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Chicago → Oakland

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MDW → OAK1 adulteconomy

24 flight options · 1 airline

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Show 8 more flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:50 amMDW
8h 25m
DAL · 2h 15m
3:15 pmOAK
Southwest Airlines
11:50 pmOAK
4h 5m
Nonstop
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:50 amMDW
6h 55m
LAS · 1h 25m
10:45 amOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 50m
10:50 amOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:50 amMDW
8h 25m
DAL · 2h 15m
3:15 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:35 pmMDW
8h 40m
DEN · 3h 20m
9:15 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK
Southwest Airlines
6:30 amOAK
4h
Nonstop
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
10:00 amMDW
4h 40m
Nonstop
12:40 pmOAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:30 pmMDW
4h 45m
Nonstop
12:15 am+1OAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
5:50 amMDW
6h 55m
LAS · 1h 25m
10:45 amOAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
5:05 amMDW
7h 45m
PHX · 1h 50m
10:50 amOAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:45 pmMDW
7h 30m
LAX · 1h 50m
9:15 pmOAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:50 amMDW
8h 25m
DAL · 2h 15m
3:15 pmOAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:35 pmMDW
8h 40m
DEN · 3h 20m
9:15 pmOAK

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

One-way 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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Why book with Axel
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  • 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
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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 AirlinesWN3174$179.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3174 / WN3220$338.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3174 / WN2871$388.702026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2990$179.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2990 / WN3220$338.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2990 / WN2871$388.702026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2691 + WN1936$169.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2995 + WN681$169.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2952 + WN1901$169.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN1191 + WN1924$169.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4606 + WN1726$169.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4415 + WN1144$169.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2691 + WN1936 / WN3220$328.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4415 + WN1144 / WN3220$328.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4606 + WN1726 / WN3220$328.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2995 + WN681 / WN3220$328.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1191 + WN1924 / WN3220$328.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2952 + WN1901 / WN3220$328.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2691 + WN1936 / WN2871$375.702026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2995 + WN681 / WN2871$375.702026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1191 + WN1924 / WN2871$375.702026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4606 + WN1726 / WN2871$375.702026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4415 + WN1144 / WN2871$375.702026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2952 + WN1901 / WN2871$375.702026-10-29T01:29:13Z

2026-11-20 · one way · $179.00

  • Southwest Airlines WN3174: MDW 2026-11-20 10:00:00 → OAK 2026-11-20 12:40:00; nonstop; 280 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $338.00

  • Southwest Airlines WN3174: MDW 2026-11-20 10:00:00 → OAK 2026-11-20 12:40:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $388.70

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

2026-11-20 · one way · $179.00

  • Southwest Airlines WN2990: MDW 2026-11-20 21:30:00 → OAK 2026-11-21 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $338.00

  • Southwest Airlines WN2990: MDW 2026-11-20 21:30:00 → OAK 2026-11-21 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $388.70

  • Southwest Airlines WN2990: MDW 2026-11-27 21:30:00 → OAK 2026-11-28 00:15:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-20 · one way · $169.00

  • Southwest Airlines WN2691 / WN1936: MDW 2026-11-20 05:50:00 → OAK 2026-11-20 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN2691: MDW 2026-11-20 05:50:00 → LAS 2026-11-20 07:45:00; layover at LAS: 85 minutes.
    • WN1936: LAS 2026-11-20 09:10:00 → OAK 2026-11-20 10:45:00.

2026-11-20 · one way · $169.00

  • Southwest Airlines WN2995 / WN681: MDW 2026-11-20 05:05:00 → OAK 2026-11-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-11-20 05:05:00 → PHX 2026-11-20 07:55:00; layover at PHX: 110 minutes.
    • WN681: PHX 2026-11-20 09:45:00 → OAK 2026-11-20 10:50:00.

2026-11-20 · one way · $169.00

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

2026-11-20 · one way · $169.00

  • Southwest Airlines WN1191 / WN1924: MDW 2026-11-20 08:50:00 → OAK 2026-11-20 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
    • WN1191: MDW 2026-11-20 08:50:00 → DAL 2026-11-20 11:20:00; layover at DAL: 135 minutes.
    • WN1924: DAL 2026-11-20 13:35:00 → OAK 2026-11-20 15:15:00.

2026-11-20 · one way · $169.00

  • Southwest Airlines WN4606 / WN1726: MDW 2026-11-20 14:35:00 → OAK 2026-11-20 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 200 minutes.
    • WN1726: DEN 2026-11-20 19:35:00 → OAK 2026-11-20 21:15:00.

2026-11-20 · one way · $169.00

  • Southwest Airlines WN4415 / WN1144: MDW 2026-11-20 15:15:00 → OAK 2026-11-20 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-11-20 15:15:00 → SAN 2026-11-20 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-11-20 20:05:00 → OAK 2026-11-20 21:35:00.

2026-11-20 → 2026-11-23 · $328.00

  • Southwest Airlines WN2691 / WN1936: MDW 2026-11-20 05:50:00 → OAK 2026-11-20 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN2691: MDW 2026-11-20 05:50:00 → LAS 2026-11-20 07:45:00; layover at LAS: 85 minutes.
    • WN1936: LAS 2026-11-20 09:10:00 → OAK 2026-11-20 10:45:00.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $328.00

  • Southwest Airlines WN4415 / WN1144: MDW 2026-11-20 15:15:00 → OAK 2026-11-20 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-11-20 15:15:00 → SAN 2026-11-20 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-11-20 20:05:00 → OAK 2026-11-20 21:35:00.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $328.00

  • Southwest Airlines WN4606 / WN1726: MDW 2026-11-20 14:35:00 → OAK 2026-11-20 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 200 minutes.
    • WN1726: DEN 2026-11-20 19:35:00 → OAK 2026-11-20 21:15:00.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $328.00

  • Southwest Airlines WN2995 / WN681: MDW 2026-11-20 05:05:00 → OAK 2026-11-20 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-11-20 05:05:00 → PHX 2026-11-20 07:55:00; layover at PHX: 110 minutes.
    • WN681: PHX 2026-11-20 09:45:00 → OAK 2026-11-20 10:50:00.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $328.00

  • Southwest Airlines WN1191 / WN1924: MDW 2026-11-20 08:50:00 → OAK 2026-11-20 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
    • WN1191: MDW 2026-11-20 08:50:00 → DAL 2026-11-20 11:20:00; layover at DAL: 135 minutes.
    • WN1924: DAL 2026-11-20 13:35:00 → OAK 2026-11-20 15:15:00.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $328.00

  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-20 15:45:00 → OAK 2026-11-20 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-20 15:45:00 → LAX 2026-11-20 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-20 20:00:00 → OAK 2026-11-20 21:15:00.
  • Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $375.70

  • Southwest Airlines WN2691 / WN1936: MDW 2026-11-27 05:50:00 → OAK 2026-11-27 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN2691: MDW 2026-11-27 05:50:00 → LAS 2026-11-27 07:45:00; layover at LAS: 85 minutes.
    • WN1936: LAS 2026-11-27 09:10:00 → OAK 2026-11-27 10:45:00.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $375.70

  • Southwest Airlines WN2995 / WN681: MDW 2026-11-27 05:05:00 → OAK 2026-11-27 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
    • WN2995: MDW 2026-11-27 05:05:00 → PHX 2026-11-27 07:55:00; layover at PHX: 110 minutes.
    • WN681: PHX 2026-11-27 09:45:00 → OAK 2026-11-27 10:50:00.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $375.70

  • Southwest Airlines WN1191 / WN1924: MDW 2026-11-27 08:50:00 → OAK 2026-11-27 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
    • WN1191: MDW 2026-11-27 08:50:00 → DAL 2026-11-27 11:20:00; layover at DAL: 135 minutes.
    • WN1924: DAL 2026-11-27 13:35:00 → OAK 2026-11-27 15:15:00.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $375.70

  • Southwest Airlines WN4606 / WN1726: MDW 2026-11-27 14:35:00 → OAK 2026-11-27 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
    • WN4606: MDW 2026-11-27 14:35:00 → DEN 2026-11-27 16:15:00; layover at DEN: 200 minutes.
    • WN1726: DEN 2026-11-27 19:35:00 → OAK 2026-11-27 21:15:00.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $375.70

  • Southwest Airlines WN4415 / WN1144: MDW 2026-11-27 15:15:00 → OAK 2026-11-27 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-11-27 15:15:00 → SAN 2026-11-27 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-11-27 20:05:00 → OAK 2026-11-27 21:35:00.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $375.70

  • Southwest Airlines WN2952 / WN1901: MDW 2026-11-27 15:45:00 → OAK 2026-11-27 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
    • WN2952: MDW 2026-11-27 15:45:00 → LAX 2026-11-27 18:10:00; layover at LAX: 110 minutes.
    • WN1901: LAX 2026-11-27 20:00:00 → OAK 2026-11-27 21:15:00.
  • Southwest Airlines WN2871: OAK 2026-12-04 06:30:00 → MDW 2026-12-04 12:30:00; nonstop; 240 minutes. Local airport times.

More dates for this route