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Oakland → Chicago

Dec 3, 2026 · return Dec 7, 2026

OAK → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
8:45 pmOAK
6h 55m
LAS · 2h 5m
5:40 am+1MDW
Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW
Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
3:40 pmOAK
7h
LAX · 1h 40m
12:40 am+1MDW
Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
7:45 amOAK
8h
SLC · 3h 25m
5:45 pmMDW
Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
1:35 pmOAK
6h 25m
SAN · 1h
10:00 pmMDW
Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Mon, Dec 7

Southwest Airlines
5:50 amOAK
4h
Nonstop
11:50 amMDW
Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

Round-trip total · 1 adult · Taxes included

Make this trip yours

OAK ⇄ 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 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 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)
2026-12-03 → 2026-12-07Southwest AirlinesWN4605 + WN4990 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-12-03 → 2026-12-07Southwest AirlinesWN3217 + WN801 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-12-03 → 2026-12-07Southwest AirlinesWN768 + WN2517 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-12-03 → 2026-12-07Southwest AirlinesWN4674 + WN4349 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-12-03 → 2026-12-07Southwest AirlinesWN3238 + WN2962 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-12-03 → 2026-12-07Southwest AirlinesWN1082 / WN2952 + WN1901$350.002026-10-29T01:51:12Z

2026-12-03 → 2026-12-07 · $340.00

  • Southwest Airlines WN4605 / WN4990: OAK 2026-12-03 20:45:00 → MDW 2026-12-04 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2026-12-03 20:45:00 → LAS 2026-12-03 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2026-12-04 00:20:00 → MDW 2026-12-04 05:40:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-07 15:45:00 → OAK 2026-12-07 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-07 15:45:00 → LAX 2026-12-07 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-07 20:00:00 → OAK 2026-12-07 21:15:00.

2026-12-03 → 2026-12-07 · $340.00

  • Southwest Airlines WN3217 / WN801: OAK 2026-12-03 08:30:00 → MDW 2026-12-03 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2026-12-03 08:30:00 → LGB 2026-12-03 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2026-12-03 11:35:00 → MDW 2026-12-03 17:20:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-07 15:45:00 → OAK 2026-12-07 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-07 15:45:00 → LAX 2026-12-07 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-07 20:00:00 → OAK 2026-12-07 21:15:00.

2026-12-03 → 2026-12-07 · $340.00

  • Southwest Airlines WN768 / WN2517: OAK 2026-12-03 15:40:00 → MDW 2026-12-04 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2026-12-03 15:40:00 → LAX 2026-12-03 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2026-12-03 18:45:00 → MDW 2026-12-04 00:40:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-07 15:45:00 → OAK 2026-12-07 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-07 15:45:00 → LAX 2026-12-07 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-07 20:00:00 → OAK 2026-12-07 21:15:00.

2026-12-03 → 2026-12-07 · $340.00

  • Southwest Airlines WN4674 / WN4349: OAK 2026-12-03 07:45:00 → MDW 2026-12-03 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2026-12-03 07:45:00 → SLC 2026-12-03 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2026-12-03 13:50:00 → MDW 2026-12-03 17:45:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-07 15:45:00 → OAK 2026-12-07 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-07 15:45:00 → LAX 2026-12-07 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-07 20:00:00 → OAK 2026-12-07 21:15:00.

2026-12-03 → 2026-12-07 · $340.00

  • Southwest Airlines WN3238 / WN2962: OAK 2026-12-03 13:35:00 → MDW 2026-12-03 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2026-12-03 13:35:00 → SAN 2026-12-03 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2026-12-03 16:05:00 → MDW 2026-12-03 22:00:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-07 15:45:00 → OAK 2026-12-07 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-07 15:45:00 → LAX 2026-12-07 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-07 20:00:00 → OAK 2026-12-07 21:15:00.

2026-12-03 → 2026-12-07 · $350.00

  • Southwest Airlines WN1082: OAK 2026-12-03 05:50:00 → MDW 2026-12-03 11:50:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-12-07 15:45:00 → OAK 2026-12-07 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-12-07 15:45:00 → LAX 2026-12-07 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-12-07 20:00:00 → OAK 2026-12-07 21:15:00.

More dates for this route