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259 € Cheap Flights from Chicago Midway to San Antonio International

Compare Chicago Midway to San Antonio International flight deals

Find the cheapest month or even day of the year to fly to San Antonio International

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Flight deals from Chicago Midway to San Antonio International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Antonio International Airport? If you want to travel next month, return fares start from 260 €. Find the lowest prices on one-way and return tickets right here.
San Antonio.259 € per passenger.Departing Mon, 28 Sep, returning Wed, 30 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 28 Sep, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Wed, 30 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
San Antonio.260 € per passenger.Departing Mon, 2 Nov, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Wed, 4 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.260 € per passenger.Departing Tue, 1 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Dec, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Tue, 8 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.260 € per passenger.Departing Sat, 31 Oct, returning Tue, 3 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 31 Oct, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.260 € per passenger.Departing Mon, 19 Oct, returning Thu, 22 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 19 Oct, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Thu, 22 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.260 € per passenger.Departing Tue, 29 Sep, returning Tue, 6 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 29 Sep, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Tue, 6 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.260 € per passenger.Departing Sat, 22 Aug, returning Sat, 29 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 22 Aug, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Sat, 29 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.260 € per passenger.Departing Thu, 26 Nov, returning Thu, 3 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 26 Nov, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Thu, 3 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
San Antonio.273 € per passenger.Departing Mon, 31 Aug, returning Mon, 7 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 31 Aug, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Mon, 7 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 273 €, select.
San Antonio.314 € per passenger.Departing Tue, 29 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 29 Dec, arriving in San Antonio International.Inbound indirect flight with Southwest Airlines, departs from San Antonio International on Sat, 2 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 314 €, select.
San Antonio.338 € per passenger.Departing Thu, 6 May, returning Wed, 19 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 6 May, arriving in San Antonio International.Inbound indirect flight with Delta, departs from San Antonio International on Wed, 19 May, arriving in Chicago Midway.Price includes taxes and charges.From 338 €, select.
San Antonio.349 € per passenger.Departing Fri, 1 Jan, returning Mon, 4 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 1 Jan, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Mon, 4 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 349 €, select.
San Antonio.364 € per passenger.Departing Fri, 25 Dec, returning Fri, 1 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 25 Dec, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Fri, 1 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 364 €, select.
San Antonio.398 € per passenger.Departing Sun, 21 Mar, returning Fri, 26 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sun, 21 Mar, arriving in San Antonio International.Inbound indirect flight with Delta, departs from San Antonio International on Fri, 26 Mar, arriving in Chicago Midway.Price includes taxes and charges.From 398 €, select.
San Antonio.452 € per passenger.Departing Wed, 29 Jul, returning Tue, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Tue, 4 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 452 €, select.
San Antonio.469 € per passenger.Departing Sat, 25 Jul, returning Tue, 28 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 25 Jul, arriving in San Antonio International.Inbound direct flight with Southwest Airlines departs from San Antonio International on Tue, 28 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 469 €, select.

Find the cheapest month to fly from Chicago Midway to San Antonio International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Antonio International flights are currently cheapest in September.
Jul
from 469 €
Aug
from 260 €
Sep
from 259 €
Oct
from 260 €
Nov
from 260 €
Dec
from 260 €
Jan
from 349 €
Feb
Find prices
Mar
from 398 €
Apr
Find prices
May
from 338 €
Jun
Find prices

Direct flights from Chicago Midway to San Antonio International

Chicago Midway to San Antonio International: Alternative routes

Compare routes from Chicago Midway to San Antonio below. You may find an airport to fly into that's cheaper, faster, or easier than San Antonio International.

San Antonio International

13km from central San Antonio
ClosestCheapest
from 259 €
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Chicago to San Antonio: Flight information

The things to know before you go.
Cheapest flight found259 €
Cheapest month to flySeptember
Average flight time2 hrs, 48 mins
Most popular airlineSouthwest Airlines
Average flights per week15

Finding cheap flights from Chicago Midway to San Antonio International: Frequently asked questions

The best price we found for a return flight from Chicago Midway to San Antonio International is 259 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 48 minutes is the average flight time from Chicago Midway to San Antonio International.
Southwest Airlines flies direct from Chicago Midway to San Antonio International.
As of July 2026, there are 15 flights per week flying from Chicago Midway to San Antonio International.
The cheapest month to fly from Chicago Midway to San Antonio International is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Antonio International Airport on Monday, 28 September 2026.
Yes – the average flight time is 2 hours and 48 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Antonio International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Antonio is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to San Antonio International.

Flying from Chicago Midway Airport (MDW) to San Antonio International Airport (SAT): what you need to know

  • Take a direct flight from Chicago Midway Airport to San Antonio International Airport and you'll be in the air for an average of 2 hours 45 minutes.

  • Chicago and San Antonio are both in the UTC-6 timezone. This means there's no time difference to adjust for.

  • Flights from MDW to SAT start from 07:40 — the earliest with Southwest Airlines. The last departure is at 22:50 with Southwest Airlines. In total, you can take your pick of eight weekly Chicago Midway Airport to San Antonio International Airport flights.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Be at the airport with enough time to board your MDW to SAT flight.

  • Flying during a peak time such as July? School holidays and other popular periods can result in longer queues at airport checkpoints. Play things extra safe and get there up to four hours before international flights and two hours before a domestic departure.

  • Flying into San Antonio (and then discovering more of the United States!) is a breeze with Southwest Airlines. This popular airline has direct flights from Chicago Midway Airport to San Antonio International Airport.

  • The airline that tops the list for bookings on this route is Southwest Airlines.

  • Southwest Airlines is the most punctual carrier offering MDW to SAT flights, with 76.55% of its services reaching their destination on time.

  • Consider adding a stopover when booking your ticket from Chicago Midway Airport to San Antonio International Airport. Simply uncheck 'Direct flights only' to break up your journey, or even explore someplace new along the way. Here are some options between MDW and SAT:

    • St Louis Airport

    • Dallas Love Field Airport

    • Houston Hobby Airport

Handy information about Chicago Midway Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • Of the departures from Chicago Midway Airport, 76% touch down on time at their destination.

  • To reach Chicago Midway Airport from central Chicago, it'll take around 25 minutes if you're going by car. This depends on traffic though. It's approximately 16 kilometres from the airport to the city centre.

  • The journey when using public transport will take about 30 minutes.

  • Searching for a convenient hotel close to MDW? If you're catching an early flight from Chicago Midway Airport to San Antonio International Airport, these stays will have you sleeping moments from check-in:

Arriving at San Antonio International Airport (SAT)

Getting from San Antonio International Airport (SAT) to central San Antonio

  • You'll find SAT at 9800 Airport Boulevard.

  • San Antonio International Airport is roughly 14 kilometres from central San Antonio. The drive time takes about 20 minutes.

  • Travelling to the centre by public transport will take you roughly 50 minutes.

When to fly to San Antonio International Airport (SAT)

  • The quietest month for a flight from Chicago Midway Airport to San Antonio International Airport is March, while July is the busiest. Pick the best time to go to San Antonio based on whether you prefer a faster pace or a more relaxed vibe.

  • Lock in your flight from Chicago Midway Airport to San Antonio International Airport for August if you'd like to visit San Antonio during its warmest month. You can expect temperatures of between 24ºC (75ºF) and 40ºC (104ºF).

  • Look for cheap tickets from MDW to SAT in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between 4ºC (39ºF) and 20ºC (68ºF) on average.

Explore more of the United States

  • San Antonio is easy to fall in love with, but there are so many other corners of the United States waiting to be explored. About 306 kilometres east of San Antonio, a visit to Houston will keep you busy. Check out popular attractions like The Museum of Fine Arts, Houston, Beck Building, Houston Museum of Natural Science and The Menil Collection.

  • If you're eager to discover another major destination in the United States, consider Dallas, about 402 kilometres north-east of San Antonio. Meyerson Symphony Centre, Winspear Opera House and Dallas Museum of Art are among its highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.