Cheap flights from San Antonio to Chicago from $98

The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from San Antonio averaging around $377.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $493. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from San Antonio because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $869.

Flying to Chicago O'Hare Intl Airport from San Antonio in the morning is the least expensive time of day to depart. momondo users have found prices as low as $505 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $860. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from San Antonio to Chicago O'Hare Intl for the best San Antonio - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from San Antonio when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $415 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from San Antonio for as low as $297 on momondo.

There are 4 cabin classes available to choose from on San Antonio to Chicago O'Hare Intl Airport 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 9% on your flight if you consider stops on a San Antonio to Chicago O'Hare Intl Airport flight.

As of November 2026, prices for San Antonio to Chicago O'Hare Intl Airport flights are approximately 74% more expensive when compared to flights at the same time last year.

Frontier and United Airlines are the most popular carriers operating from San Antonio to Chicago O'Hare Intl

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from San Antonio according to our data. American Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Detroit (DTW) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Denver (DEN) offer the lowest average round-trip price of $216.

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 6h 07m.

Detroit (DTW) has the shortest average layover time for this route: 1h 48m.

The number of flights available between San Antonio and Chicago O'Hare Intl Airport is 17 per day as of November 2026. The most frequent departure time is 7:00AM, with 51% of daily flights leaving in the afternoon.

As of November 2026, 120 flights take off from San Antonio and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Wed, with 18% of weekly flights taking off on this day.