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Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

Oakland → Chicago

Jun 25, 2027 · return Jun 28, 2027

OAK → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Fri, Jun 25 – Mon, Jun 28

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

Fri, Jun 25 – Mon, Jun 28

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

Fri, Jun 25 – Mon, Jun 28

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

Fri, Jun 25 – Mon, Jun 28

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

Fri, Jun 25 – Mon, Jun 28

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

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW
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

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Explore this route

All dates for this routeJun 24, 2027 → Jun 27, 2027Jun 26, 2027 → Jun 29, 2027
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-06-25 → 2027-06-28Southwest AirlinesWN3238 + WN2962 / WN2952 + WN1901$425.002026-10-29T01:51:12Z
2027-06-25 → 2027-06-28Southwest AirlinesWN4605 + WN4990 / WN2952 + WN1901$425.002026-10-29T01:51:12Z
2027-06-25 → 2027-06-28Southwest AirlinesWN3217 + WN801 / WN2952 + WN1901$425.002026-10-29T01:51:12Z
2027-06-25 → 2027-06-28Southwest AirlinesWN768 + WN2517 / WN2952 + WN1901$425.002026-10-29T01:51:12Z
2027-06-25 → 2027-06-28Southwest AirlinesWN4674 + WN4349 / WN2952 + WN1901$425.002026-10-29T01:51:12Z
2027-06-25 → 2027-06-28Southwest AirlinesWN2871 / WN2952 + WN1901$437.502026-10-29T01:51:12Z

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN3238 / WN2962: OAK 2027-06-25 13:35:00 → MDW 2027-06-25 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2027-06-25 13:35:00 → SAN 2027-06-25 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2027-06-25 16:05:00 → MDW 2027-06-25 22:00:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2027-06-28 15:45:00 → OAK 2027-06-28 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-06-28 15:45:00 → LAX 2027-06-28 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-06-28 20:00:00 → OAK 2027-06-28 21:15:00.

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN4605 / WN4990: OAK 2027-06-25 20:45:00 → MDW 2027-06-26 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2027-06-25 20:45:00 → LAS 2027-06-25 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2027-06-26 00:20:00 → MDW 2027-06-26 05:40:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2027-06-28 15:45:00 → OAK 2027-06-28 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-06-28 15:45:00 → LAX 2027-06-28 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-06-28 20:00:00 → OAK 2027-06-28 21:15:00.

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN3217 / WN801: OAK 2027-06-25 08:30:00 → MDW 2027-06-25 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2027-06-25 08:30:00 → LGB 2027-06-25 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2027-06-25 11:35:00 → MDW 2027-06-25 17:20:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2027-06-28 15:45:00 → OAK 2027-06-28 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-06-28 15:45:00 → LAX 2027-06-28 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-06-28 20:00:00 → OAK 2027-06-28 21:15:00.

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN768 / WN2517: OAK 2027-06-25 15:40:00 → MDW 2027-06-26 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2027-06-25 15:40:00 → LAX 2027-06-25 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2027-06-25 18:45:00 → MDW 2027-06-26 00:40:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2027-06-28 15:45:00 → OAK 2027-06-28 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-06-28 15:45:00 → LAX 2027-06-28 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-06-28 20:00:00 → OAK 2027-06-28 21:15:00.

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN4674 / WN4349: OAK 2027-06-25 07:45:00 → MDW 2027-06-25 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2027-06-25 07:45:00 → SLC 2027-06-25 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2027-06-25 13:50:00 → MDW 2027-06-25 17:45:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2027-06-28 15:45:00 → OAK 2027-06-28 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-06-28 15:45:00 → LAX 2027-06-28 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-06-28 20:00:00 → OAK 2027-06-28 21:15:00.

2027-06-25 → 2027-06-28 · $437.50

  • Southwest Airlines WN2871: OAK 2027-06-25 06:30:00 → MDW 2027-06-25 12:30:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN2952 / WN1901: MDW 2027-06-28 15:45:00 → OAK 2027-06-28 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2027-06-28 15:45:00 → LAX 2027-06-28 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2027-06-28 20:00:00 → OAK 2027-06-28 21:15:00.

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