Cheap Flights from San Antonio, TX to Chicago, IL from $29

Return flight: Chicago – San Antonio

On Cheapflightsplus.com you will find 34 direct and 173 connecting flights from San Antonio to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $29, book and save on cheap plane tickets and last minute offers. Also check out SAT-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip San Antonio to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $29 (one-way), $50 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from San Antonio to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
05:45 — 08:20
05:45 — 08:20 WN1878 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$91
06:20 — 08:55
06:20 — 08:55 WN1541 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$91
06:20 — 08:55
06:20 — 08:55 WN1838 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$93
06:30 — 09:10
06:30 — 09:10 WN1355 Southwest Airlines
San Antonio — Chicago
2h 40m
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from$94
07:00 — 09:55
07:00 — 09:55 UA2325 United Airlines
San Antonio — Chicago
2h 55m
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from$52
07:00 — 09:56
07:00 — 09:56 UA3461 United Airlines
San Antonio — Chicago
2h 56m
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from$54
07:45 — 10:30
07:45 — 10:30 UA2200 United Airlines
San Antonio — Chicago
2h 45m
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from$51
08:10 — 11:09
08:10 — 11:09 AA1062 American Airlines
San Antonio — Chicago
2h 59m
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from$53
08:10 — 11:09
08:10 — 11:09 AA1230 American Airlines
San Antonio — Chicago
2h 59m
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from$54
09:15 — 11:50
09:15 — 11:50 WN2701 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$95
09:15 — 11:50
09:15 — 11:50 WN2298 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$138
09:25 — 12:05
09:25 — 12:05 WN3640 Southwest Airlines
San Antonio — Chicago
2h 40m
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from$97
10:15 — 12:50
10:15 — 12:50 WN600 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$94
10:35 — 13:10
10:35 — 13:10 WN3164 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$108
10:45 — 13:20
10:45 — 13:20 WN652 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$93
11:15 — 13:50
11:15 — 13:50 WN2186 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$151
11:40 — 14:32
11:40 — 14:32 UA5709 United Airlines
San Antonio — Chicago
2h 52m
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from$51
11:45 — 14:20
11:45 — 14:20 WN1101 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$91
12:10 — 14:45
12:10 — 14:45 WN2116 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$151
14:00 — 16:58
14:00 — 16:58 UA3482 United Airlines
San Antonio — Chicago
2h 58m
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from$54
14:00 — 16:48
14:00 — 16:48 UA5284 United Airlines
San Antonio — Chicago
2h 48m
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from$65
14:05 — 16:40
14:05 — 16:40 WN1554 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$94
14:15 — 16:58
14:15 — 16:58 UA2376 United Airlines
San Antonio — Chicago
2h 43m
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from$51
14:35 — 17:34
14:35 — 17:34 AA2887 American Airlines
San Antonio — Chicago
2h 59m
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from$53
14:35 — 17:34
14:35 — 17:34 AA1573 American Airlines
San Antonio — Chicago
2h 59m
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from$54
14:35 — 17:37
14:35 — 17:37 AA3453 American Airlines
San Antonio — Chicago
3h 2m
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from$69
14:40 — 17:15
14:40 — 17:15 WN955 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$93
15:35 — 18:27
15:35 — 18:27 AA1706 American Airlines
San Antonio — Chicago
2h 52m
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from$171
15:55 — 18:30
15:55 — 18:30 WN3010 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$95
16:35 — 19:32
16:35 — 19:32 AA3835 American Airlines
San Antonio — Chicago
2h 57m
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from$56
16:35 — 19:32
16:35 — 19:32 AA3894 American Airlines
San Antonio — Chicago
2h 57m
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from$57
17:25 — 20:07
17:25 — 20:07 UA5995 United Airlines
San Antonio — Chicago
2h 42m
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from$51
18:00 — 20:35
18:00 — 20:35 WN586 Southwest Airlines
San Antonio — Chicago
2h 35m
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from$91
05:45 — 10:20
05:45 — 06:40 UA2108 United Airlines
San Antonio — Houston
1h 5m stop
07:45 — 10:20 UA1253 United Airlines
Houston — Chicago
4h 35m
including layover
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from$51
05:45 — 12:48
05:45 — 06:40 UA2108 United Airlines
San Antonio — Houston
3h 35m stop
10:15 — 12:48 UA1403 United Airlines
Houston — Chicago
7h 3m
including layover
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from$51
06:50 — 12:28
06:50 — 10:47 AA2212 American Airlines
San Antonio — Charlotte
43m stop
11:30 — 12:28 AA550 American Airlines
Charlotte — Chicago
5h 38m
including layover
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from$52
06:50 — 14:13
06:50 — 10:47 AA2212 American Airlines
San Antonio — Charlotte
2h 28m stop
13:15 — 14:13 AA433 American Airlines
Charlotte — Chicago
7h 23m
including layover
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from$52
07:30 — 12:45
07:30 — 08:34 UA2486 United Airlines
San Antonio — Houston
1h 26m stop
10:00 — 12:45 UA1403 United Airlines
Houston — Chicago
5h 15m
including layover
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from$51
07:30 — 14:50
07:30 — 08:30 UA2486 United Airlines
San Antonio — Houston
3h 40m stop
12:10 — 14:50 UA1752 United Airlines
Houston — Chicago
7h 20m
including layover
Find flight
from$51
09:50 — 15:53
09:50 — 13:55 AA5501 American Airlines
San Antonio — Charlotte
1h stop
14:55 — 15:53 AA2388 American Airlines
Charlotte — Chicago
6h 3m
including layover
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from$52
09:50 — 17:18
09:50 — 13:55 AA5501 American Airlines
San Antonio — Charlotte
2h 25m stop
16:20 — 17:18 AA401 American Airlines
Charlotte — Chicago
7h 28m
including layover
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from$52
10:00 — 14:50
10:00 — 11:00 UA2156 United Airlines
San Antonio — Houston
1h 10m stop
12:10 — 14:50 UA1752 United Airlines
Houston — Chicago
4h 50m
including layover
Find flight
from$51
10:00 — 17:08
10:00 — 11:00 UA2156 United Airlines
San Antonio — Houston
3h 20m stop
14:20 — 17:08 UA1899 United Airlines
Houston — Chicago
7h 8m
including layover
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from$51
11:50 — 17:08
11:50 — 12:50 UA567 United Airlines
San Antonio — Houston
1h 30m stop
14:20 — 17:08 UA1899 United Airlines
Houston — Chicago
5h 18m
including layover
Find flight
from$51
12:15 — 17:06
12:15 — 13:14 UA6158 United Airlines
San Antonio — Houston
1h 16m stop
14:30 — 17:06 UA1899 United Airlines
Houston — Chicago
4h 51m
including layover
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from$52
12:15 — 18:36
12:15 — 13:14 UA6158 United Airlines
San Antonio — Houston
2h 46m stop
16:00 — 18:36 UA1637 United Airlines
Houston — Chicago
6h 21m
including layover
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from$52
14:15 — 18:46
14:15 — 15:15 UA2024 United Airlines
San Antonio — Houston
47m stop
16:02 — 18:46 UA1637 United Airlines
Houston — Chicago
4h 31m
including layover
Find flight
from$51
16:20 — 23:58
16:20 — 17:36 F9387 Frontier Airlines
San Antonio — Denver
2h 59m stop
20:35 — 23:58 F9410 Frontier Airlines
Denver — Chicago
7h 38m
including layover
Find flight
from$37
16:20 — 21:11
16:20 — 17:20 UA1930 United Airlines
San Antonio — Houston
1h stop
18:20 — 21:11 UA1611 United Airlines
Houston — Chicago
4h 51m
including layover
Find flight
from$51
17:55 — 22:10
17:55 — 18:55 UA2111 United Airlines
San Antonio — Houston
45m stop
19:40 — 22:10 UA1009 United Airlines
Houston — Chicago
4h 15m
including layover
Find flight
from$51
19:36 — 09:32
+1 day
19:36 — 20:54 F9387 Frontier Airlines
San Antonio — Denver
9h 6m stop
06:00 — 09:32 F9412 Frontier Airlines
Denver — Chicago
13h 56m
including layover
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from$41
15:30 — 22:34
+1 day
15:30 — 16:10 SY921 Sun Country Airlines
San Antonio — Austin
18h 50m stop
11:00 — 14:39 NK518 Spirit Airlines
Austin — Miami
5h 41m stop
20:20 — 22:34 NK1 Spirit Airlines
Miami — Chicago
31h 4m
including layover
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from$29
19:34 — 15:21
+1 day
19:34 — 21:00 F9387 Frontier Airlines
San Antonio — Denver
10h 20m stop
07:20 — 10:28 NK584 Spirit Airlines
Denver — Austin
2h 13m stop
12:41 — 15:21 NK176 Spirit Airlines
Austin — Chicago
19h 47m
including layover
Find flight
from$49
*Departure and arrival times - local. Updated on May 14, 2024

Flight Information

Below we will explain in detail what the flights cost on the destination from San Antonio to Chicago depends on and how to choose the most interesting flight option for you.

Distance between San Antonio and Chicago is 1684 miles. Time difference between the cities is 0h. Airplanes depart 05:00 to 22:27 from 5 San Antonio airports and arrive 05:00 to 22:27 to 7 Chicago airports. Average flight time is 2h 40m.

  • The fastest flight 2h 35m
  • Average flight time 2h 40m
  • The earliest flight 05:00
  • The latest flight 22:27
  • Distance 1047 ml

What is the lowest airfare San Antonio to Chicago?

The cheapest plane ticket found by our users is $29. This airfare is for economy class on one-way SY921 flight by Sun Country Airlines for September 13, 2020 which leaves San Antonio in San Antonio at 15:30 am and arrives at Chicago O'Hare International at 22:34.

Economy class
$29
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Business class
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First class
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Popular Airlines on the Route

The flight San Antonio — Chicago is served by 7 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by American Airlines - 52 departures per week at the price of from $ 52 . And the most expensive tickets are offered by Delta Air Lines Inc. airline - from $ 515.

Direct flights

There are 34 nonstop flights on the route. The fastest direct flight is WN1878 by Southwest Airlines takes 2h 35m and the cheapest is SY921 by Sun Country Airlines for $51.

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Connecting Flights

There are 173 flights with layovers on the route. The fastest connecting flight is WN1122 by Southwest Airlines takes 3h 50m and the cheapest is SY921 by Sun Country Airlines for $29.

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Airports

You can fly from San Antonio to Chicago from 5 airports (Randolph AFB, Martindale AAF, San Antonio, Kelly AFB, Stinson Municipal).

San Antonio airports

  • Randolph AFB-RND
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  • Martindale AAF-MDA
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  • San Antonio-SAT
    from $29
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  • Kelly AFB-SKF
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  • Stinson Municipal-SSF
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Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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