Cheap flights from North America to Chicago from $49

The month of January is, on average, the cheapest month to fly to Chicago from North America, with most prices found around $177. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from North America to Chicago during November average around $211.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $289. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from North America to Chicago for around $364.

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 $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $360.

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 $235 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 $182 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.

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

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from North America according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 11 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of February 2026, 435 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 43% of daily flights taking off at noon.

As of February 2026, 3,045 flights take off from North America and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.