Cheap flights from San Antonio to Chicago from $75

The month of February is, on average, the cheapest month to fly to Chicago from San Antonio, with most prices found around $285. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from San Antonio to Chicago during September average around $305.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $450. 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 San Antonio to Chicago for around $817.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from San Antonio to Chicago during this time can be as low as $469. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $830.

Fly from San Antonio to Chicago Midway for the best San Antonio - Chicago flight prices

You are more likely to see cheaper flights to Chicago from San Antonio when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $384 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Antonio for as low as $271 on momondo.

There are 4 cabin classes available to choose from on San Antonio 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 33% on your flight if you consider stops on a San Antonio to Chicago flight.

As of February 2026, prices for San Antonio to Chicago flights are approximately 105% more expensive when compared to flights at the same time last year.

Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from San Antonio to Chicago

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from San Antonio according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Fort Lauderdale (FLL) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $160.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 6h 16m.

Atlanta (ATL) has the shortest average layover time for this route: 2h 25m.

As of February 2026, 21 flights take off from San Antonio and land in Chicago each day. The most common flight departure time for this route is 5:00PM, with 70% of daily flights taking off in the afternoon.

151 flights are operational weekly from San Antonio to Chicago as of February 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.