Cheap Flights from Chicago to San Antonio
Cheap Flights from Chicago to San Antonio
Looking for cheap flights from Chicago to San Antonio? 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 Chicago to San Antonio 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 Chicago to San Antonio for specific travel dates.
2027-01-01
ORD - SAT
Economy | 1 Stop
From 7,000 Pts + $5.6
2026-11-05
ORD - SAT
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-06
ORD - SAT
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-07
ORD - SAT
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - SAT
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-11
ORD - SAT
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to San Antonio 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
San Antonio is in the same time zone as Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in San Antonio
SAT · San Antonio Intl
Nearby airport alternatives
Flights Chicago - Austin · Austin is 66 mi from San Antonio
Flights Milwaukee - San Antonio · Milwaukee is 73 mi from Chicago
Flights Grand Rapids - San Antonio · Grand Rapids is 142 mi from Chicago
Flights Chicago - College Station · College Station is 146 mi from San Antonio
Flights Chicago - Laredo · Laredo is 150 mi from San Antonio
Flights Chicago - Waco · Waco is 161 mi from San Antonio
Premium cabin flights from Chicago to San Antonio
Premium cabin
2026-11-09
ORD - SAT
First | Non stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-12
ORD - SAT
First | Non stop | 2 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-13
ORD - SAT
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-14
ORD - SAT
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - SAT
First | Non stop | 4 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - SAT
First | Non stop | 1 left
From 15,000 Pts + $25.6
Selected hotels for your next stay
San Antonio (United States)
Hyatt Regency Hill Country Resort and Spa
From 15,000 Pts or $439
San Antonio (United States)
Thompson San Antonio – Riverwalk
From 15,000 Pts or $231
San Antonio, TX (USA)
JW Marriott San Antonio Hill Country Resort & Spa
From Pts or $322
Frequently Asked Questions
The cheapest route from Chicago to San Antonio 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 Chicago to San Antonio.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to San Antonio.
Chicago and San Antonio 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.
San Antonio is in the same time zone as Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in San Antonio: San Antonio Intl (SAT).
Travelers searching this route also look at other popular routes into San Antonio, plus the return trip when we track it. Fares and award space change daily.
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