$131 Find Cheap Flights from San Antonio to Chicago Midway Airport - Compare and Save

Among airlines operating San Antonio to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between San Antonio and Chicago Midway Airport.

Flights from San Antonio to Chicago Midway Airport usually depart from San Antonio (SAT) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• JetBlue: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Two cabin classes are available on flights from San Antonio to Chicago Midway Airport:

• Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $277 round-trip via Orlando (MCO), compared to $398 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Airbus A319 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Embraer 175 variants.

One-stop flights from San Antonio to Chicago Midway Airport most commonly connect through:

• Atlanta Hartsfield-Jackson (ATL) - 67% of one-stop connections
• Dallas Love Field (DAL) - 25% of one-stop connections
• Orlando (MCO) - 8% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 14% on the San Antonio to Chicago Midway Airport route. Wednesday is the cheapest departure day at $367 round-trip on average, while Tuesday is the most expensive at $425, a difference of $58. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on San Antonio to Chicago Midway Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from San Antonio to Chicago Midway Airport:

• Earliest: departs at 5:00 am and lands at 7:37 am
• Latest: departs at 4:30 pm and lands at 7:07 pm.

The flight takes about 2h 37m.

Last-minute fares on this route - booked within 2 weeks of departure - run 79% above the route average of $385. Book 10 weeks before departure for the lowest fares.

A nonstop flight from San Antonio to Chicago Midway Airport takes 2h 37m, covering 1,036 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $286 to $1,479. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from San Antonio to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $137, which is 47% below the typical average for this route.

Flying via Dallas Love Field (DAL) gives the shortest average 1-stop total travel time at 4h 57m, compared with 8h 38m via Atlanta Hartsfield-Jackson (ATL) and 21h 48m via Orlando (MCO).

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from San Antonio to Chicago Midway Airport range from $318 to $517, with an average of $385 over the past 12 months. Anything below $318 counts as a good deal.

JetBlue is the only airline on the San Antonio to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.