SAT - MDW

$143 Find Cheap Flights from San Antonio to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Antonio to Midway departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$285
Typical prices: $160-$435
Southwest
Tue 9/15Tue 9/22
SAT - MDW • Non-stop
Cheapest one-way
$143
Typical prices: $147-$278
Southwest
Wed 9/30
SAT - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $277 (round-trip)
Dallas (DAL)
Shortest trip • 5h 10m (one-way)
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 100% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from San Antonio to Midway (SAT-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Antonio to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Antonio to Midway

Tue, Sep 15 - Tue, Sep 22
Southwest Logo
9:25 am - 12:00 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
SAT
2h 45mnonstop
$285Southwest
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
9:25 am - 12:00 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
SAT
2h 45mnonstop
$285Southwest
Tue, Sep 1 - Wed, Sep 9
Southwest Logo
2:50 pm - 5:25 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
SAT
2h 45mnonstop
$285Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
2:50 pm - 5:25 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
SAT
2h 45mnonstop
$285Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
2:50 pm - 5:25 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
10:10 am - 12:50 pm
MDW
-
SAT
2h 40mnonstop
$285Southwest
Mon, Sep 28 - Tue, Sep 29
Southwest Logo
5:00 am - 7:35 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
SAT
2h 45mnonstop
$291Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
2:50 pm - 5:25 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
1:55 pm - 5:55 pm
MDW
-
SAT
4h 00m
1 stop
$291Southwest
Tue, Sep 1 - Wed, Sep 9
Southwest Logo
9:25 am - 12:00 pm
SAT
-
MDW
2h 35mnonstop
Southwest Logo
1:55 pm - 5:55 pm
MDW
-
SAT
4h 00m
1 stop
$291Southwest
Wed, Dec 16 - Mon, Dec 21
Delta Logo
6:40 am - 11:50 am
SAT
-
MDW
5h 10m
1 stop
Delta Logo
5:59 pm - 11:20 pm
MDW
-
SAT
5h 21m
1 stop
$311Delta
Tue, Dec 15 - Mon, Dec 21
Delta Logo
6:40 am - 11:50 am
SAT
-
MDW
5h 10m
1 stop
Delta Logo
5:59 pm - 11:20 pm
MDW
-
SAT
5h 21m
1 stop
$311Delta
Booking Insights

KAYAK's insights & trends for San Antonio to Midway flights

Get data-powered insights and trends into flights from San Antonio to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from San Antonio to Chicago Midway Airport?

The average price of all round-trip flights from San Antonio to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from San Antonio to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Tuesday is the cheapest day to fly and Monday is the most expensive.

What is the cheapest month to fly from San Antonio to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Antonio to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Antonio to Chicago Midway Airport is April, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $550 and $529 respectively.

Can I save money by flying with a layover from San Antonio to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $376 on average.

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Expert advice

Expert advice for your flight from San Antonio to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Brandon Schultz

Brandon Schultz

Expert on SAT

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Good to know

Low season

February

Cheapest flight

$143
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from San Antonio to Chicago Midway Airport

When to book flights from San Antonio to Midway

Are your dates flexible? Find out the best times to travel from San Antonio to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking San Antonio to Chicago Midway Airport flights

  • What is the cheapest flight from San Antonio to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from San Antonio to Chicago Midway Airport was $143 for a one-way ticket and $285 for a round-trip.

  • Do I need a passport to fly between San Antonio and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from San Antonio to Chicago Midway Airport?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the San Antonio to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from San Antonio to Chicago Midway Airport?

    The Airbus A319 is the aircraft model that flies most regularly on the San Antonio to Chicago Midway Airport flight route.

  • On which days can I fly direct from San Antonio to Chicago Midway Airport?

    There are nonstop flights from San Antonio to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from San Antonio to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Antonio to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Antonio to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Antonio is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Antonio to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to San Antonio with another airline. Booking your flights between San Antonio and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Antonio to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from San Antonio up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from San Antonio to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $285 or less one-way and $328 or less round-trip.

Prefer to fly direct from San Antonio to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San Antonio to Chicago Midway.
Find which airlines fly direct from San Antonio Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

San Antonio to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to San Antonio

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Everything you need to know for your flight from San Antonio to Midway

Information on your arrival and departure airports

San Antonio (SAT)
Midway (MDW)