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Oakland → Chicago

Jan 21, 2027 · return Jan 24, 2027

OAK → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
3:40 pmOAK
7h
LAX · 1h 40m
12:40 am+1MDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
8:45 pmOAK
6h 55m
LAS · 2h 5m
5:40 am+1MDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
7:45 amOAK
8h
SLC · 3h 25m
5:45 pmMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
1:35 pmOAK
6h 25m
SAN · 1h
10:00 pmMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
5:50 amOAK
4h
Nonstop
11:50 amMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 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 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)
2027-01-21 → 2027-01-24Southwest AirlinesWN768 + WN2517 / WN4415 + WN1144$323.002026-10-29T01:51:12Z
2027-01-21 → 2027-01-24Southwest AirlinesWN4605 + WN4990 / WN4415 + WN1144$323.002026-10-29T01:51:12Z
2027-01-21 → 2027-01-24Southwest AirlinesWN3217 + WN801 / WN4415 + WN1144$323.002026-10-29T01:51:12Z
2027-01-21 → 2027-01-24Southwest AirlinesWN4674 + WN4349 / WN4415 + WN1144$323.002026-10-29T01:51:12Z
2027-01-21 → 2027-01-24Southwest AirlinesWN3238 + WN2962 / WN4415 + WN1144$323.002026-10-29T01:51:12Z
2027-01-21 → 2027-01-24Southwest AirlinesWN1082 / WN4415 + WN1144$332.502026-10-29T01:51:12Z

2027-01-21 → 2027-01-24 · $323.00

  • Southwest Airlines WN768 / WN2517: OAK 2027-01-21 15:40:00 → MDW 2027-01-22 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2027-01-21 15:40:00 → LAX 2027-01-21 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2027-01-21 18:45:00 → MDW 2027-01-22 00:40:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

2027-01-21 → 2027-01-24 · $323.00

  • Southwest Airlines WN4605 / WN4990: OAK 2027-01-21 20:45:00 → MDW 2027-01-22 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2027-01-21 20:45:00 → LAS 2027-01-21 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2027-01-22 00:20:00 → MDW 2027-01-22 05:40:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

2027-01-21 → 2027-01-24 · $323.00

  • Southwest Airlines WN3217 / WN801: OAK 2027-01-21 08:30:00 → MDW 2027-01-21 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2027-01-21 08:30:00 → LGB 2027-01-21 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2027-01-21 11:35:00 → MDW 2027-01-21 17:20:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

2027-01-21 → 2027-01-24 · $323.00

  • Southwest Airlines WN4674 / WN4349: OAK 2027-01-21 07:45:00 → MDW 2027-01-21 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2027-01-21 07:45:00 → SLC 2027-01-21 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2027-01-21 13:50:00 → MDW 2027-01-21 17:45:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

2027-01-21 → 2027-01-24 · $323.00

  • Southwest Airlines WN3238 / WN2962: OAK 2027-01-21 13:35:00 → MDW 2027-01-21 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2027-01-21 13:35:00 → SAN 2027-01-21 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2027-01-21 16:05:00 → MDW 2027-01-21 22:00:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

2027-01-21 → 2027-01-24 · $332.50

  • Southwest Airlines WN1082: OAK 2027-01-21 05:50:00 → MDW 2027-01-21 11:50:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

More dates for this route