Basic Economy allows a personal item only; no carry-on bags permitted.
Prepay checked bags 24 hours before to save on fees.
$103+ Cheap flights from San Antonio (SAT) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
May 17 — May 241
1 adult, Economy
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Find cheap flights from San Antonio to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Antonio to Chicago are usually found in August or September, booked 70 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from San Antonio to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 12, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $217 (Mytrip) |
One-way from | $103 (Cheapflightsfares) |
Popular in | March |
Cheapest in | August |
Average price | $378 |
Good round-trip deal | $337 or less |
Good one-way deal | $223 or less |
Find flight deals from San Antonio to Chicago
Cheapest flights from San Antonio to ChicagoExplore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2025.
Explore the most affordable flight options available from San Antonio to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2025.
This Mytrip deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/301:27 pmSAT - ORD
2 stops34h 02mSpirit Airlines
Tue 6/39:55 amORD - SAT
2 stops19h 09mSpirit Airlines
Deal found 5/11![Spirit Airlines logo]()
$217
This CheapOair deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:36 pmSAT - ORD
1 stop28h 16mMultiple Airlines
Sat 5/319:02 pmORD - SAT
1 stop8h 02mMultiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$220
This FlightHub deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/16:59 pmSAT - ORD
1 stop29h 00mFrontier
Mon 9/16:00 amORD - SAT
1 stop13h 31mFrontier
Deal found 5/12![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:38 pmSAT - MDW
1 stop5h 40mFrontier
Mon 6/96:30 amMDW - SAT
1 stop10h 13mFrontier
Deal found 5/12![Frontier logo]()
$230
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/245:38 pmSAT - RFD
2 stops25h 41mMultiple Airlines
Sun 7/279:21 amRFD - SAT
1 stop7h 12mMultiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$270
This American Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/16:32 amSAT - ORD
1 stop7h 13mAmerican Airlines
Tue 7/14:40 pmORD - SAT
Nonstop2h 44mAmerican Airlines
Deal found 5/12![American Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/105:35 pmSAT - MDW
Nonstop2h 40mSouthwest
Tue 6/178:30 amMDW - SAT
Nonstop2h 50mSouthwest
Deal found 5/11![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:45 amSAT - ORD
Nonstop2h 59mUnited Airlines
Thu 5/297:10 amORD - SAT
1 stop5h 54mUnited Airlines
Deal found 5/11![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/105:20 amSAT - MDW
1 stop7h 09mDelta
Wed 6/189:24 amMDW - SAT
1 stop6h 12mDelta
Deal found 5/11![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/611:25 amSAT - ORD
1 stop5h 08mDelta
Mon 8/113:50 pmORD - SAT
1 stop5h 19mDelta
Deal found 5/12![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/135:45 amSAT - ORD
2 stops8h 40mSouthwest
Thu 9/185:45 pmORD - SAT
1 stop5h 10mSouthwest
Deal found 5/12![Southwest logo]()
$338
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/32:11 pmSAT - MDW
2 stops23h 53mMultiple Airlines
Mon 7/710:31 amMDW - SAT
2 stops26h 35mMultiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$371
Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated May 12, 2025.
Use the filters below to find and compare flights from San Antonio to Chicago that are best for you.
Fly from
San Antonio
Fly to
Chicago
Route
Depart
Return
Price
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Fri 5/30
1:27 pm-11:29 pm
2 stops34h 02m
Chicago O'Hare Intl
Tue 6/3
9:55 am-5:04 am
2 stops19h 09m
$217
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Sat 5/24
7:36 pm-11:52 pm
1 stop28h 16m
Chicago O'Hare Intl
Sat 5/31
9:02 pm-5:04 am
1 stop8h 02m
$220
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Tue 7/1
6:59 pm-11:59 pm
1 stop29h 00m
Chicago O'Hare Intl
Mon 9/1
6:00 am-7:31 pm
1 stop13h 31m
$230
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 6/6
5:38 pm-11:18 pm
1 stop5h 40m
Chicago Midway
Mon 6/9
6:30 am-4:43 pm
1 stop10h 13m
$230
San AntonioChicago
SAT - RFD
SATRFD
San Antonio
Thu 7/24
5:38 pm-7:19 pm
2 stops25h 41m
Chicago Greater Rockford
Sun 7/27
9:21 am-4:33 pm
1 stop7h 12m
$270
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Tue 7/1
6:32 am-1:45 pm
1 stop7h 13m
Chicago O'Hare Intl
Tue 7/1
4:40 pm-7:24 pm
Nonstop2h 44m
$272
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Tue 6/10
5:35 pm-8:15 pm
Nonstop2h 40m
Chicago Midway
Tue 6/17
8:30 am-11:20 am
Nonstop2h 50m
$297
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Wed 5/28
6:45 am-9:44 am
Nonstop2h 59m
Chicago O'Hare Intl
Thu 5/29
7:10 am-1:04 pm
1 stop5h 54m
$303
San AntonioChicago
SAT - MDW
SATMDW
San Antonio
Fri 5/30
6:25 am-1:15 pm
1 stop6h 50m
Chicago Midway
Fri 5/30
6:31 pm-12:28 am
1 stop5h 57m
$317
San AntonioChicago
SAT - ORD
SATORD
San Antonio
Wed 8/6
11:25 am-4:33 pm
1 stop5h 08m
Chicago O'Hare Intl
Mon 8/11
3:50 pm-9:09 pm
1 stop5h 19m
$325
Showing 1-10 of 24 results
Compare providers for flights from San Antonio to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Antonio to Chicago in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Antonio-Chicago flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on San Antonio-Chicago flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Antonio-Chicago flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Antonio-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
The best insider tips for San Antonio to Chicago flights
Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your San Antonio to Chicago trip
Airlines
![United Airlines]()
United Airlines
![Southwest]()
Southwest
Enjoy free snacks and non-alcoholic drinks, plus in-flight entertainment on your device.
Two free checked bags included, even oversized items like skis or golf clubs.
Airports
Our travel experts
Best time to book a flight from San Antonio to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Antonio with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Antonio to Chicago
How far ahead should I book a flight from San Antonio to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San Antonio to Chicago. Price data was last updated on May 9, 2025.
To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 70 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from San Antonio to Chicago?
Currently, August is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $245). Flying from San Antonio to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SAT to CHI?
Find hourly flight availability from San Antonio to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 12, 2025.
When flying from San Antonio to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 67% versus a flight at noon.
What is the cheapest day to fly from San Antonio to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Antonio to Chicago. Price data was last updated on May 11, 2025.
Travelers seeking maximum savings on their San Antonio to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from San Antonio to Chicago
Explore weekly flight availability from San Antonio to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 12, 2025.
The most flights from SAT to CHI are scheduled on a Monday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 12, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from San Antonio to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.1
Comfort
7.9
Boarding
8.1
Overall
8.0
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Food
7.1
Comfort
7.9
Boarding
8.1
Overall
8.0
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Food
7.1
Comfort
7.9
Boarding
8.1
Overall
8.0
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Food
7.1
Comfort
7.9
Boarding
8.1
Overall
8.0
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Food
7.1
Comfort
7.9
Boarding
8.1
Overall
8.0
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Crew
8.5
Food
7.1
Comfort
7.9
Boarding
8.1
Overall
8.0
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Related info for your journey
Find useful and relevant information for your journey from San Antonio to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near San Antonio?
Book flights to San Antonio if you plan to visit one of these locationsMerrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
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Alternative routes for San Antonio to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from San Antonio to Chicago
Discover the top 6 airlines that operate flights from San Antonio to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$111 | Average$250 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$114 | Average$189 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$222 | Average$427 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$253 | Average$390 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$287 | Average$468 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$301 | Average$437 | FlexibilityNo cancel fee | On-timeN/A |