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Midway

$119+ Cheap flights from Oakland, CA (OAK) to Midway (MDW)

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MDW
May 18 — May 251
Mon 5/18
Mon 5/25
1 adult, Economy
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Cheap flight deals from Oakland to Midway

Cheapest flights from Oakland to Midway
Explore the most affordable flight options available from Oakland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.

This Southwest deal was found by Cheapflights users on 4/14. 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 5/1911:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Tue 6/28:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 4/14$237
This Southwest deal was found by Cheapflights users on 4/13. 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 5/68:50 pm
OAK
-
MDW
1 stop6h 50m
Southwest
Tue 5/128:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 4/13$247
This Southwest deal was found by Cheapflights users on 4/13. 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 5/911:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Wed 5/138:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 4/13$251
This Southwest deal was found by Cheapflights users on 4/15. 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.
Wed 5/138:15 am
OAK
-
MDW
1 stop6h 45m
Southwest
Wed 5/204:30 pm
MDW
-
OAK
1 stop6h 15m
Southwest
Deal found 4/15$257
This Southwest deal was found by Cheapflights users on 4/15. 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.
Mon 5/1811:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Thu 5/219:50 pm
MDW
-
OAK
Nonstop4h 35m
Southwest
Deal found 4/15$265
This Southwest deal was found by Cheapflights users on 4/13. 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 5/288:55 pm
OAK
-
MDW
1 stop6h 05m
Southwest
Tue 6/95:25 pm
MDW
-
OAK
1 stop7h 00m
Southwest
Deal found 4/13$271
This Southwest deal was found by Cheapflights users on 4/15. 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 5/911:55 pm
OAK
-
MDW
Nonstop4h 05m
Southwest
Sat 5/165:10 am
MDW
-
OAK
1 stop6h 50m
Southwest
Deal found 4/15$275

Find flight deals from Oakland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Midway (MDW). 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 April 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Southwest)

One-way from

$119
(Southwest)

Popular in

November

Cheapest in

February

Average price

$476

Good round-trip deal

$380 or less

Good one-way deal

$201 or less
Provider with most accurate pricing for Oakland-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Chicago Midway flights.
Search Deals
From Oakland to Chicago Midway
Search Deals
One-way flight from Oakland to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Oakland to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Oakland to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Midway 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 April 18, 2026.
Use the filters below to find and compare flights from Oakland to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 5/11

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Tue 5/12

8:50 pm-11:25 pm

Nonstop4h 35m

$251

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 5/19

8:50 pm-5:40 am

1 stop6h 50m

Chicago Midway

Tue 6/2

6:05 pm-10:35 pm

1 stop6h 30m

$257

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 5/4

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Tue 5/12

7:30 am-1:30 pm

1 stop8h 00m

$261

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 5/9

8:05 am-5:50 pm

1 stop7h 45m

Chicago Midway

Wed 5/13

8:50 pm-11:25 pm

Nonstop4h 35m

$261

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 5/28

8:55 pm-5:00 am

1 stop6h 05m

Chicago Midway

Tue 6/2

2:55 pm-8:35 pm

1 stop7h 40m

$271

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 8/18

5:55 am-9:46 pm

2 stops13h 51m

Chicago Midway

Sat 8/22

9:20 am-4:31 pm

2 stops9h 11m

$301

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 6/17

9:00 pm-5:25 am

1 stop6h 25m

Chicago Midway

Sat 7/11

10:15 am-4:25 pm

2 stops8h 10m

$336

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 5/23

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Tue 5/26

3:55 pm-8:20 pm

1 stop6h 25m

$352
Quickest round-trip

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 6/15

11:55 pm-6:00 am

Nonstop4h 05m

Chicago Midway

Tue 6/23

9:00 pm-11:30 pm

Nonstop4h 30m

$353

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 9/25

11:55 pm-5:55 am

Nonstop4h 00m

Chicago Midway

Wed 9/30

10:15 am-2:45 pm

1 stop6h 30m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Oakland to Midway

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 Oakland to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 Oakland, California-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Chicago Midway Airport 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 Oakland, California-Chicago Midway Airport 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 Oakland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oakland 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 Oakland to Chicago Midway Airport

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

Currently, February is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $288). Flying from Oakland, California to Chicago Midway Airport in November is currently the most expensive (average of $647). 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 OAK to MDW?

Find hourly flight availability from Oakland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 18, 2026.

When flying from Oakland, California to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 57% versus a flight at noon.

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

The best insider tips for Oakland to Chicago Midway Airport 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 Oakland to Chicago Midway Airport 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 18, 2026.
Peruse reviews from past customers who have flown with Southwest from Oakland to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,330 reviews
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Midway. 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 from for flights from Oakland to Chicago Midway?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Chicago Midway from Oakland. Booking flights from Oakland (OAK) to Chicago Midway should be relatively easy as there is 1 daily outbound flight to Chicago Midway from 1 airline.

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

    Southwest can get you from Oakland, California to Chicago Midway Airport in just under 4h 05m. Your travel time will be generally consistent. There are 1839 mi between Oakland, California and Chicago Midway Airport. All flights are typically nonstop.

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

    Southwest, at $274, was found to be the cheapest airline from Oakland, California to Chicago Midway Airport.. Southwest is 41% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Looking for the cheapest flight from Oakland, California to Chicago Midway Airport? While on average our users pay $378, our data indicates the cheapest price to be $132. The most popular route (Oakland - Chicago Midway), is priced around $237.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Midway 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 Oakland, California to Chicago Midway Airport?

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $288). Flying from Oakland, California to Chicago Midway Airport in November is currently the most expensive (average of $647). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Oakland to Midway

Discover the top airline that operate flights from Oakland to Midway. 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 April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$274Average$475FlexibilityNo cancel feeOn-time63%

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