Cheap flights from San Antonio to Chicago from $130 SAT → ORD

Found recently, and the cheapest we hold

What have prices looked like?

Over 50 days, 24 Sept to 12 Nov, the cheapest return we saw each day was $227 to $442.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 14-night return fares leaving within 3 days of 20 Dec to compare.

Every date we hold

3 fares on 2 departure dates

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 41 days, 30 Sept to 12 Nov, the cheapest one-way we saw each day was $123 to $322.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other one-way fares leaving within 3 days of 25 Nov to compare.

Every date we hold

3 fares on 3 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $130.

Return

Fares 14 to 29 days before departure were typically 53% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 12 Nov (50 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 7 to 13 days before departure were typically 10% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 30 Sept and 12 Nov (41 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from San Antonio to Chicago?

The cheapest return found recently is $382 with Frontier Airlines, 20 Dec to 3 Jan 2027, found 3 days ago. The cheapest return we hold, of any age, is $300 with Frontier Airlines, 19 Dec to 4 Jan 2027, found 6 days ago.

How much is a one-way flight from San Antonio to Chicago?

The cheapest one-way found recently is $130 with Frontier Airlines, 25 Nov, found 3 days ago. The cheapest one-way fare on each of 3 departure dates is usually $152 to $208.

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

November 2026 is the cheapest month for a one-way, from $130, 25 Nov, found 3 days ago.

How far ahead should I book a flight from San Antonio to Chicago?

In 50 days of prices between 24 Sept and 12 Nov, return fares 14 to 29 days before departure were typically 53% lower than 0 to 6 days before departure. In 41 days of prices between 30 Sept and 12 Nov, one-way fares 7 to 13 days before departure were typically 10% lower than 0 to 6 days before departure.

Is there a direct flight from San Antonio to Chicago?

Yes, the cheapest nonstop one-way found recently is $242 with American Airlines, 2 Jan 2027, found 3 days ago.

How long is the flight from San Antonio to Chicago?

The cheapest nonstop one-way found recently, with American Airlines on 2 Jan 2027, takes 3 h 1 min from San Antonio International Airport (SAT) to O'Hare International Airport (ORD). The cheapest one-way found recently, with Frontier Airlines on 25 Nov, takes 12 h 36 min with 1 stop.

Which airlines have the cheapest flights from San Antonio to Chicago?

Between 25 Nov and 2 Jan 2027, Frontier Airlines has the cheapest one-way on 2 of the 3 departure dates we hold, and American Airlines on 1.