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Cheap flights from San Antonio to Chicago from $66

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 2/18. 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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Cheap round-trip flights

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Frontier Logo
8:25 pm - 11:58 am
SAT
-
ORD
15h 33m1 stop
Frontier Logo
4:29 pm - 10:40 am
ORD
-
SAT
18h 11m2 stops
$207Frontier
Thu, Feb 12 - Sat, Feb 14
Multiple Airlines Logo
6:30 am - 3:52 pm
SAT
-
ORD
9h 22m1 stop
Multiple Airlines Logo
5:05 am - 4:19 pm
ORD
-
SAT
11h 14m1 stop
$210Multiple Airlines
Wed, Feb 11 - Sun, Feb 15
Multiple Airlines Logo
6:30 am - 7:52 pm
SAT
-
MDW
13h 22m1 stop
Multiple Airlines Logo
1:00 pm - 11:52 pm
MDW
-
SAT
10h 52m1 stop
$210Multiple Airlines
Fri, Jan 30 - Sun, Feb 1
Spirit Airlines Logo
10:26 am - 11:47 pm
SAT
-
ORD
13h 21m1 stop
Spirit Airlines Logo
10:44 am - 11:59 pm
ORD
-
SAT
13h 15m1 stop
$213Spirit Airlines
Wed, Feb 18 - Sun, Feb 22
Frontier Logo
5:36 pm - 10:51 am
SAT
-
ORD
17h 15m2 stops
Frontier Logo
6:30 pm - 12:17 am
ORD
-
SAT
29h 47m1 stop
$215Frontier
Tue, Mar 3 - Mon, Mar 9
Multiple Airlines Logo
9:41 pm - 10:38 pm
SAT
-
ORD
24h 57m2 stops
Multiple Airlines Logo
5:32 pm - 9:40 am
ORD
-
SAT
16h 08m1 stop
$216Multiple Airlines
Mon, Jan 26 - Wed, Jan 28
Multiple Airlines Logo
6:30 am - 3:52 pm
SAT
-
ORD
9h 22m1 stop
Multiple Airlines Logo
6:00 am - 4:41 pm
ORD
-
SAT
34h 41m2 stops
$217Multiple Airlines
Wed, Feb 11 - Mon, Feb 16
Multiple Airlines Logo
1:57 pm - 7:34 am
SAT
-
ORD
17h 37m2 stops
Multiple Airlines Logo
8:16 pm - 9:30 am
ORD
-
SAT
13h 14m1 stop
$218Multiple Airlines
Sat, Feb 14 - Mon, Mar 2
Frontier Logo
5:04 pm - 10:37 pm
SAT
-
MDW
5h 33m1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
SAT
10h 20m1 stop
$218Frontier
Fri, Feb 27 - Mon, Mar 2
Delta Logo
4:29 pm - 10:07 pm
SAT
-
MDW
5h 38m1 stop
Delta Logo
6:45 am - 12:45 pm
MDW
-
SAT
6h 00m1 stop
$281Delta
Sat, Jan 17 - Sun, Jan 18

Spirit Airlines flights from San Antonio to Chicago

Our best Spirit Airlines deals on San Antonio to Chicago flight tickets
Spirit Airlines
Feb 18
SAT10:26 amSan Antonio
13h 21m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 22
ORD10:44 amChicago O'Hare Intl
13h 15m
1 stop
SAT11:59 pmSan Antonio
$213
Find similar
Spirit Airlines
Jan 21
SAT6:30 amSan Antonio
6h 43m
1 stop
ORD1:13 pmChicago O'Hare Intl
Jan 24
ORD7:20 amChicago O'Hare Intl
16h 32m
2 stops
SAT11:52 pmSan Antonio
$226
Find similar
Spirit Airlines
Apr 1
SAT10:26 amSan Antonio
13h 15m
1 stop
ORD11:41 pmChicago O'Hare Intl
Apr 6
ORD7:41 pmChicago O'Hare Intl
13h 41m
1 stop
SAT9:22 amSan Antonio
$228
Find similar

American Airlines flights from San Antonio to Chicago

Our best American Airlines deals on San Antonio to Chicago flight tickets
American Airlines
Jan 17
SAT6:01 amSan Antonio
2h 52m
ORD8:53 amChicago O'Hare Intl
Jan 18
ORD7:35 pmChicago O'Hare Intl
3h 07m
SAT10:42 pmSan Antonio
$261
Find similar
American Airlines
Feb 18
SAT5:00 pmSan Antonio
2h 57m
ORD7:57 pmChicago O'Hare Intl
Feb 25
ORD2:58 pmChicago O'Hare Intl
7h 56m
1 stop
SAT10:54 pmSan Antonio
$272
Find similar
American Airlines
Feb 18
SAT1:36 pmSan Antonio
2h 57m
ORD4:33 pmChicago O'Hare Intl
Feb 25
ORD2:58 pmChicago O'Hare Intl
7h 56m
1 stop
SAT10:54 pmSan Antonio
$273
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 January 2, 2026.
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 - ORD

SATORD

San Antonio

Thu 2/12

8:25 pm-11:58 am

1 stop15h 33m

Chicago O'Hare Intl

Sat 2/14

4:29 pm-10:40 am

2 stops18h 11m

$207

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 2/11

6:30 am-3:52 pm

1 stop9h 22m

Chicago O'Hare Intl

Sun 2/15

5:05 am-4:19 pm

1 stop11h 14m

$210

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 1/30

6:30 am-7:52 pm

1 stop13h 22m

Chicago Midway

Sun 2/1

1:00 pm-11:52 pm

1 stop10h 52m

$210

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 2/18

10:26 am-11:47 pm

1 stop13h 21m

Chicago O'Hare Intl

Sun 2/22

10:44 am-11:59 pm

1 stop13h 15m

$213

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 3/3

5:36 pm-10:51 am

2 stops17h 15m

Chicago O'Hare Intl

Mon 3/9

6:30 pm-12:17 am

1 stop29h 47m

$215

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Mon 1/26

9:41 pm-10:38 pm

2 stops24h 57m

Chicago O'Hare Intl

Wed 1/28

5:32 pm-9:40 am

1 stop16h 08m

$216

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 2/11

6:30 am-3:52 pm

1 stop9h 22m

Chicago O'Hare Intl

Mon 2/16

6:00 am-4:41 pm

2 stops34h 41m

$217

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 2/14

1:57 pm-7:34 am

2 stops17h 37m

Chicago O'Hare Intl

Mon 3/2

8:16 pm-9:30 am

1 stop13h 14m

$218

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/27

5:04 pm-10:37 pm

1 stop5h 33m

Chicago Midway

Mon 3/2

6:00 am-4:20 pm

1 stop10h 20m

$218

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

4:29 pm-10:07 pm

1 stop5h 38m

Chicago Midway

Sun 1/18

6:45 am-12:45 pm

1 stop6h 00m

$281

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 September is, on average, the cheapest month to fly to Chicago from San Antonio, with most prices found around $305. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from San Antonio to Chicago during August average around $308.

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 $443. 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 $849.

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 morning. Flights from San Antonio to Chicago during this time can be as low as $465. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $881.

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 $390 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 $263 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?

You could potentially save up to 32% on your flight if you consider stops on a San Antonio to Chicago flight.

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

As of January 2026, prices for San Antonio to Chicago flights are approximately 58% 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

$196

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from San Antonio in the past 72 hours is $196. The best round-trip flight deal from San Antonio to Chicago found on momondo in the last 72 hours is $346.
The fastest flight from San Antonio to Chicago takes 2h 30m
Direct flights go from San Antonio to Chicago every day.
There are 3 airports in Chicago. From San Antonio there are direct flights to 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 30m, 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
FrontierPriceFrom $97Free CancellationRating
5.7
3,069 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $191Free CancellationRating
6.3
8,258 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.2
11,074 reviews
Search American Airlines flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,254 reviews
Search Southwest flights
United AirlinesPriceFrom $276Free CancellationRating
7.4
9,132 reviews
Search United Airlines flights

  • Southwest Flights From San Antonio to Chicago

    Southwest operates around 5 flights from San Antonio to Chicago every week. The average price of these flights found in the last 72 hours has been $422, but momondo users have found Southwest deals from San Antonio to Chicago from as low as $256 round-trip. Southwest has been scored 8.0/10 in 4,254 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 $276, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $450 round-trip. United Airlines operates 8 flights out of San Antonio into Chicago in an average week, so prices vary by time and availability. 9,132 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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
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