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Chicago → San Jose

Dec 21, 2026 · return Dec 27, 2026

MDW → SJC1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
3:50 pmMDW
4h 40m
Nonstop
6:30 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
6:05 pmMDW
7h 15m
PHX · 1h 20m
11:20 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
3:15 pmMDW
7h 45m
SAN · 1h 55m
9:00 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
10:00 amMDW
6h 55m
LAS · 1h 25m
2:55 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
9:55 amMDW
8h 55m
BUR · 3h
4:50 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
10:05 amMDW
7h 55m
LAX · 2h 15m
4:00 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sun, Dec 27

Southwest Airlines
9:55 amMDW
8h 50m
BNA · 2h 25m
4:45 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SJC

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 → 2026-12-27Southwest AirlinesWN2386 / WN3895$490.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN3035 / WN3895$490.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN2998 + WN3507 / WN3895$469.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN4415 + WN3749 / WN3895$469.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN142 + WN1226 / WN3895$469.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN2905 + WN2917 / WN3895$469.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN1517 + WN2538 / WN3895$469.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-27Southwest AirlinesWN725 + WN364 / WN3895$469.002026-10-29T01:29:13Z

2026-12-21 → 2026-12-27 · $490.00

  • Southwest Airlines WN2386: MDW 2026-12-21 15:50:00 → SJC 2026-12-21 18:30:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $490.00

  • Southwest Airlines WN3035: MDW 2026-12-21 09:55:00 → SJC 2026-12-21 12:35:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $469.00

  • Southwest Airlines WN2998 / WN3507: MDW 2026-12-21 18:05:00 → SJC 2026-12-21 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
    • WN2998: MDW 2026-12-21 18:05:00 → PHX 2026-12-21 21:00:00; layover at PHX: 80 minutes.
    • WN3507: PHX 2026-12-21 22:20:00 → SJC 2026-12-21 23:20:00.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $469.00

  • Southwest Airlines WN4415 / WN3749: MDW 2026-12-21 15:15:00 → SJC 2026-12-21 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN4415: MDW 2026-12-21 15:15:00 → SAN 2026-12-21 17:35:00; layover at SAN: 115 minutes.
    • WN3749: SAN 2026-12-21 19:30:00 → SJC 2026-12-21 21:00:00.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $469.00

  • Southwest Airlines WN142 / WN1226: MDW 2026-12-21 10:00:00 → SJC 2026-12-21 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN142: MDW 2026-12-21 10:00:00 → LAS 2026-12-21 11:55:00; layover at LAS: 85 minutes.
    • WN1226: LAS 2026-12-21 13:20:00 → SJC 2026-12-21 14:55:00.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $469.00

  • Southwest Airlines WN2905 / WN2917: MDW 2026-12-21 09:55:00 → SJC 2026-12-21 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
    • WN2905: MDW 2026-12-21 09:55:00 → BUR 2026-12-21 12:30:00; layover at BUR: 180 minutes.
    • WN2917: BUR 2026-12-21 15:30:00 → SJC 2026-12-21 16:50:00.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $469.00

  • Southwest Airlines WN1517 / WN2538: MDW 2026-12-21 10:05:00 → SJC 2026-12-21 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
    • WN1517: MDW 2026-12-21 10:05:00 → LAX 2026-12-21 12:30:00; layover at LAX: 135 minutes.
    • WN2538: LAX 2026-12-21 14:45:00 → SJC 2026-12-21 16:00:00.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-21 → 2026-12-27 · $469.00

  • Southwest Airlines WN725 / WN364: MDW 2026-12-21 09:55:00 → SJC 2026-12-21 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
    • WN725: MDW 2026-12-21 09:55:00 → BNA 2026-12-21 11:30:00; layover at BNA: 145 minutes.
    • WN364: BNA 2026-12-21 13:55:00 → SJC 2026-12-21 16:45:00.
  • Southwest Airlines WN3895: SJC 2026-12-27 23:00:00 → MDW 2026-12-28 05:00:00; nonstop; 240 minutes. Local airport times.

More dates for this route