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$100+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MDW
May 25 — Jun 11
Sun 5/25
Sun 6/1
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 May 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$267
(Southwest)

One-way from

$100
(Southwest)

Popular in

January

Cheapest in

July

Average price

$416

Good round-trip deal

$381 or less

Good one-way deal

$200 or less
Provider with most accurate pricing for Oakland-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Oakland-Chicago Midway flights.
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From Oakland to Chicago Midway
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One-way flight from Oakland to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 20, 2025.

This Southwest deal was found by Cheapflights users on 5/20. 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 7/98:05 pmOAK - MDW
1 stop6h 55mSouthwest
Thu 7/108:00 pmMDW - OAK
1 stop6h 05mSouthwest
Deal found 5/20$267
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:00 amOAK - MDW
2 stops10h 45mDelta
Fri 5/301:08 pmMDW - OAK
2 stops12h 41mDelta
Deal found 5/19$287
This Mytrip deal was found by Cheapflights users on 5/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/55:45 amOAK - MDW
3 stops30h 18mMultiple Airlines
Sun 6/88:09 pmMDW - OAK
2 stops22h 32mMultiple Airlines
Deal found 5/19$528

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 May 20, 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

Wed 7/9

8:05 pm-5:00 am

1 stop6h 55m

Chicago Midway

Thu 7/10

8:00 pm-12:05 am

1 stop6h 05m

$267

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 7/11

4:55 pm-8:44 am

2 stops13h 49m

Chicago Midway

Tue 7/15

12:43 pm-11:55 pm

2 stops13h 12m

$298

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 6/5

5:45 am-2:03 pm

3 stops30h 18m

Chicago Midway

Sun 6/8

8:09 pm-4:41 pm

2 stops22h 32m

$528

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 5/28

8:30 pm-5:15 am

1 stop6h 45m

$100

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 6/26

9:38 pm-2:56 pm

1 stop15h 18m

$127

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 8/22

4:58 pm-9:16 am

2 stops14h 18m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 eDreams the most. eDreams 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, 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 May 20, 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 morning, which can drop the price by up to 14% versus a flight in the afternoon.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 20, 2025.
Read reviews from past customers who have flown Southwest and Delta from Oakland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,289 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,289 reviews
Southwest
8.0
Very good
4,289 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,289 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Food

7.1

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • What are the cheapest airlines flying 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. An alternate airline flying to your destination would be Delta. Southwest is 35% 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 $340, our data indicates the cheapest price to be $128. The most popular route (Oakland - Chicago Midway), is priced around $257.

  • 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 Oakland?

Book flights to Oakland if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Oakland to Midway

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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 May 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$276Average$416FlexibilityNo cancel feeOn-time63%

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