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Chicago → Oakland

Jan 21, 2027 · return Jan 24, 2027

MDW → OAK1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Sun, Jan 24

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

Thu, Jan 21 – Sun, Jan 24

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

Thu, Jan 21 – Sun, Jan 24

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

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

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

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
2:35 pmMDW
8h 40m
DEN · 3h 20m
9:15 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

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

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 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 AirlinesWN3174 / WN3220$321.102026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN2990 / WN3220$321.102026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN2995 + WN681 / WN3220$311.602026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN4415 + WN1144 / WN3220$311.602026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN3174 / WN4605 + WN4990$311.602026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN2691 + WN1936 / WN3220$311.602026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN4606 + WN1726 / WN3220$311.602026-10-29T01:29:13Z
2027-01-21 → 2027-01-24Southwest AirlinesWN2952 + WN1901 / WN3220$311.602026-10-29T01:29:13Z

2027-01-21 → 2027-01-24 · $321.10

  • Southwest Airlines WN3174: MDW 2027-01-21 10:00:00 → OAK 2027-01-21 12:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $321.10

  • Southwest Airlines WN2990: MDW 2027-01-21 21:30:00 → OAK 2027-01-22 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $311.60

  • Southwest Airlines WN2995 / WN681: MDW 2027-01-21 05:05:00 → OAK 2027-01-21 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2027-01-21 05:05:00 → PHX 2027-01-21 07:55:00; layover at PHX: 110 minutes.
    • WN681: PHX 2027-01-21 09:45:00 → OAK 2027-01-21 10:50:00.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $311.60

  • Southwest Airlines WN4415 / WN1144: MDW 2027-01-21 15:15:00 → OAK 2027-01-21 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2027-01-21 15:15:00 → SAN 2027-01-21 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2027-01-21 20:05:00 → OAK 2027-01-21 21:35:00.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $311.60

  • Southwest Airlines WN3174: MDW 2027-01-21 10:00:00 → OAK 2027-01-21 12:45:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN4605 / WN4990: OAK 2027-01-24 20:45:00 → MDW 2027-01-25 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2027-01-24 20:45:00 → LAS 2027-01-24 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2027-01-25 00:20:00 → MDW 2027-01-25 05:40:00.

2027-01-21 → 2027-01-24 · $311.60

  • Southwest Airlines WN2691 / WN1936: MDW 2027-01-21 05:50:00 → OAK 2027-01-21 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN2691: MDW 2027-01-21 05:50:00 → LAS 2027-01-21 07:45:00; layover at LAS: 85 minutes.
    • WN1936: LAS 2027-01-21 09:10:00 → OAK 2027-01-21 10:45:00.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $311.60

  • Southwest Airlines WN4606 / WN1726: MDW 2027-01-21 14:35:00 → OAK 2027-01-21 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
    • WN4606: MDW 2027-01-21 14:35:00 → DEN 2027-01-21 16:15:00; layover at DEN: 200 minutes.
    • WN1726: DEN 2027-01-21 19:35:00 → OAK 2027-01-21 21:15:00.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $311.60

  • Southwest Airlines WN2952 / WN1901: MDW 2027-01-21 15:45:00 → OAK 2027-01-21 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-01-21 15:45:00 → LAX 2027-01-21 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-01-21 20:00:00 → OAK 2027-01-21 21:15:00.
  • Southwest Airlines WN3220: OAK 2027-01-24 23:50:00 → MDW 2027-01-25 05:55:00; nonstop; 245 minutes. Local airport times.

More dates for this route