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How to get from San Antonio to Chicago

No nonstop flights. The fastest way is via Houston: about 6h 28m including the connection. Other options: via Dallas, Atlanta, Monterrey and Charlotte. Two tickets from $138.

Flights from San Antonio to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: San Antonio to Chicago

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from San Antonio to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $130 25 November 2026, with a connection Cheapest nonstop $165 15 November 2026, AA Cheapest in the next 7 days $165 15 November, Sun Cheapest weekend departure $242 Sat, 2 January 2027 Cheapest month November 2026 tickets from $130

Where to connect

Options with one connection, fastest first

fastest, via Houston
6h 28m
two tickets, via Dallas
$138
connection options
5
straight-line distance
1,053 mi (1,694 km)
fastest
Via Houston
6h 28m
with the connection
San Antonio to Houston flight 1h
Connection of about 3h Arrival: George Bush Intercontinental, William P. Hobby. Departure to Chicago: George Bush Intercontinental, William P. Hobby.
Houston to Chicago flight 2h 28m
two ticketsfrom $349
Via Dallas
6h 42m
with the connection
San Antonio to Dallas flight 1h 10m
Connection of about 3h Arrival: Dallas Love Field, Dallas/Fort Worth International. Departure to Chicago: Dallas Love Field, Dallas/Fort Worth International.
Dallas to Chicago flight 2h 32m
two ticketsfrom $138
Via Atlanta
7h 30m
with the connection
San Antonio to Atlanta flight 2h 19m
Connection of about 3h
Atlanta to Chicago flight 2h 11m
two ticketsfrom $364
Via Monterrey
Mexico
7h 35m
with the connection
San Antonio to Monterrey flight 1h 10m
Connection of about 3h
Monterrey to Chicago flight 3h 25m
Via Charlotte
8h 7m
with the connection
San Antonio to Charlotte flight 2h 50m
Connection of about 3h
Charlotte to Chicago flight 2h 17m
two ticketsfrom $586

One ticket or two

How the options are calculated and what to keep in mind at the connection

Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Nearest nonstop flights

The closest you can get without a connection

Frequently asked questions

Is there a nonstop flight from San Antonio to Chicago?
There are no nonstop flights in the schedule. You will need a connection, the fastest is via Houston.
What is the fastest way to fly from San Antonio to Chicago?
Via Houston: 1h to the connection, 2h 28m after it, about 6h 28m in total with 3h for the connection.
How much does a flight from San Antonio to Chicago with a connection cost?
Two nonstop tickets via Dallas from $138. This is the sum of the lowest known prices for each leg, and their dates may not match.
Which cities can you connect in between San Antonio and Chicago?
Houston (6h 28m total), Dallas (6h 42m total), Atlanta (7h 30m total), Monterrey (7h 35m total) and Charlotte (8h 7m total).
How far is Chicago from San Antonio?
1,053 mi (1,694 km) in a straight line between the cities.
How much time should I allow for the connection?
The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.