How long is the flight from San Antonio to Chicago?

Frontier, United Airlines, and Southwest can get you from San Antonio to Chicago in just under 2h 35m. Your travel time can differ by up to 7h 48m. San Antonio and Chicago are separated by a distance of 1036 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

Cheapflights users have booked flights from San Antonio to Chicago round-trip from $97. Other airlines that can offer you cheap pricing are Spirit Airlines, from $208, and American Airlines, from $235. These flights start at 74% lower than the current average price 3 months from now.

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

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $139. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from San Antonio to Chicago for a low price.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from San Antonio to Chicago?

When deciding which route to take from San Antonio to Chicago consider San Antonio - Chicago O'Hare Intl, San Antonio - Chicago Midway or San Antonio - Chicago Greater Rockford as they are the most popular.

What are the cheapest flights from San Antonio to Chicago?

On average you can expect to pay $1,181 for a flight from San Antonio to Chicago. The cheapest flight overall is $158 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $152.

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

The top 3 most reliable airlines when flying from San Antonio to Chicago are ANA (87%), United Airlines (86%) and Japan Airlines (84%).

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

When booking a flight from San Antonio to Chicago, you may want to consider flying on American Airlines, United Airlines or Southwest as they are the most popular for this route.

Most accurate provider : When it comes to deals on San Antonio-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on San Antonio-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Antonio-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

If you book a flight to Chicago from San Antonio, you will be flying from San Antonio, which is the city’s only airport. San Antonio (SAT) is located 7.6 mi from the center of San Antonio. There are 30 flights from San Antonio to Chicago per day from 5 different airlines.

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

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

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

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

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

Yes. Cheapflights offers flight deals from San Antonio to Chicago 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+ Cheap Flights from San Antonio to Chicago

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

Airfare is below average for this route at the moment. San Antonio to Chicago flights typically cost between $280 and $477 in November. The cheapest round-trip price found within the last 3 days was $159 on Spirit Airlines (Nov 4-Nov 12).

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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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Cheapflights Tip: The best prices from San Antonio to Chicago are usually found in September or August, booked 70 days in advance, depart on a Thursday or Friday and return on a Wednesday

Find flight deals from San Antonio to Chicago

Cheapest flights from San Antonio to Chicago
Explore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

Tue 11/47:37 pmSAT - ORD

1 stop14h 10mSpirit Airlines

Wed 11/1210:52 amORD - SAT

1 stop7h 40mSpirit Airlines

Deal found 10/12

$159

Fri 10/315:35 pmSAT - ORD

1 stop6h 04mFrontier

Fri 11/75:11 amORD - SAT

1 stop11h 29mFrontier

Deal found 10/12

$160

Sat 11/13:12 pmSAT - ORD

1 stop8h 17mFrontier

Mon 11/35:05 amORD - SAT

1 stop11h 35mFrontier

Deal found 10/14

$161

Tue 11/47:37 pmSAT - ORD

1 stop14h 10mMultiple Airlines

Mon 11/105:05 amORD - SAT

1 stop11h 35mMultiple Airlines

Deal found 10/13

$162

Thu 12/1110:13 amSAT - MDW

1 stop10h 23mFrontier

Mon 12/156:00 amMDW - SAT

1 stop11h 47mFrontier

Deal found 10/13

$162

Tue 11/47:37 pmSAT - ORD

1 stop14h 10mSpirit Airlines

Tue 11/1110:52 amORD - SAT

1 stop7h 40mSpirit Airlines

Deal found 10/13

$163

Mon 11/38:25 pmSAT - ORD

2 stops14h 49mMultiple Airlines

Wed 11/1210:52 amORD - SAT

1 stop7h 40mMultiple Airlines

Deal found 10/12

$164

Wed 11/57:37 pmSAT - ORD

1 stop15h 35mSpirit Airlines

Tue 11/115:10 amORD - SAT

1 stop13h 22mSpirit Airlines

Deal found 10/12

$165

Mon 11/35:35 pmSAT - ORD

1 stop17h 39mFrontier

Thu 11/66:00 amORD - SAT

1 stop13h 06mFrontier

Deal found 10/12

$167

Wed 11/57:37 pmSAT - ORD

1 stop15h 35mMultiple Airlines

Mon 11/105:05 amORD - SAT

1 stop11h 35mMultiple Airlines

Deal found 10/12

$168

Mon 10/275:45 pmSAT - ORD

1 stop17h 29mFrontier

Thu 11/66:00 amORD - SAT

1 stop13h 06mFrontier

Deal found 10/12

$170

Mon 10/275:45 pmSAT - ORD

1 stop17h 29mMultiple Airlines

Tue 11/410:52 amORD - SAT

1 stop7h 40mMultiple Airlines

Deal found 10/12

$171

Best flights from San Antonio to Chicago
Discover carefully curated flight deals from San Antonio to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2025.

Fri 12/510:13 amSAT - MDW

1 stop10h 23mFrontier

Mon 12/86:00 amMDW - SAT

1 stop11h 47mFrontier

Deal found 10/14

$296

Sat 11/82:04 pmSAT - ORD

Nonstop2h 46mUnited Airlines

Sat 11/158:55 amORD - SAT

Nonstop3h 13mUnited Airlines

Deal found 10/11

$297

Wed 11/126:40 amSAT - MDW

Nonstop2h 35mSouthwest

Wed 11/194:55 pmMDW - SAT

Nonstop2h 55mSouthwest

Deal found 10/13

$297

Fri 10/315:25 amSAT - MDW

1 stop7h 03mDelta

Tue 11/45:09 pmMDW - SAT

1 stop7h 11mDelta

Deal found 10/12

$307

Fri 10/2410:54 amSAT - RFD

1 stop25h 16mMultiple Airlines

Sun 10/261:44 pmRFD - SAT

1 stop9h 56mMultiple Airlines

Deal found 10/13

$408

Tue 11/45:25 amSAT - ORD

1 stop7h 15mDelta

Tue 11/45:51 pmORD - SAT

1 stop6h 29mDelta

Deal found 10/14

$317

Sat 11/86:50 amSAT - MDW

1 stop4h 55mSouthwest

Sat 11/81:15 pmMDW - SAT

1 stop7h 35mSouthwest

Deal found 10/11

$317

Thu 11/67:05 amSAT - ORD

Nonstop2h 47mUnited Airlines

Sat 11/87:10 amORD - SAT

1 stop5h 46mUnited Airlines

Deal found 10/11

$332

Tue 11/411:35 amSAT - MDW

1 stop6h 50mDelta

Sat 11/84:23 pmMDW - SAT

1 stop7h 57mDelta

Deal found 10/13

$317

Thu 11/133:45 pmSAT - MDW

Nonstop2h 35mSouthwest

Thu 11/275:45 amMDW - SAT

1 stop6h 35mSouthwest

Deal found 10/12

$322

Tue 11/411:40 amSAT - ORD

1 stop5h 28mUnited Airlines

Thu 11/61:03 pmORD - SAT

Nonstop3h 17mUnited Airlines

Deal found 10/12

$332

Sat 11/85:15 pmSAT - MDW

1 stop4h 59mDelta

Wed 11/125:34 pmMDW - SAT

1 stop7h 04mDelta

Deal found 10/13

$317

Wed 12/105:15 pmSAT - MDW

1 stop6h 34mDelta

Tue 12/169:34 amMDW - SAT

1 stop6h 30mDelta

Deal found 10/11

$317

Fri 12/55:20 pmSAT - ORD

Nonstop2h 57mUnited Airlines

Mon 12/810:35 amORD - SAT

1 stop6h 19mUnited Airlines

Deal found 10/12

$357

Wed 11/55:25 amSAT - MDW

1 stop7h 03mDelta

Tue 11/116:00 amMDW - SAT

1 stop7h 41mDelta

Deal found 10/13

$317

Fri 10/312:04 pmSAT - ORD

Nonstop2h 46mUnited Airlines

Wed 11/51:03 pmORD - SAT

Nonstop3h 17mUnited Airlines

Deal found 10/14

$367

Sat 10/257:00 amSAT - RFD

3 stops26h 24mMultiple Airlines

Sun 10/261:44 pmRFD - SAT

1 stop9h 56mMultiple Airlines

Deal found 10/12

$513

Tue 12/236:40 amSAT - ORD

Nonstop2h 51mUnited Airlines

Tue 12/237:41 pmORD - SAT

Nonstop3h 13mUnited Airlines

Deal found 10/11

$376

Tue 11/42:04 pmSAT - ORD

Nonstop2h 46mUnited Airlines

Wed 11/59:10 amORD - SAT

Nonstop3h 15mUnited Airlines

Deal found 10/14

$377

Wed 11/57:05 amSAT - ORD

Nonstop2h 47mUnited Airlines

Sat 11/88:55 amORD - SAT

Nonstop3h 13mUnited Airlines

Deal found 10/13

$377

Mon 12/222:16 pmSAT - RFD

1 stop21h 09mMultiple Airlines

Sat 12/2712:15 pmRFD - SAT

1 stop17h 15mMultiple Airlines

Deal found 10/14

$658

Tue 11/47:05 amSAT - ORD

Nonstop2h 47mUnited Airlines

Tue 11/48:08 pmORD - SAT

Nonstop3h 08mUnited Airlines

Deal found 10/14

$377

Last-minute flights from San Antonio to Chicago
Discover last-minute flight deals from San Antonio to Chicago. Data last updated October 14, 2025 and is based on user searches.

Mon 10/207:10 pmSAT - ORD

2 stops21h 30mFrontier

Mon 11/35:05 amORD - SAT

1 stop11h 35mFrontier

Deal found 10/13

$175

Mon 10/205:45 pmSAT - ORD

1 stop5h 54mFrontier

Wed 10/227:15 amORD - SAT

1 stop8h 01mFrontier

Deal found 10/13

$198

Fri 10/247:10 pmSAT - ORD

1 stop23h 23mFrontier

Sun 11/166:00 amORD - SAT

1 stop13h 30mFrontier

Deal found 10/12

$179

Fri 10/247:10 pmSAT - ORD

1 stop23h 23mFrontier

Mon 10/278:15 amORD - SAT

1 stop10h 00mFrontier

Deal found 10/13

$181

Fri 10/247:10 pmSAT - MDW

1 stop15h 11mFrontier

Mon 10/276:15 amMDW - SAT

1 stop10h 35mFrontier

Deal found 10/13

$181

Fri 10/247:00 amSAT - ORD

2 stops40h 29mMultiple Airlines

Mon 10/278:15 amORD - SAT

1 stop10h 00mMultiple Airlines

Deal found 10/12

$204

Mon 10/2710:54 amSAT - MDW

1 stop10h 52mFrontier

Thu 11/612:30 pmMDW - SAT

1 stop6h 36mFrontier

Deal found 10/12

$172

Mon 10/275:45 pmSAT - MDW

1 stop17h 53mFrontier

Fri 10/316:20 amMDW - SAT

1 stop10h 20mFrontier

Deal found 10/12

$198

Sun 11/29:59 amSAT - MDW

1 stop7h 23mFrontier

Thu 11/612:30 pmMDW - SAT

1 stop6h 36mFrontier

Deal found 10/12

$200

Mon 11/310:04 amSAT - MDW

1 stop6h 48mFrontier

Fri 11/76:15 amMDW - SAT

1 stop10h 25mFrontier

Deal found 10/12

$217

Wed 11/510:58 amSAT - MDW

1 stop22h 14mMultiple Airlines

Thu 11/61:37 pmMDW - SAT

2 stops29h 53mMultiple Airlines

Deal found 10/12

$215

Sat 11/83:12 pmSAT - MDW

1 stop20h 18mFrontier

Sat 11/151:37 pmMDW - SAT

2 stops29h 53mFrontier

Deal found 10/11

$199

One-way flights from San Antonio to Chicago
Search for one-way flight options from San Antonio to Chicago. Find affordable one-way fares based on user searches. Data last updated October 14, 2025.

Sat 11/153:12 pmSAT - ORD

1 stop8h 17mFrontier

Deal found 10/13

$80

Wed 11/53:23 pmSAT - ORD

1 stop14h 09mSpirit Airlines

Deal found 10/12

$81

Wed 11/56:45 amSAT - ORD

2 stops18h 14mMultiple Airlines

Deal found 10/12

$86

Mon 12/1510:13 amSAT - MDW

1 stop10h 23mFrontier

Deal found 10/13

$86

Sun 11/168:25 pmSAT - ORD

1 stop27h 50mFrontier

Deal found 10/12

$87

Sat 11/153:12 pmSAT - MDW

1 stop20h 18mFrontier

Deal found 10/13

$87

Sun 11/168:25 pmSAT - MDW

1 stop15h 05mFrontier

Deal found 10/12

$88

Sat 12/136:33 pmSAT - MDW

1 stop18h 37mFrontier

Deal found 10/14

$91

Fri 12/510:13 amSAT - ORD

1 stop8h 21mFrontier

Deal found 10/12

$92

Wed 11/127:37 pmSAT - MDW

2 stops26h 26mMultiple Airlines

Deal found 10/12

$92

Thu 1/1510:13 amSAT - ORD

1 stop8h 37mFrontier

Deal found 10/13

$93

Tue 11/187:37 pmSAT - ORD

1 stop14h 10mSpirit Airlines

Deal found 10/12

$94

Cheap flight deals from San Antonio to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$159 (Kiwi.com)
One-way from	$80 (Priceline)
Popular in	March
Cheapest in	September
Average price	$362
Good round-trip deal	$317 or less
Good one-way deal	$220 or less

Provider with most accurate pricing for San Antonio-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for San Antonio-Chicago (CHI) flights.

Search Deals

From San Antonio to Chicago (CHI)

Search Deals

One-way flight from San Antonio to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2025

Search Deals

Price to beat on a round-trip flight from San Antonio to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from San Antonio to Chicago (CHI).

Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 12/5

10:13 am-8:36 pm

1 stop10h 23m

Chicago Midway

Mon 12/8

6:00 am-5:47 pm

1 stop11h 47m

$296

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 11/8

2:04 pm-4:50 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sat 11/15

8:55 am-12:08 pm

Nonstop3h 13m

$297

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 11/12

6:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Wed 11/19

4:55 pm-7:50 pm

Nonstop2h 55m

$297

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 10/31

5:25 am-12:28 pm

1 stop7h 03m

Chicago Midway

Tue 11/4

5:09 pm-12:20 am

1 stop7h 11m

$307

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 11/4

5:25 am-12:40 pm

1 stop7h 15m

Chicago O'Hare Intl

Tue 11/4

5:51 pm-12:20 am

1 stop6h 29m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 11/8

6:50 am-11:45 am

1 stop4h 55m

Chicago Midway

Sat 11/8

1:15 pm-8:50 pm

1 stop7h 35m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 11/4

11:35 am-6:25 pm

1 stop6h 50m

Chicago Midway

Sat 11/8

4:23 pm-12:20 am

1 stop7h 57m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 11/8

5:15 pm-10:14 pm

1 stop4h 59m

Chicago Midway

Wed 11/12

5:34 pm-12:38 am

1 stop7h 04m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 12/10

5:15 pm-11:49 pm

1 stop6h 34m

Chicago Midway

Tue 12/16

9:34 am-4:04 pm

1 stop6h 30m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 11/5

5:25 am-12:28 pm

1 stop7h 03m

Chicago Midway

Tue 11/11

6:00 am-1:41 pm

1 stop7h 41m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 50 results

...

Compare providers for flights from San Antonio to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Antonio to Chicago in October.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
JustAirTicket	Price Accuracy-	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars
Justfly.com	Price Accuracy3 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy2 stars	Trust Score*1 star
CheapOair	Price Accuracy3 stars	Trust Score*3 stars
CheapTicketsDeal	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on San Antonio-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on San Antonio-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Antonio-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San Antonio to Chicago

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

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 70 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, March is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $59). Flying from San Antonio to Chicago in January is currently the most expensive (average of $186). 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 time of day to fly from SAT to CHI?

When flying from San Antonio to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 64% versus a flight at noon.

Weekly flight availability from San Antonio to Chicago

The most flights from SAT to CHI are scheduled on a Monday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 on average).

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

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

Orlando (MCO) – chosen by Cheapflights users on 60% of 1-stop itineraries from San Antonio to Chicago on Cheapflights.

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

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $173.

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

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 10h 05m.

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

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 12m.

The best insider tips for San Antonio to Chicago flights

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

Airports

SAT

Parking at SAT is convenient with a new seven-story garage and economy lots offering shuttle service for longer trips.

ORD

For a quick city transfer, take the “L” train from ORD to downtown Chicago, avoiding potential traffic delays.

MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a cost-effective travel option.

Our travel experts

Ramsey Qubein

Expert on ORD, MDW and SAT

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from San Antonio to Chicago. 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.

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest

8.0

Very good

4,238 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines

7.4

Good

8,976 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

American Airlines

7.2

Good

11,042 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Spirit Airlines

6.3

Okay

8,096 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Frontier

5.8

Fair

3,135 reviews

Southwest

8.0

Very good

4,238 reviews

Reviews

1 / 20

8.0

Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

What airport do you fly from for flights from San Antonio to Chicago?
If you book a flight to Chicago from San Antonio, you will be flying from San Antonio, which is the city’s only airport. San Antonio (SAT) is located 7.6 mi from the center of San Antonio. There are 30 flights from San Antonio to Chicago per day from 5 different airlines.
How long is the flight from San Antonio to Chicago?
Frontier, United Airlines, and Southwest can get you from San Antonio to Chicago in just under 2h 35m. Your travel time can differ by up to 7h 48m. San Antonio and Chicago are separated by a distance of 1036 mi. Both multi-stop and nonstop flights can be found to your destination and back.
What are the cheapest airlines flying from San Antonio to Chicago round-trip?
Cheapflights users have booked flights from San Antonio to Chicago round-trip from $97. Other airlines that can offer you cheap pricing are Spirit Airlines, from $208, and American Airlines, from $235. These flights start at 74% lower than the current average price 3 months from now.
What are the cheapest airlines to fly from San Antonio to Chicago one-way?
The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $139. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from San Antonio to Chicago for a low price.
What are the most popular routes from San Antonio to Chicago?
When deciding which route to take from San Antonio to Chicago consider San Antonio - Chicago O'Hare Intl, San Antonio - Chicago Midway or San Antonio - Chicago Greater Rockford as they are the most popular.
What are the most reliable airlines from San Antonio to Chicago?
The top 3 most reliable airlines when flying from San Antonio to Chicago are ANA (87%), United Airlines (86%) and Japan Airlines (84%).
What are the cheapest flights from San Antonio to Chicago?
On average you can expect to pay $1,181 for a flight from San Antonio to Chicago. The cheapest flight overall is $158 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $152.
Can I find deals for flights from San Antonio to Chicago that include hotel bookings?
Yes. In addition to deals on San Antonio to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from San Antonio to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Antonio to Chicago.
Can I find deals for business class flights from San Antonio to Chicago?
Yes. Cheapflights offers flight deals from San Antonio to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from San Antonio to Chicago?
Currently, March is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $59). Flying from San Antonio to Chicago in January is currently the most expensive (average of $186). 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.

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Top 5 airlines flying from San Antonio to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$97	Average$210	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$208	Average$302	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$235	Average$393	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$256	Average$425	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$290	Average$488	FlexibilityNo cancel fee	On-time69%

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

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 11/15. 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 San Antonio to Chicago are usually found in September or August, booked 70 days in advance, depart on a Thursday or Friday and return on a Wednesday

Find flight deals from San Antonio to Chicago

Cheapest flights from San Antonio to ChicagoExplore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

Explore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

Cheap flight deals from San Antonio to Chicago

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

Compare providers for flights from San Antonio to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Antonio to Chicago in October.

Best time to book a flight from San Antonio to Chicago

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

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from San Antonio to Chicago. Price data was last updated on October 10, 2025.

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

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

Find hourly flight availability from San Antonio to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

Weekly flight availability from San Antonio to Chicago

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

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

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

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

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

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

Shortest average travel time for 1-stop one-way flights from San Antonio to Chicago, 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 San Antonio to Chicago?

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

The best insider tips for San Antonio to Chicago flights

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

Airports

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Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from San Antonio to Chicago. 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 San Antonio to Chicago. 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 from for flights from San Antonio to Chicago?

How long is the flight from San Antonio to Chicago?

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

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

What are the most popular routes from San Antonio to Chicago?

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

What are the cheapest flights from San Antonio to Chicago?

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

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

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

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

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Alternative routes for San Antonio to Chicago

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Cheapest flights from San Antonio to Chicago
Explore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.