Chicago Vacation Packages

Things to do in Chicago

Chicago is perfect for family-friendly, outdoor, and city-themed vacations. Visitors can explore a variety of attractions, from shopping districts to entertainment venues, and enjoy educational experiences. Key highlights include the iconic Ferris wheel, along with options for cheap vacation packages and golf vacations. Plan your trip to experience the vibrant culture and diverse activities that Chicago has to offer.

Shopping

In Chicago, Woodfield Mall offers a vibrant shopping experience with entertainment and family-friendly amenities. For unique gifts, visit LEGOLAND® Discovery Center. Chicago Place Mall caters to shoppers with a mix of businesses and city vibes, perfect for finding souvenirs and more.

Recreation

At Wrigley Field, soak in the vibrant sports atmosphere while cheering for the Cubs. Experience the charm of the Chicago Theatre with its captivating performances, perfect for a romantic night out. For music lovers, the Aragon Ballroom offers exhilarating concerts in a stunning historic venue.

Adventure

Experience the thrills at Great Wolf Lodge Water Park, where you can splash down water slides and enjoy family-friendly attractions. For arcade fun, head to Galloping Ghost for classic games and excitement. If you seek nature, hike along Salt Creek Trail for stunning scenery and outdoor adventure.

Nightlife

Chicago's nightlife is vibrant and diverse. Visit Dave & Buster's for a fun atmosphere with drinks and games. For a more intimate experience, Kingston Mines offers live music and a romantic vibe. Blues on Halstead is perfect for enjoying soulful tunes in a lively setting with a city backdrop.

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

Find the best attractions in Chicago

Chicago is a fantastic destination for families and outdoor enthusiasts, offering a vibrant mix of urban parks, beautiful beaches, and renowned colleges. Explore downtown Chicago and discover top attractions that cater to a variety of interests, from cultural experiences to family-friendly activities. Whether you're seeking a city adventure or a relaxing day outdoors, this city has something for everyone to enjoy.

• Navy Pier: Experience the vibrant atmosphere of Navy Pier, where you can enjoy stunning views of Lake Michigan, dine at waterfront restaurants, and explore unique shops. The pier often hosts events and entertainment, making it a lively destination for all ages.
• Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with high-end shops, historic buildings, and cultural attractions. Stroll along this iconic avenue to soak in the dynamic city vibe and discover local art and architecture.
• McCormick Place: As the largest convention centre in North America, McCormick Place hosts major events, trade shows, and conferences. The modern facilities and diverse offerings make it a hub for business and innovation in Chicago.

Best time to go to Chicago

The best time to visit Chicago is dependant 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 with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly	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	Average	Slightly 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.