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San Antonio → Chicago

Jan 21, 2027 · one way

SAT → MDW1 adulteconomyOne way

8 flight options · 2 airlines

Nonstop flights

Thu, Jan 21 · One way

Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

One-way total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 · One way

Delta Air Lines
11:00 amSAT
5h 18m
ATL · 1h 8m
4:18 pmMDW

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
1:00 pmSAT
6h 40m
HOU · 3h 20m
7:40 pmMDW

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
7:10 amSAT
5h 45m
BNA · 2h
12:55 pmMDW

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Southwest Airlines
2:35 pmSAT
6h 25m
DAL · 3h 10m
9:00 pmMDW

One-way total · 1 adult · Taxes included

Thu, Jan 21 · One way

Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

SAT ⇄ MDW

Economy

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

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-21 · one waySouthwest AirlinesWN3791$165.002026-10-29T02:06:15Z
2027-01-21 · one wayDelta Air LinesDL1676 + DL1728$190.002026-10-29T02:06:15Z
2027-01-21 · one waySouthwest AirlinesWN2348$165.002026-10-29T02:06:15Z
2027-01-21 · one waySouthwest AirlinesWN4494 + WN2134$155.002026-10-29T02:06:15Z
2027-01-21 · one waySouthwest AirlinesWN2991 + WN1005$155.002026-10-29T02:06:15Z
2027-01-21 · one waySouthwest AirlinesWN3801 + WN4175$155.002026-10-29T02:06:15Z
2027-01-21 · one waySouthwest AirlinesWN1506 + WN1433$155.002026-10-29T02:06:15Z
2027-01-21 · one wayDelta Air LinesDL2497 + DL4688$190.002026-10-29T02:06:15Z

2027-01-21 · one way · $165.00

  • Southwest Airlines WN3791: SAT 2027-01-21 14:50:00 → MDW 2027-01-21 17:25:00; nonstop; 155 minutes. Local airport times.

2027-01-21 · one way · $190.00

  • Delta Air Lines DL1676 / DL1728: SAT 2027-01-21 11:00:00 → MDW 2027-01-21 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2027-01-21 11:00:00 → ATL 2027-01-21 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2027-01-21 15:25:00 → MDW 2027-01-21 16:18:00.

2027-01-21 · one way · $165.00

  • Southwest Airlines WN2348: SAT 2027-01-21 06:25:00 → MDW 2027-01-21 08:55:00; nonstop; 150 minutes. Local airport times.

2027-01-21 · one way · $155.00

  • Southwest Airlines WN4494 / WN2134: SAT 2027-01-21 13:00:00 → MDW 2027-01-21 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
    • WN4494: SAT 2027-01-21 13:00:00 → HOU 2027-01-21 13:55:00; layover at HOU: 200 minutes.
    • WN2134: HOU 2027-01-21 17:15:00 → MDW 2027-01-21 19:40:00.

2027-01-21 · one way · $155.00

  • Southwest Airlines WN2991 / WN1005: SAT 2027-01-21 07:10:00 → MDW 2027-01-21 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
    • WN2991: SAT 2027-01-21 07:10:00 → BNA 2027-01-21 09:25:00; layover at BNA: 120 minutes.
    • WN1005: BNA 2027-01-21 11:25:00 → MDW 2027-01-21 12:55:00.

2027-01-21 · one way · $155.00

  • Southwest Airlines WN3801 / WN4175: SAT 2027-01-21 15:20:00 → MDW 2027-01-21 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2027-01-21 15:20:00 → STL 2027-01-21 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2027-01-21 18:55:00 → MDW 2027-01-21 20:00:00.

2027-01-21 · one way · $155.00

  • Southwest Airlines WN1506 / WN1433: SAT 2027-01-21 14:35:00 → MDW 2027-01-21 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2027-01-21 14:35:00 → DAL 2027-01-21 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2027-01-21 18:50:00 → MDW 2027-01-21 21:00:00.

2027-01-21 · one way · $190.00

  • Delta Air Lines DL2497 / DL4688: SAT 2027-01-21 05:25:00 → MDW 2027-01-21 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2027-01-21 05:25:00 → DTW 2027-01-21 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2027-01-21 12:44:00 → MDW 2027-01-21 13:01:00.

More dates for this route