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$129+ Cheap flights from Midway (MDW) to Oakland (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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAK
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$240
(eDestinos)

One-way from

$129
(Southwest)
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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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 November 20, 2024.

This Southwest deal was found by Cheapflights users on 11/20. 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 12/115:10 pmMDW - OAK
Nonstop4h 45mSouthwest
Sun 12/155:30 amOAK - MDW
1 stop6h 55mSouthwest
Deal found 11/20$292
This Delta deal was found by Cheapflights users on 11/18. 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.
Tue 12/109:30 amMDW - OAK
2 stops8h 46mDelta
Wed 12/186:00 amOAK - MDW
2 stops9h 01mDelta
Deal found 11/18$367
This eDestinos deal was found by Cheapflights users on 11/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2012:09 pmMDW - OAK
2 stops29h 50mMultiple Airlines
Sun 11/248:01 pmOAK - MDW
2 stops37h 43mMultiple Airlines
Deal found 11/18$552
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Tue 12/37:50 pmMDW - OAK
2 stops25h 13mVolaris
Tue 12/317:50 pmOAK - MDW
1 stop10h 55mVolaris
Deal found 11/19$910

Find flights from Midway to Oakland within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 1/3

1:24 pm-9:43 am

2 stops22h 19m

Oakland

Fri 1/10

12:41 pm-11:48 am

2 stops45h 07m

$240

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/8

9:40 am-12:35 pm

Nonstop4h 55m

Oakland

Tue 2/18

11:25 am-5:30 pm

Nonstop4h 05m

$258

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 12/10

9:30 am-4:16 pm

2 stops8h 46m

Oakland

Wed 12/18

6:00 am-5:01 pm

2 stops9h 01m

$367

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 4/1

10:41 pm-12:14 pm

1 stop15h 33m

Oakland

Fri 4/4

12:30 pm-7:14 pm

3 stops28h 44m

$712

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 1/7

9:40 am-12:35 pm

Nonstop4h 55m

$129

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 1/7

1:26 pm-11:56 pm

2 stops12h 30m

$133

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 1/5

6:31 pm-8:30 pm

3 stops27h 59m

$258

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sun 3/30

10:14 pm-10:00 am

1 stop13h 46m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 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.

Travel insights for flights from Midway to Oakland

Get recent, data-driven insights about flights from Midway to Oakland including ideal travel times, pricing trends, and more.

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

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $179). Flying from Chicago Midway Airport to Oakland, California in July is currently the most expensive (average of $243). 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 November 20, 2024.

It’s typically best to fly out from Chicago Midway Airport to Oakland, California in the morning. Doing so could potentially save you 46% on the flight price compared to flying at noon, 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 November 20, 2024.
Read through reviews of airlines operating flights from Chicago to Oakland, such as Delta, Volaris and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 $258. Other airlines that can offer you cheap pricing are Delta, from $367, and Volaris, from $712.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Oakland, California one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Oakland, California are Southwest ($129), Delta ($133), and Volaris ($297).

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

    Looking at all options, your cheapest flight can be booked for $119. While the most popular route (Chicago Midway - Oakland) can be booked for $258 on average our data indicates $492 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, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $179). Flying from Chicago Midway Airport to Oakland, California in July is currently the most expensive (average of $243). 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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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$242Average$352FlexibilityNo cancel feeOn-time63%
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