What’s the fastest layover option from Chicago to San Antonio?

Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 9h 22m.

What’s the top layover airport for flights from Chicago to San Antonio?

Orlando (MCO) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to San Antonio on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San Antonio?

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $227.

How much does it cost to fly round-trip from Chicago to San Antonio?

Airfare is below average for this route at the moment. Chicago to San Antonio flights typically cost between $295 and $494 in October. The cheapest round-trip price found within the last 3 days was $158 on Frontier (Oct 16-Oct 18).

Which airport typically offers the quickest layover for flights from Chicago to San Antonio?

Flights via Orlando (MCO) offer the fastest connection on this route, with an average layover time of 2h 47m.

How long is the flight from Chicago to San Antonio?

Departing from Chicago to San Antonio will take you 2h 50m. The distance between Chicago and San Antonio is about 1036 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from Chicago to San Antonio round-trip?

Cheapflights users have booked flights from Chicago to San Antonio round-trip from $125. Other airlines that can offer you cheap pricing are Spirit Airlines, from $172, and American Airlines, from $194. Frontier is priced at 68% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Chicago to San Antonio one-way?

One-way options have recently been found by users for as low as $80 on Frontier. Other airlines that offer cheap prices include American Airlines from $127 and United Airlines from $159 one-way.

What is the cheapest month to book a flight from Chicago to San Antonio?

Currently, August is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $295). Flying from Chicago to San Antonio in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Chicago to San Antonio?

Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to San Antonio

The most flights from CHI to SAT are scheduled on a Monday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

In terms of precipitation, rainfall in San Antonio ranges from 1.6 - 3.7 inches per month. May is typically the wettest month, when rainfall can reach 3.7 in. December is typically the driest time to visit San Antonio when rainfall is around 1.6 in.

If weather is an important factor for your trip to San Antonio, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

What are the cheapest flights from Chicago to San Antonio?

Looking at all options, your cheapest flight can be booked for $143. While the most popular route (Chicago O'Hare Intl - San Antonio) can be booked for $146 on average, our data indicates $703 when flying from Chicago to San Antonio.

What are the most reliable airlines from Chicago to San Antonio?

Consider SkyWest Airlines (96%), Republic Airways (85%) or Air Canada (81%) when booking your flight. These represent the most reliable airlines when flying from Chicago to San Antonio.

What are the most popular airlines that fly from Chicago to San Antonio?

Before booking your flight from Chicago to San Antonio check out the most popular airlines for this route: American Airlines, Frontier or Spirit Airlines.

What is the cheapest time of day to fly from CHI to SAT?

It’s typically best to fly out from Chicago to San Antonio at noon. Doing so could potentially save you 12% on the flight price compared to flying in the morning, which is usually more expensive.

What airport do you fly into for flights to San Antonio from Chicago?

San Antonio (SAT) is the airport you will fly into if you book a flight from Chicago to San Antonio. You should not have trouble finding flights to San Antonio from Chicago; the airport handles an average of 20 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 5 airlines have flights to the San Antonio airport from Chicago. It is only a 7.6 mi journey from San Antonio (SAT) to San Antonio’s city center.

Can I find deals for flights from Chicago to San Antonio that include hotel bookings?

Yes. In addition to deals on Chicago to San Antonio flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to San Antonio?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Antonio.

Can I find deals for business class flights from Chicago to San Antonio?

Yes. Cheapflights offers flight deals from Chicago to San Antonio by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$80+ Flights from Chicago to San Antonio

Round-trip from	$158 (Frontier)
One-way from	$80 (Cheapflightsfares)
Popular in	March
Cheapest in	October
Average price	$406
Good round-trip deal	$295 or less
Good one-way deal	$153 or less

ORD

Expect long walks between terminals at ORD; plan extra time for navigating this busy airport.

MDW

Use the 'L' train for a quick, cost-effective way to reach MDW from downtown Chicago in under 30 minutes.

SAT

For a quick ride to downtown San Antonio, use rideshare services from SAT, taking about 15 minutes.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$125	Average$217	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$172	Average$288	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$194	Average$400	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$203	Average$501	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$261	Average$474	FlexibilityNo cancel fee	On-time69%

$80+ Cheap flights from Chicago (CHI) to San Antonio (SAT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/4. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in October or August, booked 71 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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Cheapest flights from Chicago to San AntonioExplore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

Explore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

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Use the filters below to find and compare flights from Chicago to San Antonio that are best for you.

The best insider tips for Chicago to San Antonio flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Antonio trip

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MDW

SAT

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Best time to book a flight from Chicago to San Antonio

Have a flexible travel schedule? Discover the best time to fly to San Antonio from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San Antonio

What is the cheapest month to book a flight from Chicago to San Antonio?

What is the cheapest time of day to fly from CHI to SAT?

Find hourly flight availability from Chicago to San Antonio. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

What is the cheapest day to fly from Chicago to San Antonio?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Antonio. Price data was last updated on September 14, 2025.

Weekly flight availability from Chicago to San Antonio

How much does it cost to fly round-trip from Chicago to San Antonio?

What’s the top layover airport for flights from Chicago to San Antonio?

Share of 1-stop round-trip flights from Chicago to San Antonio chosen by Cheapflights users in the past 12 months, using the same layover each way.

What’s the cheapest layover airport for flights from Chicago to San Antonio?

Average round-trip fare for 1-stop flights from Chicago to San Antonio, chosen by Cheapflights users in the past 12 months, with the same layover each way.

What’s the fastest layover option from Chicago to San Antonio?

Shortest average travel time for 1-stop one-way flights from Chicago to San Antonio, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Which airport typically offers the quickest layover for flights from Chicago to San Antonio?

Average layover duration for 1-stop one-way flights from Chicago to San Antonio, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Reviews of airlines servicing San Antonio

Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Antonio. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to San Antonio from Chicago?

How long is the flight from Chicago to San Antonio?

What are the cheapest airlines flying from Chicago to San Antonio round-trip?

What are the cheapest airlines to fly from Chicago to San Antonio one-way?

What are the most reliable airlines from Chicago to San Antonio?

What are the cheapest flights from Chicago to San Antonio?

Can I find deals for flights from Chicago to San Antonio that include hotel bookings?

How can I find direct flights from Chicago to San Antonio?

Can I find deals for business class flights from Chicago to San Antonio?

What is the cheapest month to book a flight from Chicago to San Antonio?

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Alternative routes for Chicago to San Antonio

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Top 5 airlines flying from Chicago to San Antonio

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Cheapest flights from Chicago to San Antonio
Explore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.