Cheap flights to
Chicago

There is no perfect calculation for the exact date you should book a flight. However, there is a range. We call it the Goldilocks Window because it’s not too far away from your departure date, but not too close either; it’s that sweet spot when you’re most likely to find a great deal. This just-right time is 1–3 months before a domestic flight and 2–8 months before an international flight.

If you plan to travel during peak season or your dates aren’t flexible, start looking even earlier. This means if you hope to take a vacation during the December holiday season, it’s smart to start looking for flights in July.

We know it’s tempting to hold out for a last minute deal, but those deals are very rare. In fact, fare jumps happen 21, 14, and 7 days ahead of travel dates, so it’s best to book before those points.

The Greek Islands Trick is one of our beloved tips for getting to expensive islands during peak travel seasons, but it works for Chicago, too. Basically, you get as close as you can to your final destination, then find another short flight or an alternate travel mode for your last leg.

So, if flights to Chicago in July are crazy expensive, look for flights to Indianapolis; Milwaukee; Madison, Wisconsin; or Grand Rapids, Michigan. From there, you can take the train, bus, or rent a car. It takes more time but could save you a few hundred bucks.

Travelers living near, say, Houston who are looking to fly to Chicago may never have considered flying out of another airport. Why would you when you have such a large airport right there? Believe it or not, there may be situations when you could save money by flying out of another airport. We see deals from airports all over the country, so it’s worth looking around. If there’s another airport within driving distance, like Austin or New Orleans, compare prices to Houston before booking.

If you’re traveling from outside of the US, it could even be worth flying to an alternative airport. If you live in Athens, for example, look for flights from Dublin or London to Chicago. If you see a great deal, it could be worth taking a budget airline flight to one of those cities before heading across the ocean.

Summer is by far the busiest travel season in Chicago. If you can, look for flights during shoulder seasons, like April and May or September and October, when the weather isn’t too cold and there are fewer crowds and cheaper prices. And if you can stand the cold, you’ll likely find some amazing flight and hotel deals in January and February.

If you plan to travel during the summer, at least try to look for fares on what are generally the cheapest days to fly: Tuesdays, Wednesdays, and Saturdays. Avoid Fridays and Sundays, the most expensive days to fly, if you can.

Flight alerts are your friend. They will help save time searching for flights and help you avoid frustration when you miss a deal. Simply set a flight alert for the dates you hope to travel (or multiple dates if you’re flexible), and wait for an alert telling you prices have dropped. It’s best to do this well before your trip so you can see prices drop during the Goldilocks Window we talked about.

O’Hare is one of the world’s busiest airports, serving more than 30 million passengers per year and with direct flights from more than 240 cities around the world. It’s a hub for both United and American, plus serves numerous international airlines, along with Delta and Southwest flights. Add on Midway, with another 8.8 million passengers and lots of Southwest and low-fare carriers, and your odds of finding a decent flight to Chicago are pretty high.