$119+ Cheap flights from San Antonio (SAT) to Midway (MDW)
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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Sep 16 — Sep 231
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from San Antonio to Midway 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.Cheap flight deals from San Antonio to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Antonio to MidwayExplore the most affordable flight options available from San Antonio to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
Explore the most affordable flight options available from San Antonio to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/17. 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 9/299:20 am -
1 stop7h 15m
Thu 10/19:20 pm -
Nonstop2h 45m
Deal found 8/17![Southwest logo]()
$267
This Faresmojo deal was found by Cheapflights users on 8/13. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:21 pm -
1 stop6h 23m
Fri 9/185:10 pm -
1 stop6h 58m
Deal found 8/13![JetBlue logo]()
$271
This Southwest deal was found by Cheapflights users on 8/15. 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 9/126:55 am -
2 stops6h 25m
Mon 9/148:35 pm -
Nonstop2h 45m
Deal found 8/15![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 11/29:15 am -
Nonstop2h 40m
Fri 11/62:35 pm -
2 stops7h 35m
Deal found 8/13![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 8/17. 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 9/298:00 am -
1 stop8h 15m
Thu 10/19:29 am -
1 stop6h 24m
Deal found 8/17![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/112:55 pm -
1 stop6h 05m
Mon 9/148:35 pm -
Nonstop2h 45m
Deal found 8/14![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 8/17. 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.
Fri 10/162:35 pm -
Nonstop2h 40m
Fri 10/239:20 pm -
Nonstop2h 45m
Deal found 8/17![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 10/2911:40 am -
1 stop5h 55m
Tue 11/33:45 pm -
2 stops5h 55m
Deal found 8/14![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 10/302:35 pm -
Nonstop2h 40m
Tue 11/33:45 pm -
2 stops5h 55m
Deal found 8/14![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 8/14. 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 10/2712:55 pm -
2 stops6h 30m
Mon 11/22:35 pm -
2 stops7h 35m
Deal found 8/14![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/14. 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 9/82:35 pm -
1 stop6h 15m
Fri 9/187:30 am -
1 stop6h 10m
Deal found 8/14![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/112:55 pm -
1 stop6h 05m
Fri 9/188:35 pm -
Nonstop2h 45m
Deal found 8/14![Southwest logo]()
$289
Best flights from San Antonio to MidwayDiscover carefully curated flight deals from San Antonio to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
Discover carefully curated flight deals from San Antonio to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 17, 2026.
This Delta deal was found by Cheapflights users on 8/16. 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 10/75:15 am -
1 stop7h 32m
Sat 10/1011:33 am -
1 stop8h 15m
Deal found 8/16![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/14. 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 9/512:55 pm -
1 stop6h 20m
Sat 9/129:05 am -
1 stop7h 45m
Deal found 8/14![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 12/1710:51 am -
1 stop5h 23m
Mon 12/215:59 pm -
1 stop5h 21m
Deal found 8/13![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 10/2211:40 am -
1 stop3h 50m
Fri 10/309:55 am -
2 stops5h 20m
Deal found 8/14![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 10/152:35 pm -
Nonstop2h 40m
Sat 10/176:20 pm -
Nonstop2h 45m
Deal found 8/12![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 8/16. 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.
Mon 11/25:30 am -
1 stop5h 13m
Thu 11/511:39 am -
1 stop5h 35m
Deal found 8/16![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 8/12. 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 9/2611:10 am -
Nonstop2h 35m
Sat 10/36:20 pm -
Nonstop2h 45m
Deal found 8/12![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 8/15. 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 9/126:55 am -
2 stops6h 25m
Mon 9/145:25 am -
1 stop5h 45m
Deal found 8/15![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 9/176:10 pm -
1 stop5h 40m
Mon 9/215:50 pm -
1 stop5h 10m
Deal found 8/14![Southwest logo]()
$389
Last-minute flights from San Antonio to MidwayDiscover last-minute flight deals from San Antonio to Midway. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Midway. Data last updated August 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/14. 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 9/512:55 pm -
1 stop6h 20m
Sat 9/1210:05 am -
2 stops5h 55m
Deal found 8/14![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/14. 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 9/82:35 pm -
1 stop6h 15m
Fri 9/187:30 am -
1 stop6h 10m
Deal found 8/14![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 9/105:00 am -
Nonstop2h 35m
Mon 9/148:35 pm -
Nonstop2h 45m
Deal found 8/14![Southwest logo]()
$303
This Faresmojo deal was found by Cheapflights users on 8/13. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:21 pm -
1 stop6h 23m
Fri 9/185:10 pm -
1 stop6h 58m
Deal found 8/13![JetBlue logo]()
$271
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/112:55 pm -
1 stop6h 05m
Mon 9/148:35 pm -
Nonstop2h 45m
Deal found 8/14![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 8/14. 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.
Fri 9/112:55 pm -
1 stop6h 05m
Fri 9/188:35 pm -
Nonstop2h 45m
Deal found 8/14![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 8/15. 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 9/126:55 am -
2 stops6h 25m
Mon 9/148:35 pm -
Nonstop2h 45m
Deal found 8/15![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/13. 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 9/1511:40 am -
1 stop5h 20m
Fri 9/185:30 am -
1 stop5h 05m
Deal found 8/13![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 8/14. 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 9/1511:40 am -
1 stop5h 20m
Sat 9/1910:05 am -
2 stops5h 55m
Deal found 8/14![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 8/17. 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 9/299:20 am -
1 stop7h 15m
Thu 10/19:20 pm -
Nonstop2h 45m
Deal found 8/17![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 8/17. 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 9/298:00 am -
1 stop8h 15m
Thu 10/19:29 am -
1 stop6h 24m
Deal found 8/17![Delta logo]()
$277
One-way flights from San Antonio to MidwaySearch for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
Search for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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.
Wed 9/92:50 pm -
Nonstop2h 35m
Deal found 8/13![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 8/14. 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 10/1312:55 pm -
2 stops6h 30m
Deal found 8/14![Southwest logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:19 pm -
2 stops26h 32m
Deal found 8/13![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:03 am -
2 stops13h 40m
Deal found 8/14![Frontier logo]()
$137
This Delta deal was found by Cheapflights users on 8/17. 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 9/1611:36 am -
1 stop6h 57m
Deal found 8/17![Delta logo]()
$139
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 9/105:00 am -
Nonstop2h 35m
Deal found 8/17![Southwest logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:34 pm -
2 stops25h 09m
Deal found 8/13![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:08 am -
2 stops23h 50m
Deal found 8/13![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:50 pm -
2 stops19h 56m
Deal found 8/13![Frontier logo]()
$146
Find flight deals from San Antonio to Midway
Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Midway (MDW). 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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $271 (Faresmojo) |
One-way from | $119 (Southwest) |
Popular in | March |
Cheapest in | February |
Average price | $472 |
Good round-trip deal | $350 or less |
Good one-way deal | $285 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Antonio to Midway 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 August 17, 2026.
Use the filters below to find and compare flights from San Antonio to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Wed 10/7
5:15 am-12:47 pm
1 stop7h 32m
Chicago Midway
Sat 10/10
11:33 am-7:48 pm
1 stop8h 15m
$277
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 9/5
12:55 pm-7:15 pm
1 stop6h 20m
Chicago Midway
Sat 9/12
9:05 am-4:50 pm
1 stop7h 45m
$277
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 12/17
10:51 am-4:14 pm
1 stop5h 23m
Chicago Midway
Mon 12/21
5:59 pm-11:20 pm
1 stop5h 21m
$292
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 10/22
11:40 am-3:30 pm
1 stop3h 50m
Chicago Midway
Fri 10/30
9:55 am-3:15 pm
2 stops5h 20m
$293
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 10/15
2:35 pm-5:15 pm
Nonstop2h 40m
Chicago Midway
Sat 10/17
6:20 pm-9:05 pm
Nonstop2h 45m
$307
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Mon 11/2
5:30 am-10:43 am
1 stop5h 13m
Chicago Midway
Thu 11/5
11:39 am-5:14 pm
1 stop5h 35m
$308
Quickest round-trip
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 9/26
11:10 am-1:45 pm
Nonstop2h 35m
Chicago Midway
Sat 10/3
6:20 pm-9:05 pm
Nonstop2h 45m
$327
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 9/12
6:55 am-1:20 pm
2 stops6h 25m
Chicago Midway
Mon 9/14
5:25 am-11:10 am
1 stop5h 45m
$338
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 9/17
6:10 pm-11:50 pm
1 stop5h 40m
Chicago Midway
Mon 9/21
5:50 pm-11:00 pm
1 stop5h 10m
$389
Cheapest one-way
Quickest one-way
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Wed 9/9
2:50 pm-5:25 pm
Nonstop2h 35m
$119
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from San Antonio to Midway
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 Midway in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on San Antonio-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Antonio-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from San Antonio to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from San Antonio with our price prediction graph.
SAT-MDW
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 Midway Airport
What is the cheapest time of day to fly from SAT to MDW?
Find hourly flight availability from San Antonio to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 17, 2026.
It’s typically best to fly out from San Antonio to Chicago Midway Airport in the evening. Doing so could potentially save you 41% on the flight price compared to flying in the afternoon, which is usually more expensive.
How much does it cost to fly round-trip from San Antonio to Chicago Midway Airport?
Airfare is below average for this route at the moment.
San Antonio to Chicago Midway Airport flights typically cost between $370 and $705 in September.The cheapest round-trip price found within the last 5 days was $271 on JetBlue (Sep 11-Sep 18).
The best insider tips for San Antonio to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Antonio to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated August 17, 2026.
Read reviews from past customers who have flown Southwest from San Antonio to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Antonio to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from San Antonio
Popular flights
Alternative routes for San Antonio to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Antonio to Midway by cabin class
Find flights from San Antonio to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
San Antonio and Midway flights
Browse other San Antonio and Midway flight options. Last updated on August 17, 2026.
Other flights from San Antonio
Browse through other flights departing from San Antonio. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from San Antonio to Midway
Discover the top airline that operate flights from San Antonio to Midway. 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 August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$456 | FlexibilityNo cancel fee | On-time63% |