoor beauty while enjoying a round of golf.

Adventure

Galloping Ghost is an exhilarating arcade adventure zone in Chicago, offering a vibrant atmosphere filled with classic games for all ages. Odyssey Fun World promises thrilling rides and arcade excitement, while The People's Choice Family Fun Center invites families to enjoy a delightful mix of games and activities.

Nightlife

Chicago's nightlife offers vibrant experiences with venues like Dave & Buster's, where you can enjoy drinks and fun entertainment vibes. For a romantic atmosphere, visit Kingston Mines or Blues on Halstead, both nightclubs that provide a lively mix of music and city allure.

Find the best attractions in Chicago

Chicago offers an ideal blend of family-friendly activities, outdoor adventures, and urban experiences. Visitors can explore urban parks, scenic beaches, and renowned universities, all while immersing themselves in the city's rich culture. For an unforgettable experience, be sure to spend time in downtown Chicago, where a wealth of attractions awaits, catering to diverse interests and providing lasting memories for all travellers.

• Navy Pier: Experience the vibrant atmosphere of Navy Pier, a lively jetty that offers stunning views of Lake Michigan. Enjoy a variety of entertainment options, including rides, restaurants, and shops, making it perfect for a fun day out with friends or family.
• Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with luxurious shops, fine dining, and iconic architecture. Stroll along this vibrant thoroughfare to soak up the city's dynamic energy and discover unique boutiques.
• Millennium Park: A must-visit urban park, Millennium Park features beautiful green spaces, public art installations like the famous Cloud Gate sculpture, and family-friendly events. It's an ideal spot for relaxation and enjoying outdoor activities in the heart of the city.

Best time to go to Chicago

The best time to visit Chicago 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.

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	Slightly High	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	Average	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

Tips to save on your trip to Chicago

• Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
• 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.