Cheap flights from San Antonio to Chicago

One-way fares from $165 · SAT → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → San Antonio
Cheapest fare
$165

Frontier Airlines · Mon, Nov 16

Cheapest month
November

from $165

Direct flights
Not recently

Usually 1+ stop

Quickest trip
4h 55m

1,690 km

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Cheapest month to fly from San Antonio to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $165

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Frontier Airlines
Depart20:20 Mon, Nov 16SAT → ORD 4h 55m · 1 stop
$165one way, per person
View deal
Frontier Airlines
Depart20:20 Thu, Nov 12SAT → ORD 4h 55m · 1 stop
$180one way, per person
View deal
Frontier Airlines
Depart20:20 Mon, Nov 9SAT → ORD 4h 55m · 1 stop
$183one way, per person
View deal
Frontier Airlines
Depart20:11 Fri, Nov 6SAT → ORD 4h 55m · 1 stop
$212one way, per person
View deal
See every date in November 2026 →

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Where to stay, what to do and getting around, from our travel partners.

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About flights from San Antonio to Chicago

San Antonio (SAT) and Chicago (CHI) are about 1,690 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 4h 55m. Over the next few months, one-way fares start from $165, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from San Antonio to Chicago?

The cheapest one-way fare we've seen recently is $165 with Frontier Airlines, departing Monday, November 16, 2026.

What is the cheapest month to fly from San Antonio to Chicago?

November 2026 currently has the lowest fares, from $165 one way.

Are there direct flights from San Antonio to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from San Antonio to Chicago?

The quickest journey we've seen takes about 4h 55m. San Antonio and Chicago are around 1,690 km apart.

Which airlines fly from San Antonio to Chicago?

Recent fares on this route were with Frontier Airlines.

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