CHI - SAT

$105 Find Cheap Flights from Chicago to San Antonio

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Antonio departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Antonio

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Antonio, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Antonio, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$292
Typical prices: $413-$255
Frontier
Fri 6/5Mon 6/8
ORD - SAT • 2 stops
Cheapest non-stop
$297
Typical prices: $447-$297
American Airlines
Tue 6/2Tue 6/16
ORD - SAT • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags offer great value.
Midway's shorter security lines ease your travel.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $297 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 3h 04m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $138 (round-trip)
Shortest trip • 4h 25m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 55% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Chicago to San Antonio (CHI-SAT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Antonio that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to San Antonio

Fri, Jun 5 - Mon, Jun 8
Multiple Airlines Logo
1:50 pm - 6:59 pm
ORD
-
SAT
29h 09m
2 stops
Multiple Airlines Logo
5:26 pm - 12:25 pm
SAT
-
ORD
18h 59m
1 stop
$292Multiple Airlines
Tue, Jun 2 - Tue, Jun 16
American Airlines Logo
10:00 am - 12:52 pm
ORD
-
SAT
2h 52mnonstop
American Airlines Logo
6:24 pm - 9:29 pm
SAT
-
ORD
3h 05mnonstop
$297American Airlines
Tue, May 26 - Tue, Jun 2
Southwest Logo
9:00 pm - 11:50 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
2:35 pm - 5:10 pm
SAT
-
MDW
2h 35mnonstop
$297Southwest
Wed, May 13 - Mon, May 18
Multiple Airlines Logo
9:37 pm - 6:59 pm
ORD
-
SAT
21h 22m
1 stop
Multiple Airlines Logo
7:54 pm - 10:14 pm
SAT
-
ORD
26h 20m
2 stops
$298Multiple Airlines
Tue, May 26 - Thu, May 28
Multiple Airlines Logo
6:55 am - 6:59 pm
ORD
-
SAT
12h 04m
2 stops
Multiple Airlines Logo
5:26 pm - 12:37 pm
SAT
-
ORD
19h 11m
1 stop
$299Multiple Airlines
Mon, Jun 15 - Wed, Jun 17
Frontier Logo
9:48 pm - 6:56 pm
ORD
-
SAT
21h 08m
1 stop
Frontier Logo
8:56 pm - 5:32 am
SAT
-
ORD
8h 36m
1 stop
$301Frontier
Sat, May 16 - Tue, May 19
United Airlines Logo
9:05 am - 12:15 pm
ORD
-
SAT
3h 10mnonstop
United Airlines Logo
5:34 pm - 8:36 pm
SAT
-
ORD
3h 02mnonstop
$303United Airlines
Sat, May 16 - Tue, May 19
Southwest Logo
10:45 am - 1:35 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
2:35 pm - 5:10 pm
SAT
-
MDW
2h 35mnonstop
$303Southwest
Sun, May 24 - Sun, May 31
Frontier Logo
9:37 pm - 6:59 pm
ORD
-
SAT
21h 22m
1 stop
Frontier Logo
7:54 pm - 8:32 pm
SAT
-
ORD
24h 38m
1 stop
$304Frontier
Tue, Jun 2 - Tue, Jun 16
Delta Logo
6:23 am - 1:31 pm
MDW
-
SAT
7h 08m
1 stop
Delta Logo
11:30 am - 6:31 pm
SAT
-
MDW
7h 01m
1 stop
$317Delta
Booking Insights

KAYAK's insights & trends for Chicago to San Antonio flights

Get data-powered insights and trends into flights from Chicago to San Antonio to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to San Antonio?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to San Antonio departing in June.

What is the cheapest Chicago to San Antonio flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Chicago to San Antonio costs $303 on the route between Chicago O'Hare Intl Airport (ORD) and San Antonio (SAT). The most popular route is between Chicago O'Hare Intl Airport (ORD) and San Antonio (SAT).

What’s the cheapest day of the week to fly from Chicago to San Antonio?

The average price of all round-trip flights from Chicago to San Antonio clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to San Antonio on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to San Antonio. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Antonio, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to San Antonio is January, where tickets cost $88 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $188 and $186 respectively.

Can I save money by flying with a layover from Chicago to San Antonio?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $346 on average.

How far in advance should I book a flight from Chicago to San Antonio?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San Antonio, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to San Antonio, you should book around 4 weeks before departure, which saves you about 55% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to San Antonio

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Brandon Schultz

Brandon Schultz

Expert on SAT

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago O'Hare Airport to San Antonio

When to book flights from Chicago to San Antonio

Are your dates flexible? Find out the best times to travel from Chicago to San Antonio based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to San Antonio

  • How can I get downtown from San Antonio International Airport?

    SAT is connected to the public bus system, and VIA bus route 5 provides regular services between the airport and downtown San Antonio. SuperShuttle also offers door-to-door shuttle services from SAT to downtown San Antonio and the surrounding neighborhoods. You can get tickets from Terminal A's baggage claim area. Taxis are also available at SAT, and you'll find them on the lower levels of Terminals A and B, around baggage claim. If you wish to self-drive, take a rental car from Terminal A's baggage claim area.

  • Does San Antonio International Airport offer accessible services?

    SAT is a fully accessible airport. The airport has provided ramps and elevators for barrier-free access. PRM also get accessible restrooms, wheelchair services, fast-track services, and reserved parking spots. Low-vision passengers at ORD will have free Air services, braille signage, and tactile guide paths. TTY telephones and visual paging services are available for the hard-of-hearing.

  • Which family services are offered at Chicago Midway International Airport?

    MDW has provided private spaces for nursing mothers to feed their babies. These rooms include a sink, a wash area, and comfortable seating. You'll find the nursing rooms on Concourse C beside the yoga room. Also available at MDW are the baby changing facilities, which are provided in all washrooms. The airport has provided a special family lane for parents traveling with kids for quicker transition. Additionally, most airport restaurants offer kid menus and high chairs for babies.

  • Which airlines have lounges at Chicago O'Hare International Airport?

    Air France, American Airlines, Swiss Air, Delta, and United Airlines have lounges at ORD. You can access these lounges by paying at the door, except for the Delta lounge, which is a members-only lounge. The Swiss Air and Air France lounges are in Terminal 5 airside. American Airlines has several locations, Concourses G, L, and H/K. The Delta lounge is in Terminal 2 near Gate E6, while United Club has several locations around Concourses B, C, and F.

  • What is the cheapest flight from Chicago to San Antonio?

    In the last 3 days, the lowest price for a flight from Chicago to San Antonio was $96 for a one-way ticket and $292 for a round-trip.

  • Do I need a passport to fly between Chicago and San Antonio?

    No, a passport isn't needed to fly from Chicago to San Antonio. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to San Antonio?

    Chicago is served by 2 major airports and there is only 1 main airport in San Antonio. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at San Antonio.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to San Antonio?

    American Airlines, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to San Antonio flight route.

  • Which aircraft models fly most regularly from Chicago to San Antonio?

    The Embraer 175 is the aircraft model that flies most regularly on the Chicago to San Antonio flight route.

  • Which airline alliances offer flights from Chicago to San Antonio?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San Antonio, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to San Antonio?

    There are nonstop flights from Chicago to San Antonio on a daily basis.

  • Which is the best airline for flights from Chicago to San Antonio, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San Antonio are Southwest and United Airlines. With an average price for the route of $380 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $413 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to San Antonio?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San Antonio.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Antonio?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Antonio from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San Antonio?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Antonio with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Antonio?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Antonio from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to San Antonio

  • Looking for a cheap flight? 25% of our users found flights on this route for $191 or less one-way and $353 or less round-trip.
  • Chicago O'Hare International Airport (ORD) has nine concourses in four terminals. The airport has provided an automated people mover running every 5-10min for easy movement between terminals and around the airport complex.
  • Around 532 kg of carbon is emitted on flights from Chicago to San Antonio. You can fly more sustainably with Southwest Airlines, which emits 43% less carbon per passenger on this route.
  • Are you traveling with your pet? San Antonio International Airport (SAT) is a pet-friendly airport with designated spaces for your furry friend's potty needs. You'll find pet relief areas in Terminal B near the west exit and airside in both terminals.
  • Are you nervous before your flight? Chicago Midway International Airport (MDW) has a yoga room where you can relax with a few stretches. The yoga room is airside on Concourse C, and it comes with a wall-mounted TV that shows the poses to follow.
  • Seaway National Bank runs a full-service branch at ORD if you're looking for banking services at ORD. The bank offers banking, currency exchange, and copying services and has two locations at ORD. The first is in Terminal 2 near the main hall landside, and the other in Terminal 5 on the lower level.

Prefer to fly direct from Chicago to San Antonio?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to San Antonio.
Find which airlines fly direct from Chicago to San Antonio Airport, which days they fly and book direct flights.

Direct departures

Chicago to San Antonio

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

San Antonio to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 4 airlines serving from Chicago to San Antonio

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Antonio. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to San Antonio? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4314 reviews
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The seat was not comfortable. 1D. My back was sore all night and the next day.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

Got home at 3am after deboarding the plane. No compensation offered by American

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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

Information on your arrival and departure airports