Route guide · 1,037 miles
Cheap Flights from San Antonio to Chicago
SAT → MDW · Nonstop 2h 36m · Live round-trip fares
The run from San Antonio (SAT) to Chicago (MDW) is 1,037 miles of sky, and ticket prices on it are anything but steady. One week can cost double the next. Booking about 3–6 weeks in advance — and watching fares with a free Airfare Deal alert — is how regulars on this route keep costs down.
Live fares for SAT → MDW are updating. Use the search below for real-time prices.
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Updated daily
Flight time
2h 36m
Nonstop, typical
Distance
1,037 mi
SAT → MDW
Book ahead
3–6 weeks
Best window, typically
Nonstop airlines
1
Southwest Airlines
Nonstop flights from San Antonio to Chicago
The fastest way between the two cities is the nonstop: about 2h 36m for the 1,037-mile run from SAT to MDW. Those flights are flown by Southwest Airlines. Prices behave best when you book 3–6 weeks out.
Booking insights: San Antonio → Chicago
- Distance: 1,037 miles · nonstop flight time: 2h 36m.
- Fares tend to bottom out when you book about 3–6 weeks ahead — earlier than that rarely helps, later usually hurts.
- If your dates flex by a day or two, shifting to a midweek departure is the easiest saving there is.
- A free fare alert beats daily checking: we watch this route and ping you when prices drop.
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Flying from San Antonio to Chicago: what you need to know
The flight
The nonstop from SAT to MDW runs about 2h 36m over 1,037 miles. It's a comfortable mid-range flight: long enough that seat choice matters a little, short enough that paying up for extras rarely does.
Airlines on this route
Southwest Airlines flies this route nonstop. That matters more than it sounds: the cheapest fare on one carrier is rarely the same product as the cheapest on another. Checked-bag fees, free seat selection and change rules all differ, so compare the full trip cost before you pick a winner. See our airline guides for exactly what each carrier charges — then send an enquiry and we'll confirm the all-in price for your dates.
Leaving from San Antonio (SAT)
Plan to be at the airport two hours before a domestic departure — ninety minutes can work at smaller airports outside peak times, but security lines are the one variable you can't control. If you're checking a bag, add time rather than cutting it close. Our San Antonio airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Chicago (MDW)
Before you land, know how you're getting from the airport to where you're staying — it's the part of the trip people forget to plan. The Chicago airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Chicago to San Antonio fares — prices on the return direction often move on a different rhythm.
When to book
For a trip of 1,037 miles, booking 3–6 weeks ahead typically lands you in the sweet spot. Leave it to the final two weeks and prices usually climb as the cheapest seats sell out. If your dates are flexible, midweek departures are where the lower fares hide on most domestic routes.
Good to know before you go
- If you're traveling with only a carry-on, you can skip the bag-drop line entirely with mobile check-in.
- Download the airline's app before you fly; gate changes and delays show up there first.
- Nonstop time on this route is about 2h 36m — a one-stop itinerary needs to be a lot cheaper to be worth the extra hours.
- Tuesday and Wednesday departures are typically the cheapest days on domestic routes.
- Screenshot your fare before you enquire — prices move, and a saved fare helps our team match or beat it.
San Antonio to Chicago flight FAQs
How long is the flight from SAT to MDW?
Plan on about 2h 36m in the air for a nonstop from San Antonio to Chicago — the route runs roughly 1,037 miles. Connecting flights typically add 2–4 hours.
Are there nonstop flights from San Antonio to Chicago?
Southwest Airlines typically operate nonstop flights from SAT to MDW. Nonstops are usually cheapest when booked 3–6 weeks ahead of departure.
What is the cheapest month to fly from San Antonio to Chicago?
Fares from San Antonio to Chicago tend to ease outside the peak summer and holiday rush — the late-summer and early-fall shoulder weeks are usually kinder on the wallet. Set a free Airfare Deal alert and we'll flag the dips for your dates.
How much are last minute flights from SAT to MDW?
Book inside the final week and you'll usually pay a premium on SAT to MDW. Fares booked 3–6 weeks ahead are almost always kinder.
What is a good round-trip deal from San Antonio to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from San Antonio to Chicago?
You'll mainly see Southwest Airlines on San Antonio to Chicago. Checking each against the live fares below is the surest way to find the lowest price for your dates.
How early should I get to San Antonio airport for this flight?
Plan on two hours before departure for a domestic flight — ninety minutes can work at smaller airports outside peak times. If you're checking a bag, earlier is better; the bag-drop line, not the flight, is what runs late.
Do the cheapest fares on this route include a checked bag?
Usually not. Basic economy fares on most airlines include a carry-on but charge extra for checked bags, and seat selection can cost more too. Add up the real total before comparing — a slightly higher regular fare sometimes works out cheaper. Our team confirms the full breakdown with you before you pay.
More cheap flights from San Antonio
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