$109 Cheap Flights from San Antonio (SAT) to Chicago (ORD)

View $109 flight on Sat, Aug 8, 2026Opens in a new window

Popular airlines from San Antonio International Airport (SAT) to Chicago O'Hare Intl. Airport (ORD)

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

Prices were available within the past 7 days and start at $109 for one-way flights and $190 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Jun 17 - Wed, Jun 24
SAT
San Antonio
ORD
Chicago
$190 Roundtrip, found 21 hours ago
$190
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Jun 17 from San Antonio to Chicago, returning Wed, Jun 24, priced at $190 found 21 hours ago
Frontier Airlines
Tue, Jul 21 - Tue, Aug 4
SAT
San Antonio
ORD
Chicago
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from San Antonio to Chicago, returning Tue, Aug 4, priced at $200 found 2 days ago
Frontier Airlines
Mon, Jun 29 - Tue, Jun 30
SAT
San Antonio
ORD
Chicago
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jun 29 from San Antonio to Chicago, returning Tue, Jun 30, priced at $209 found 1 day ago
Frontier Airlines
Sun, Aug 2 - Wed, Aug 12
SAT
San Antonio
ORD
Chicago
$210 Roundtrip, found 23 hours ago
$210
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sun, Aug 2 from San Antonio to Chicago, returning Wed, Aug 12, priced at $210 found 23 hours ago
Frontier Airlines
Tue, Jul 21 - Sat, Aug 8
SAT
San Antonio
ORD
Chicago
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from San Antonio to Chicago, returning Sat, Aug 8, priced at $214 found 2 days ago
Frontier Airlines
Fri, Jul 17 - Tue, Aug 4
SAT
San Antonio
ORD
Chicago
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jul 17 from San Antonio to Chicago, returning Tue, Aug 4, priced at $220 found 2 days ago
United
Wed, Aug 5 - Wed, Aug 12
SAT
San Antonio
ORD
Chicago
$253 Roundtrip, found 4 hours ago
$253
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Aug 5 from San Antonio to Chicago, returning Wed, Aug 12, priced at $253 found 4 hours ago
American Airlines
Tue, Jun 9 - Wed, Jun 17
SAT
San Antonio
ORD
Chicago
$305 Roundtrip, just found
$305
Roundtrip
just found
Select American Airlines flight, departing Tue, Jun 9 from San Antonio to Chicago, returning Wed, Jun 17, priced at $305 just found
Delta
Tue, Jun 9 - Wed, Jun 17
SAT
San Antonio
ORD
Chicago
$325 Roundtrip, just found
$325
Roundtrip
just found
Select Delta flight, departing Tue, Jun 9 from San Antonio to Chicago, returning Wed, Jun 17, priced at $325 just found
Southwest Airlines
Thu, May 28 - Fri, May 29
SAT
San Antonio
ORD
Chicago
$387 Roundtrip, just found
$387
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, May 28 from San Antonio to Chicago, returning Fri, May 29, priced at $387 just found

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $553
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $553

Frequently asked questions

How much does a flight from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $109 and cheap return flights from $190 San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $177 to $759, and return flights typically cost between $333 and $1393. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from SAT to ORD is June when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
2 airlines operate nonstop service from SAT to ORD:

  • American Airlines operates around 34 direct flights from SAT to ORD every week
  • United operates around 22 direct flights from SAT to ORD every week

What is the cheapest airline that flies from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering nonstop flights from San Antonio (SAT) to Chicago (ORD) with tickets starting from around $364. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from San Antonio, TX (SAT) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. American Airlines also offers the most daily flights from SAT to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can find approximately 8 nonstop flights per day from San Antonio Intl. (SAT) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from San Antonio International Airport (SAT) to O'Hare International Airport (ORD) typically leaves at around 5:00 AM, operated by American Airlines. An early departure like this allows you to make the most of your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the early morning, from 6am to 9am. About 31% of passengers prefer this time window. Major carriers like American Airlines and United Airlines offer flights during this window. This timing works well for travelers looking to maximize their day in Chicago upon arrival.
How long does it take to fly from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from SAT to ORD usually take about 3 hours, traveling roughly 1,043 miles. If you opt for a connecting flight, expect to add around 4 hours 20 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
First class seats are offered on the SAT to ORD route. First class cabins are available on:

  • Delta Air Lines
  • American Airlines
  • United Airlines
  • Spirit Airlines

How much is a business class flight from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from San Antonio, TX (SAT) to Chicago, IL (ORD) typically costs between $795 - $1,139. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from San Antonio Intl. (SAT)?
From San Antonio Intl. (SAT), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Love Field (DAL), William P. Hobby (HOU), Baltimore Washington Intl. Thurgood Marshall (BWI) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your San Antonio, TX (SAT-San Antonio Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
San Antonio Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Southwest Airlines, United
Roundtrip price
$190
Distance
1042 mi
Average flight time
3 hours 13 mins

Book with confidence

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 June. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $109 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.

 

San Antonio to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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