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Cheap flights Chicago — San Antonio

Chicago (MDW, US) San Antonio (SAT, US)
from $317 1 694 km ~2h 30m 1 flights found 1 airlines cheapest on Monday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $317 on 15.11.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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December 2026
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January 2027
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Prices found for 2 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
16 Nov 2026, Mon
Southwest Airlines WN 3024
06:30
MDW Chicago Midway International Airport
09:25
SAT San Antonio International Airport
2h 55m Direct
Farera
$317
View this ticket
Route characteristics
Distance
1 694 km
Flight time
2h 30m
Time difference
+0h
Minimum price
from $317 (15.11.2026)
Average price
$317
Maximum price
$317
Cheapest day
Monday
Departure airports (1)
MDW Chicago Midway International Airport
Arrival airports (1)
SAT San Antonio International Airport
Airlines (1)
WN Southwest Airlines
Agencies (1)
Farera
Airlines — cheapest prices 1
Southwest Airlines
Southwest Airlines
Low-cost 1 flights · 1 days
$317
Where to buy tickets 1
Farera
1 tickets · 1 days
from $317
Airports

From — Chicago (1)

  • MDW Chicago Midway International Airport

To — San Antonio (1)

  • SAT San Antonio International Airport
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Frequently asked questions about the route Chicago — San Antonio
How long is the flight from Chicago to San Antonio?
Approximate flight time — 2h 30m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Chicago to San Antonio?
The straight-line distance — 1 694 km.
How much do flights from Chicago to San Antonio cost?
The minimum price over 3 months — from $317 on 15.11.2026.
What is the average ticket price?
The average price — $317. Range: $317 — $317.
What is the time difference between Chicago and San Antonio?
The difference — +0h.
From which airports does Chicago operate flights?
From Chicago: MDW (Chicago Midway International Airport).
To which airports in San Antonio do flights arrive?
To San Antonio: SAT (San Antonio International Airport).
Which airlines fly this route?
This route is served by 1 airline: Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $317. Total direct flights found: 1.
Which day of the week is cheapest?
The cheapest day of the week — Monday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Chicago — San Antonio

Flights Chicago — San Antonio is a popular route. The straight-line distance is 1 694 km. Flight time 2h 30m. Time difference +0h.

From Chicago (MDW) flights depart from 1 airport: MDW. To San Antonio (SAT) — 1 arrival airport: SAT.

1 airline operate on this route: Southwest Airlines.

The minimum price for the next 3 months — from $317 (15.11.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $317, ranging from $317 to $317. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Monday.

Other destinations in United States from Chicago
Omaha
US
Pittsburgh
US
Phoenix
US
Philadelphia
US
Portland
US
Norfolk
US
Ontario
US
New Orleans
US

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