$55 Cheap Flights from San Antonio (SAT) to Chicago (CHI)

View $55 flight on Mon, Dec 8, 2025Opens in a new window

Popular airlines from San Antonio International Airport (SAT) to Chicago

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

Prices were available within the past 7 days and start at $55 for one-way flights and $110 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Nov 15 - Thu, Nov 20
SAT
San Antonio
ORD
Chicago
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 15 from San Antonio to Chicago, returning Thu, Nov 20, priced at $110 just found
Frontier Airlines
Sat, Nov 15 - Tue, Nov 18
SAT
San Antonio
ORD
Chicago
$119 Roundtrip, found 2 hours ago
$119
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from San Antonio to Chicago, returning Tue, Nov 18, priced at $119 found 2 hours ago
Frontier Airlines
Sat, Nov 15 - Mon, Nov 17
SAT
San Antonio
ORD
Chicago
$120 Roundtrip, found 2 hours ago
$120
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from San Antonio to Chicago, returning Mon, Nov 17, priced at $120 found 2 hours ago
Frontier Airlines
Sat, Nov 15 - Wed, Nov 19
SAT
San Antonio
ORD
Chicago
$124 Roundtrip, found 2 hours ago
$124
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from San Antonio to Chicago, returning Wed, Nov 19, priced at $124 found 2 hours ago
Frontier Airlines
Thu, Nov 13 - Wed, Nov 19
SAT
San Antonio
ORD
Chicago
$124 Roundtrip, found 23 hours ago
$124
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from San Antonio to Chicago, returning Wed, Nov 19, priced at $124 found 23 hours ago
Frontier Airlines
Sat, Nov 15 - Thu, Nov 20
SAT
San Antonio
ORD
Chicago
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 15 from San Antonio to Chicago, returning Thu, Nov 20, priced at $130 just found
Spirit Airlines
Thu, Dec 4 - Thu, Dec 11
SAT
San Antonio
ORD
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Dec 4 from San Antonio to Chicago, returning Thu, Dec 11, priced at $137 just found
American Airlines
Sat, Dec 13 - Sun, Dec 14
SAT
San Antonio
RFD
Rockford
$163 Roundtrip, found 4 days ago
$163
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Dec 13 from San Antonio to Rockford, returning Sun, Dec 14, priced at $163 found 4 days ago
Southwest Airlines
Wed, Feb 18 - Sat, Feb 21
SAT
San Antonio
MDW
Chicago
$195 Roundtrip, found 4 days ago
$195
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Feb 18 from San Antonio to Chicago, returning Sat, Feb 21, priced at $195 found 4 days ago
Delta
Tue, Dec 9 - Tue, Dec 30
SAT
San Antonio
MDW
Chicago
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Dec 9 from San Antonio to Chicago, returning Tue, Dec 30, priced at $197 found 4 days ago

Find the cheapest month to fly from San Antonio (SAT) to Chicago (CHI)

February is typically the cheapest month to fly

From $120 - $356 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $230
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $230
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $445
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $445
Select flight to Greater Rockford RFD. Average driving time to city center is 1 hour 30 minutes. Flights from $424
RFD
Greater Rockford
Average driving time to city center1 h 30 min
Flights from $424
Flights from San Antonio (SAT) to Chicago (ORD)
Origin airport
San Antonio Intl.
Destination airport
O'Hare Intl.
Roundtrip price
$110
Distance
1042 mi

San Antonio to Chicago Flights

The cheapest times to fly from San Antonio to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Antonio to Chicago are during the month of November. You can find some of the cheapest flights from San Antonio to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Antonio to Chicago

Sunday is one of the best days to book for cheap flights from San Antonio to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Antonio to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Antonio to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $55 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Antonio to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Antonio to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much is a flight from San Antonio Airport to Chicago, IL (CHI-All Airports)?
Pack your bags, because round-trip flights from San Antonio Airport to Chicago, IL (CHI-All Airports) start from $110. That's based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book today to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from SAT to Chicago, IL (CHI-All Airports)?
This varies from airline to airline, as each one has its own set of terms and conditions. Head to the Customer Service Portal, where you'll find easy instructions on how to cancel online.
How do I find cheap flights from San Antonio Airport to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for San Antonio Airport to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from San Antonio Intl. Airport (SAT) to Chicago, IL (CHI-All Airports)?
The flight distance from San Antonio Intl. Airport (SAT) to Chicago, IL (CHI-All Airports) is 1025 mi. Pack yourself a drink, some snacks and a good movie. Keep yourself entertained and the hours will fly by.
Which airlines fly direct from San Antonio Airport to Chicago, IL (CHI-All Airports)?
United Airlines (UA) is one of the preferred choices for many travelers flying between SAT and Chicago, IL (CHI-All Airports). Choose from the 91 flights it offers on this route each month. If you'd like more options, have a look at the ticket prices from Southwest Airlines (WN). This airlines operates 60 monthly flights between these airports.
Are San Antonio Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
It is possible to pick up an amazing last-minute deal from San Antonio Airport to Chicago, IL (CHI-All Airports), but it can also be hit-or-miss. As many airlines release seats up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can feel confident knowing you're always seeing the latest offers.

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*Available to One Key members.