Cheap Flights from San Antonio to Chicago
Browse current best options from San Antonio. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
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Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from San Antonio to Chicago
Explore current cheapest deals departing from San Antonio to Chicago
Round trip
Sort by: Cheapest
August 18 - August 26
SAT - Chicago
$254
$212
Round trip
August 19 - August 25
SAT - Chicago
$264
$212
Round trip
July 22 - July 29
SAT - Chicago
$257
$230
Round trip
July 8 - July 14
SAT - Chicago
$268
$231
Round trip
July 15 - July 21
SAT - Chicago
$263
$231
Round trip
July 15 - July 22
SAT - Chicago
$263
$231
Round trip
July 7 - July 14
SAT - Chicago
$268
$232
Round trip
August 4 - August 25
SAT - Chicago
$144
$234
Round trip
August 19 - August 25
SAT - Chicago
$175
$234
Round trip
August 12 - August 15
SAT - Chicago
$275
$234
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from San Antonio to Chicago
How much is a round trip from San Antonio to Chicago
Regular price: $208 - $290
Prices are currently within the regular range.
The regular price range for flights from San Antonio to Chicago is $208 to $290. The current lowest deal is $212 with Frontier Airlines, for travel from Aug 18 to Aug 26.
now $212
Low $208
High $290
The cheapest time to fly from San Antonio to Chicago
Flights from San Antonio to Chicago are cheapest in January, with a median price of $229. The most expensive month to fly is February, with a median price of $692. Prices are generally lower from January to December.
January
Flights from $229
February
Flights from $692
Direct flights from San Antonio to Chicago
Southwest Airlines
United Airlines
Last-minute flights going from San Antonio to Chicago
Tue, Jun 16
SAT - Chicago
San Antonio (SAT) - Chicago (ORD)
Frontier Airlines
$432
$352
One-way
Tue, Jun 16
SAT - Chicago
San Antonio (SAT) - Chicago (ORD)
Frontier Airlines
$429
$391
One-way
Wed, Jun 17
SAT - Chicago
San Antonio (SAT) - Chicago (ORD)
Frontier Airlines
$432
$391
One-way
Thu, Jun 18
SAT - Chicago
San Antonio (SAT) - Chicago (ORD)
Frontier Airlines
$387
$342
One-way
Thu, Jun 18
SAT - Chicago
San Antonio (SAT) - Chicago (ORD)
Frontier Airlines
$427
$390
One-way
Thu, Jun 18
SAT - Chicago
San Antonio (SAT) - Chicago (ORD)
Frontier Airlines
$434
$391
One-way
Biggest price drops on these dates for flights from San Antonio to Chicago
Nov 12 - Nov 15
$384 → $270
30%
Jun 20 - Jun 21
$436 → $342
22%
Jun 19 - Jun 21
$434 → $342
21%
Jun 20 - Jun 23
$430 → $342
20%
Popular Airports to fly from San Antonio to Chicago
San Antonio - Chicago route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares for San Antonio to Chicago are above the typical level, with a median price of $455.
📅 Best time to fly
January is historically the cheapest month to fly.
Historically, January is the cheapest month to fly from San Antonio to Chicago, with a median price of $229.
⏱️ Flight duration
Connecting flights typically take 19h 31m.
Flights from San Antonio to Chicago typically take 19h 31m, with most flights having 2 stopovers.
✈️ Airlines & availability
Connecting flights are dominant on this route.
Only 19.4% of recent deals are for direct flights, making connecting flights dominant.
🏆 Airline highlight
Frontier Airlines offers a recent deal for $212.
A recent deal from Frontier Airlines to Chicago O Hare International Airport was found for $212.
🎯 Booking tip
Deals appear frequently, with over 1 deal per day.
Historically, deals for this route appear frequently, with more than 1 deal per day.
San Antonio main airports to depart from
San Antonio International (SAT)
San Antonio International offers the cheapest flights to Chicago, making it a good value departure option.
📍 ~15 km from San Antonio city center (reachable by car)
💸 Flights from ~$212
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights from San Antonio to Chicago.
📍 ~25 km from Chicago city center (reachable by car)
💸 Flights from ~$212
Chicago Midway International (MDW)
Chicago Midway International Airport is another choice for your trip from San Antonio to Chicago.
📍 ~15 km from Chicago city center (reachable by car)
💸 Flights from ~$234
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves the Chicago area for flights from San Antonio.
📍 ~110 km from Chicago city center (reachable by car)
💸 Flights from ~$393
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic).
💸 Flights from ~$286
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, with direct commuter rail connections.
📍 ~125 km from Chicago (reachable by rail).
💸 Flights from ~$298
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, a good alternative for travelers on Chicago's eastern side.
📍 ~205 km from Chicago (requires a significant drive).
💸 Flights from ~$269
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport, less congested than Chicago or Milwaukee airports.
📍 ~200 km from Chicago.
💸 Flights from ~$231
Fort Wayne International (FWA)
Fort Wayne International offers stable regional service, an alternative for southeastern Chicago suburbs.
📍 ~240 km from Chicago (significant distance).
💸 Flights from ~$294
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from San Antonio to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From SAT
Elite
Sep 03
Chicago, United States
84% AI deal score
$1,358
$671
Save $687
From SAT
Elite
Sep 17
Chicago, United States
84% AI deal score
$1,371
$675
Save $696
From SAT
Elite
Jul 06
Chicago, United States
81% AI deal score
$1,698
$887
Save $811
From SAT
Elite
Aug 01
Chicago, United States
79% AI deal score
$1,085
$742
Save $343
From SAT
Elite
Aug 01
Chicago, United States
79% AI deal score
$1,070
$742
Save $328
From SAT
Elite
Aug 26
Chicago, United States
78% AI deal score
$1,004
$715
Save $289
From SAT
Elite
Aug 01
Chicago, United States
78% AI deal score
$1,032
$750
Save $282
From SAT
Elite
Jul 21
Chicago, United States
78% AI deal score
$1,365
$812
Save $553
From SAT
Elite
Jul 06
Chicago, United States
77% AI deal score
$3,640
$2,056
Save $1,584
From SAT
Elite
Aug 05
Chicago, United States
77% AI deal score
$923
$707
Save $216
From SAT
Elite
Aug 04
Chicago, United States
77% AI deal score
$930
$715
Save $215
From SAT
Elite
Oct 11
Chicago, United States
77% AI deal score
$1,291
$858
Save $433
From SAT
Elite
Jun 30
Chicago, United States
76% AI deal score
$866
$711
Save $155
From SAT
Elite
Sep 10
Chicago, United States
76% AI deal score
$1,309
$826
Save $483
From SAT
Elite
Jul 08
Chicago, United States
72% AI deal score
$3,320
$1,946
Save $1,374
From SAT
Elite
Jul 21
Chicago, United States
72% AI deal score
$3,187
$1,952
Save $1,235
From SAT
Elite
Jul 21
Chicago, United States
72% AI deal score
$3,317
$1,952
Save $1,365
From SAT
Elite
Jul 21
Chicago, United States
72% AI deal score
$3,571
$2,026
Save $1,545
From SAT
Elite
Jul 06
Chicago, United States
72% AI deal score
$3,222
$2,030
Save $1,192
From SAT
Elite
Jul 13
Chicago, United States
72% AI deal score
$3,324
$2,030
Save $1,294
From SAT
Elite
Nov 23
Chicago, United States
72% AI deal score
$967
$750
Save $217
From SAT
Elite
Aug 05
Chicago, United States
71% AI deal score
$2,803
$1,951
Save $852
From SAT
Elite
Jul 08
Chicago, United States
71% AI deal score
$3,226
$1,952
Save $1,274
From SAT
Elite
Aug 06
Chicago, United States
71% AI deal score
$2,805
$1,952
Save $853
From SAT
Elite
Aug 10
Chicago, United States
71% AI deal score
$2,816
$1,982
Save $834
From SAT
Elite
Oct 23
Chicago, United States
71% AI deal score
$2,900
$2,001
Save $899
From SAT
Elite
Oct 22
Chicago, United States
71% AI deal score
$2,905
$2,030
Save $875
From SAT
Elite
Oct 23
Chicago, United States
71% AI deal score
$2,964
$2,057
Save $907
From SAT
Elite
Jul 13
Chicago, United States
71% AI deal score
$3,197
$2,121
Save $1,076
From SAT
Elite
Jul 01
Chicago, United States
71% AI deal score
$3,275
$2,193
Save $1,082
From SAT
Elite
Jul 01
Chicago, United States
71% AI deal score
$3,426
$2,271
Save $1,155
From SAT
Elite
Sep 22
Chicago, United States
71% AI deal score
$872
$715
Save $157
From SAT
Elite
Jul 28
Chicago, United States
71% AI deal score
$879
$742
Save $137
From SAT
Elite
Jul 22
Chicago, United States
71% AI deal score
$896
$742
Save $154
From SAT
Elite
Jul 21
Chicago, United States
71% AI deal score
$899
$742
Save $157
From SAT
Elite
Oct 13
Chicago, United States
71% AI deal score
$881
$659
Save $222
From SAT
Elite
Aug 31
Chicago, United States
71% AI deal score
$941
$667
Save $274
From SAT
Elite
Aug 06
Chicago, United States
71% AI deal score
$942
$675
Save $267
From SAT
Elite
Aug 08
Chicago, United States
71% AI deal score
$915
$675
Save $240
From SAT
Elite
Aug 01
Chicago, United States
71% AI deal score
$946
$694
Save $252
From SAT
Elite
Oct 13
Chicago, United States
71% AI deal score
$919
$694
Save $225
From SAT
Elite
Aug 12
Chicago, United States
70% AI deal score
$2,822
$1,956
Save $866
From SAT
Elite
Oct 03
Chicago, United States
70% AI deal score
$2,776
$2,000
Save $776
From SAT
Elite
Oct 03
Chicago, United States
70% AI deal score
$2,776
$2,056
Save $720
From SAT
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Oct 22
Chicago, United States
70% AI deal score
$2,900
$2,086
Save $814
From SAT
Elite
Jun 26
Chicago, United States
70% AI deal score
$3,349
$2,381
Save $968
From SAT
Elite
Sep 24
Chicago, United States
70% AI deal score
$885
$742
Save $143
From SAT
Elite
Jul 24
Chicago, United States
70% AI deal score
$880
$762
Save $118
From SAT
Elite
Sep 25
Chicago, United States
70% AI deal score
$908
$770
Save $138
From SAT
Elite
Oct 29
Chicago, United States
70% AI deal score
$931
$788
Save $143
From SAT
Elite
Jul 08
Chicago, United States
70% AI deal score
$940
$811
Save $129
From SAT
Elite
Jul 06
Chicago, United States
70% AI deal score
$951
$817
Save $134
From SAT
Elite
Jul 15
Chicago, United States
70% AI deal score
$749
$659
Save $90
From SAT
Elite
Jun 27
Chicago, United States
69% AI deal score
$3,199
$2,607
Save $592
From SAT
Elite
Jun 26
Chicago, United States
69% AI deal score
$3,221
$2,660
Save $561
From SAT
Elite
Jul 07
Chicago, United States
69% AI deal score
$923
$811
Save $112
From SAT
Elite
Jul 14
Chicago, United States
69% AI deal score
$730
$659
Save $71
From SAT
Elite
Jul 15
Chicago, United States
69% AI deal score
$730
$659
Save $71
From SAT
Elite
Jul 08
Chicago, United States
69% AI deal score
$728
$659
Save $69
From SAT
Elite
Jul 15
Chicago, United States
69% AI deal score
$749
$667
Save $82
From SAT
Elite
Jul 14
Chicago, United States
68% AI deal score
$804
$742
Save $62
From SAT
Elite
Jul 30
Chicago, United States
68% AI deal score
$894
$815
Save $79
From SAT
Elite
Jun 20
Chicago, United States
68% AI deal score
$926
$846
Save $80
From SAT
Elite
Jul 22
Chicago, United States
68% AI deal score
$730
$665
Save $65
From SAT
Elite
Jul 16
Chicago, United States
67% AI deal score
$820
$777
Save $43
From SAT
Elite
Oct 11
Chicago, United States
67% AI deal score
$850
$788
Save $62
From SAT
Elite
Jul 04
Chicago, United States
67% AI deal score
$873
$815
Save $58
From SAT
Elite
Jul 15
Chicago, United States
67% AI deal score
$893
$848
Save $45
From SAT
Elite
Jul 11
Chicago, United States
67% AI deal score
$909
$848
Save $61
From SAT
Elite
Nov 25
Chicago, United States
67% AI deal score
$1,489
$1,188
Save $301
From SAT
Elite
Jul 22
Chicago, United States
67% AI deal score
$736
$694
Save $42
From SAT
Elite
Jul 22
Chicago, United States
67% AI deal score
$743
$694
Save $49
From SAT
Elite
Jul 15
Chicago, United States
67% AI deal score
$736
$694
Save $42
From SAT
Elite
Jul 28
Chicago, United States
67% AI deal score
$731
$694
Save $37
From SAT
Elite
Jul 21
Chicago, United States
67% AI deal score
$729
$694
Save $35
From SAT
Elite
Nov 21
Chicago, United States
67% AI deal score
$817
$767
Save $50
From SAT
Elite
Jun 26
Chicago, United States
66% AI deal score
$3,559
$3,388
Save $171
From SAT
Elite
Nov 13
Chicago, United States
66% AI deal score
$814
$787
Save $27
From SAT
Elite
Jul 19
Chicago, United States
49% AI deal score
$1,632
$1,498
Save $134
From SAT
Elite
Jul 21
Chicago, United States
49% AI deal score
$743
$694
Save $49
From SAT
Elite
Jul 15
Chicago, United States
48% AI deal score
$1,652
$1,526
Save $126
From SAT
Elite
Jul 25
Chicago, United States
46% AI deal score
$1,648
$1,630
Save $18
From SAT
Elite
Nov 07
Chicago, United States
45% AI deal score
$1,349
From SAT
Elite
Dec 04
Chicago, United States
44% AI deal score
$1,253
From SAT
Elite
Dec 03
Chicago, United States
43% AI deal score
$1,349
From SAT
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Jul 13
Chicago, United States
40% AI deal score
$1,595
From SAT
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Jul 16
Chicago, United States
39% AI deal score
$1,595
From SAT
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Jul 29
Chicago, United States
38% AI deal score
$1,701
From SAT
Elite
Jul 16
Chicago, United States
38% AI deal score
$2,031
From SAT
Elite
Jun 18
Chicago, United States
38% AI deal score
$2,462
From SAT
Elite
Jul 16
Chicago, United States
37% AI deal score
$1,796
From SAT
Elite
Aug 29
Chicago, United States
37% AI deal score
$1,887
From SAT
Elite
Aug 15
Chicago, United States
37% AI deal score
$1,926
From SAT
Elite
Aug 17
Chicago, United States
37% AI deal score
$1,937
From SAT
Elite
Jul 14
Chicago, United States
37% AI deal score
$2,021
From SAT
Elite
Jul 06
Chicago, United States
37% AI deal score
$2,183
From SAT
Elite
Dec 30
Chicago, United States
37% AI deal score
$2,183
From SAT
Elite
Jun 27
Chicago, United States
36% AI deal score
$2,183
From SAT
Elite
Jul 01
Chicago, United States
36% AI deal score
$2,249
From SAT
Elite
Jul 17
Chicago, United States
36% AI deal score
$2,404