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Oakland

$119+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAK
May 31 — Jun 71
Sun 5/31
Sun 6/7
1 adult, Economy
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Cheap 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 May 1, 2026.

This Southwest deal was found by Cheapflights users on 4/30. 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 8/198:35 pm
MDW
-
OAK
Nonstop4h 30m
Southwest
Wed 8/266:55 pm
OAK
-
MDW
1 stop7h 35m
Southwest
Deal found 4/30$247
This Southwest deal was found by Cheapflights users on 4/29. 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 5/235:55 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Tue 5/2611:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 4/29$251
This Southwest deal was found by Cheapflights users on 4/27. 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 6/33:55 pm
MDW
-
OAK
1 stop6h 25m
Southwest
Mon 6/85:10 am
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 4/27$257
This Southwest deal was found by Cheapflights users on 4/29. 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 5/235:55 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Mon 5/2511:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 4/29$265
This Southwest deal was found by Cheapflights users on 4/27. 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 5/306:00 am
MDW
-
OAK
2 stops8h 25m
Southwest
Wed 6/311:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 4/27$266
This Southwest deal was found by Cheapflights users on 4/29. 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 5/235:55 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Sat 5/308:05 am
OAK
-
MDW
1 stop7h 45m
Southwest
Deal found 4/29$275
This Southwest deal was found by Cheapflights users on 4/26. 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 6/28:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Mon 6/811:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Deal found 4/26$286

Find 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 May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Southwest)

One-way from

$119
(Southwest)

Popular in

November

Cheapest in

September

Average price

$343

Good round-trip deal

$364 or less

Good one-way deal

$221 or less
Provider with most accurate pricing for Chicago Midway-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Oakland flights.
Search Deals
From Chicago Midway to Oakland
Search Deals
One-way flight from Chicago Midway to Oakland
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($141 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Oakland.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Oakland.
Search Deals

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 May 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Oakland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 5/30

6:00 am-12:25 pm

2 stops8h 25m

Oakland

Wed 6/3

11:55 pm-6:00 am

Nonstop4h 05m

$266

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 6/4

9:40 pm-12:10 am

Nonstop4h 30m

Oakland

Sat 6/6

2:10 pm-9:55 pm

1 stop5h 45m

$275

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 5/31

6:55 am-1:20 pm

1 stop8h 25m

Oakland

Wed 6/3

10:45 am-7:55 pm

2 stops7h 10m

$328

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 6/8

5:20 am-9:45 am

1 stop6h 25m

Oakland

Fri 6/12

9:05 pm-5:25 am

1 stop6h 20m

$329

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 5/26

6:23 am-4:25 pm

2 stops12h 02m

Oakland

Tue 6/2

6:00 am-5:56 pm

2 stops9h 56m

$333
Quickest round-trip

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 7/16

9:40 pm-12:10 am

Nonstop4h 30m

Oakland

Mon 7/20

11:55 pm-6:00 am

Nonstop4h 05m

$335

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 8/4

2:15 pm-8:40 pm

2 stops8h 25m

Oakland

Tue 8/11

6:15 am-5:10 pm

2 stops8h 55m

$341

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 9/22

10:30 am-4:00 pm

2 stops7h 30m

Oakland

Sat 9/26

11:55 pm-5:55 am

Nonstop4h 00m

$346

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 6/18

8:35 pm-12:50 am

1 stop6h 15m

Oakland

Mon 6/22

11:55 pm-6:00 am

Nonstop4h 05m

$354

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 6/11

6:40 pm-11:10 pm

1 stop6h 30m

Oakland

Mon 6/15

4:00 pm-12:15 am

1 stop6h 15m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Midway to Oakland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Oakland in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Oakland, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Oakland, California flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Oakland, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 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 May 1, 2026.

It’s typically best to fly out from Chicago Midway Airport to Oakland, California in the evening. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost to fly round-trip from Chicago Midway Airport to Oakland, California?

The best insider tips for Chicago Midway Airport to Oakland flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Oakland trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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

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 May 1, 2026.
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
4,317 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,317 reviews
Southwest
8.0
Very good
4,317 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 8h 25m. Southwest provides one of the quickest options available for as low as $266. The distance between Chicago Midway Airport and Oakland, California is about 1839 mi. This flight may include one or multiple stops.

  • 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 $275. This flight start at 32% 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 $133. While the most popular route (Chicago Midway - Oakland) can be booked for $251 on average, our data indicates $380 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$275Average$408FlexibilityNo cancel feeOn-time63%

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