Cheap flights from North America to Chicago from $82

The month of January is, on average, the cheapest month to fly to Chicago from North America, with most prices found around $267. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from North America to Chicago during February average around $275.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $344. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from North America to Chicago for around $423.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from North America to Chicago during this time can be as low as $345. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $383.

Fly from Newark to Chicago Midway for the best North America - Chicago flight prices

You are more likely to see cheaper flights to Chicago from North America when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $256 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from North America for as low as $177 on momondo.

There are 4 cabin classes available to choose from on North America to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

JetBlue, Delta, and United Airlines are the most popular carriers operating from North America to Chicago

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from North America according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 13 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 15% of flights between North America and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 146 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

As of October 2026, 471 flights take off from North America and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 38% of daily flights taking off in the afternoon.

As of October 2026, 3,297 flights take off from North America and land in Chicago each week. The most common flight departure day for this route is Tue, with 21% of weekly flights taking off on this day.