Cheap flights from Springfield to Chicago from $180

The month of February is, on average, the cheapest month to fly to Chicago from Springfield, with most prices found around $230. If you’re not able to fly to Chicago in February, then December is your next best option. Flight prices from Springfield to Chicago during December average around $259.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $430. 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 Springfield to Chicago for around $669.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Springfield to Chicago during this time can be as low as $465. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $638.

Fly from Springfield-Branson to Chicago O'Hare Intl for the best Springfield-Branson - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Springfield when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $308 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Springfield for as low as $219 on momondo.

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

You could potentially save up to 52% on your flight if you consider stops on a Springfield to Chicago flight.

As of September 2026, prices for Springfield to Chicago flights are approximately 99% more expensive when compared to flights at the same time last year.

United Airlines is the most popular carrier operating from Springfield-Branson to Chicago

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Springfield according to our data. American Airlines is the first choice among our users, with 69% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

13 flights are operational daily from Springfield to Chicago as of September 2026. The most popular departure time for this route is 3:00PM, with 56% of flights per day taking off at noon.

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