The third largest city in the United States, Chicago, is serviced by two international airports (O'Hare and Midway), 52 airlines, and countless cheap flights. Collectively, the airports can support about 1,450 daily direct flights to more than 245 destinations. With that many flights, there are plenty of deals to be found.
In general, the more you know, the more it will help you make the decision that's best for you. Set airfare alerts for your trip to Chicago, and watch routes to familiarize yourself with standard costs (and to better recognize a deal).
The best strategy for finding a cheap flight can vary greatly depending on your unique travel plans. If you don't have a set time frame to travel, looking at a range of dates is one nearly surefire way to find a deal.
As for when to buy, that varies, too. The earlier you look, the greater your chance of finding a deal. Flight prices typically remain relatively stable between five and two months before a flight, and then they rise — or fall — depending on the route’s popularity.
Usually airfare rises. But not always. That’s why customized alerts and apps, like the farecaster app Hopper, help identify those last-minute deals and unexpected price drops.
Looking at low-cost carriers is a great way to find a great, cheap flight to Chicago. Five budget airlines fly into Chicago’s two main airports.
At this time, Southwest Airlines is the only low-cost airline servicing Midway International Airport.
A sixth budget carrier, Allegiant Air, flies into Chicago Rockford International Airport, located (a not insignificant) 85 miles northwest of downtown Chicago.
Travelers who want a cheap flight to Chicago by traveling with one of these airlines should be wary of ancillary fees. Many no-frills carriers, though not all, will charge for checked bags, seat assignments, and other "perks" when you book the most affordable ticket class.
Where to Find a Good Deal
Online search engines are another great place to look for good deals on flights to Chicago. Tools such as Google Flights, Kayak, and Momondo let shoppers compare prices, see the fare difference between dates, and search all area airports. Keep in mind, however, that Southwest won't appear in most search results, so you'll have to go directly to their website to comparison shop.
When to Buy
Summertime is Chicago’s peak tourism season, with downtown beaches and historic ballparks tempting visitors from around the world. It’s also, consequently, the most expensive time to go. Come winter, prices go down, but so do temperatures. And pretty drastically at that.
Travel during the shoulder seasons (spring and fall) to avoid both the worst prices and the worst weather.
In general, you have a better chance of finding a deal by shopping for flights in advance, rather than last minute. (Though there are exceptions to this, like all rules.) And while traveling on less popular days (or unpopular times) can help you book cheaper fares (think: Tuesdays, Wednesdays, and Saturdays) your best bet will always be closely watching your route of choice, so you can spot a flash sale or price drop right when it happens.