HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oakland

$95+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAK
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Oakland with Cheapflights

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 junio 12, 2025.

Round-trip from

$227
(Southwest)

One-way from

$95
(Southwest)

Popular in

July

Cheapest in

November

Average price

$444

Good round-trip deal

$342 or less

Good one-way deal

$258 or less
From Chicago Midway to Oakland
Search Deals
One-way flight from Chicago Midway to Oakland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Oakland.
Search Deals
Price to beat on a 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 junio 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
jue. 9/1110:50 amMDW - OAK
1 stop6h 15mSouthwest
lun. 9/158:30 pmOAK - MDW
1 stop6h 40mSouthwest
Deal found 6/11$199
This Delta deal was found by Cheapflights users on 6/10. 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.
mar. 7/19:24 amMDW - OAK
2 stops8h 52mDelta
mar. 7/84:55 pmOAK - MDW
2 stops13h 49mDelta
Deal found 6/10$308
This Mytrip deal was found by Cheapflights users on 6/10. 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.
jue. 7/1011:37 amMDW - OAK
3 stops22h 51mMultiple Airlines
dom. 7/136:00 amOAK - MDW
2 stops25h 41mMultiple Airlines
Deal found 6/10$491

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 junio 12, 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

jue. 7/3

7:20 am-9:50 am

Nonstop4h 30m

Oakland

lun. 7/7

9:15 pm-5:00 am

1 stop5h 45m

$227

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mar. 7/1

9:24 am-4:16 pm

2 stops8h 52m

Oakland

mar. 7/8

4:55 pm-8:44 am

2 stops13h 49m

$308

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

jue. 7/10

11:37 am-8:28 am

3 stops22h 51m

Oakland

dom. 7/13

6:00 am-9:41 am

2 stops25h 41m

$491

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

sáb. 8/23

10:55 am-3:10 pm

1 stop6h 15m

$95

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

lun. 8/11

9:12 am-8:28 am

2 stops25h 16m

$132

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

mié. 8/27

9:15 am-4:16 pm

2 stops9h 01m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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

Use the Orange Line train for a quick, cost-effective trip to MDW, taking less than 30 minutes from the city center.

Read more about MDWby Ramsey Qubein
OAK

For a cost-effective trip from OAK to San Francisco, use BART. It's efficient and connects directly to the airport terminals.

Read more about OAKby Bill Fink
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 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 junio 12, 2025.

It’s typically best to fly out from Chicago Midway Airport to Oakland, California at noon. Doing so could potentially save you 38% 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 junio 12, 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
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

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 $227. Another airline that can offer you cheap pricing is Delta. These flights start at 42% 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 $81. While the most popular route (Chicago Midway - Oakland) can be booked for $199 on average our data indicates $529 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.

See more FAQs

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.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Ontario flights
Midway to Las Vegas flights
O'Hare Intl to Burbank flights
Midway to Los Angeles flights
Midway to San Francisco flights
O'Hare Intl to Oakland flights
O'Hare Intl to Reno flights
O'Hare Intl to Sacramento flights
O'Hare Intl to San Jose flights
Midway to San Diego flights
O'Hare Intl to Palm Springs flights
Midway to Santa Ana flights
Rockford to Las Vegas flights
Midway to Ontario flights
Midway to Reno flights
O'Hare Intl to Fresno flights
O'Hare Intl to Santa Barbara flights
Midway to Palm Springs flights
Midway to Burbank flights
Midway to Sacramento flights
O'Hare Intl to Long Beach flights
Midway to San Jose flights
O'Hare Intl to Monterey flights
Midway to Long Beach flights
Midway to Fresno flights
O'Hare Intl to San Luis Obispo flights
O'Hare Intl to Santa Rosa flights
O'Hare Intl to Medford flights
O'Hare Intl to Arcata flights
Midway to Medford flights
O'Hare Intl to Tijuana flights
O'Hare Intl to Redding flights
O'Hare Intl to Bakersfield flights
Midway to Tijuana flights
O'Hare Intl to Yuma flights
O'Hare Intl to Merced flights
O'Hare Intl to Mexicali flights
Midway to Mexicali flights
O'Hare Intl to Mammoth Lakes flights

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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$247Average$361FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.