Chicago Vacation Deals

Stroll museums and parks filled with art, and catch live blues  any night of the week in Chicago’s bustling Downtown district. Or catch a lively sports game in this home to the Cubs and White Sox baseball teams, and the Chicago Bulls basketball team.

This metropolis is the third largest city in America, but getting around is easy thanks to the efficient above ground train, the ‘L’. Get your bearings from the tallest skyscraper in the US, Willis Tower, which defines the city’s skyline. The viewing platform, 1,353 feet (412 meters) above the busy streets, offers unparalleled vistas of Lake Michigan, Navy Pier, and other main attractions.

Lincoln Park, just north of downtown, has beaches, sporting grounds and landscaped gardens. Soak up the history of the Windy City at the Chicago History Museum, located on the southern end of the park. Take a stroll through the indoor gardens of the Lincoln Park Conservatory, or spend an afternoon at the Lincoln Park Zoo. This public zoo houses more than 1,000 animals. Brookfield Zoo, 12 miles west of the city center, is more than double the size and features dolphin displays, big cats, a variety of primates and more.

Head back into the Loop district downtown for some of the best shopping in the city, along Michigan Avenue’s Magnificent Mile. It’s a good place for lunch or dinner, or people watching while you sip a coffee or beer. Just south of the Magnificent Mile is the expansive Art Institute of Chicago well worth a visit for its collection of European and American masterpieces that include Monet, Van Gogh, and much more. Nearby is Millennium Park, a meeting place with public art and spectacular summer concerts.

Chicago’s Museum Campus is located in the South Loop, just a few miles by car or a few stops on the “L” from downtown. The Field Museum is filled with natural history, while the Museum of Science has interactive exhibits such as a mock coal mine and an airplane.

Some of America’s most influential figures came from Chicago. Visit the Ernest Hemingway Museum and House, where the famous writer was born. Architect Frank Lloyd Wright’s first house is in the pretty Oak Park neighborhood (called the Frank Lloyd Wright Home and Studio). He designed many houses and buildings in the area, including Unity Temple, considered one of his best. On your way back into town, stop off at the Garfield Park Conservatory, an urban oasis of rare and exotic plants.

No trip to Chicago would be complete without catching a baseball game at the legendary Wrigley Field. At night, head to Navy Pier, packed with lively bars and restaurants. Another option is to head out for a night of blues at one of Chicago's legendary clubs. Check out B.L.U.E.S. near downtown on Chicago's north side or Kingston Mines a few miles north near Lincoln Park. Both of these long established venues have music every night of the week.

For more details on interesting local attractions and activities, check out our things to do in Chicago page. 

Best time to visit Chicago

The ideal time to visit the Windy City is summer or fall. The summer months offer an endless selection of special events and outdoor activities, but also the biggest crowds and hot, muggy weather. However, autumn days are generally sunny, and the crowds are smaller at major tourist attractions. The first snow doesn’t appear until late November at the earliest. If you don’t mind being indoors, winter is a great time to visit. The weather may be blustery, but there are no lines at most attractions and the hotel rates are lower.

Peak season:A popular travel period is autumn (September–November), when the weather is moderate and the kids are back in school, making the city’s attractions less crowded. Spring and summer are also busy times. Spring weather can be unpredictable and summer can be warm; however, travelers enjoy endless special events.

Value season:If you’re looking for the cheapest hotel rates and don’t mind being indoors, travel between December and March. Added bonus: You won't have to wait to get into museums and other city attractions.

Accommodation in Chicago

Chicago is well-loved by tourists, and boasts a broad range of places to stay. Expedia's Chicago lodging guide is your go-to place.

Fine examples of slightly more premium lodgings in Chicago are The Peninsula Chicago, 108 East Superior Street, and the Waldorf Astoria Chicago, 11 E. Walton Street. Cheaper accommodations worth considering include the Old Chicago Inn, at 3222 N Sheffield Ave, and the Inn at Lincoln Park, at 601 West Diversey Parkway.

One of the highlights of any trip to Chicago is McCormick Place. If you'd prefer to stay within easy walking distance of the must-see attraction, the Hyatt Regency McCormick Place and the Chicago South Loop Hotel are both popular options.

Popular Activities in Chicago

Lying on a beach doing not much is pleasant enough, but there's nothing like throwing yourself into awesome new experiences on your vacation!

The really good news is that Chicago has loads of things to do. Here are just some of our picks:

• Bikes, Bites & Brews Bike Tour
• Bobby’s ‘Tike’ Hike- Kid’s Edition
• Helicopter Flight at Night
• Indoor Skydiving Experience
• Historic Skyscrapers Walking Tour
• Lakefront Neighborhoods Bike Tour

Got a little time on your side? Make your way to our Chicago things to do page for a full range of options.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.