$133+ Cheap flights from San Antonio (SAT) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Nov 1 — Nov 81
Round-trip
1 adult, Economy
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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
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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
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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 October 2, 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 October 2, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/71:32 pm -
1 stop7h 10m
Thu 12/178:07 pm -
1 stop24h 05m
Deal found 9/30![Frontier logo]()
$281
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:06 pm -
1 stop7h 41m
Sun 11/298:42 pm -
1 stop14h 29m
Deal found 9/29![Frontier logo]()
$324
This Cheapflightsfares deal was found by Cheapflights users on 9/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/289:07 pm -
1 stop21h 55m
Thu 12/318:07 pm -
1 stop24h 05m
Deal found 9/30![Frontier logo]()
$335
This Southwest deal was found by Cheapflights users on 9/29. 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 10/292:35 pm -
Nonstop2h 40m
Mon 11/29:30 pm -
Nonstop2h 50m
Deal found 9/29![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/30. 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 10/226:45 pm -
1 stop5h 35m
Mon 10/269:20 pm -
Nonstop2h 50m
Deal found 9/30![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 9/30. 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
Tue 10/278:45 pm -
Nonstop2h 50m
Deal found 9/30![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/30. 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 10/307:55 pm -
1 stop5h 15m
Tue 11/38:50 pm -
Nonstop2h 50m
Deal found 9/30![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 9/29. 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 9/29![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 9/30. 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.
Fri 10/305:30 am -
1 stop6h 24m
Mon 11/211:38 am -
1 stop8h 10m
Deal found 9/30![Delta logo]()
$370
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 October 2, 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 October 2, 2026.
This Southwest deal was found by Cheapflights users on 9/27. 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 11/119:50 am -
Nonstop2h 30m
Wed 11/188:50 pm -
Nonstop2h 55m
Deal found 9/27![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 10/1. 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.
Sat 11/215:10 pm -
1 stop5h 44m
Thu 11/266:00 am -
1 stop6h 39m
Deal found 10/1![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 9/28. 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 10/222:35 pm -
Nonstop2h 40m
Mon 10/269:20 pm -
Nonstop2h 50m
Deal found 9/28![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 10/1. 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 12/3011:47 am -
1 stop5h 57m
Wed 1/65:25 pm -
1 stop7h 03m
Deal found 10/1![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 9/27. 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 10/276:50 am -
1 stop4h 35m
Thu 10/299:45 am -
Nonstop2h 45m
Deal found 9/27![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 9/29. 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 10/295:15 am -
1 stop7h 32m
Mon 11/211:38 am -
1 stop8h 10m
Deal found 9/29![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 10/2. 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 12/152:40 pm -
Nonstop2h 35m
Wed 12/163:45 pm -
2 stops5h 55m
Deal found 10/2![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/29. 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 2/105:55 am -
1 stop5h 55m
Mon 2/155:10 pm -
1 stop7h 00m
Deal found 9/29![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 9/27. 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.
Fri 10/2311:36 am -
1 stop6h 24m
Tue 10/275:09 pm -
1 stop7h 24m
Deal found 9/27![Delta logo]()
$398
This Southwest deal was found by Cheapflights users on 9/29. 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 11/76:35 am -
2 stops7h 55m
Wed 11/117:05 am -
1 stop6h 10m
Deal found 9/29![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 9/30. 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 11/164:35 pm -
1 stop6h 35m
Thu 11/1910:15 am -
2 stops7h 25m
Deal found 9/30![Southwest logo]()
$402
Last-minute flights from San Antonio to MidwayDiscover last-minute flight deals from San Antonio to Midway. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Antonio to Midway. Data last updated October 2, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/30. 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 10/226:45 pm -
1 stop5h 35m
Mon 10/269:20 pm -
Nonstop2h 50m
Deal found 9/30![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 9/30. 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
Tue 10/278:45 pm -
Nonstop2h 50m
Deal found 9/30![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/29. 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 9/29![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 9/27. 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 10/278:55 am -
Nonstop2h 40m
Thu 10/299:20 pm -
Nonstop2h 50m
Deal found 9/27![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 9/29. 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 10/292:35 pm -
Nonstop2h 40m
Mon 11/29:30 pm -
Nonstop2h 50m
Deal found 9/29![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/30. 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 10/307:55 pm -
1 stop5h 15m
Tue 11/38:50 pm -
Nonstop2h 50m
Deal found 9/30![Southwest logo]()
$360
This Delta deal was found by Cheapflights users on 9/30. 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.
Fri 10/305:30 am -
1 stop6h 24m
Mon 11/211:38 am -
1 stop8h 10m
Deal found 9/30![Delta logo]()
$370
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:06 pm -
1 stop7h 41m
Sun 11/298:42 pm -
1 stop14h 29m
Deal found 9/29![Frontier logo]()
$324
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 October 2, 2026.
Search for one-way flight options from San Antonio to Midway. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This Trip.com deal was found by Cheapflights users on 9/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/71:32 pm -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 9/29. 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.
Wed 11/2512:06 pm -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/208:21 pm -
2 stops39h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$141
This Priceline deal was found by Cheapflights users on 9/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:32 pm -
1 stop7h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/2710:29 pm -
2 stops49h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/2610:34 pm -
2 stops49h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 10/288:20 pm -
2 stops21h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$151
This Jetabroad deal was found by Cheapflights users on 10/1. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2711:55 am -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Sat 10/318:20 pm -
2 stops40h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 11/28:20 pm -
2 stops21h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 9/29. 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 10/288:55 am -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Fri 10/3010:29 pm -
2 stops19h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$170
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 October 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Cheapflightsfares) |
One-way from | $133 (Trip.com) |
Popular in | November |
Cheapest in | February |
Average price | $444 |
Good round-trip deal | $388 or less |
Good one-way deal | $227 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 7,457,451 searches. Data last updated October 2, 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 10/28
8:55 am-11:35 am
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 10/31
9:30 am-12:10 pm
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 10/29
2:35 pm-5:15 pm
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 10/22
5:15 am-12:47 pm
1 stop7h 32m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 11/26
5:30 am-11:25 am
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 1/30
4:25 pm-10:10 pm
1 stop5h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Mon 10/26
7:55 pm-1:10 am
1 stop5h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 12/31
11:47 am-5:44 pm
1 stop5h 57m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 10/27
2:25 pm-5:05 pm
Nonstop2h 40m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$182
Quickest round-trip
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 11/7
7:00 am-9:35 am
Nonstop2h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$182
Showing 1-10 of 22 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 October.
| 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 October 2, 2026.
It’s typically best to fly out from San Antonio to Chicago Midway Airport in the evening. Doing so could potentially save you 46% 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 $377 and $598 in December.The cheapest round-trip price found within the last 5 days was $281 on Frontier (Dec 7-Dec 17).
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 October 2, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
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
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Alternative routes for San Antonio to Midway
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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 7,457,451 searches. Data last updated October 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$313 | Average$481 | FlexibilityNo cancel fee | On-time63% |