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$100+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAK
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(Southwest)

One-way from

$100
(Southwest)

Popular in

July

Cheapest in

November

Average price

$375

Good round-trip deal

$287 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Chicago Midway-Oakland flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Oakland flights.
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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. 18% potential increase in price ($92 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Southwest deal was found by Cheapflights users on 4/28. 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 5/295:05 amMDW - OAK
1 stop6h 45mSouthwest
Sun 6/15:55 amOAK - MDW
Nonstop4h 10mSouthwest
Deal found 4/28$247
This Delta deal was found by Cheapflights users on 4/28. 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 5/281:55 pmMDW - OAK
2 stops11h 54mDelta
Tue 6/36:00 amOAK - MDW
2 stops9h 45mDelta
Deal found 4/28$267
This Mytrip deal was found by Cheapflights users on 4/28. 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 5/298:20 pmMDW - OAK
3 stops28h 05mMultiple Airlines
Wed 6/45:45 amOAK - MDW
3 stops35h 34mMultiple Airlines
Deal found 4/28$430

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 April 29, 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

Thu 5/29

5:05 am-9:50 am

1 stop6h 45m

Oakland

Sun 6/1

5:55 am-12:05 pm

Nonstop4h 10m

$247

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 5/28

1:08 pm-11:49 pm

2 stops12h 41m

Oakland

Mon 6/2

6:00 am-5:45 pm

2 stops9h 45m

$267

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 5/29

8:20 pm-4:41 pm

2 stops22h 21m

Oakland

Wed 6/4

5:45 am-7:19 pm

3 stops35h 34m

$399

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 7/4

2:45 pm-7:05 pm

1 stop6h 20m

$100

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 6/16

9:12 am-11:26 pm

2 stops40h 14m

$127

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 6/24

9:21 am-4:16 pm

2 stops8h 55m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 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 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 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 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 April 29, 2025.

It’s typically best to fly out from Chicago Midway Airport to Oakland, California at noon. Doing so could potentially save you 35% on the flight price compared to flying in the morning, which is usually more expensive.

Rainfall in Oakland by month

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

In terms of precipitation, rainfall in Oakland, California ranges from 0.0 - 4.8 inches per month. January is typically the wettest month, when rainfall can reach 4.8 in. July is typically the driest time to visit Oakland, California when rainfall is around 0.0 in.

Temperature in Oakland by month

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

If weather is an important factor for your trip to Oakland, California, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 April 29, 2025.
Read through reviews of airlines operating flights from Chicago to Oakland, such as Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

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
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

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
7,929 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

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 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 1 inbound flight from Chicago Midway per day.

  • What are the cheapest airlines flying 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. Another airline that can offer you cheap pricing is Delta. These flights start at 38% 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 $98. While the most popular route (Chicago Midway - Oakland) can be booked for $247 on average our data indicates $275 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.

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Alternative routes for Midway to Oakland

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$247Average$363FlexibilityNo cancel feeOn-time63%

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