MDW - SAT

$104 Find Cheap Flights from Chicago Midway Airport to San Antonio - Compare and Save

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Everything you should know

Cheapest round-trip
$316
Typical prices: $333-$497
Southwest
Mon 11/26Mon 12/10
MDW - SAT • 2 stops
Cheapest non-stop
$324
Typical prices: $355-$517
Southwest
Sat 12/15Sat 1/6
MDW - SAT • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 55m
Direct flights
+1
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 13% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $152 (round-trip)
Shortest trip • 4h 23m (one-way)
Insights
Insights
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We hope you love your trip to San Antonio!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Antonio

Thu, Nov 26 - Thu, Dec 10
Southwest Logo
10:10 am - 4:35 pmMDW  Chicago Midway-SAT San Antonio
6h 25m2 stops Oklahoma City Will Rogers World Houston Hobby
Southwest Logo
2:50 pm - 8:25 pmSAT  San Antonio-MDW Chicago Midway
5h 35m1 stop Atlanta Hartsfield-Jackson
$316Southwest
Fri, Nov 20 - Thu, Nov 26
Southwest Logo
9:30 pm - 12:25 amMDW  Chicago Midway-SAT San Antonio
2h 55mnonstop
Southwest Logo
12:05 pm - 4:05 pmSAT  San Antonio-MDW Chicago Midway
4h 00m1 stop Dallas Love Field
$321Southwest
Fri, Nov 20 - Thu, Nov 26
Southwest Logo
9:30 pm - 12:25 amMDW  Chicago Midway-SAT San Antonio
2h 55mnonstop
Southwest Logo
10:50 am - 4:05 pmSAT  San Antonio-MDW Chicago Midway
5h 15m1 stop Dallas Love Field
$321Southwest
Tue, Dec 15 - Wed, Jan 6
Southwest Logo
8:50 pm - 11:45 pmMDW  Chicago Midway-SAT San Antonio
2h 55mnonstop
Southwest Logo
1:55 pm - 4:40 pmSAT  San Antonio-MDW Chicago Midway
2h 45mnonstop
$324Southwest
Wed, Dec 9 - Fri, Dec 11
Delta Logo
11:28 am - 7:59 pmMDW  Chicago Midway-SAT San Antonio
8h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:16 am - 12:04 pmSAT  San Antonio-MDW Chicago Midway
6h 48m1 stop Atlanta Hartsfield-Jackson
$331Delta
Tue, Nov 24 - Mon, Nov 30
Frontier Logo
8:42 pm - 11:11 amMDW  Chicago Midway-SAT San Antonio
14h 29m1 stop Orlando
Frontier Logo
12:06 pm - 7:47 pmSAT  San Antonio-MDW Chicago Midway
7h 41m1 stop Orlando
$333Frontier
Tue, Nov 24 - Fri, Nov 27
Frontier Logo
8:42 pm - 11:11 amMDW  Chicago Midway-SAT San Antonio
14h 29m1 stop Orlando
Frontier Logo
12:06 pm - 7:47 pmSAT  San Antonio-MDW Chicago Midway
7h 41m1 stop Orlando
$334Frontier
Mon, Nov 23 - Tue, Dec 1
Frontier Logo
8:42 pm - 9:16 pmMDW  Chicago Midway-SAT San Antonio
24h 34m2 stops Orlando Las Vegas Harry Reid Intl
Frontier Logo
8:03 pm - 9:26 amSAT  San Antonio-MDW Chicago Midway
13h 23m2 stops Las Vegas Harry Reid Intl Dallas/Fort Worth
$339Frontier
Sun, Nov 22 - Thu, Dec 3
Delta Logo
6:00 am - 12:39 pmMDW  Chicago Midway-SAT San Antonio
6h 39m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:50 am - 6:01 pmSAT  San Antonio-MDW Chicago Midway
6h 11m1 stop Detroit Metropolitan Wayne County
$364Delta
Thu, Nov 19 - Sun, Nov 22
Delta Logo
9:30 am - 4:05 pmMDW  Chicago Midway-SAT San Antonio
6h 35m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:30 am - 12:51 pmSAT  San Antonio-MDW Chicago Midway
7h 21m1 stop Detroit Metropolitan Wayne County
$364Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to San Antonio flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to San Antonio?

Round-trip flights from Chicago Midway Airport to San Antonio typically range from $333 to $497. The lowest price found in the past 5 days was $316, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Friday is the cheapest day of the week to fly from Chicago Midway Airport to San Antonio. It’s 8% cheaper than the average day, while Monday is the most expensive, with prices 20% higher.

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

•January is the cheapest month to fly from Chicago Midway Airport to San Antonio at $342 round-trip.
•July ($501) and November ($490) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 46% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to San Antonio the cheapest?

Flights from Chicago Midway Airport to San Antonio are cheapest 4 weeks before departure. Booking in this window typically costs about 50% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Midway to San Antonio

 
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.

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.

Key details for Chicago Midway Airport to San Antonio flights

Low season

August

Cheapest flight

$104
Beat the crowds with an average 23% drop in travelers.
The most popular month to fly with an average 32% increase in travelers.
One-way flight from Chicago Midway Airport to San Antonio

When to book flights from Midway to San Antonio

Are your dates flexible? Find out the best times to travel from Midway to San Antonio based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to San Antonio flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to San Antonio?

    These are the earliest and latest flight times available from Chicago Midway Airport to San Antonio:

    • Earliest: departs at 9:45 am and lands at 12:40 pm
    • Latest: departs at 11:00 pm and lands at 1:55 am.

    The flight takes about 2h 55m.

  • What cabin classes can I book on flights from Chicago Midway Airport to San Antonio?

    Only Economy Class is available on flights from Chicago Midway Airport to San Antonio.

  • How long is a flight from Chicago Midway Airport to San Antonio?

    A nonstop flight from Chicago Midway Airport to San Antonio takes 2h 55m, covering 1,036 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to San Antonio flight?

    Round-trip flights from Chicago Midway Airport to San Antonio range from $333 to $497, with an average of $395 over the past 12 months. Anything below $333 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to San Antonio flights?

    Last-minute fares on this route (booked within two weeks of departure) run 52% above the $395 route average. Book 4 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to San Antonio?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $152 round-trip via Denver Intl (DEN), compared to $408 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to San Antonio?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to San Antonio?

    The Airbus A319 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • How are flight departures from Chicago Midway Airport to San Antonio spread across the day?

    Morning is the busiest departure period on Chicago Midway Airport to San Antonio flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from Chicago Midway Airport to San Antonio changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $316 to $2,290. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Chicago Midway Airport to San Antonio looking right now?

    One-way fares from Chicago Midway Airport to San Antonio are currently lower than usual. Average one-way flight prices are about $143, which is 37% below the typical average for this route.

  • What car rental options are available at San Antonio Airport (SAT)?

    San Antonio Airport (SAT) hosts 5 major car rental companies, with daily rates averaging $53 for economy cars. Top options include:

    • Europcar
    • Fox
    • Dollar
    • Hertz
    • Alamo

  • Which airports can I use when flying from Chicago Midway Airport to San Antonio?

    Flights from Chicago Midway Airport to San Antonio usually depart from Chicago Midway (MDW) and arrive at San Antonio (SAT).

  • Which airports do connecting flights from Chicago Midway Airport to San Antonio pass through?

    One-stop flights from Chicago Midway Airport to San Antonio most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 46% of one-stop connections
    • Denver Intl (DEN) - 38% of one-stop connections
    • Houston Hobby (HOU) - 8% of one-stop connections
    • Nashville Intl (BNA) - 4% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to San Antonio?

    Yes. Flexible dates can save you up to 24% on flights from Chicago Midway Airport to San Antonio. Friday is the cheapest departure day at $367 round-trip on average, while Monday is the most expensive at $477, a difference of $110.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to San Antonio?

    Only Southwest operates flights between Chicago Midway Airport and San Antonio.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to San Antonio?

    Flying via Houston Hobby (HOU) gives the shortest average 1-stop total travel time at 4h 23m, compared with 4h 42m via Nashville Intl (BNA) and 8h 22m via Atlanta Hartsfield-Jackson (ATL).

  • What popular places can I visit in San Antonio?

    Some of the most popular sights in San Antonio are San Antonio River Walk, SeaWorld San Antonio and Alamodome. These are among the most viewed places in San Antonio on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to San Antonio flights?

    Among airlines operating Chicago Midway Airport to San Antonio flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to San Antonio flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to San Antonio flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Friday departure and avoid flying on Monday. On this route, Friday flights average $367, about $110 less than Monday fares (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 4 weeks before you fly. On this route, that window historically saves about 50% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to San Antonio trip for January. Fares historically average $342 round-trip in that month - typically $159 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $152 round-trip on this route - about $256 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to San Antonio Airport.

    • Wyndham Garden San Antonio Airport
    • Heritage Inn & Suites San Antonio Airport, Trademark Wyndham
    • La Quinta Inn & Suites by Wyndham San Antonio Airport

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

 
Find which airlines fly direct from Chicago Midway Airport to San Antonio Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Antonio

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

San Antonio to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from Midway to San Antonio

Complete your trip to San Antonio with a hotel stay or car rental