FlightsFlights to Chicago
"One of the 50 Websites that make the web great."
"Hipmunk is the best travel site on the Web. Period."
"Stands out for its fun, interactive and deal-scoring features."
“The cheapest time of year to fly into Chicago is during the winter months -- typically just before or just after Christmas.”

Flying into Beautiful Chicago

Two of the busiest airports in the United States are in Chicago: O'Hare International Airport and Chicago Midway International Airport. The largest of these is O'Hare International Airport -- the second busiest airport in the world -- serving 200 destinations, both domestic and international. Chicago Midway International Airport is the second largest airport in the city and is home to budget airlines that fly domestically. With almost 90 million passengers passing through these two Chicago airports every year, there's plenty of opportunity to find a cheap flight to suit your needs.
Roundtrip Flights to Chicago
Washington (IAD) Chicago (ORD)Fri May 01-Sun May 03$364
Baltimore (BWI) Chicago (ORD)Fri May 08-Sun May 10$217
Baltimore (BWI) Chicago (ORD)Fri May 15-Sun May 17$216
Baltimore (BWI) Chicago (ORD)Fri May 22-Sun May 24$231
Washington (IAD) Chicago (ORD)Fri May 29-Sun May 31$144
Baltimore (BWI) Chicago (ORD)Fri Jun 05-Sun Jun 07$196
Hotels in Chicago
The Palmer House Hilton
3.4
6316 reviews
$119 avg/night
Congress Plaza Hotel
2.7
10876 reviews
$119 avg/night
Sofitel Chicago Water Tower
4.3
2975 reviews
$128 avg/night
Thompson Chicago
4.4
952 reviews
$144 avg/night
Other Top Flight Destinations
More About Flights to Chicago

Finding Cheap Flights to Chicago

O'Hare International Airport is the second largest hub for United Airlines and American Airlines, with more than 1000 departures per day. Check the websites of both airlines as they're likely to have the cheapest flights. You'll also find regular flights with Delta, Spirit Airlines, and Frontier Airlines. You can buy day passes to multiple lounges at the airport, including American Admirals Club Lounge, Delta Sky Club Lounge, and United Club. O'Hare won the accolade of "Best Airport in North America" by readers of Business Traveler Magazine and Global Traveler Magazine, making it an excellent choice to fly in and out of. 

If you'll be flying into Chicago Midway International Airport, check Southwest Airlines' prices before you look anywhere else. It's a major focus city for Southwest and is one of their biggest hubs, so it's not difficult to find a cheap flight to Chicago with them. Chicago Midway International Airport ranked highest for customer satisfaction at medium-sized airports in a 2008 study from J.D. Power and Associates, making both Chicago airports a fantastic option for travelers. Please note that Chicago Midway International Airport doesn't have any lounges, so bear this in mind if you're planning for a long stay at the airport.

How to Get to Chicago From the Airports

Getting to downtown Chicago from either of the city's airports is simple. From O'Hare International Airport, you'll be able to pick up a car from any of the rental car companies in the arrivals hall. You'll be able to choose from Alamo, Avis, Budget, Dollar, Enterprise, Hertz, National, and Thrifty. The cheapest option for transferring downtown, however, is to take the El (elevated train) from O'Hare International Airport via the Blue Line -- it shouldn't cost more than two dollars.

If you need privacy and comfort for your journey, you can hire a taxi from outside the arrivals hall, which will cost roughly $45 to get to downtown. The Continental Airport Express bus offers an alternative way of getting downtown; it leaves every 15 minutes. For $27, it'll take you from O'Hare International Airport to your downtown hotel.

If you're flying into Chicago Midway International Airport, arranging transport is quicker and easier. Like with O'Hare International Airport, the cheapest transport available is via the El. To get from Chicago Midway International Airport to downtown Chicago, take the Orange Line, and it'll cost just two dollars. You can also rent a car from the arrivals desk -- Alamo, Avis, Budget, Enterprise, Hertz, National, and Thrifty are all available. Additionally, you can take a taxi downtown for roughly $25, or take the Continental Airport Express bus for $22, which leaves every 15 minutes.

The Cheapest Time to Fly Is Winter

The cheapest time of year to fly into Chicago is during the winter months -- typically just before or just after Christmas and New Year's. The cold weather and snow in Chicago deters most tourists from visiting during this time, leading to winter flights being much cheaper in price.

If you don't prefer your attractions with crowds and sweltering heat, and the thought of trudging through lots of snow puts you off, consider traveling during spring or fall. Traveling in the shoulder season means that you'll have the most pleasant weather, prices will still be low, and the crowds will be smaller. If you time your visit to coincide within the school semester, prices will be cheaper still. Look into flying in March or October. 

If possible, try to avoid flying between June and August, which is when most visitors head to Chicago. Flights and accommodations will be at their highest, and the streets will likely be crowded and noisy. If you do decide to travel in summer, try to avoid visiting when one of Chicago's famous summer festivals are on. The Chicago Blues Festival, Chicago Jazz Festival, and Chicago Pride Fest are most popular.

Chicago Midway International Airport Is Your Best Choice

Deciding whether to fly into O'Hare International Airport or Chicago Midway International Airport depends on what you're looking for. The simplest way to figure this out is to look at whether you'll be flying domestically or internationally. O'Hare International Airport will be your only option if you're looking to fly from or to somewhere outside of the United States and Mexico.

If you'll be flying domestically, then the decision becomes a little trickier. In terms of distance, O'Hare International Airport is 17 miles northwest of the Chicago Loop, which is one of Chicago's biggest attractions. Chicago Midway International Airport is closer at only eight miles to the southwest of the Chicago Loop.  

Furthermore, you're looking for the least amount of hassle. Therefore, both in navigating the airport and traveling downtown, Chicago Midway International Airport is the best option. It's a smaller airport, so making your way through the airport and collecting your luggage is far faster than at O'Hare International Airport. Additionally, because Chicago Midway International Airport is half the distance away from downtown Chicago, getting to your hotel will take less time -- and with a shorter distance to travel, will also be cheaper. 

If you're on a tight budget, then check the flights to O'Hare International Airport before you book. Since it is the United States' second busiest airport, there is a larger choice of flights to choose from. With hundreds of flights passing through each day, you might be able to find a cheaper price that makes all the added hassle worth it. 

Where to Fly to and From Chicago

The two main airlines operating from O'Hare International Airport are United Airlines and American Airlines, which both list the airport as their second largest hub for flights. In addition, O'Hare is a hub airport for Air Choice One as well as a focus city for Spirit Airlines. O'Hare offers plenty of seasonal flights to three of the most popular cities in Europe: London, Paris, and Rome.

If you'll be flying into O'Hare International Airport, you'll find dozens of high-class airlines, including Delta, British Airways, and Continental Airlines. Direct flights are available from London Heathrow and London Gatwick, with a flight time of 8.5 hours. If the direct flights are pricey, take a look at some of the many indirect flights that connect on the East Coast; examples of these are New York City, Philadelphia, Boston; and Washington, D.C.

Chicago Midway International Airport is ideal for travelers who are looking for budget flights throughout the United States. Southwest is the main airline here, and it flies to and from more than 60 cities across the country. Seasonally, travelers will be able to visit several Mexican cities, which are flown to by both Frontier Airlines and Volaris. If you'll be flying into Chicago Midway International Airport, you'll likely find a bargain because most of the operators are budget airlines. 

Budget Activities to Keep You Entertained

Chicago is a lively city with hundreds of events taking place, no matter what time of year that you decide to visit. Most of the outdoor activities take place in the summer when the weather is warm and there's not a snowflake in sight. Thousands fly in for the Chicago Blues Festival in June, and July's Taste of Chicago is a must-visit festival. Taste of Chicago is the largest outdoor food festival in the world, and there you'll find delicious food samples, live music, and plenty of attractions for adults and children

The highlight of any winter in Chicago is ice skating at Millennium Park and, if you arrive an hour before the rink opens on Thursdays to Sundays, you'll receive a free ice skating lesson. Christmas brings plenty of celebrations to Chicago, too, with the Tree Lighting Ceremony at Daley Plaza and the Christmas Parade a day later.

If you're a sports fan, you won't want to miss the Chicago Cubs and Chicago White Sox home openers, which take in April. Another popular event in Chicago's spring is the St. Patrick's Day Parade, which you can guarantee turning into an enormous party given the large amount of Irish Americans calling this city home. Watch the green dye pass along the river, smile at the hundreds of shamrocks that fill the streets, and enjoy the sound of bagpipes filling the air.

Quantcast