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$68+ Cheap flights from Midway (MDW) to Oakland, CA (OAK)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAK
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midway to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Oakland (OAK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Round-trip from

$227
(Southwest)

One-way from

$68
(Mytrip)

Popular in

September

Cheapest in

November

Average price

$397

Good round-trip deal

$354 or less

Good one-way deal

$127 or less
From Chicago Midway to Oakland
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One-way flight from Chicago Midway to Oakland
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Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Oakland.
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Price to beat on a one-way flight from Chicago Midway to Oakland.
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Find flight deals from Midway to Oakland

Cheapest flights from Midway to Oakland
Explore the most affordable flight options available from Midway to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/101:50 pmMDW - OAK
1 stop6h 20mSouthwest
Mon 10/135:50 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 8/18$227
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/63:25 pmMDW - OAK
Nonstop4h 30mSouthwest
Sun 9/145:50 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 8/15$247
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/261:15 pmMDW - OAK
Nonstop4h 30mSouthwest
Sun 9/285:50 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 8/15$253
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/303:10 pmMDW - OAK
Nonstop4h 30mSouthwest
Tue 10/78:35 pmOAK - MDW
1 stop6h 40mSouthwest
Deal found 8/16$267
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:10 pmMDW - OAK
1 stop6h 25mSouthwest
Mon 9/85:15 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 8/16$277
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:00 amMDW - OAK
1 stop6h 00mSouthwest
Tue 9/2311:20 amOAK - MDW
2 stops7h 30mSouthwest
Deal found 8/17$282
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:50 amMDW - OAK
1 stop6h 15mSouthwest
Tue 9/301:35 pmOAK - MDW
1 stop5h 15mSouthwest
Deal found 8/17$286
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/261:15 pmMDW - OAK
Nonstop4h 30mSouthwest
Mon 9/293:55 pmOAK - MDW
1 stop6h 35mSouthwest
Deal found 8/15$292

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Oakland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Oakland that are best for you.

Fly from

Midway

Fly to

Oakland

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 10/10

1:50 pm-6:10 pm

1 stop6h 20m

Oakland

Mon 10/13

5:50 am-11:55 am

Nonstop4h 05m

$227

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 9/6

3:25 pm-5:55 pm

Nonstop4h 30m

Oakland

Sun 9/14

5:50 am-11:55 am

Nonstop4h 05m

$247

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 9/26

1:15 pm-3:45 pm

Nonstop4h 30m

Oakland

Sun 9/28

5:50 am-11:55 am

Nonstop4h 05m

$253

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 9/26

1:15 pm-3:45 pm

Nonstop4h 30m

Oakland

Mon 9/29

5:15 am-11:20 am

Nonstop4h 05m

$253

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 9/30

3:10 pm-5:40 pm

Nonstop4h 30m

Oakland

Tue 10/7

8:35 pm-5:15 am

1 stop6h 40m

$267

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 10/3

1:50 pm-6:10 pm

1 stop6h 20m

Oakland

Sun 10/5

6:40 am-12:45 pm

Nonstop4h 05m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 9/4

5:10 pm-9:35 pm

1 stop6h 25m

Oakland

Mon 9/8

5:15 am-11:20 am

Nonstop4h 05m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 9/16

8:25 am-12:50 pm

1 stop6h 25m

Oakland

Wed 9/17

9:40 am-7:05 pm

1 stop7h 25m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 9/17

6:00 am-10:00 am

1 stop6h 00m

Oakland

Tue 9/23

7:10 pm-5:15 am

1 stop8h 05m

$277

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 11/27

8:25 am-11:10 am

Nonstop4h 45m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 15 results
1
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The best insider tips for Chicago Midway Airport to Oakland flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Oakland trip
Airports
MDW

Use the Orange Line train for a quick, cost-effective trip to MDW, taking less than 30 minutes from the city center.

Read more about MDWby Ramsey Qubein
OAK

For a cost-effective trip from OAK to San Francisco, use BART. It's efficient and connects directly to the airport terminals.

Read more about OAKby Bill Fink
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Bill Fink

Bill Fink

Expert on OAK

Bill Fink

Bill Fink

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Read more

Best time to book a flight from Midway to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Oakland

What is the cheapest month to book a flight from Chicago Midway Airport to Oakland, California?

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $183). Flying from Chicago Midway Airport to Oakland, California in November is currently the most expensive (average of $259). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to OAK?

Find hourly flight availability from Midway to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

It’s typically best to fly out from Chicago Midway Airport to Oakland, California at noon. Doing so could potentially save you 39% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oakland. Reviews last updated August 18, 2025.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Oakland from Chicago Midway?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Oakland. 1 airline have flights to Oakland from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Oakland should not be difficult; the airport handles an average of 2 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Oakland, California?

    A quick flight from Chicago Midway Airport to Oakland, California can take about 6h 20m. Southwest provides one of the quickest options available for as low as $227. The distance between Chicago Midway Airport and Oakland, California is about 1839 mi.

  • What is the cheapest airline to fly from Chicago Midway Airport to Oakland, California round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Oakland, California round-trip from $247. This flight start at 35% lower than the current average price 3 months from now.

  • What are the cheapest flights from Chicago Midway Airport to Oakland, California?

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Chicago Midway - Oakland) can be booked for $267 on average our data indicates $442 when flying from Chicago Midway Airport to Oakland, California.

  • Can I find deals for flights from Midway to Oakland that include hotel bookings?

    Yes. In addition to deals on Midway to Oakland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Oakland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Oakland.

  • Can I find deals for business class flights from Midway to Oakland?

    Yes. Cheapflights offers flight deals from Midway to Oakland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Oakland, California?

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $183). Flying from Chicago Midway Airport to Oakland, California in November is currently the most expensive (average of $259). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Oakland

Discover the top airline that operate flights from Midway to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$247Average$368FlexibilityNo cancel feeOn-time63%

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