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Chicago → San Diego

Dec 21, 2026 · return Jan 4, 2027

MDW → SAN1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
3:15 pmMDW
4h 20m
Nonstop
5:35 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
1:20 pmMDW
7h 15m
CMH · 1h 20m
6:35 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
9:55 amMDW
7h
BNA · 1h
2:55 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
3:45 pmMDW
7h 5m
ABQ · 1h 55m
8:50 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
2:35 pmMDW
6h 10m
DEN · 1h 10m
6:45 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
10:15 amMDW
7h 35m
HOU · 1h 35m
3:50 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

Southwest Airlines
5:05 amMDW
6h 35m
PHX · 1h 25m
9:40 amSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SAN

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)
2026-12-21 → 2027-01-04Southwest AirlinesWN1987 / WN1981$411.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN4415 / WN1981$411.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN1354 + WN225 / WN1981$390.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN725 + WN1079 / WN1981$390.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN153 + WN167 / WN1981$390.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN4606 + WN1780 / WN1981$390.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN4395 + WN3167 / WN1981$390.252026-10-29T01:29:13Z
2026-12-21 → 2027-01-04Southwest AirlinesWN2995 + WN2447 / WN1981$390.252026-10-29T01:29:13Z

2026-12-21 → 2027-01-04 · $411.25

  • Southwest Airlines WN1987: MDW 2026-12-21 20:55:00 → SAN 2026-12-21 23:25:00; nonstop; 270 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $411.25

  • Southwest Airlines WN4415: MDW 2026-12-21 15:15:00 → SAN 2026-12-21 17:35:00; nonstop; 260 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $390.25

  • Southwest Airlines WN1354 / WN225: MDW 2026-12-21 13:20:00 → SAN 2026-12-21 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
    • WN1354: MDW 2026-12-21 13:20:00 → CMH 2026-12-21 15:25:00; layover at CMH: 80 minutes.
    • WN225: CMH 2026-12-21 16:45:00 → SAN 2026-12-21 18:35:00.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $390.25

  • Southwest Airlines WN725 / WN1079: MDW 2026-12-21 09:55:00 → SAN 2026-12-21 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
    • WN725: MDW 2026-12-21 09:55:00 → BNA 2026-12-21 11:30:00; layover at BNA: 60 minutes.
    • WN1079: BNA 2026-12-21 12:30:00 → SAN 2026-12-21 14:55:00.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $390.25

  • Southwest Airlines WN153 / WN167: MDW 2026-12-21 15:45:00 → SAN 2026-12-21 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
    • WN153: MDW 2026-12-21 15:45:00 → ABQ 2026-12-21 17:55:00; layover at ABQ: 115 minutes.
    • WN167: ABQ 2026-12-21 19:50:00 → SAN 2026-12-21 20:50:00.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $390.25

  • Southwest Airlines WN4606 / WN1780: MDW 2026-12-21 14:35:00 → SAN 2026-12-21 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN4606: MDW 2026-12-21 14:35:00 → DEN 2026-12-21 16:15:00; layover at DEN: 70 minutes.
    • WN1780: DEN 2026-12-21 17:25:00 → SAN 2026-12-21 18:45:00.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $390.25

  • Southwest Airlines WN4395 / WN3167: MDW 2026-12-21 10:15:00 → SAN 2026-12-21 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
    • WN4395: MDW 2026-12-21 10:15:00 → HOU 2026-12-21 12:50:00; layover at HOU: 95 minutes.
    • WN3167: HOU 2026-12-21 14:25:00 → SAN 2026-12-21 15:50:00.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $390.25

  • Southwest Airlines WN2995 / WN2447: MDW 2026-12-21 05:05:00 → SAN 2026-12-21 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
    • WN2995: MDW 2026-12-21 05:05:00 → PHX 2026-12-21 07:55:00; layover at PHX: 85 minutes.
    • WN2447: PHX 2026-12-21 09:20:00 → SAN 2026-12-21 09:40:00.
  • Southwest Airlines WN1981: SAN 2027-01-04 12:00:00 → MDW 2027-01-04 17:55:00; nonstop; 235 minutes. Local airport times.

More dates for this route