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Midway

$93+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$297
(Southwest)

One-way from

$93
(Southwest)

Popular in

January

Cheapest in

February

Average price

$544

Good round-trip deal

$366 or less

Good one-way deal

$208 or less
From Oakland to Chicago Midway
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One-way flight from Oakland to Chicago Midway
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High demand for flights, 1% potential price rise
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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 September 2025
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Price to beat on a round-trip flight from Oakland to Chicago Midway.
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Price to beat on a one-way flight from Oakland to Chicago Midway.
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Find 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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 10/275:50 amOAK - MDW
Nonstop4h 05mSouthwest
Wed 11/54:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 9/14$297
This Southwest deal was found by Cheapflights users on 9/13. 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.
Fri 10/248:45 pmOAK - MDW
1 stop6h 15mSouthwest
Sun 10/268:00 amMDW - OAK
1 stop6h 25mSouthwest
Deal found 9/13$308
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 10/221:15 pmOAK - MDW
1 stop6h 45mSouthwest
Wed 10/297:50 amMDW - OAK
1 stop6h 30mSouthwest
Deal found 9/14$317
This Southwest deal was found by Cheapflights users on 9/13. 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 10/233:25 pmOAK - MDW
1 stop6h 25mSouthwest
Sun 10/268:00 amMDW - OAK
1 stop6h 25mSouthwest
Deal found 9/13$320
This Southwest deal was found by Cheapflights users on 9/13. 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 12/67:40 amOAK - MDW
2 stops6h 50mSouthwest
Mon 12/87:05 amMDW - OAK
2 stops8h 50mSouthwest
Deal found 9/13$327
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/232:25 pmOAK - MDW
1 stop7h 25mSouthwest
Mon 10/276:25 pmMDW - OAK
1 stop7h 40mSouthwest
Deal found 9/14$330
This Southwest deal was found by Cheapflights users on 9/13. 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.
Fri 12/125:25 amOAK - MDW
Nonstop4h 05mSouthwest
Mon 12/154:05 pmMDW - OAK
Nonstop4h 35mSouthwest
Deal found 9/13$336
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:30 amOAK - MDW
1 stop12h 22mMultiple Airlines
Sun 9/2810:13 amMDW - OAK
2 stops39h 19mMultiple Airlines
Deal found 9/14$344

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 September 15, 2025.
Use the filters below to find and compare flights from Oakland to Chicago Midway Airport that are best for you.

Fly from

Oakland

Fly to

Midway

Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 10/27

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Wed 11/5

4:15 pm-8:45 pm

1 stop6h 30m

$307

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 10/24

8:45 pm-5:00 am

1 stop6h 15m

Chicago Midway

Sun 10/26

8:00 am-12:25 pm

1 stop6h 25m

$308

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 11/13

12:20 pm-9:55 pm

2 stops7h 35m

Chicago Midway

Sat 11/15

2:05 pm-4:45 pm

Nonstop4h 40m

$312

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 10/22

1:15 pm-10:00 pm

1 stop6h 45m

Chicago Midway

Wed 10/29

7:50 am-12:20 pm

1 stop6h 30m

$317

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 10/23

3:25 pm-11:50 pm

1 stop6h 25m

Chicago Midway

Sun 10/26

8:00 am-12:25 pm

1 stop6h 25m

$320

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 12/12

5:25 am-11:30 am

Nonstop4h 05m

Chicago Midway

Mon 12/15

4:15 pm-8:45 pm

1 stop6h 30m

$346

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 1/25

12:25 pm-10:25 pm

1 stop8h 00m

Chicago Midway

Sat 1/31

9:45 am-4:40 pm

2 stops8h 55m

$367

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 10/15

1:15 pm-10:00 pm

1 stop6h 45m

$94

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 10/3

10:56 am-10:28 am

2 stops21h 32m

$128

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 1/27

5:55 am-6:08 pm

2 stops10h 13m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 18 results
1
2

The best insider tips for Oakland to Chicago Midway Airport 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 Oakland to Chicago Midway Airport trip
Airports
OAK

For a smooth departure, OAK offers quick TSA security checks, especially compared to larger airports like SFO.

Read more about OAKby Bill Fink
MDW

Use the Orange Line train for a quick, cost-effective trip from MDW to downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
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 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, April is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $160). Flying from Oakland, California to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 15, 2025.

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 6% versus a flight at noon.

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 September 15, 2025.
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
4,245 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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 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 $267, was found to be the cheapest airline from Oakland, California to Chicago Midway Airport.. Southwest is 42% 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 $350, our data indicates the cheapest price to be $98. The most popular route (Oakland - Chicago Midway), is priced around $297.

  • 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, April is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $160). Flying from Oakland, California to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Oakland to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$267Average$440FlexibilityNo cancel feeOn-time63%

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