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Cheap flights San Antonio — Chicago

San Antonio (SAT, US) Chicago (MDW, US)
from $262 1 694 km ~2h 30m 8 flights found 3 airlines cheapest on Tuesday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $262 on 17.11.2026
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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Su
December 2026
Mo
Tu
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January 2027
Mo
Tu
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Prices found for 5 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
17 Nov 2026, Tue
Frontier Airlines F9 1654
02:13
SAT San Antonio International Airport
08:49
MDW Chicago Midway International Airport
6h 36m 2 stops
Kupi.com
$262
View this ticket
19 Nov 2026, Thu
Breeze Airways MX 1011
18:25
SAT San Antonio International Airport
03:41
MDW Chicago Midway International Airport
9h 16m 3 stops
Kiwi.com
$305
View this ticket
16 Nov 2026, Mon
Southwest Airlines WN 2348
18:50
SAT San Antonio International Airport
21:20
MDW Chicago Midway International Airport
2h 30m Direct
Farera
$317
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 2348
18:15
SAT San Antonio International Airport
20:55
MDW Chicago Midway International Airport
2h 40m Direct
Farera
$322
View this ticket
19 Nov 2026, Thu
Southwest Airlines WN 3382
23:35
SAT San Antonio International Airport
02:15
MDW Chicago Midway International Airport
2h 40m Direct
Farera
$333
View this ticket
Route characteristics
Distance
1 694 km
Flight time
2h 30m
Time difference
+0h
Minimum price
from $262 (17.11.2026)
Average price
$298
Maximum price
$322
Departures per week
1
Cheapest day
Tuesday
Departure airports (1)
SAT San Antonio International Airport
Arrival airports (1)
MDW Chicago Midway International Airport
Airlines (3)
F9 Frontier Airlines MX Breeze Airways WN Southwest Airlines
Agencies (4)
Kupi.com Lucky2Go Kiwi.com Farera
Prices by day of week
Monday
$317
avg $317
Tuesday
$262
avg $262
Cheapest
Thursday
$305
avg $319
Sunday
$322
avg $322
Airlines — cheapest prices 3
Frontier Airlines
Frontier Airlines
Low-cost 2 flights · 2 days
$262
Breeze Airways
Breeze Airways
Low-cost 1 flights · 1 days
$305
Southwest Airlines
Southwest Airlines
Low-cost 5 flights · 5 days
$317
Where to buy tickets 4
Kupi.com
1 tickets · 1 days
from $262
Lucky2Go
1 tickets · 1 days
from $301
Kiwi.com
1 tickets · 1 days
from $305
Farera
5 tickets · 5 days
from $317
Airports

From — San Antonio (1)

  • SAT San Antonio International Airport

To — Chicago (1)

  • MDW Chicago Midway International Airport
Other destinations from San Antonio
Atlanta
US · Hub
Nashville
US
Boston
US
Baltimore
US
Chattanooga
US
Chicago
US
Charlotte
US · Hub
Corpus Christi
US
Cancun
MX
Cincinnati
US
Denver
US · Hub
Dallas
US · Hub
Frequently asked questions about the route San Antonio — Chicago
How long is the flight from San Antonio to Chicago?
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 San Antonio to Chicago?
The straight-line distance — 1 694 km.
How much do flights from San Antonio to Chicago cost?
The minimum price over 3 months — from $262 on 17.11.2026.
What is the average ticket price?
The average price — $298. Range: $262 — $322.
What is the time difference between San Antonio and Chicago?
The difference — +0h.
From which airports does San Antonio operate flights?
From San Antonio: SAT (San Antonio International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport).
Which airlines fly this route?
This route is served by 3 airlines: Frontier Airlines, Breeze Airways, Southwest Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $317. Total direct flights found: 3.
Which day of the week is cheapest?
The cheapest day of the week — Tuesday.
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 San Antonio — Chicago

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

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

3 airlines operate on this route: Frontier Airlines, Breeze Airways, Southwest Airlines.

The minimum price for the next 3 months — from $262 (17.11.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $298, ranging from $262 to $322. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Tuesday.

Other destinations in United States from San Antonio
Ontario
US
Palm Springs
US
Pensacola
US
Phoenix
US
Philadelphia
US
Orlando
US
New Orleans
US
Kansas City
US

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