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Chicago → San Diego

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MDW → SAN1 adulteconomy

24 flight options · 1 airline

Round-trip flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:20 amMDW
4h 25m
Nonstop
12:45 pmSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:15 pmMDW
4h 20m
Nonstop
5:35 pmSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
10:20 amMDW
4h 25m
Nonstop
12:45 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:45 pmMDW
7h 5m
ABQ · 1h 55m
8:50 pmSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:35 pmMDW
6h 10m
DEN · 1h 10m
6:45 pmSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:05 amMDW
6h 35m
PHX · 1h 25m
9:40 amSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
1:20 pmMDW
7h 15m
CMH · 1h 20m
6:35 pmSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Show 8 more flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:55 amMDW
7h
BNA · 1h
2:55 pmSAN
Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:10 amMDW
4h 25m
Nonstop
12:35 pmSAN
Southwest Airlines
12:10 pmSAN
5h 35m
OMA · 1h 5m
7:45 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
10:20 amMDW
4h 25m
Nonstop
12:45 pmSAN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
5:05 amMDW
6h 35m
PHX · 1h 25m
9:40 amSAN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:15 amMDW
7h 35m
HOU · 1h 35m
3:50 pmSAN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:55 amMDW
7h
BNA · 1h
2:55 pmSAN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
1:20 pmMDW
7h 15m
CMH · 1h 20m
6:35 pmSAN

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:35 pmMDW
6h 10m
DEN · 1h 10m
6:45 pmSAN

One-way 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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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN1456$249.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1456 / WN1156$411.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4415 / WN1981$472.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4415$249.752026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4415 / WN1156$411.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1456 / WN1981$472.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN153 + WN167$229.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2995 + WN2447$229.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4395 + WN3167$229.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN725 + WN1079$229.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN1354 + WN225$229.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4606 + WN1780$229.502026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN153 + WN167 / WN1156$391.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4606 + WN1780 / WN1156$391.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2995 + WN2447 / WN1156$391.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1354 + WN225 / WN1156$391.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN725 + WN1079 / WN1156$391.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1456 / WN399 + WN1407$396.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2995 + WN2447 / WN1981$452.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN725 + WN1079 / WN1981$452.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN153 + WN167 / WN1981$452.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1354 + WN225 / WN1981$452.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4395 + WN3167 / WN1981$452.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4606 + WN1780 / WN1981$452.252026-10-29T01:29:13Z

2026-11-20 · one way · $249.75

  • Southwest Airlines WN1456: MDW 2026-11-20 10:20:00 → SAN 2026-11-20 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • Southwest Airlines WN1456: MDW 2026-11-27 10:20:00 → SAN 2026-11-27 12:45:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $472.50

  • Southwest Airlines WN4415: MDW 2026-11-20 15:15:00 → SAN 2026-11-20 17:35:00; nonstop; 260 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 · one way · $249.75

  • Southwest Airlines WN4415: MDW 2026-11-20 15:15:00 → SAN 2026-11-20 17:35:00; nonstop; 260 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • Southwest Airlines WN4415: MDW 2026-11-27 15:15:00 → SAN 2026-11-27 17:35:00; nonstop; 260 minutes. Local airport times.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $472.50

  • Southwest Airlines WN1456: MDW 2026-11-20 10:20:00 → SAN 2026-11-20 12:45:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 · one way · $229.50

  • Southwest Airlines WN153 / WN167: MDW 2026-11-20 15:45:00 → SAN 2026-11-20 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
    • WN153: MDW 2026-11-20 15:45:00 → ABQ 2026-11-20 17:55:00; layover at ABQ: 115 minutes.
    • WN167: ABQ 2026-11-20 19:50:00 → SAN 2026-11-20 20:50:00.

2026-11-20 · one way · $229.50

  • Southwest Airlines WN2995 / WN2447: MDW 2026-11-20 05:05:00 → SAN 2026-11-20 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
    • WN2995: MDW 2026-11-20 05:05:00 → PHX 2026-11-20 07:55:00; layover at PHX: 85 minutes.
    • WN2447: PHX 2026-11-20 09:20:00 → SAN 2026-11-20 09:40:00.

2026-11-20 · one way · $229.50

  • Southwest Airlines WN4395 / WN3167: MDW 2026-11-20 10:15:00 → SAN 2026-11-20 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
    • WN4395: MDW 2026-11-20 10:15:00 → HOU 2026-11-20 12:50:00; layover at HOU: 95 minutes.
    • WN3167: HOU 2026-11-20 14:25:00 → SAN 2026-11-20 15:50:00.

2026-11-20 · one way · $229.50

  • Southwest Airlines WN725 / WN1079: MDW 2026-11-20 09:55:00 → SAN 2026-11-20 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
    • WN725: MDW 2026-11-20 09:55:00 → BNA 2026-11-20 11:30:00; layover at BNA: 60 minutes.
    • WN1079: BNA 2026-11-20 12:30:00 → SAN 2026-11-20 14:55:00.

2026-11-20 · one way · $229.50

  • Southwest Airlines WN1354 / WN225: MDW 2026-11-20 13:20:00 → SAN 2026-11-20 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
    • WN1354: MDW 2026-11-20 13:20:00 → CMH 2026-11-20 15:25:00; layover at CMH: 80 minutes.
    • WN225: CMH 2026-11-20 16:45:00 → SAN 2026-11-20 18:35:00.

2026-11-20 · one way · $229.50

  • Southwest Airlines WN4606 / WN1780: MDW 2026-11-20 14:35:00 → SAN 2026-11-20 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 70 minutes.
    • WN1780: DEN 2026-11-20 17:25:00 → SAN 2026-11-20 18:45:00.

2026-11-27 → 2026-12-04 · $391.00

  • Southwest Airlines WN153 / WN167: MDW 2026-11-27 15:45:00 → SAN 2026-11-27 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
    • WN153: MDW 2026-11-27 15:45:00 → ABQ 2026-11-27 17:55:00; layover at ABQ: 115 minutes.
    • WN167: ABQ 2026-11-27 19:50:00 → SAN 2026-11-27 20:50:00.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $391.00

  • Southwest Airlines WN4606 / WN1780: MDW 2026-11-27 14:35:00 → SAN 2026-11-27 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN4606: MDW 2026-11-27 14:35:00 → DEN 2026-11-27 16:15:00; layover at DEN: 70 minutes.
    • WN1780: DEN 2026-11-27 17:25:00 → SAN 2026-11-27 18:45:00.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $391.00

  • Southwest Airlines WN2995 / WN2447: MDW 2026-11-27 05:05:00 → SAN 2026-11-27 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
    • WN2995: MDW 2026-11-27 05:05:00 → PHX 2026-11-27 07:55:00; layover at PHX: 85 minutes.
    • WN2447: PHX 2026-11-27 09:20:00 → SAN 2026-11-27 09:40:00.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $391.00

  • Southwest Airlines WN1354 / WN225: MDW 2026-11-27 13:20:00 → SAN 2026-11-27 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
    • WN1354: MDW 2026-11-27 13:20:00 → CMH 2026-11-27 15:25:00; layover at CMH: 80 minutes.
    • WN225: CMH 2026-11-27 16:45:00 → SAN 2026-11-27 18:35:00.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $391.00

  • Southwest Airlines WN725 / WN1079: MDW 2026-11-27 09:55:00 → SAN 2026-11-27 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
    • WN725: MDW 2026-11-27 09:55:00 → BNA 2026-11-27 11:30:00; layover at BNA: 60 minutes.
    • WN1079: BNA 2026-11-27 12:30:00 → SAN 2026-11-27 14:55:00.
  • Southwest Airlines WN1156: SAN 2026-12-04 11:45:00 → MDW 2026-12-04 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $396.25

  • Southwest Airlines WN1456: MDW 2026-11-27 10:10:00 → SAN 2026-11-27 12:35:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN399 / WN1407: SAN 2026-12-04 12:10:00 → MDW 2026-12-04 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
    • WN399: SAN 2026-12-04 12:10:00 → OMA 2026-12-04 17:15:00; layover at OMA: 65 minutes.
    • WN1407: OMA 2026-12-04 18:20:00 → MDW 2026-12-04 19:45:00.

2026-11-20 → 2026-11-23 · $452.25

  • Southwest Airlines WN2995 / WN2447: MDW 2026-11-20 05:05:00 → SAN 2026-11-20 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
    • WN2995: MDW 2026-11-20 05:05:00 → PHX 2026-11-20 07:55:00; layover at PHX: 85 minutes.
    • WN2447: PHX 2026-11-20 09:20:00 → SAN 2026-11-20 09:40:00.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $452.25

  • Southwest Airlines WN725 / WN1079: MDW 2026-11-20 09:55:00 → SAN 2026-11-20 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
    • WN725: MDW 2026-11-20 09:55:00 → BNA 2026-11-20 11:30:00; layover at BNA: 60 minutes.
    • WN1079: BNA 2026-11-20 12:30:00 → SAN 2026-11-20 14:55:00.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $452.25

  • Southwest Airlines WN153 / WN167: MDW 2026-11-20 15:45:00 → SAN 2026-11-20 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
    • WN153: MDW 2026-11-20 15:45:00 → ABQ 2026-11-20 17:55:00; layover at ABQ: 115 minutes.
    • WN167: ABQ 2026-11-20 19:50:00 → SAN 2026-11-20 20:50:00.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $452.25

  • Southwest Airlines WN1354 / WN225: MDW 2026-11-20 13:20:00 → SAN 2026-11-20 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
    • WN1354: MDW 2026-11-20 13:20:00 → CMH 2026-11-20 15:25:00; layover at CMH: 80 minutes.
    • WN225: CMH 2026-11-20 16:45:00 → SAN 2026-11-20 18:35:00.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $452.25

  • Southwest Airlines WN4395 / WN3167: MDW 2026-11-20 10:15:00 → SAN 2026-11-20 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
    • WN4395: MDW 2026-11-20 10:15:00 → HOU 2026-11-20 12:50:00; layover at HOU: 95 minutes.
    • WN3167: HOU 2026-11-20 14:25:00 → SAN 2026-11-20 15:50:00.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $452.25

  • Southwest Airlines WN4606 / WN1780: MDW 2026-11-20 14:35:00 → SAN 2026-11-20 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 70 minutes.
    • WN1780: DEN 2026-11-20 17:25:00 → SAN 2026-11-20 18:45:00.
  • Southwest Airlines WN1981: SAN 2026-11-23 12:00:00 → MDW 2026-11-23 17:55:00; nonstop; 235 minutes. Local airport times.

More dates for this route