Cheap flights from St. Louis to Chicago from $50

The month of October is, on average, the cheapest month to fly to Chicago from St. Louis, with most prices found around $287. If you’re not able to fly to Chicago in October, then August is your next best option. Flight prices from St. Louis to Chicago during August average around $288.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $620. 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 St. Louis to Chicago for around $800.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from St. Louis to Chicago during this time can be as low as $581. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,130.

Fly from Lambert-St Louis to Chicago Midway for the best Lambert-St Louis - Chicago flight prices

You are more likely to see cheaper flights to Chicago from St. Louis when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $345 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from St. Louis for as low as $97 on momondo.

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

No. A direct flight is the cheapest option for a flight between St. Louis to Chicago.

As of August 2026, prices for St. Louis to Chicago flights are approximately 17% cheaper when compared to flights at the same time last year.

Southwest, United Airlines, and Frontier are the most popular carriers operating from Lambert-St Louis to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from St. Louis according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of August 2026, there are 41 flights per day flying from St. Louis to Chicago. The most common time of day flights depart is 9:00AM, with 44% of flights taking off at noon.

291 flights are operational weekly from St. Louis to Chicago as of August 2026. The most popular departure day for this route is Tue, with 23% of flights per week taking off on this day.