What airlines fly to Chicago?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from San Antonio according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which layover airport has the shortest travel time from San Antonio to Chicago?

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 6h 16m.

What is the cheapest airline that flies from San Antonio to Chicago?

United Airlines, Southwest, and Delta are the most popular carriers operating from San Antonio to Chicago

Which airport is the most popular layover for flights between San Antonio and Chicago?

Fort Lauderdale (FLL) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from San Antonio to Chicago?

Atlanta (ATL) has the shortest average layover time for this route: 2h 25m.

How many flights depart from San Antonio to Chicago on average per day?

As of May 2026, 26 flights take off from San Antonio and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 49% of daily flights taking off in the afternoon.

Which layover airport offers the lowest fares from San Antonio to Chicago?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $160.

How many flights depart from San Antonio to Chicago on average per week?

186 flights are operational weekly from San Antonio to Chicago as of May 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

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?

The number of operators available for flights from San Antonio Airport to Chicago is 5 as of May 2026.

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.

$145 Cheap Flights from San Antonio to Chicago in 2026

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

Prices are currently low for flights on this route. Typical prices usually range from $493 to $309. The lowest price recently found on this route was $293.

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Find the cheapest flights from San Antonio to Chicago

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One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:54 pm - 8:32 pm

SAT

ORD

24h 38m

1 stop

9:37 pm - 6:59 pm

ORD

SAT

21h 22m

1 stop

$293Frontier

Wed, May 20 - Sun, May 24

7:54 pm - 8:32 pm

SAT

ORD

24h 38m

1 stop

9:48 pm - 6:56 pm

ORD

SAT

21h 08m

1 stop

$296Frontier

Mon, May 18 - Tue, Jun 9

6:49 am - 9:45 am

SAT

ORD

2h 56mnonstop

8:03 pm - 11:02 pm

ORD

SAT

2h 59mnonstop

$297United Airlines

Wed, May 20 - Tue, May 26

2:35 pm - 5:10 pm

SAT

MDW

2h 35mnonstop

9:00 pm - 11:50 pm

MDW

SAT

2h 50mnonstop

$297Southwest

Tue, May 26 - Tue, Jun 2

6:27 pm - 9:44 pm

SAT

ORD

3h 17mnonstop

10:00 am - 12:52 pm

ORD

SAT

2h 52mnonstop

$298American Airlines

Tue, May 26 - Tue, Jun 2

4:44 pm - 11:59 pm

SAT

ORD

7h 15m

1 stop

9:57 pm - 6:54 pm

ORD

SAT

20h 57m

1 stop

$300Multiple Airlines

Wed, Jul 1 - Mon, Jul 13

8:59 pm - 5:28 am

SAT

ORD

8h 29m

1 stop

9:57 pm - 6:54 pm

ORD

SAT

20h 57m

1 stop

$301Frontier

Wed, Jul 22 - Mon, Jul 27

7:54 pm - 8:32 pm

SAT

ORD

24h 38m

1 stop

5:05 am - 4:16 pm

ORD

SAT

11h 11m

1 stop

$302Multiple Airlines

Wed, May 27 - Sun, May 31

6:27 pm - 9:44 pm

SAT

ORD

3h 17mnonstop

9:10 pm - 12:01 am

ORD

SAT

2h 51mnonstop

$303American Airlines

Thu, May 28 - Wed, Jun 3

9:25 am - 12:00 pm

SAT

MDW

2h 35mnonstop

1:55 pm - 5:55 pm

MDW

SAT

4h 00m

1 stop

$303Southwest

Wed, Aug 12 - Tue, Aug 18

Spirit Airlines flights from San Antonio to Chicago

Our best Spirit Airlines deals on San Antonio to Chicago flight tickets

Spirit Airlines

Jun 28

SAT7:42 pmSan Antonio

13h 40m

1 stop

ORD9:22 amChicago O'Hare Intl

Jul 9

ORD5:10 amChicago O'Hare Intl

13h 27m

1 stop

SAT6:37 pmSan Antonio

$335

Spirit Airlines

May 14

SAT5:26 pmSan Antonio

14h 56m

1 stop

ORD8:22 amChicago O'Hare Intl

May 17

ORD5:05 amChicago O'Hare Intl

11h 11m

1 stop

SAT4:16 pmSan Antonio

$363

American Airlines flights from San Antonio to Chicago

Our best American Airlines deals on San Antonio to Chicago flight tickets

American Airlines

May 26

SAT6:27 pmSan Antonio

3h 17m

ORD9:44 pmChicago O'Hare Intl

Jun 2

ORD10:00 amChicago O'Hare Intl

2h 52m

SAT12:52 pmSan Antonio

$298

American Airlines

May 28

SAT6:27 pmSan Antonio

3h 17m

ORD9:44 pmChicago O'Hare Intl

Jun 3

ORD9:10 pmChicago O'Hare Intl

2h 51m

SAT12:01 amSan Antonio

$303

American Airlines

May 26

SAT6:04 amSan Antonio

2h 59m

ORD9:03 amChicago O'Hare Intl

Jun 2

ORD4:44 pmChicago O'Hare Intl

5h 16m

1 stop

SAT10:00 pmSan Antonio

$308

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 5/20

7:54 pm-8:32 pm

1 stop24h 38m

Chicago O'Hare Intl

Sun 5/24

9:37 pm-6:59 pm

1 stop21h 22m

$293

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Mon 5/18

7:54 pm-8:32 pm

1 stop24h 38m

Chicago O'Hare Intl

Tue 6/9

9:48 pm-6:56 pm

1 stop21h 08m

$296

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 5/20

6:49 am-9:45 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 5/26

8:03 pm-11:02 pm

Nonstop2h 59m

$297

Quickest round-trip

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 5/26

2:35 pm-5:10 pm

Nonstop2h 35m

Chicago Midway

Tue 6/2

9:00 pm-11:50 pm

Nonstop2h 50m

$297

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 5/26

6:27 pm-9:44 pm

Nonstop3h 17m

Chicago O'Hare Intl

Tue 6/2

10:00 am-12:52 pm

Nonstop2h 52m

$298

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 7/1

4:44 pm-11:59 pm

1 stop7h 15m

Chicago O'Hare Intl

Mon 7/13

9:57 pm-6:54 pm

1 stop20h 57m

$300

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 7/22

8:59 pm-5:28 am

1 stop8h 29m

Chicago O'Hare Intl

Mon 7/27

9:57 pm-6:54 pm

1 stop20h 57m

$301

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 5/27

7:54 pm-8:32 pm

1 stop24h 38m

Chicago O'Hare Intl

Sun 5/31

5:05 am-4:16 pm

1 stop11h 11m

$302

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Thu 5/28

6:27 pm-9:44 pm

Nonstop3h 17m

Chicago O'Hare Intl

Wed 6/3

9:10 pm-12:01 am

Nonstop2h 51m

$303

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 8/12

9:25 am-12:00 pm

Nonstop2h 35m

Chicago Midway

Tue 8/18

1:55 pm-5:55 pm

1 stop4h 00m

$303

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Layovers

Other information

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 $96. If you’re not able to fly to Chicago in August, then October is your next best option. Flight prices from San Antonio to Chicago during October average around $98.

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 $787.

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 $476. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $792.

What is the cheapest San Antonio to Chicago flight route?

Fly from San Antonio to Chicago Midway for the best San Antonio - Chicago flight prices

How far in advance should I book a flight from San Antonio 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 $387 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 $294 on momondo.

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

As of May 2026, prices for San Antonio to Chicago flights are approximately 160% 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	$221
Fastest flight time	2h 35m
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 $221. The best round-trip flight deal from San Antonio to Chicago found on momondo in the last 72 hours is $367.

The fastest flight from San Antonio to Chicago takes 2h 35m

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

Frequently asked questions about flying from San Antonio to Chicago

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?
The number of operators available for flights from San Antonio Airport to Chicago is 5 as of May 2026.
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?
Based on momondo bookings for flights between San Antonio and Chicago, the leading plane model is Boeing 737-800, making up 20.24% of the total bookings. Other popular models include Embraer 175 with 18.62%, Airbus A319 with 14.83%, and Boeing 737 MAX 8 with 12.30%.
What is the most popular airline from San Antonio to Chicago?
Based on momondo bookings for flights between San Antonio and Chicago, the leading airline is American Airlines, making up 39% of the total bookings. Other popular airlines include United Airlines with 27%, Southwest with 20%, and Frontier with 10%.

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
Frontier	PriceFrom $96	Free Cancellation	Rating 5.6 2,971 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $98	Free Cancellation	Rating 6.3 8,640 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $217	Free Cancellation	Rating 7.1 11,673 reviews	Search American Airlines flights
Southwest	PriceFrom $256	Free Cancellation	Rating 8.0 4,314 reviews	Search Southwest flights
United Airlines	PriceFrom $261	Free Cancellation	Rating 7.4 9,679 reviews	Search United Airlines flights

Southwest Flights From San Antonio to Chicago
Southwest operates around 11 flights from San Antonio to Chicago every week. The average price of these flights found in the last 72 hours has been $400, 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 4,314 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 $261, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $431 round-trip. United Airlines operates 14 flights out of San Antonio into Chicago in an average week, so prices vary by time and availability. 9,679 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

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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Cheap flights from San Antonio to Chicago from $145

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 7/26. 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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How to get the cheapest flight ticket from San Antonio to Chicago

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

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest San Antonio to Chicago flight route?

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

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

What is the cheapest airline that flies from San Antonio to Chicago?

What airlines fly to Chicago?

Which airport is the most popular layover for flights between San Antonio and Chicago?

Which layover airport offers the lowest fares from San Antonio to Chicago?

Which layover airport has the shortest travel time from San Antonio to Chicago?

Which layover airport has the shortest connection time from San Antonio to Chicago?

How many flights depart from San Antonio to Chicago on average per day?

How many flights depart from San Antonio to Chicago on average per week?

When to book flights from San Antonio to Chicago

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

Fastest flight time

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Airports in Chicago

Frequently asked questions about flying 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

Southwest Flights From San Antonio to Chicago

United Airlines Flights From San Antonio to Chicago

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An easier way to manage your Chicago trip

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Airports listed have a maximum distance of 78.5 mi from Chicago

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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