Cheap flights from San Antonio to Chicago

Flights overview

Useful information for finding cheap flights from San Antonio to Chicago and booking your next trip
Cheapest round-trip flights $180
Frontier 1 stop 15 hr Sat, May 9 — Sun, May 10
The cheapest round-trip flight from San Antonio to Chicago is currently $180
Cheapest one-way flight $96
Frontier 1 stop 19 hr Mon, Apr 13
The cheapest one-way flight from San Antonio to Chicago is currently $96
Cheapest nonstop flights $277
Southwest Nonstop 3 hr Sat, Apr 11 — Mon, Apr 13
The cheapest nonstop round-trip flight from San Antonio to Chicago is currently $277
Last-minute weekend getaway $530
Frontier 1 stop 24 hr Sat, Mar 14 — Mon, Mar 16
The cheapest last-minute weekend getaway from San Antonio to Chicago is currently $530
Cheapest business class flights $447
Frontier 1 stop 19 hr Sat, May 9 — Sun, May 10
The cheapest business class round-trip flight from San Antonio to Chicago is currently $447
Fastest flight 2 hr 30 min The fastest nonstop flight from San Antonio to Chicago takes 2 hr 30 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from San Antonio to Chicago is typically September. The most expensive month to fly is typically March.
September
Cheapest
Typical prices: $145–235
March
Most expensive
Typical prices: $240–380

Popular airlines from San Antonio to Chicago

  • Southwest
    Nonstop
    from $277
    Typical price: $305–630
    14 weekly nonstop flights
    SAT - MDW Every day
    2389 weekly connecting flights
    SAT - MDW, ORD Every day
  • American
    Nonstop
    from $277
    Typical price: $285–630
    20 weekly nonstop flights
    SAT - ORD Every day
    759 weekly connecting flights
    SAT - ORD Every day
  • United
    Nonstop
    from $277
    Typical price: $295–630
    20 weekly nonstop flights
    SAT - ORD Every day
    484 weekly connecting flights
    SAT - ORD Every day
  • Delta
    from $297
    Typical price: $330–740
    385 weekly connecting flights
    SAT - MDW, ORD Every day
  • Frontier
    from $201
    Typical price: $180–415
    39 weekly connecting flights
    SAT - MDW, ORD Every day
  • Spirit
    from $302
    Typical price: $220–430
    22 weekly connecting flights
    SAT - ORD Every day

Popular airports near San Antonio

  • San Antonio International Airport (SAT)
    San Antonio United States 19 min 7 mi
  • Austin-Bergstrom International Airport (AUS)
    Austin United States 1 hr 22 min 72 mi
  • George Bush Intercontinental Airport (IAH)
    Houston United States 3 hr 10 min 193 mi
  • William P. Hobby Airport (HOU)
    Houston United States 3 hr 15 min 193 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 59 min 165 mi

Frequently asked questions about flying from San Antonio to Chicago

The cheapest flights from San Antonio to Chicago are usually in September. Typical ticket prices in September range from $145 to $235.
The cheapest round-trip flight from San Antonio to Chicago recently found on Google Flights was with Frontier from $180. The cheapest one-way flight was with Frontier from $96.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Antonio to Chicago is $277, flying from Apr 11 to Apr 13.
  • The cheapest American flight from San Antonio to Chicago is $277, flying from May 9 to May 11.
  • The cheapest United flight from San Antonio to Chicago is $277, flying from Apr 18 to Apr 20.
  • The cheapest Delta flight from San Antonio to Chicago is $297, flying from Apr 18 to Apr 20.
  • The cheapest Frontier flight from San Antonio to Chicago is $201, flying from Apr 16 to Apr 20.
  • The cheapest Spirit flight from San Antonio to Chicago is $302, flying from May 14 to May 18.
The cheapest round-trip flight from San Antonio to Chicago starts at $180 from Sat, May 9 to Sun, May 10. The cheapest one-way flight starts at $96 and departs on Mon, Apr 13.
2 hr 30 min is the shortest flight time from San Antonio to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from San Antonio to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from San Antonio to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from San Antonio to Chicago.

In terms of nonstop flights, American is the most popular. American offers 20 nonstop flights and 759 connecting flights per week. American flies from San Antonio International Airport (SAT) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 14 nonstop flights and 2,389 connecting flights per week. Southwest flies from San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from San Antonio to Chicago are:
  • United offers 20 nonstop flights and 484 connecting flights per week. United flies from San Antonio International Airport (SAT) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 385 connecting flights per week. Delta flies from San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Frontier offers 39 connecting flights per week. Frontier flies from San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Spirit offers 22 connecting flights per week. Spirit flies from San Antonio International Airport (SAT) to Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between San Antonio and Chicago.
The cheapest round-trip flight from San Antonio to Chicago recently found on Google Flights was with Frontier from $180. The cheapest one-way flight was with Frontier from $96.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Antonio to Chicago is $277, flying from Apr 11 to Apr 13.
  • The cheapest American flight from San Antonio to Chicago is $277, flying from May 9 to May 11.
  • The cheapest United flight from San Antonio to Chicago is $277, flying from Apr 18 to Apr 20.
  • The cheapest Delta flight from San Antonio to Chicago is $297, flying from Apr 18 to Apr 20.
  • The cheapest Frontier flight from San Antonio to Chicago is $201, flying from Apr 16 to Apr 20.
  • The cheapest Spirit flight from San Antonio to Chicago is $302, flying from May 14 to May 18.
Southwest, American and United fly direct from San Antonio to Chicago.
  • There are 14 Southwest direct flights from San Antonio to Chicago per week. Flights are available every day.
  • There are 20 American direct flights from San Antonio to Chicago per week. Flights are available every day.
  • There are 20 United direct flights from San Antonio to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between San Antonio and Chicago at price $530 is offered by Frontier from Sat, Mar 14 to Mon, Mar 16.
Southwest, American and United fly direct from San Antonio to Chicago.
  • There are 14 Southwest direct flights from San Antonio to Chicago per week. Flights are available every day.
  • There are 20 American direct flights from San Antonio to Chicago per week. Flights are available every day.
  • There are 20 United direct flights from San Antonio to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from San Antonio to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between San Antonio and Chicago start at $277 from Sat, Apr 11 to Mon, Apr 13 with Southwest.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from San Antonio to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between San Antonio and Chicago start at $447 from Sat, May 9 to Sun, May 10 with Frontier.
The cheapest economy class round-trip flights between San Antonio and Chicago start at $180 from Sat, May 9 to Sun, May 10.
To book business class trips from San Antonio to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between San Antonio and Chicago starts at $530 from Sat, Mar 14 to Mon, Mar 16 with Frontier.
The cheapest last-minute deal between San Antonio and Chicago at price $530 is offered by Frontier from Sat, Mar 14 to Mon, Mar 16.
To find last-minute flight deals from San Antonio to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

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