Cheap Flights to Chicago

Visit Chicago

The juxtaposition of the natural beauty of Lake Michigan and the urban skyline of the city make Chicago truly beautiful. Therefore, it’s not difficult to see why over 35 million people journey to Chi-Town. It lures with attractions like the art installations of Millennium Park, the iconic Art Institute of Chicago, and the Lincoln Park Zoo. All you’ll need are your bags and a good pair of walking shoes to hit the city streets in search of the bets deep dish pizza. Book your flights to Chicago today on and get ready to be blown away by the Windy City.

When to book Chicago flights

Chicago is no stranger to the seasons, so when you travel to Chi-town, be sure to pack accordingly. Despite dramatically varying temperatures, each season offers something unique to Chicago’s tourists. Cold temperatures in the winter are ideal for exploring the Adler Planetarium and applauding after a performance at the Chicago Theatre; whereas the warm winds of spring are conducive to playing in the arcade at Navy Pier and beaming at the Chicago Botanic Garden. Travelers flock to the city during the summer to cheer on the Cubs at Wrigley Field and sing along at the Lollapalooza music festival. And even if you travel to Chicago in autumn, you’ll be met with events such as the Windy City Wine Festival and the Chicago International Film Festival.

Book your flight with Expedia

Chicago flights don’t need to cost an arm and a leg. After all, you’ll need plenty of spending money in your budget to buy tickets to see a performance by the Second City improvisational theatre troupe. Instead, browse our carefully curated collection of flights to Chicago right here on and select the one best suiting your travel and budgetary needs. What’s more, when you make your travel arrangements with us, you always receive our best prices thanks to our Best Price Guarantee. Meaning you can book confidently and get back to researching the best beaches of Lake Michigan for lounging.

Chicago Airports

Book your flight into either the O’Hare International Airport (ORD) or the Midway International Airport (MDW). O’Hare is a mere 17 miles west of the downtown district while Midway is roughly 11 miles southwest of the city. O’Hare transports close to 55 million passengers each year and is one of the busiest airports in the world. Although Midway has less traffic, it still serves close to 19 million passengers each year. Fortunately, the city of Chicago is very eco-conscious and works to reduce their environmental impact. These efforts are visible at both the ORD and MDW facilities, through programs that monitor waste management, water conservation, and electricity usage.

Transportation from the Airport

Chicago is a bustling hub known for its convenient and numerous public transportation options. If you are arriving at O’Hare, use the Chicago Transit Authority’s (CTA) Blue Line train. This railway will take you to the Forest Park terminal in downtown Chicago where you’ll have the option to hop on a connecting line. Additionally, Metra’s North Central Service train transports passengers to Union Station downtown as well as the north central suburbs.

Adversely, from the Midway Airport you can take CTA’s Orange Line train which makes frequent stops from the airport to downtown Chicago. Both airports are serviced by Pace buses as well throughout the city and its surrounding neighborhoods.

What’s more, you always have the option to rent a car ahead of time here on This way, you can avoid the hassle of navigating bus routes and focus on enjoying your trip to the Windy City instead.

Frequently asked questions

Looking to compare flights to Chicago to find the best Chicago flight deals? No travel company presents more choices than Expedia: more airlines such as , cheaper flights, fewer stops, and more departure and arrival times. The average flight time to Chicago is approximately (hr(s) & min(s). Cheapest flight to Chicago is from one-way and round-trip, book now while seats available! Expedia provides the cheapest flights to Chicago and you may find even greater savings if you combine your flight to Chicago with a hotel stay. 

Using the Expedia booking engine is simple: just type in your points of travel and preferred dates and does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. You can book your Chicago flights with full confidence knowing that you’ve found the best deal online.

If you're looking to compare flights to Chicago, no travel company presents more choices than Expedia - more airlines, cheaper flights, fewer stops, and more departure and arrival times. Expedia provides the cheapest flights to Chicago and you may find even greater savings if you combine your flight to Chicago with a hotel stay.