Cheap Flights from San Antonio to Chicago
Cheap Flights from San Antonio to Chicago
Looking for cheap flights from San Antonio to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from San Antonio to Chicago vary by season, cabin, and date, but available award flights can start around 7,000–7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from San Antonio to Chicago for specific travel dates.
2026-12-26
SAT - ORD
Economy | 1 Stop
From 7,000 Pts + $11.2
2026-12-26
SAT - ORD
Economy | 1 Stop
From 7,000 Pts + $11.2
2026-11-09
SAT - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
SAT - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-11
SAT - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-13
SAT - ORD
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
San Antonio to Chicago flight facts
Distance
1,036 mi
1,666 km in a straight line
Estimated flight time
about 2h 30m
In the air, for the straight-line distance
Time difference
Same time zone
Chicago is in the same time zone as San Antonio.
Airports in San Antonio
SAT · San Antonio Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Austin - Chicago · Austin is 66 mi from San Antonio
Flights San Antonio - Milwaukee · Milwaukee is 73 mi from Chicago
Flights Killeen - Chicago · Killeen is 113 mi from San Antonio
Flights San Antonio - Grand Rapids · Grand Rapids is 142 mi from Chicago
Flights College Station - Chicago · College Station is 146 mi from San Antonio
Flights Laredo - Chicago · Laredo is 150 mi from San Antonio
Premium cabin flights from San Antonio to Chicago
Premium cabin
2026-11-12
SAT - ORD
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-12
SAT - ORD
First | Non stop | 2 left
From 20,000 Pts + $5.6
Premium cabin
2026-11-06
SAT - ORD
First | 1 Stop
From 21,500 Pts + $5.6
Premium cabin
2026-11-07
SAT - ORD
First | Non stop
From 21,500 Pts + $5.6
Premium cabin
2026-11-05
SAT - ORD
First | 1 Stop
From 24,000 Pts + $5.6
Premium cabin
2026-11-08
SAT - ORD
First | 1 Stop
From 24,500 Pts + $5.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from San Antonio to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from San Antonio to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from San Antonio to Chicago.
San Antonio and Chicago are about 1,036 miles (1,666 km) apart in a straight line.
Flying the 1,036-mile straight-line distance takes about 2h 30m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is in the same time zone as San Antonio.
Departures from San Antonio: San Antonio Intl (SAT). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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