WarBird Flight is an independent booking service, not affiliated with United Airlines. Fares are recorded lows for the route across carriers; the agent quotes United Airlines's current fare on the call.

CHI → SAT · about 2h 45m nonstop · 1,042 miles · 4 airlines
Fares shown are recorded lows. An agent confirms today's live price on the call.
Chicago is a United Airlines hub, so United Airlines typically offers several daily departures on CHI–SAT, with nonstop service where demand supports it and connections through its other hubs otherwise. The nonstop flight time is about 2h 45m.
Fare classes available: Basic Economy, Economy, Economy Plus, Premium Plus / First / Polaris. United has no change fees on Economy and above for travel within the US or between the US and Mexico, the Caribbean, or international destinations originating in the US. Fare difference applies.
The lowest one-way fare we have on record for this route is $231 on Southwest, and $306 round-trip. Fares like that usually show up on off-peak days and for travel booked a few weeks out; an agent can check whether a similar fare is available for your dates.
Because Delta Air Lines treats San Antonio as a hub, this pairing tends to have frequent departures throughout the day. American Airlines and Southwest Airlines also compete here, which keeps fares in check.
The 1,042 miles between Chicago and San Antonio works out to about 2h 45m in the air, the range where nonstops are common on busy days and connections through a hub fill in the rest. Ask the agent to compare both; the one-stop is sometimes cheaper by a wide margin.
Recorded lows on CHI–SAT have come from American and Southwest recently. The cheapest carrier on a given day depends on how full each flight is, so a live comparison usually beats any rule of thumb.
From the Midwest, the expensive weeks cluster around Thanksgiving, Christmas, and spring break in March; May, early June, September, and October tend to price lowest.
Tuesday, Wednesday, and Saturday departures are usually the cheapest days on domestic routes; Friday and Sunday are the most expensive. Early-morning and late-evening flights are often priced below the midday departures.
For domestic travel, booking three to eight weeks ahead usually captures the best price. Inside two weeks, fares climb; more than four months out, airlines have not yet released their cheapest inventory.
The same city pair priced from each airport combination. Differences on the same day are often larger than the drive between airports.
Fares from a neighboring airport are sometimes far lower than the drive is long. Agents quote all of these on one call.
Licensed agents at our partner agency handle these by phone, 24/7. No charge for a quote.
Chicago is a United Airlines hub, so nonstop service is likely on this route. The agent confirms the schedule for your dates.
The lowest one-way fare we have recorded recently is $231, and $306 round-trip. Fares change daily; call (708) 866-8751 for today's price.
A nonstop flight takes about 2h 45m to cover 1,042 miles. Connecting itineraries add two to five hours depending on the layover.
Delta Air Lines, United Airlines, American Airlines, and Southwest Airlines are the carriers most likely to serve this route. We book all of them.
Yes. Licensed agents at our partner agency book United and United Express flights in every cabin and can compare them with other carriers on your route.
On most domestic routes, no. Only a personal item is included. Economy fares include a full-size carry-on.
All airlines, Chicago to San Antonio · United Airlines booking