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Chicago → San Jose

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MDW → SJC1 adulteconomy

23 flight options · 1 airline

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:10 amMDW
4h 45m
Nonstop
12:55 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:00 amMDW
6h 55m
LAS · 1h 25m
2:55 pmSJC
Southwest Airlines
8:45 pmSJC
7h 20m
SEA · 1h 5m
6:05 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:15 pmMDW
7h 45m
SAN · 1h 55m
9:00 pmSJC
Southwest Airlines
8:45 pmSJC
7h 20m
SEA · 1h 5m
6:05 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:55 amMDW
8h 50m
BNA · 2h 25m
4:45 pmSJC
Southwest Airlines
8:45 pmSJC
7h 20m
SEA · 1h 5m
6:05 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:05 amMDW
7h 55m
LAX · 2h 15m
4:00 pmSJC
Southwest Airlines
8:45 pmSJC
7h 20m
SEA · 1h 5m
6:05 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:05 pmMDW
7h 15m
PHX · 1h 20m
11:20 pmSJC
Southwest Airlines
8:45 pmSJC
7h 20m
SEA · 1h 5m
6:05 am+1MDW

Round-trip total · 1 adult · Taxes included

Show 7 more flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
10:10 amMDW
4h 45m
Nonstop
12:55 pmSJC
Southwest Airlines
7:45 amSJC
7h 15m
HOU · 1h 15m
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
3:50 pmMDW
4h 40m
Nonstop
6:30 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:55 amMDW
8h 50m
BNA · 2h 25m
4:45 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:05 amMDW
7h 55m
LAX · 2h 15m
4:00 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:05 pmMDW
7h 15m
PHX · 1h 20m
11:20 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:15 pmMDW
7h 45m
SAN · 1h 55m
9:00 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:00 amMDW
6h 55m
LAS · 1h 25m
2:55 pmSJC

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:55 amMDW
8h 55m
BUR · 3h
4:50 pmSJC

One-way 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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Why book with Axel
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  • 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
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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 AirlinesWN2386$180.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3035 / WN4230$411.252026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3035 / WN4230$411.252026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN3035$180.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2386 / WN4230$411.252026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN725 + WN364$165.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN1517 + WN2538$165.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2998 + WN3507$165.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4415 + WN3749$165.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN142 + WN1226$165.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2905 + WN2917$165.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN142 + WN1226 / WN2612 + WN4975$376.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4415 + WN3749 / WN2612 + WN4975$376.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN725 + WN364 / WN2612 + WN4975$376.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1517 + WN2538 / WN2612 + WN4975$376.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2998 + WN3507 / WN2612 + WN4975$376.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3035 / WN3883 + WN2133$391.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4415 + WN3749 / WN4230$396.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN142 + WN1226 / WN4230$396.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2998 + WN3507 / WN4230$396.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1517 + WN2538 / WN4230$396.252026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3035 / WN2612 + WN4975$396.252026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN725 + WN364 / WN4230$396.252026-10-29T01:29:13Z

2026-11-20 · one way · $180.00

  • Southwest Airlines WN2386: MDW 2026-11-20 15:50:00 → SJC 2026-11-20 18:30:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $411.25

  • Southwest Airlines WN3035: MDW 2026-11-20 09:55:00 → SJC 2026-11-20 12:35:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • Southwest Airlines WN3035: MDW 2026-11-27 10:10:00 → SJC 2026-11-27 12:55:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN4230: SJC 2026-12-04 23:00:00 → MDW 2026-12-05 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-20 · one way · $180.00

  • Southwest Airlines WN3035: MDW 2026-11-20 09:55:00 → SJC 2026-11-20 12:35:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $411.25

  • Southwest Airlines WN2386: MDW 2026-11-20 15:50:00 → SJC 2026-11-20 18:30:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-20 · one way · $165.00

  • Southwest Airlines WN725 / WN364: MDW 2026-11-20 09:55:00 → SJC 2026-11-20 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
    • WN725: MDW 2026-11-20 09:55:00 → BNA 2026-11-20 11:30:00; layover at BNA: 145 minutes.
    • WN364: BNA 2026-11-20 13:55:00 → SJC 2026-11-20 16:45:00.

2026-11-20 · one way · $165.00

  • Southwest Airlines WN1517 / WN2538: MDW 2026-11-20 10:05:00 → SJC 2026-11-20 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
    • WN1517: MDW 2026-11-20 10:05:00 → LAX 2026-11-20 12:30:00; layover at LAX: 135 minutes.
    • WN2538: LAX 2026-11-20 14:45:00 → SJC 2026-11-20 16:00:00.

2026-11-20 · one way · $165.00

  • Southwest Airlines WN2998 / WN3507: MDW 2026-11-20 18:05:00 → SJC 2026-11-20 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
    • WN2998: MDW 2026-11-20 18:05:00 → PHX 2026-11-20 21:00:00; layover at PHX: 80 minutes.
    • WN3507: PHX 2026-11-20 22:20:00 → SJC 2026-11-20 23:20:00.

2026-11-20 · one way · $165.00

  • Southwest Airlines WN4415 / WN3749: MDW 2026-11-20 15:15:00 → SJC 2026-11-20 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN4415: MDW 2026-11-20 15:15:00 → SAN 2026-11-20 17:35:00; layover at SAN: 115 minutes.
    • WN3749: SAN 2026-11-20 19:30:00 → SJC 2026-11-20 21:00:00.

2026-11-20 · one way · $165.00

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

2026-11-20 · one way · $165.00

  • Southwest Airlines WN2905 / WN2917: MDW 2026-11-20 09:55:00 → SJC 2026-11-20 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
    • WN2905: MDW 2026-11-20 09:55:00 → BUR 2026-11-20 12:30:00; layover at BUR: 180 minutes.
    • WN2917: BUR 2026-11-20 15:30:00 → SJC 2026-11-20 16:50:00.

2026-11-27 → 2026-12-04 · $376.00

  • Southwest Airlines WN142 / WN1226: MDW 2026-11-27 10:00:00 → SJC 2026-11-27 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN142: MDW 2026-11-27 10:00:00 → LAS 2026-11-27 11:55:00; layover at LAS: 85 minutes.
    • WN1226: LAS 2026-11-27 13:20:00 → SJC 2026-11-27 14:55:00.
  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-27 → 2026-12-04 · $376.00

  • Southwest Airlines WN4415 / WN3749: MDW 2026-11-27 15:15:00 → SJC 2026-11-27 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN4415: MDW 2026-11-27 15:15:00 → SAN 2026-11-27 17:35:00; layover at SAN: 115 minutes.
    • WN3749: SAN 2026-11-27 19:30:00 → SJC 2026-11-27 21:00:00.
  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-27 → 2026-12-04 · $376.00

  • Southwest Airlines WN725 / WN364: MDW 2026-11-27 09:55:00 → SJC 2026-11-27 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
    • WN725: MDW 2026-11-27 09:55:00 → BNA 2026-11-27 11:30:00; layover at BNA: 145 minutes.
    • WN364: BNA 2026-11-27 13:55:00 → SJC 2026-11-27 16:45:00.
  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-27 → 2026-12-04 · $376.00

  • Southwest Airlines WN1517 / WN2538: MDW 2026-11-27 10:05:00 → SJC 2026-11-27 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
    • WN1517: MDW 2026-11-27 10:05:00 → LAX 2026-11-27 12:30:00; layover at LAX: 135 minutes.
    • WN2538: LAX 2026-11-27 14:45:00 → SJC 2026-11-27 16:00:00.
  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-27 → 2026-12-04 · $376.00

  • Southwest Airlines WN2998 / WN3507: MDW 2026-11-27 18:05:00 → SJC 2026-11-27 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
    • WN2998: MDW 2026-11-27 18:05:00 → PHX 2026-11-27 21:00:00; layover at PHX: 80 minutes.
    • WN3507: PHX 2026-11-27 22:20:00 → SJC 2026-11-27 23:20:00.
  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-20 → 2026-11-23 · $391.00

  • Southwest Airlines WN3035: MDW 2026-11-20 10:10:00 → SJC 2026-11-20 12:55:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3883 / WN2133: SJC 2026-11-23 07:45:00 → MDW 2026-11-23 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
    • WN3883: SJC 2026-11-23 07:45:00 → HOU 2026-11-23 13:20:00; layover at HOU: 75 minutes.
    • WN2133: HOU 2026-11-23 14:35:00 → MDW 2026-11-23 17:00:00.

2026-11-20 → 2026-11-23 · $396.25

  • Southwest Airlines WN4415 / WN3749: MDW 2026-11-20 15:15:00 → SJC 2026-11-20 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN4415: MDW 2026-11-20 15:15:00 → SAN 2026-11-20 17:35:00; layover at SAN: 115 minutes.
    • WN3749: SAN 2026-11-20 19:30:00 → SJC 2026-11-20 21:00:00.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $396.25

  • Southwest Airlines WN142 / WN1226: MDW 2026-11-20 10:00:00 → SJC 2026-11-20 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN142: MDW 2026-11-20 10:00:00 → LAS 2026-11-20 11:55:00; layover at LAS: 85 minutes.
    • WN1226: LAS 2026-11-20 13:20:00 → SJC 2026-11-20 14:55:00.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $396.25

  • Southwest Airlines WN2998 / WN3507: MDW 2026-11-20 18:05:00 → SJC 2026-11-20 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
    • WN2998: MDW 2026-11-20 18:05:00 → PHX 2026-11-20 21:00:00; layover at PHX: 80 minutes.
    • WN3507: PHX 2026-11-20 22:20:00 → SJC 2026-11-20 23:20:00.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $396.25

  • Southwest Airlines WN1517 / WN2538: MDW 2026-11-20 10:05:00 → SJC 2026-11-20 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
    • WN1517: MDW 2026-11-20 10:05:00 → LAX 2026-11-20 12:30:00; layover at LAX: 135 minutes.
    • WN2538: LAX 2026-11-20 14:45:00 → SJC 2026-11-20 16:00:00.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $396.25

  • Southwest Airlines WN3035: MDW 2026-11-27 09:55:00 → SJC 2026-11-27 12:35:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
    • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
    • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-20 → 2026-11-23 · $396.25

  • Southwest Airlines WN725 / WN364: MDW 2026-11-20 09:55:00 → SJC 2026-11-20 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
    • WN725: MDW 2026-11-20 09:55:00 → BNA 2026-11-20 11:30:00; layover at BNA: 145 minutes.
    • WN364: BNA 2026-11-20 13:55:00 → SJC 2026-11-20 16:45:00.
  • Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

More dates for this route