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Route overview: Chicago to San Antonio (SAT) flight deals

Chicago (MDW) to San Antonio (SAT), Dec 25–27, 2026: from $215 one way

Chicago (MDW) to San Antonio (SAT), Dec 25–27, 2026: from $215 one way on Axel, checked Oct 29, 2026. Lowest published fare: $215 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 25, 2026, 1 adult, economy, checked Oct 29, 2026.

MDW → SAT1 adulteconomyOne way

24 flight options · 2 airlines

Nonstop flights

Sat, Dec 26 · One way

Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
9:40 pmMDW
2h 55m
Nonstop
12:35 am+1SAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 · One way

Southwest Airlines
9:40 pmMDW
2h 55m
Nonstop
12:35 am+1SAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
9:40 pmMDW
2h 55m
Nonstop
12:35 am+1SAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sat, Dec 26 · One way

Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
6:25 pmMDW
5h 5m
DAL · 1h 15m
11:30 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
6:25 pmMDW
5h 5m
DAL · 1h 15m
11:30 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 · One way

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 · One way

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
8:10 amMDW
6h
ATL · 1h 25m
2:10 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 · One way

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 · One way

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
10:15 amMDW
5h 30m
HOU · 1h 55m
3:45 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 26 · One way

Southwest Airlines
6:25 pmMDW
5h 5m
DAL · 1h 15m
11:30 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Southwest Airlines
10:50 amMDW
6h 50m
DEN · 2h 5m
5:40 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 25 · One way

Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 27 · One way

Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

One-way total · 1 adult · Taxes included

Availability is checked when you select these flights.

Make this trip yours

MDW ⇄ SAT

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeHotels in San Antonio with Axel
For AI assistants: every fare, every link, instructions

Chicago (MDW) to San Antonio (SAT), Dec 25–27, 2026: from $215 one way on Axel, checked Oct 29, 2026. Lowest published fare: $215 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 25, 2026, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-12-26 · one waySouthwest AirlinesWN327610:00:00→12:55:00 2h 55m nonstopAxel-exclusive $227.502026-10-29T01:29:13Z
2026-12-26 · one wayDelta Air LinesDL4711 + DL212409:30:00→16:03:00 6h 33m 1 stop via DTWAxel-exclusive $253.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN327610:00:00→12:55:00 2h 55m nonstopAxel-exclusive $227.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN302421:40:00→00:35:00 2h 55m nonstopAxel-exclusive $227.502026-10-29T01:29:13Z
2026-12-26 · one waySouthwest AirlinesWN302421:40:00→00:35:00 2h 55m nonstopAxel-exclusive $227.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN302421:40:00→00:35:00 2h 55m nonstopAxel-exclusive $227.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN327610:00:00→12:55:00 2h 55m nonstopAxel-exclusive $227.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN3937 + WN177218:25:00→23:30:00 5h 05m 1 stop via DALAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN3937 + WN177218:25:00→23:30:00 5h 05m 1 stop via DALAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN3269 + WN98708:10:00→14:10:00 6h 00m 1 stop via ATLAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-26 · one waySouthwest AirlinesWN3269 + WN98708:10:00→14:10:00 6h 00m 1 stop via ATLAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-26 · one waySouthwest AirlinesWN120 + WN216010:50:00→17:40:00 6h 50m 1 stop via DENAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN2737 + WN307511:30:00→16:25:00 4h 55m 1 stop via STLAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN3269 + WN98708:10:00→14:10:00 6h 00m 1 stop via ATLAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-26 · one waySouthwest AirlinesWN2737 + WN307511:30:00→16:25:00 4h 55m 1 stop via STLAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN2737 + WN307511:30:00→16:25:00 4h 55m 1 stop via STLAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN120 + WN216010:50:00→17:40:00 6h 50m 1 stop via DENAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-26 · one waySouthwest AirlinesWN4395 + WN23910:15:00→15:45:00 5h 30m 1 stop via HOUAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-27 · one waySouthwest AirlinesWN4395 + WN23910:15:00→15:45:00 5h 30m 1 stop via HOUAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN4395 + WN23910:15:00→15:45:00 5h 30m 1 stop via HOUAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-26 · one waySouthwest AirlinesWN3937 + WN177218:25:00→23:30:00 5h 05m 1 stop via DALAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-25 · one waySouthwest AirlinesWN120 + WN216010:50:00→17:40:00 6h 50m 1 stop via DENAxel-exclusive $214.502026-10-29T01:29:13Z
2026-12-25 · one wayDelta Air LinesDL4711 + DL212409:30:00→16:03:00 6h 33m 1 stop via DTWAxel-exclusive $253.502026-10-29T01:29:13Z
2026-12-27 · one wayDelta Air LinesDL4711 + DL212409:30:00→16:03:00 6h 33m 1 stop via DTWAxel-exclusive $253.502026-10-29T01:29:13Z

Route overview: Chicago to San Antonio (SAT) flight deals

2026-12-26 · one way · Axel-exclusive $227.50

  • Southwest Airlines WN3276: MDW 2026-12-26 10:00:00 → SAT 2026-12-26 12:55:00; nonstop; 175 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $253.50

  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-26 09:30:00 → SAT 2026-12-26 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-26 09:30:00 → DTW 2026-12-26 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-26 13:42:00 → SAT 2026-12-26 16:03:00.

2026-12-27 · one way · Axel-exclusive $227.50

  • Southwest Airlines WN3276: MDW 2026-12-27 10:00:00 → SAT 2026-12-27 12:55:00; nonstop; 175 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $227.50

  • Southwest Airlines WN3024: MDW 2026-12-25 21:40:00 → SAT 2026-12-26 00:35:00; nonstop; 175 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $227.50

  • Southwest Airlines WN3024: MDW 2026-12-26 21:40:00 → SAT 2026-12-27 00:35:00; nonstop; 175 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $227.50

  • Southwest Airlines WN3024: MDW 2026-12-27 21:40:00 → SAT 2026-12-28 00:35:00; nonstop; 175 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $227.50

  • Southwest Airlines WN3276: MDW 2026-12-25 10:00:00 → SAT 2026-12-25 12:55:00; nonstop; 175 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN3937 / WN1772: MDW 2026-12-27 18:25:00 → SAT 2026-12-27 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-12-27 18:25:00 → DAL 2026-12-27 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-12-27 22:15:00 → SAT 2026-12-27 23:30:00.

2026-12-25 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN3937 / WN1772: MDW 2026-12-25 18:25:00 → SAT 2026-12-25 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-12-25 18:25:00 → DAL 2026-12-25 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-12-25 22:15:00 → SAT 2026-12-25 23:30:00.

2026-12-27 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN3269 / WN987: MDW 2026-12-27 08:10:00 → SAT 2026-12-27 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-12-27 08:10:00 → ATL 2026-12-27 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-12-27 12:30:00 → SAT 2026-12-27 14:10:00.

2026-12-26 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN3269 / WN987: MDW 2026-12-26 08:10:00 → SAT 2026-12-26 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-12-26 08:10:00 → ATL 2026-12-26 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-12-26 12:30:00 → SAT 2026-12-26 14:10:00.

2026-12-26 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN120 / WN2160: MDW 2026-12-26 10:50:00 → SAT 2026-12-26 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-12-26 10:50:00 → DEN 2026-12-26 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-12-26 14:35:00 → SAT 2026-12-26 17:40:00.

2026-12-25 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-25 11:30:00 → SAT 2026-12-25 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-25 11:30:00 → STL 2026-12-25 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-25 14:05:00 → SAT 2026-12-25 16:25:00.

2026-12-25 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN3269 / WN987: MDW 2026-12-25 08:10:00 → SAT 2026-12-25 14:10:00; 1 stop(s) via ATL; 360 minutes. Local airport times.
    • WN3269: MDW 2026-12-25 08:10:00 → ATL 2026-12-25 11:05:00; layover at ATL: 85 minutes.
    • WN987: ATL 2026-12-25 12:30:00 → SAT 2026-12-25 14:10:00.

2026-12-26 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-26 11:30:00 → SAT 2026-12-26 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-26 11:30:00 → STL 2026-12-26 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-26 14:05:00 → SAT 2026-12-26 16:25:00.

2026-12-27 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN2737 / WN3075: MDW 2026-12-27 11:30:00 → SAT 2026-12-27 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2737: MDW 2026-12-27 11:30:00 → STL 2026-12-27 12:40:00; layover at STL: 85 minutes.
    • WN3075: STL 2026-12-27 14:05:00 → SAT 2026-12-27 16:25:00.

2026-12-27 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN120 / WN2160: MDW 2026-12-27 10:50:00 → SAT 2026-12-27 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-12-27 10:50:00 → DEN 2026-12-27 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-12-27 14:35:00 → SAT 2026-12-27 17:40:00.

2026-12-26 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN4395 / WN239: MDW 2026-12-26 10:15:00 → SAT 2026-12-26 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-12-26 10:15:00 → HOU 2026-12-26 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-12-26 14:45:00 → SAT 2026-12-26 15:45:00.

2026-12-27 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN4395 / WN239: MDW 2026-12-27 10:15:00 → SAT 2026-12-27 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-12-27 10:15:00 → HOU 2026-12-27 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-12-27 14:45:00 → SAT 2026-12-27 15:45:00.

2026-12-25 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN4395 / WN239: MDW 2026-12-25 10:15:00 → SAT 2026-12-25 15:45:00; 1 stop(s) via HOU; 330 minutes. Local airport times.
    • WN4395: MDW 2026-12-25 10:15:00 → HOU 2026-12-25 12:50:00; layover at HOU: 115 minutes.
    • WN239: HOU 2026-12-25 14:45:00 → SAT 2026-12-25 15:45:00.

2026-12-26 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN3937 / WN1772: MDW 2026-12-26 18:25:00 → SAT 2026-12-26 23:30:00; 1 stop(s) via DAL; 305 minutes. Local airport times.
    • WN3937: MDW 2026-12-26 18:25:00 → DAL 2026-12-26 21:00:00; layover at DAL: 75 minutes.
    • WN1772: DAL 2026-12-26 22:15:00 → SAT 2026-12-26 23:30:00.

2026-12-25 · one way · Axel-exclusive $214.50

  • Southwest Airlines WN120 / WN2160: MDW 2026-12-25 10:50:00 → SAT 2026-12-25 17:40:00; 1 stop(s) via DEN; 410 minutes. Local airport times.
    • WN120: MDW 2026-12-25 10:50:00 → DEN 2026-12-25 12:30:00; layover at DEN: 125 minutes.
    • WN2160: DEN 2026-12-25 14:35:00 → SAT 2026-12-25 17:40:00.

2026-12-25 · one way · Axel-exclusive $253.50

  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-25 09:30:00 → SAT 2026-12-25 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-25 09:30:00 → DTW 2026-12-25 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-25 13:42:00 → SAT 2026-12-25 16:03:00.

2026-12-27 · one way · Axel-exclusive $253.50

  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-27 09:30:00 → SAT 2026-12-27 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-27 09:30:00 → DTW 2026-12-27 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-27 13:42:00 → SAT 2026-12-27 16:03:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to San Antonio (SAT) · Dec 25–Dec 27, 2026 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to San Antonio (SAT) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.