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Cheap flights from San Antonio to Chicago from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Antonio to Chicago departing on 9/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from San Antonio to Chicago (SAT-CHI)

Cheap round-trip flights

Frontier Logo
5:45 pm - 11:25 pmSAT-MDW
5h 40m1 stop
Frontier Logo
9:44 am - 4:50 pmMDW-SAT
7h 06m1 stop
$144Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
5:40 pm - 12:10 amSAT-ORD
6h 30m1 stop
Frontier Logo
6:00 am - 7:15 pmORD-SAT
13h 15m1 stop
$146Frontier
Find Deal
Fri, Sep 19 - Mon, Sep 22
Logo
3:22 pm - 9:28 pmSAT-ORD
6h 06m1 stop
Logo
9:00 am - 8:52 pmORD-SAT
11h 52m1 stop
$175
Find Deal
Sat, Sep 6 - Tue, Sep 9
Logo
5:40 pm - 12:10 amSAT-ORD
6h 30m1 stop
Logo
6:30 am - 1:49 pmORD-SAT
7h 19m1 stop
$191
Find Deal
Fri, Sep 19 - Sun, Sep 28
Spirit Airlines Logo
12:45 pm - 9:58 pmSAT-ORD
9h 13m1 stop
Spirit Airlines Logo
11:15 am - 8:52 pmORD-SAT
9h 37m1 stop
$203Spirit Airlines
Find Deal
Mon, Sep 8 - Wed, Sep 10
Spirit Airlines Logo
6:00 am - 5:04 pmSAT-ORD
11h 04m1 stop
Spirit Airlines Logo
10:18 am - 10:27 pmORD-SAT
12h 09m1 stop
$206Spirit Airlines
Find Deal
Sat, Nov 8 - Mon, Nov 10
American Airlines Logo
1:44 pm - 9:45 pmSAT-ORD
8h 01m1 stop
American Airlines Logo
1:20 pm - 10:13 pmORD-SAT
8h 53m1 stop
$209American Airlines
Find Deal
Wed, Sep 10 - Tue, Sep 16
American Airlines Logo
10:13 am - 7:16 pmSAT-ORD
9h 03m1 stop
American Airlines Logo
3:08 pm - 11:00 pmORD-SAT
7h 52m1 stop
$218American Airlines
Find Deal
Wed, Sep 3 - Sat, Sep 6
Southwest Logo
2:40 pm - 5:15 pmSAT-MDW
2h 35mnonstop
Southwest Logo
8:25 am - 11:10 amMDW-SAT
2h 45mnonstop
$257Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
6:30 am - 9:05 amSAT-MDW
2h 35mnonstop
Southwest Logo
12:50 pm - 6:15 pmMDW-SAT
5h 25m1 stop
$267Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10

Spirit Airlines flights from San Antonio to Chicago

Our best Spirit Airlines deals on San Antonio to Chicago flight tickets
Spirit Airlines
Sep 8
SAT12:45 pmSan Antonio
9h 13m
1 stop
ORD9:58 pmChicago O'Hare Intl
Sep 10
ORD11:15 amChicago O'Hare Intl
9h 37m
1 stop
SAT8:52 pmSan Antonio
$203
Find similar
Spirit Airlines
Nov 8
SAT6:00 amSan Antonio
11h 04m
1 stop
ORD5:04 pmChicago O'Hare Intl
Nov 10
ORD10:18 amChicago O'Hare Intl
12h 09m
1 stop
SAT10:27 pmSan Antonio
$206
Find similar
Spirit Airlines
Sep 16
SAT9:47 pmSan Antonio
20h 27m
2 stops
ORD6:14 pmChicago O'Hare Intl
Sep 20
ORD12:46 pmChicago O'Hare Intl
8h 06m
1 stop
SAT8:52 pmSan Antonio
$212
Find similar

Frontier flights from San Antonio to Chicago

Our best Frontier deals on San Antonio to Chicago flight tickets
Frontier
Oct 17
SAT5:45 pmSan Antonio
5h 40m
1 stop
MDW11:25 pmChicago Midway
Oct 20
MDW9:44 amChicago Midway
7h 06m
1 stop
SAT4:50 pmSan Antonio
$144
Find similar
Frontier
Sep 19
SAT5:40 pmSan Antonio
6h 30m
1 stop
ORD12:10 amChicago O'Hare Intl
Sep 22
ORD6:00 amChicago O'Hare Intl
13h 15m
1 stop
SAT7:15 pmSan Antonio
$146
Find similar
Frontier
Sep 26
SAT5:40 pmSan Antonio
6h 30m
1 stop
ORD12:10 amChicago O'Hare Intl
Sep 27
ORD8:25 amChicago O'Hare Intl
24h 45m
1 stop
SAT9:10 amSan Antonio
$147
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Antonio to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 14, 2025.
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 10/17

5:45 pm-11:25 pm

1 stop5h 40m

Chicago Midway

Mon 10/20

9:44 am-4:50 pm

1 stop7h 06m

$144

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Fri 9/19

5:40 pm-12:10 am

1 stop6h 30m

Chicago O'Hare Intl

Mon 9/22

6:00 am-7:15 pm

1 stop13h 15m

$146

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 9/6

3:22 pm-9:28 pm

1 stop6h 06m

Chicago O'Hare Intl

Tue 9/9

9:00 am-8:52 pm

1 stop11h 52m

$175

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Fri 9/19

5:40 pm-12:10 am

1 stop6h 30m

Chicago O'Hare Intl

Sun 9/28

6:30 am-1:49 pm

1 stop7h 19m

$191

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Mon 9/8

12:45 pm-9:58 pm

1 stop9h 13m

Chicago O'Hare Intl

Wed 9/10

11:15 am-8:52 pm

1 stop9h 37m

$203

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 11/8

6:00 am-5:04 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 11/10

10:18 am-10:27 pm

1 stop12h 09m

$206

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 9/10

1:44 pm-9:45 pm

1 stop8h 01m

Chicago O'Hare Intl

Tue 9/16

1:20 pm-10:13 pm

1 stop8h 53m

$209

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 9/3

10:13 am-7:16 pm

1 stop9h 03m

Chicago O'Hare Intl

Sat 9/6

3:08 pm-11:00 pm

1 stop7h 52m

$218

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/3

2:40 pm-5:15 pm

Nonstop2h 35m

Chicago Midway

Wed 9/10

8:25 am-11:10 am

Nonstop2h 45m

$257

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/3

6:30 am-9:05 am

Nonstop2h 35m

Chicago Midway

Wed 9/10

12:50 pm-6:15 pm

1 stop5h 25m

$267

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Antonio to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between San Antonio and Chicago?

What is the cheapest month to fly to Chicago?

The month of August 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 August, then September is your next best option. Flight prices from San Antonio to Chicago during September average around $340.

What is the cheapest day to depart on your flight to Chicago?

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 $855.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Antonio to Chicago during this time can be as low as $278. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $878.

What is the cheapest San Antonio to Chicago flight route?

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

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

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 $402 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 $312 on momondo.

What cabin class options are available on San Antonio to Chicago flights?

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.

Can stopping save me money on San Antonio to Chicago flights?

No. A direct flight is the cheapest option for a flight between San Antonio to Chicago.

How have San Antonio to Chicago flight prices changed over time?

As of August 2025, prices for San Antonio to Chicago flights are approximately 11% more expensive when compared to flights at the same time last year.

When to book flights from San Antonio to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San Antonio to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Antonio to Chicago (SAT to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Antonio to Chicago

Best Price Found

$72

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from San Antonio in the past 72 hours is $72. The best round-trip flight deal from San Antonio to Chicago found on momondo in the last 72 hours is $144.
The fastest flight from San Antonio to Chicago takes 2h 35m
Direct flights go from San Antonio to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is San Antonio to Chicago by plane?

    There are 1052.0 mi between San Antonio and Chicago. Flights usually cover this in 2h 35m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from San Antonio Airport to Chicago?

    Prices for flights from San Antonio Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from San Antonio Airport to Chicago?

  • How old do you have to be to fly from San Antonio Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Antonio Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San Antonio to Chicago?

  • What is the most popular airline from San Antonio to Chicago?

Best airlines flying from San Antonio to Chicago

Compare and see reviews for airlines that fly from San Antonio to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $111Free CancellationRating
6.3
8,045 reviews
Search Spirit Airlines flights
FrontierPriceFrom $114Free CancellationRating
5.8
3,219 reviews
Search Frontier flights
American AirlinesPriceFrom $208Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $245Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
United AirlinesPriceFrom $283Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights

  • Southwest Flights From San Antonio to Chicago

    Southwest operates around 10 flights from San Antonio to Chicago every week. The average price of these flights found in the last 72 hours has been $436, but momondo users have found Southwest deals from San Antonio to Chicago from as low as $245 round-trip. Southwest has been scored 8.0/10 in 4,244 reviews.

  • United Airlines Flights From San Antonio to Chicago

    The best United Airlines deal for San Antonio to Chicago flight tickets found on momondo in the last 72 hours was $283, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $491 round-trip. United Airlines operates 8 flights out of San Antonio into Chicago in an average week, so prices vary by time and availability. 8,916 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San Antonio to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San Antonio to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from San Antonio to Chicago with flexible booking policies on momondo?

Flights from San Antonio to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from San Antonio to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from San Antonio. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from San Antonio to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from San Antonio are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport