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San Jose → Chicago

Dec 13, 2026 · return Dec 27, 2026

SJC → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sun, Dec 13 – Sun, Dec 27

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

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
6:00 amSJC
4h 10m
Nonstop
12:10 pmMDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

One-stop flights

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
7:20 amSJC
8h
LGB · 3h
5:20 pmMDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
7:15 amSJC
7h 50m
PDX · 2h 15m
5:05 pmMDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
7:45 amSJC
7h 15m
HOU · 1h 15m
5:00 pmMDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
8:45 pmSJC
7h 20m
SEA · 1h 5m
6:05 am+1MDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
8:05 pmSJC
7h 50m
LAX · 2h 30m
5:55 am+1MDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
1:40 pmSJC
5h 50m
DEN · 1h
9:30 pmMDW
Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

Round-trip total · 1 adult · Taxes included

Make this trip yours

SJC ⇄ 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)
2026-12-13 → 2026-12-27Southwest AirlinesWN3895 / WN3035$428.752026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN266 / WN3035$428.752026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN433 + WN801 / WN3035$411.252026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN3901 + WN696 / WN3035$411.252026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN3883 + WN2133 / WN3035$411.252026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN2612 + WN4975 / WN3035$411.252026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN3818 + WN2518 / WN3035$411.252026-10-29T01:21:21Z
2026-12-13 → 2026-12-27Southwest AirlinesWN3877 + WN776 / WN3035$411.252026-10-29T01:21:21Z

2026-12-13 → 2026-12-27 · $428.75

  • Southwest Airlines WN3895: SJC 2026-12-13 23:00:00 → MDW 2026-12-14 05:00:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $428.75

  • Southwest Airlines WN266: SJC 2026-12-13 06:00:00 → MDW 2026-12-13 12:10:00; nonstop; 250 minutes. Local airport times.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $411.25

  • Southwest Airlines WN433 / WN801: SJC 2026-12-13 07:20:00 → MDW 2026-12-13 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
    • WN433: SJC 2026-12-13 07:20:00 → LGB 2026-12-13 08:35:00; layover at LGB: 180 minutes.
    • WN801: LGB 2026-12-13 11:35:00 → MDW 2026-12-13 17:20:00.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $411.25

  • Southwest Airlines WN3901 / WN696: SJC 2026-12-13 07:15:00 → MDW 2026-12-13 17:05:00; 1 stop(s) via PDX; 470 minutes. Local airport times.
    • WN3901: SJC 2026-12-13 07:15:00 → PDX 2026-12-13 09:05:00; layover at PDX: 135 minutes.
    • WN696: PDX 2026-12-13 11:20:00 → MDW 2026-12-13 17:05:00.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $411.25

  • Southwest Airlines WN3883 / WN2133: SJC 2026-12-13 07:45:00 → MDW 2026-12-13 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
    • WN3883: SJC 2026-12-13 07:45:00 → HOU 2026-12-13 13:20:00; layover at HOU: 75 minutes.
    • WN2133: HOU 2026-12-13 14:35:00 → MDW 2026-12-13 17:00:00.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $411.25

  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-13 20:45:00 → MDW 2026-12-14 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-13 20:45:00 → SEA 2026-12-13 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-14 00:15:00 → MDW 2026-12-14 06:05:00.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $411.25

  • Southwest Airlines WN3818 / WN2518: SJC 2026-12-13 20:05:00 → MDW 2026-12-14 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
    • WN3818: SJC 2026-12-13 20:05:00 → LAX 2026-12-13 21:25:00; layover at LAX: 150 minutes.
    • WN2518: LAX 2026-12-13 23:55:00 → MDW 2026-12-14 05:55:00.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $411.25

  • Southwest Airlines WN3877 / WN776: SJC 2026-12-13 13:40:00 → MDW 2026-12-13 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
    • WN3877: SJC 2026-12-13 13:40:00 → DEN 2026-12-13 17:05:00; layover at DEN: 60 minutes.
    • WN776: DEN 2026-12-13 18:05:00 → MDW 2026-12-13 21:30:00.
  • Southwest Airlines WN3035: MDW 2026-12-27 09:55:00 → SJC 2026-12-27 12:35:00; nonstop; 280 minutes. Local airport times.

More dates for this route