Cheap flights from the United States to Chicago from $91

The month of January is, on average, the cheapest month to fly to Chicago from United States, with most prices found around $249. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from United States to Chicago during September average around $256.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $319. 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 United States to Chicago for around $392.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from United States to Chicago during this time can be as low as $302. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $371.

Fly from Dallas/Fort Worth to Chicago Midway for the best United States - Chicago flight prices

You are more likely to see cheaper flights to Chicago from United States when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $243 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from United States for as low as $174 on momondo.

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

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from United States according to our data. United Airlines is the first choice among our users, with 36% 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.

Historically, on average around 15% of flights between United States and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 152 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 10% of their flights experiencing any sort of delay.

As of July 2026, 369 flights take off from United States and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 40% of daily flights taking off in the afternoon.

As of July 2026, 2,589 flights take off from United States and land in Chicago each week. The most common flight departure day for this route is Wed, with 23% of weekly flights taking off on this day.