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Route overview: Chicago to San Diego (SAN) flight deals

Chicago → San Diego

Nov 21, 2026 · return Dec 1, 2026

MDW → SAN1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

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

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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Explore this route

All dates for this routeNov 20, 2026 → Nov 30, 2026Nov 22, 2026 → Dec 2, 2026
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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Chicago to San Diego (SAN) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-21 → 2026-12-01Southwest AirlinesWN1456 / WN1981$411.252026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN4415 / WN1981$411.252026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN2995 + WN2447 / WN1981$391.002026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN4395 + WN3167 / WN1981$391.002026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN1354 + WN225 / WN1981$391.002026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN725 + WN1079 / WN1981$391.002026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN153 + WN167 / WN1981$391.002026-10-29T01:29:13Z
2026-11-21 → 2026-12-01Southwest AirlinesWN4606 + WN1780 / WN1981$391.002026-10-29T01:29:13Z

2026-11-21 → 2026-12-01 · $411.25

  • Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $411.25

  • Southwest Airlines WN4415: MDW 2026-11-21 15:15:00 → SAN 2026-11-21 17:35:00; nonstop; 260 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $391.00

  • Southwest Airlines WN2995 / WN2447: MDW 2026-11-21 05:05:00 → SAN 2026-11-21 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
    • WN2995: MDW 2026-11-21 05:05:00 → PHX 2026-11-21 07:55:00; layover at PHX: 85 minutes.
    • WN2447: PHX 2026-11-21 09:20:00 → SAN 2026-11-21 09:40:00.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $391.00

  • Southwest Airlines WN4395 / WN3167: MDW 2026-11-21 10:15:00 → SAN 2026-11-21 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
    • WN4395: MDW 2026-11-21 10:15:00 → HOU 2026-11-21 12:50:00; layover at HOU: 95 minutes.
    • WN3167: HOU 2026-11-21 14:25:00 → SAN 2026-11-21 15:50:00.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $391.00

  • Southwest Airlines WN1354 / WN225: MDW 2026-11-21 13:20:00 → SAN 2026-11-21 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
    • WN1354: MDW 2026-11-21 13:20:00 → CMH 2026-11-21 15:25:00; layover at CMH: 80 minutes.
    • WN225: CMH 2026-11-21 16:45:00 → SAN 2026-11-21 18:35:00.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $391.00

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

2026-11-21 → 2026-12-01 · $391.00

  • Southwest Airlines WN153 / WN167: MDW 2026-11-21 15:45:00 → SAN 2026-11-21 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
    • WN153: MDW 2026-11-21 15:45:00 → ABQ 2026-11-21 17:55:00; layover at ABQ: 115 minutes.
    • WN167: ABQ 2026-11-21 19:50:00 → SAN 2026-11-21 20:50:00.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $391.00

  • Southwest Airlines WN4606 / WN1780: MDW 2026-11-21 14:35:00 → SAN 2026-11-21 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN4606: MDW 2026-11-21 14:35:00 → DEN 2026-11-21 16:15:00; layover at DEN: 70 minutes.
    • WN1780: DEN 2026-11-21 17:25:00 → SAN 2026-11-21 18:45:00.
  • Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to San Diego (SAN) · Nov 21, 2026 · return Dec 1, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • 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 Diego (SAN) 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.