Cheap Flights to Chicago


Flights to Chicago, Illinois

Chicagoans call it the Windy City, New Yorkers call it the Second City, but everyone knows it as the best place to get deep-dish pizza! Forget rivalries between the Cubs and White Sox or the Bears and Green Bay Packers, the debate over whether deep-dish reigns supreme over thin crust is one that will impassion any Chicago native. As you board your cheap flight to Chicago, remember to order a slice, or a whole pie, when you get there.

Wrigley and Willis, What More?

If you see any two structures when you visit Chicago, make sure they're Wrigley Field and Willis Tower. Wrigley Field is home to the Cubs, and any visitor should catch a game if they're traveling to the area during baseball season. You don't have to be a sports fan to appreciate this ballpark. Opened in 1914, Wrigley field still has the old-school charm of the great ballpark era, and visitors will love taking photos with the iconic marquee, watching players chase balls into the ivy, and even see the wooden scoreboard get an update in between innings.

Willis Tower, previously known as the Sears Tower, is the second largest skyscraper in the United States. Standing at 1,451 feet and 108 stories, this building is easily identifiable on the Chicago skyline and is regularly used as a landmark. If you're brave, your plane tickets to Chicago will be worth the purchase just to stand out on the Ledge, a glass box extending from the 103rd floor, and take in the view of the whole city. You don't have to look down, but it's hard not to.

Rock Out and Dive In

If you're looking to spend a significant amount of time on your feet in Chicago, make Grant Park your home base for discovering everything the city has to offer. This 319-acre park is known as Chicago's "front yard," and includes attractions like the Art Institute of Chicago and Buckingham Fountain. Visitors interested in a particular event, like Grant Music Fest or Lollapalooza, will want to book well in advance in order to find cheap flights to Chicago.

When you do step indoors, make sure it's to visit the Shedd Aquarium, home to 32,000 marine animals representing 1,500 species. Take a behind the scenes tour to meet a penguin in person, train the Beluga whales, or, to really get your heart pumping, feed the sharks.

It's a Magnificent City

If you would rather take in the culture and feel of the city when you visit Chicago, then see and be seen at the Magnificent Mile. This 13-block stretch on North Michigan Avenue runs from the banks of the Chicago River to Oaks Street. It's home to 460 stores, 275 restaurants, and 60 hotels. If your idea of a great vacation is endless shopping and great food, plan your trip around the Magnificent Mile � just be sure to find a cheap flight to Chicago from Travelocity to increase your shopping budget first.

Present-day Chicago is a beautiful sight to behold, and its history is incredibly rich. If you want to learn more about what makes this town great, visit the DuSable Museum of African American History, which regularly rotates its temporary exhibits, so it's worth seeing more than once. Afterward, take a tour of the Chicago History Museum to learn why they dye the river green each year.

When to Visit

The best time to find cheap flights to Chicago is in the winter, but that's not when most tourists try to visit. Many locals would recommend visiting between April and October, when the snow has melted and temperatures climb into the 70s. This is also when most of the festivals and outdoor concerts are. If you do like the cold, consider flights to Chicago, IL, in December to experience the city during the holidays.

Whenever you plan to visit, you can always find cheap tickets to Chicago with Travelocity. Book with us now, and you'll be ordering peanuts at Wrigley field before you know it!

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Experience Chicago

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Chicago Airports

  • Midway Intl. (MDW)
  • O'Hare Intl. (ORD)