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Oakland → Chicago

May 29, 2027 · return Jun 5, 2027

OAK → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sat, May 29 – Sat, Jun 5

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

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

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

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, May 29 – Sat, Jun 5

Southwest Airlines
11:25 amOAK
8h 5m
DEN · 3h 15m
9:30 pmMDW
Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
1:35 pmOAK
6h 25m
SAN · 1h
10:00 pmMDW
Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW
Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
3:40 pmOAK
7h
LAX · 1h 40m
12:40 am+1MDW
Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
8:45 pmOAK
6h 55m
LAS · 2h 5m
5:40 am+1MDW
Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
7:45 amOAK
8h
SLC · 3h 25m
5:45 pmMDW
Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

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 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
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)
2027-05-29 → 2027-06-05Southwest AirlinesWN3220 / WN2990$495.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN1082 / WN2990$495.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN3203 + WN776 / WN2990$480.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN3238 + WN2962 / WN2990$480.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN3217 + WN801 / WN2990$480.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN768 + WN2517 / WN2990$480.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN4605 + WN4990 / WN2990$480.002026-10-29T01:51:12Z
2027-05-29 → 2027-06-05Southwest AirlinesWN4674 + WN4349 / WN2990$480.002026-10-29T01:51:12Z

2027-05-29 → 2027-06-05 · $495.00

  • Southwest Airlines WN3220: OAK 2027-05-29 23:50:00 → MDW 2027-05-30 05:55:00; nonstop; 245 minutes. Local airport times.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $495.00

  • Southwest Airlines WN1082: OAK 2027-05-29 05:50:00 → MDW 2027-05-29 11:50:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $480.00

  • Southwest Airlines WN3203 / WN776: OAK 2027-05-29 11:25:00 → MDW 2027-05-29 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
    • WN3203: OAK 2027-05-29 11:25:00 → DEN 2027-05-29 14:50:00; layover at DEN: 195 minutes.
    • WN776: DEN 2027-05-29 18:05:00 → MDW 2027-05-29 21:30:00.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $480.00

  • Southwest Airlines WN3238 / WN2962: OAK 2027-05-29 13:35:00 → MDW 2027-05-29 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2027-05-29 13:35:00 → SAN 2027-05-29 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2027-05-29 16:05:00 → MDW 2027-05-29 22:00:00.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $480.00

  • Southwest Airlines WN3217 / WN801: OAK 2027-05-29 08:30:00 → MDW 2027-05-29 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2027-05-29 08:30:00 → LGB 2027-05-29 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2027-05-29 11:35:00 → MDW 2027-05-29 17:20:00.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $480.00

  • Southwest Airlines WN768 / WN2517: OAK 2027-05-29 15:40:00 → MDW 2027-05-30 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2027-05-29 15:40:00 → LAX 2027-05-29 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2027-05-29 18:45:00 → MDW 2027-05-30 00:40:00.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $480.00

  • Southwest Airlines WN4605 / WN4990: OAK 2027-05-29 20:45:00 → MDW 2027-05-30 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2027-05-29 20:45:00 → LAS 2027-05-29 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2027-05-30 00:20:00 → MDW 2027-05-30 05:40:00.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $480.00

  • Southwest Airlines WN4674 / WN4349: OAK 2027-05-29 07:45:00 → MDW 2027-05-29 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2027-05-29 07:45:00 → SLC 2027-05-29 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2027-05-29 13:50:00 → MDW 2027-05-29 17:45:00.
  • Southwest Airlines WN2990: MDW 2027-06-05 21:30:00 → OAK 2027-06-06 00:15:00; nonstop; 285 minutes. Local airport times.

More dates for this route