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Chicago → Oakland

Dec 1, 2026 · return Dec 6, 2026

MDW → OAK1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
8:45 pmMDW
4h 50m
Nonstop
11:35 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
10:00 amMDW
4h 45m
Nonstop
12:45 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK
Southwest Airlines
8:45 pmOAK
6h 55m
LAS · 2h 5m
5:40 am+1MDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
5:50 amMDW
6h 55m
LAS · 1h 25m
10:45 amOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
8:50 amMDW
8h 25m
DAL · 2h 15m
3:15 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 1 – Sun, Dec 6

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 50m
10:50 amOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ OAK

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 routeOct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 13, 2026 → Nov 16, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 11, 2026 → Dec 14, 2026Dec 12, 2026 → Dec 19, 2026Dec 22, 2026 → Dec 27, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Dec 30, 2026 → Jan 2, 2027Jan 8, 2027 → Jan 11, 2027Jan 9, 2027 → Jan 16, 2027Jan 15, 2027 → Jan 18, 2027Jan 22, 2027 → Jan 25, 2027Jan 23, 2027 → Jan 30, 2027Feb 5, 2027 → Feb 8, 2027Feb 6, 2027 → Feb 13, 2027Feb 12, 2027 → Feb 15, 2027Mar 5, 2027 → Mar 8, 2027Mar 6, 2027 → Mar 13, 2027Mar 25, 2027 → Mar 29, 2027Apr 2, 2027 → Apr 5, 2027Apr 3, 2027 → Apr 10, 2027Apr 30, 2027 → May 3, 2027May 1, 2027 → May 8, 2027May 28, 2027 → May 31, 2027May 29, 2027 → Jun 5, 2027Jun 25, 2027 → Jun 28, 2027Jun 26, 2027 → Jul 3, 2027Jul 2, 2027 → Jul 6, 2027Jul 23, 2027 → Jul 26, 2027Jul 24, 2027 → Jul 31, 2027Aug 20, 2027 → Aug 23, 2027Aug 21, 2027 → Aug 28, 2027Sep 3, 2027 → Sep 6, 2027Sep 17, 2027 → Sep 20, 2027Oct 30, 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)
2026-12-01 → 2026-12-06Southwest AirlinesWN1364 / WN3220$338.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN3174 / WN3220$338.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN3174 / WN4605 + WN4990$328.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN4415 + WN1144 / WN3220$328.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN2952 + WN1901 / WN3220$328.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN2691 + WN1936 / WN3220$328.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN1191 + WN1924 / WN3220$328.002026-10-29T01:29:13Z
2026-12-01 → 2026-12-06Southwest AirlinesWN2995 + WN681 / WN3220$328.002026-10-29T01:29:13Z

2026-12-01 → 2026-12-06 · $338.00

  • Southwest Airlines WN1364: MDW 2026-12-01 20:45:00 → OAK 2026-12-01 23:35:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $338.00

  • Southwest Airlines WN3174: MDW 2026-12-01 10:00:00 → OAK 2026-12-01 12:45:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $328.00

  • Southwest Airlines WN3174: MDW 2026-12-01 10:00:00 → OAK 2026-12-01 12:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN4605 / WN4990: OAK 2026-12-06 20:45:00 → MDW 2026-12-07 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2026-12-06 20:45:00 → LAS 2026-12-06 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2026-12-07 00:20:00 → MDW 2026-12-07 05:40:00.

2026-12-01 → 2026-12-06 · $328.00

  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-01 15:15:00 → OAK 2026-12-01 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-01 15:15:00 → SAN 2026-12-01 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-01 20:05:00 → OAK 2026-12-01 21:35:00.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $328.00

  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-01 15:45:00 → OAK 2026-12-01 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-01 15:45:00 → LAX 2026-12-01 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-01 20:00:00 → OAK 2026-12-01 21:15:00.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $328.00

  • Southwest Airlines WN2691 / WN1936: MDW 2026-12-01 05:50:00 → OAK 2026-12-01 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN2691: MDW 2026-12-01 05:50:00 → LAS 2026-12-01 07:45:00; layover at LAS: 85 minutes.
    • WN1936: LAS 2026-12-01 09:10:00 → OAK 2026-12-01 10:45:00.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $328.00

  • Southwest Airlines WN1191 / WN1924: MDW 2026-12-01 08:50:00 → OAK 2026-12-01 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
    • WN1191: MDW 2026-12-01 08:50:00 → DAL 2026-12-01 11:20:00; layover at DAL: 135 minutes.
    • WN1924: DAL 2026-12-01 13:35:00 → OAK 2026-12-01 15:15:00.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

2026-12-01 → 2026-12-06 · $328.00

  • Southwest Airlines WN2995 / WN681: MDW 2026-12-01 05:05:00 → OAK 2026-12-01 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-12-01 05:05:00 → PHX 2026-12-01 07:55:00; layover at PHX: 110 minutes.
    • WN681: PHX 2026-12-01 09:45:00 → OAK 2026-12-01 10:50:00.
  • Southwest Airlines WN3220: OAK 2026-12-06 23:50:00 → MDW 2026-12-07 05:55:00; nonstop; 245 minutes. Local airport times.

More dates for this route