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 $266. Another airline that can offer you cheap pricing is Southwest.

What is the cheapest day to fly from Chicago Midway Airport to Oakland, California?

Travelers seeking maximum savings on their Chicago Midway Airport to Oakland, California flight should consider departing on Saturday mornings when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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

Looking at all options, your cheapest flight can be booked for $171. While the most popular route (Chicago Midway - Oakland) can be booked for $258 on average our data indicates $298 when flying from Chicago Midway Airport to Oakland, California.

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

Users have found that leaving on a Wednesday can be a cost-effective option. It’s possible to save up to 92% on your flight compared to booking on days when demand is much higher.

How far in advance should I book a flight from Chicago Midway Airport to Oakland, California?

Users have found that booking a flight from Chicago Midway Airport to Oakland, California at least 59 days early can save you up to 87% on average compared to booking a flight this week. If booking 59 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Oakland, California for as little as $317 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $466 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to Oakland, California?

Our data shows that April tends to be the cheapest month to fly to Oakland, California from Chicago Midway Airport. Users have commonly found prices around $315 for the month, but tickets can be as low as $98. Due to multiple factors, prepare for potentially higher prices in March.

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.

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 0 inbound flights from Chicago Midway per day.

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.

$87+ Flights from Chicago Midway Airport to Oakland, CA

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheap flight deals from Midway to Oakland

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$266 (Delta)
One-way from	$87 (Southwest)

Provider with most accurate pricing for Chicago Midway-Oakland flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago Midway-Oakland flights.

Search Deals

From Chicago Midway to Oakland

Search Deals

One-way flight from Chicago Midway to Oakland

Search Deals

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 December 18, 2024.

Mon 12/237:20 pmMDW - OAK

1 stop6h 35mSouthwest

Tue 1/78:55 amOAK - MDW

1 stop5h 55mSouthwest

Deal found 12/17

$486

Thu 12/1912:10 pmMDW - OAK

2 stops14h 10mDelta

Tue 12/315:30 amOAK - MDW

2 stops9h 41mDelta

Deal found 12/17

$740

Thu 12/2610:44 amMDW - OAK

3 stops14h 08mMultiple Airlines

Thu 1/24:52 pmOAK - MDW

2 stops24h 40mMultiple Airlines

Deal found 12/17

$747

Best flights from Midway to Oakland
Discover carefully curated flight deals from Midway to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2024.

Wed 1/810:57 amMDW - OAK

2 stops14h 59mDelta

Sat 1/116:00 amOAK - MDW

2 stops9h 47mDelta

Deal found 12/18

$266

Wed 1/89:40 amMDW - OAK

Nonstop4h 55mSouthwest

Sat 1/117:40 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 12/17

$296

Last-minute flights from Midway to Oakland
Discover last-minute flight deals from Midway to Oakland. Data last updated December 18, 2024 and is based on user searches.

Mon 12/237:20 pmMDW - OAK

1 stop6h 35mSouthwest

Tue 1/78:55 amOAK - MDW

1 stop5h 55mSouthwest

Deal found 12/17

$486

Mon 12/236:00 amMDW - OAK

2 stops12h 27mDelta

Tue 1/76:00 amOAK - MDW

2 stops9h 47mDelta

Deal found 12/17

$1,138

Thu 12/2610:44 amMDW - OAK

3 stops14h 08mMultiple Airlines

Thu 1/24:52 pmOAK - MDW

2 stops24h 40mMultiple Airlines

Deal found 12/17

$747

Wed 1/810:57 amMDW - OAK

2 stops14h 59mDelta

Sat 1/116:00 amOAK - MDW

2 stops9h 47mDelta

Deal found 12/18

$266

Wed 1/89:40 amMDW - OAK

Nonstop4h 55mSouthwest

Sat 1/117:40 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 12/17

$296

One-way flights from Midway to Oakland
Search for one-way flight options from Midway to Oakland. Find affordable one-way fares based on user searches. Data last updated December 18, 2024.

Tue 2/49:40 amMDW - OAK

Nonstop4h 55mSouthwest

Deal found 12/18

$87

Tue 1/212:08 pmMDW - OAK

2 stops11h 48mDelta

Deal found 12/17

$133

Find flights from Midway to Oakland within your budget

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/8

10:57 am-11:56 pm

2 stops14h 59m

Oakland

Sat 1/11

6:00 am-5:47 pm

2 stops9h 47m

$266

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 1/8

9:40 am-12:35 pm

Nonstop4h 55m

Oakland

Sat 1/11

7:40 am-1:45 pm

Nonstop4h 05m

$296

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 2/4

9:40 am-12:35 pm

Nonstop4h 55m

$99

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 1/21

2:08 pm-11:56 pm

2 stops11h 48m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Compare providers for flights from Midway to Oakland

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Oakland in December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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 $177). 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?

It’s typically best to fly out from Chicago Midway Airport to Oakland, California in the morning. Doing so could potentially save you 44% on the flight price compared to flying at noon, which is usually more expensive.

Rainfall in Oakland 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

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

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

Southwest

8.1

Very good

4,848 reviews

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

4,848 reviews

Southwest

8.1

Very good

4,848 reviews

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

8,604 reviews

Southwest

8.1

Very good

4,848 reviews

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

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 0 inbound flights 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 $266. Another airline that can offer you cheap pricing is Southwest.
What are the cheapest flights from Chicago Midway Airport to Oakland, California?
Looking at all options, your cheapest flight can be booked for $171. While the most popular route (Chicago Midway - Oakland) can be booked for $258 on average our data indicates $298 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 $177). 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.

See more FAQs

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Top airline flying from Midway to Oakland

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$242	Average$355	FlexibilityNo cancel fee	On-time63%

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$87+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Oakland with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Oakland

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Find flight deals from Midway to Oakland

Cheapest flights from Midway to OaklandExplore 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 December 18, 2024.

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 December 18, 2024.

Find flights from Midway to Oakland within your budget

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 December.

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.

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?

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 December 18, 2024.

Rainfall in Oakland by month

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

Temperature in Oakland by month

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

Reviews of airlines servicing Oakland

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

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?

What are the cheapest airlines flying from Chicago Midway Airport to Oakland, California round-trip?

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

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

How can I find direct flights from Midway to Oakland?

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Oakland

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Midway to Oakland

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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 December 18, 2024.