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Not ready to book? to track prices.Southwest flights from San Antonio to Chicago Midway Airport
Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Frontier flights from San Antonio to Chicago Midway Airport
Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
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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
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 1/5
1:00 pm-7:55 pm
1 stop6h 55m
Chicago Midway
Sat 1/9
10:10 am-1:10 pm
Nonstop3h 00m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 12/12
12:05 pm-2:40 pm
Nonstop2h 35m
Chicago Midway
Wed 12/16
8:50 am-1:15 pm
1 stop4h 25m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Thu 11/5
8:25 pm-1:10 am
1 stop4h 45m
Chicago Midway
Sat 11/7
6:25 pm-9:25 pm
Nonstop3h 00m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 11/17
2:40 pm-5:15 pm
Nonstop2h 35m
Chicago Midway
Tue 11/24
9:50 am-2:55 pm
1 stop5h 05m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 11/7
6:25 am-2:15 pm
2 stops7h 50m
Chicago Midway
Thu 11/12
9:30 pm-12:25 am
Nonstop2h 55m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 11/7
6:25 am-2:15 pm
2 stops7h 50m
Chicago Midway
Wed 11/11
8:50 pm-11:45 pm
Nonstop2h 55m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Sat 11/14
6:05 am-12:55 pm
2 stops6h 50m
Chicago Midway
Sat 11/14
6:25 pm-9:25 pm
Nonstop3h 00m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Wed 1/27
1:45 pm-4:15 pm
Nonstop2h 30m
Chicago Midway
Sat 1/30
9:30 am-3:45 pm
2 stops6h 15m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Mon 11/2
5:00 pm-10:33 pm
1 stop5h 33m
Chicago Midway
Thu 11/5
11:38 am-7:48 pm
1 stop8h 10m
San AntonioChicago
SAT San Antonio - MDW Chicago Midway
SATMDW
San Antonio
Tue 11/3
5:15 am-12:47 pm
1 stop7h 32m
Chicago Midway
Tue 11/10
1:05 pm-7:48 pm
1 stop6h 43m
See travel insights to Chicago from
How to get the cheapest flight ticket from San Antonio to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between San Antonio and Chicago Midway Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $444 to $650.The lowest price recently found on this route was $271.
What is the cheapest month to fly to Chicago Midway Airport?
The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of April, then departing from San Antonio during the month February is also very affordable. Most momondo users find prices during this month for around $260.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Antonio. The lowest ticket price found for a Wednesday departure recently was $378. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from San Antonio because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $512.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from San Antonio at noon is the least expensive time of day to depart. momondo users have found prices as low as $401 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $529. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest San Antonio to Chicago Midway flight route?
Fly from San Antonio to Chicago Midway for the best San Antonio - Chicago Midway flight prices
What cabin class options are available on San Antonio to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on San Antonio to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on San Antonio to Chicago Midway Airport flights?
You could potentially save up to 1% on your flight if you consider stops on a San Antonio to Chicago Midway Airport flight.
When to book flights from San Antonio to Chicago Midway Airport
Cheap San Antonio to Chicago Midway Airport (SAT to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Antonio to Chicago Midway Airport
Frequently asked questions about flying from San Antonio to Chicago Midway Airport
How far is San Antonio to Chicago Midway by plane?
The straight-line distance from San Antonio to Chicago Midway is 1043.4 mi. By plane, this route typically takes 2h 30m.
When did momondo last update prices for flights from San Antonio Airport to Chicago Midway Airport?
Prices for flights from San Antonio Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from San Antonio Airport to Chicago Midway Airport?
As of October 2026, there is 1 operator available to choose from for flights from San Antonio Airport to Chicago Midway Airport.
How old do you have to be to fly from San Antonio Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Antonio Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from San Antonio to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from San Antonio to Chicago Midway Airport is Airbus A319, representing 20.36% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 15.27%, Airbus A320-100/200 at 14.67%, and Embraer 175 at 13.77%.
What is the most popular airline from San Antonio to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from San Antonio to Chicago Midway Airport is Southwest (100% of total bookings).
Best airlines flying from San Antonio to Chicago Midway Airport
Compare and see reviews for airlines that fly from San Antonio to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $315 | Free Cancellation | Rating 7.9 4,228 reviews |
Southwest Flights From San Antonio to Chicago Midway Airport
Southwest flies from San Antonio to Chicago Midway Airport around 6 times per week, with 4,228 momondo users rating the airline 7.9/10. The cheapest Southwest deal from San Antonio to Chicago Midway Airport in the last 72 hours was $315 (round-trip), much lower than the average airfare cost of $510 for Southwest flights on this route.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from San Antonio to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Antonio to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from San Antonio to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for San Antonio to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from San Antonio to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from San Antonio.
I’m not ready to book a flight from San Antonio to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for San Antonio to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.