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Oakland → Chicago

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OAK → MDW1 adulteconomy

22 flight options · 1 airline

Round-trip flights

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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, Nov 27 – Fri, Dec 4

Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW
Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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, Nov 20 – Mon, Nov 23

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, Nov 20 – Mon, Nov 23

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, Nov 20 – Mon, Nov 23

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, Nov 20 – Mon, Nov 23

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

Show 6 more flights

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
1:35 pmOAK
6h 25m
SAN · 1h
10:00 pmMDW
Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:40 pmOAK
7h
LAX · 1h 40m
12:40 am+1MDW
Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW
Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:45 amOAK
8h
SLC · 3h 25m
5:45 pmMDW
Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
11:25 amOAK
8h 5m
DEN · 3h 15m
9:30 pmMDW
Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:45 amOAK
8h
SLC · 3h 25m
5:45 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:40 pmOAK
7h
LAX · 1h 40m
12:40 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
1:35 pmOAK
6h 25m
SAN · 1h
10:00 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:45 pmOAK
6h 55m
LAS · 2h 5m
5:40 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:25 amOAK
8h 5m
DEN · 3h 15m
9:30 pmMDW

One-way 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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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN2871$185.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3220 / WN3174$432.002026-10-29T01:51:12Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3217 + WN801 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN3220$185.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2871 / WN3174$432.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN4674 + WN4349$175.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN3217 + WN801$175.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN768 + WN2517$175.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN3238 + WN2962$175.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN4605 + WN4990$175.002026-10-29T01:51:12Z
2026-11-20 · one waySouthwest AirlinesWN3203 + WN776$175.002026-10-29T01:51:12Z
2026-11-20 → 2026-11-23Southwest AirlinesWN768 + WN2517 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4674 + WN4349 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4605 + WN4990 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3238 + WN2962 / WN2952 + WN1901$340.002026-10-29T01:51:12Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2871 / WN2952 + WN1901$350.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4605 + WN4990 / WN3174$418.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3238 + WN2962 / WN3174$418.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN768 + WN2517 / WN3174$418.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3217 + WN801 / WN3174$418.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4674 + WN4349 / WN3174$418.002026-10-29T01:51:12Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3203 + WN776 / WN3174$418.002026-10-29T01:51:12Z

2026-11-20 · one way · $185.00

  • Southwest Airlines WN2871: OAK 2026-11-20 06:30:00 → MDW 2026-11-20 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $432.00

  • Southwest Airlines WN3220: OAK 2026-11-27 23:50:00 → MDW 2026-11-28 05:55:00; nonstop; 245 minutes. Local airport times.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN3217 / WN801: OAK 2026-11-20 08:30:00 → MDW 2026-11-20 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2026-11-20 08:30:00 → LGB 2026-11-20 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2026-11-20 11:35:00 → MDW 2026-11-20 17:20:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.

2026-11-20 · one way · $185.00

  • Southwest Airlines WN3220: OAK 2026-11-20 23:50:00 → MDW 2026-11-21 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $432.00

  • Southwest Airlines WN2871: OAK 2026-11-27 06:30:00 → MDW 2026-11-27 12:30:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN4674 / WN4349: OAK 2026-11-20 07:45:00 → MDW 2026-11-20 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2026-11-20 07:45:00 → SLC 2026-11-20 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2026-11-20 13:50:00 → MDW 2026-11-20 17:45:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3217 / WN801: OAK 2026-11-20 08:30:00 → MDW 2026-11-20 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2026-11-20 08:30:00 → LGB 2026-11-20 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2026-11-20 11:35:00 → MDW 2026-11-20 17:20:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN768 / WN2517: OAK 2026-11-20 15:40:00 → MDW 2026-11-21 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2026-11-20 15:40:00 → LAX 2026-11-20 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2026-11-20 18:45:00 → MDW 2026-11-21 00:40:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3238 / WN2962: OAK 2026-11-20 13:35:00 → MDW 2026-11-20 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2026-11-20 13:35:00 → SAN 2026-11-20 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2026-11-20 16:05:00 → MDW 2026-11-20 22:00:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN4605 / WN4990: OAK 2026-11-20 20:45:00 → MDW 2026-11-21 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2026-11-20 20:45:00 → LAS 2026-11-20 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2026-11-21 00:20:00 → MDW 2026-11-21 05:40:00.

2026-11-20 · one way · $175.00

  • Southwest Airlines WN3203 / WN776: OAK 2026-11-20 11:25:00 → MDW 2026-11-20 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
    • WN3203: OAK 2026-11-20 11:25:00 → DEN 2026-11-20 14:50:00; layover at DEN: 195 minutes.
    • WN776: DEN 2026-11-20 18:05:00 → MDW 2026-11-20 21:30:00.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN768 / WN2517: OAK 2026-11-20 15:40:00 → MDW 2026-11-21 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2026-11-20 15:40:00 → LAX 2026-11-20 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2026-11-20 18:45:00 → MDW 2026-11-21 00:40:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN4674 / WN4349: OAK 2026-11-20 07:45:00 → MDW 2026-11-20 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2026-11-20 07:45:00 → SLC 2026-11-20 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2026-11-20 13:50:00 → MDW 2026-11-20 17:45:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN4605 / WN4990: OAK 2026-11-20 20:45:00 → MDW 2026-11-21 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2026-11-20 20:45:00 → LAS 2026-11-20 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2026-11-21 00:20:00 → MDW 2026-11-21 05:40:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.

2026-11-20 → 2026-11-23 · $340.00

  • Southwest Airlines WN3238 / WN2962: OAK 2026-11-20 13:35:00 → MDW 2026-11-20 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2026-11-20 13:35:00 → SAN 2026-11-20 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2026-11-20 16:05:00 → MDW 2026-11-20 22:00:00.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.

2026-11-20 → 2026-11-23 · $350.00

  • Southwest Airlines WN2871: OAK 2026-11-20 06:30:00 → MDW 2026-11-20 12:30:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.

2026-11-27 → 2026-12-04 · $418.00

  • Southwest Airlines WN4605 / WN4990: OAK 2026-11-27 20:45:00 → MDW 2026-11-28 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2026-11-27 20:45:00 → LAS 2026-11-27 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2026-11-28 00:20:00 → MDW 2026-11-28 05:40:00.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $418.00

  • Southwest Airlines WN3238 / WN2962: OAK 2026-11-27 13:35:00 → MDW 2026-11-27 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2026-11-27 13:35:00 → SAN 2026-11-27 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2026-11-27 16:05:00 → MDW 2026-11-27 22:00:00.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $418.00

  • Southwest Airlines WN768 / WN2517: OAK 2026-11-27 15:40:00 → MDW 2026-11-28 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2026-11-27 15:40:00 → LAX 2026-11-27 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2026-11-27 18:45:00 → MDW 2026-11-28 00:40:00.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $418.00

  • Southwest Airlines WN3217 / WN801: OAK 2026-11-27 08:30:00 → MDW 2026-11-27 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2026-11-27 08:30:00 → LGB 2026-11-27 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2026-11-27 11:35:00 → MDW 2026-11-27 17:20:00.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $418.00

  • Southwest Airlines WN4674 / WN4349: OAK 2026-11-27 07:45:00 → MDW 2026-11-27 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2026-11-27 07:45:00 → SLC 2026-11-27 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2026-11-27 13:50:00 → MDW 2026-11-27 17:45:00.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $418.00

  • Southwest Airlines WN3203 / WN776: OAK 2026-11-27 11:25:00 → MDW 2026-11-27 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
    • WN3203: OAK 2026-11-27 11:25:00 → DEN 2026-11-27 14:50:00; layover at DEN: 195 minutes.
    • WN776: DEN 2026-11-27 18:05:00 → MDW 2026-11-27 21:30:00.
  • Southwest Airlines WN3174: MDW 2026-12-04 10:00:00 → OAK 2026-12-04 12:40:00; nonstop; 280 minutes. Local airport times.

More dates for this route