SAT - MDW

$100 Find Cheap Flights from San Antonio to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$306
Typical prices: $341-$533
Southwest
Mon 12/10Mon 12/17
SAT - MDW • 2 stops
Cheapest non-stop
$324
Typical prices: $349-$544
Southwest
Tue 12/4Sat 12/8
SAT - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 36m
Direct flights
+1
Direct flights
+1
When to book
10 weeks
in advance
Our data shows that travelers who book at least 10 weeks in advance save around 55% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 27% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $277 (round-trip)
Dallas Love Field (DAL)
Shortest trip • 5h 20m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
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Expert advice
Flight Deals

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

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

Recent round-trip flight deals from San Antonio to Midway

Thu, Dec 10 - Thu, Dec 17
Southwest Logo
9:50 am - 5:15 pmSAT  San Antonio-MDW Chicago Midway
7h 25m2 stops Dallas Love Field Milwaukee-Mitchell
Southwest Logo
9:30 pm - 12:25 amMDW  Chicago Midway-SAT San Antonio
2h 55mnonstop
$306Southwest
Mon, Dec 7 - Thu, Dec 10
Southwest Logo
3:20 pm - 9:35 pmSAT  San Antonio-MDW Chicago Midway
6h 15m1 stop Lambert-St Louis
Southwest Logo
9:55 am - 4:20 pmMDW  Chicago Midway-SAT San Antonio
6h 25m1 stop Atlanta Hartsfield-Jackson
$311Southwest
Thu, Nov 19 - Mon, Nov 23
Delta Logo
5:30 am - 12:51 pmSAT  San Antonio-MDW Chicago Midway
7h 21m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:13 pm - 12:33 amMDW  Chicago Midway-SAT San Antonio
7h 20m1 stop Atlanta Hartsfield-Jackson
$311Delta
Mon, Dec 7 - Thu, Dec 17
Delta Logo
6:33 am - 11:59 amSAT  San Antonio-MDW Chicago Midway
5h 26m1 stop Minneapolis St Paul
Delta Logo
11:28 am - 5:31 pmMDW  Chicago Midway-SAT San Antonio
6h 03m1 stop Atlanta Hartsfield-Jackson
$311Delta
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
2:50 pm - 8:25 pmSAT  San Antonio-MDW Chicago Midway
5h 35m1 stop Atlanta Hartsfield-Jackson
Southwest Logo
6:40 am - 12:15 pmMDW  Chicago Midway-SAT San Antonio
5h 35m1 stop Houston Hobby
$311Southwest
Mon, Dec 7 - Thu, Dec 17
Delta Logo
6:33 am - 11:59 amSAT  San Antonio-MDW Chicago Midway
5h 26m1 stop Minneapolis St Paul
Delta Logo
5:12 pm - 12:35 amMDW  Chicago Midway-SAT San Antonio
7h 23m1 stop Atlanta Hartsfield-Jackson
$311Delta
Tue, Dec 1 - Tue, Dec 1
Delta Logo
5:16 am - 12:04 pmSAT  San Antonio-MDW Chicago Midway
6h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:12 pm - 12:35 amMDW  Chicago Midway-SAT San Antonio
7h 23m1 stop Atlanta Hartsfield-Jackson
$311Delta
Sat, Nov 21 - Mon, Nov 23
Delta Logo
11:45 am - 6:04 pmSAT  San Antonio-MDW Chicago Midway
6h 19m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 4:05 pmMDW  Chicago Midway-SAT San Antonio
6h 35m1 stop Detroit Metropolitan Wayne County
$311Delta
Thu, Nov 19 - Thu, Nov 26
Delta Logo
5:30 am - 10:24 amSAT  San Antonio-MDW Chicago Midway
4h 54m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 12:39 pmMDW  Chicago Midway-SAT San Antonio
6h 39m1 stop Atlanta Hartsfield-Jackson
$311Delta
Wed, Dec 9 - Sat, Dec 12
Delta Logo
6:16 am - 12:04 pmSAT  San Antonio-MDW Chicago Midway
5h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:08 pm - 11:35 pmMDW  Chicago Midway-SAT San Antonio
7h 27m1 stop Atlanta Hartsfield-Jackson
$311Delta
Booking Insights

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

Round-trip flights from San Antonio to Chicago Midway Airport typically range from $341 to $533. The lowest price found in the past 5 days was $306, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from San Antonio to Chicago Midway Airport. It’s 9% cheaper than the average day, while Friday is the most expensive, with prices 18% higher.

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

•February is the cheapest month to fly from San Antonio to Chicago Midway Airport at $295 round-trip.
•November ($485) and October ($452) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 64% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from San Antonio to Chicago Midway Airport are cheapest 10 weeks before departure. Booking in this window typically costs about 55% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from San Antonio to Midway

 
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

Key details for San Antonio to Chicago Midway Airport flights

Low season

January

Cheapest flight

$100
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 60% increase in travelers.
One-way 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

Your San Antonio to Chicago Midway Airport 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 San Antonio to Chicago Midway Airport?

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

    • Earliest: departs at 5:00 am and lands at 7:36 am
    • Latest: departs at 4:30 pm and lands at 7:06 pm.

    The flight takes about 2h 36m.

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

    Two cabin classes are available on flights from San Antonio to Chicago Midway Airport:

    • Economy Class
    • First Class

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

    A nonstop flight from San Antonio to Chicago Midway Airport takes 2h 36m, covering 1,036 miles.

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

    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 San Antonio to Chicago Midway Airport flight?

    Round-trip flights from San Antonio to Chicago Midway Airport range from $341 to $533, with an average of $402 over the past 12 months. Anything below $341 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 71% above the $402 route average. Book 10 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $277 round-trip via Orlando (MCO), compared to $409 for nonstop.

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

    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 San Antonio to Chicago Midway Airport?

    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 Embraer 175 variants.

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

    Morning is the busiest departure period on San Antonio to Chicago Midway Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from San Antonio to Chicago Midway Airport 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 $306 to $2,238. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on San Antonio to Chicago Midway Airport flights?

    JetBlue is the only airline on the San Antonio to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

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

    One-way fares from San Antonio to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $134, which is 50% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

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

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 71% of one-stop connections
    • Dallas Love Field (DAL) - 14% of one-stop connections
    • Orlando (MCO) - 14% of one-stop connections

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

    Yes. Flexible dates can save you up to 23% on flights from San Antonio to Chicago Midway Airport. Wednesday is the cheapest departure day at $367 round-trip on average, while Friday is the most expensive at $476, a difference of $109.

    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 San Antonio to Chicago Midway Airport?

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

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

    Flying via Dallas Love Field (DAL) gives the shortest average 1-stop total travel time at 5h 20m, compared with 8h 17m via Atlanta Hartsfield-Jackson (ATL) and 21h 48m via Orlando (MCO).

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

    Among airlines operating San Antonio to Chicago Midway Airport 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 San Antonio to Chicago Midway Airport flights?

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

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: 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 San Antonio to Chicago Midway Airport 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 Wednesday departure and avoid flying on Friday. On this route, Wednesday flights average $367, about $109 less than Friday fares (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 10 weeks before you fly. On this route, that window historically saves about 55% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your San Antonio to Chicago Midway Airport trip for February. Fares historically average $295 round-trip in that month - typically $190 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $277 round-trip on this route - about $132 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 Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

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

 
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

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Sunday

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See more direct flights

Direct returns

Chicago Midway to San Antonio

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Friday

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More options for your flight from San Antonio to Midway

Complete your trip to Chicago with a hotel stay or car rental

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