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Cheap flights from Midway (MDW) to Oakland (OAK) from $122

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 5/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — OAK
May 8 — May 151
From?
To?
Wed 5/8
Wed 5/15
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 May 3, 2024.

Round-trip from

$268
From Chicago Midway to Oakland
Search Deals

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 57 days early can save you up to 40% on average compared to booking a flight this week. If booking 57 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 $354 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 $517 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 September tends to be the cheapest month to fly to Oakland, California from Chicago Midway Airport. Users have commonly found prices around $338 for the month, but tickets can be as low as $119. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from Chicago Midway Airport to Oakland, California (MDW - OAK)?

When flying from Chicago Midway Airport to Oakland, California, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Southwest flights from Midway to Oakland

Explore cheap flight options specifically provided by Southwest for the route between Midway and Oakland. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 3, 2024.
Take a peek at the cheapest Southwest flights we've detected traveling from Chicago to Oakland. Be sure to come back soon if the deals available don't appeal to you at this time.
Mon 5/207:00 pmMDW - OAK
1 stop6h 25mSouthwest
Wed 5/223:05 pmOAK - MDW
1 stop6h 15mSouthwest
Deal found 5/2$391
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/223:05 pmOAK - MDW
1 stop6h 15mSouthwest
Deal found 5/2$421
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/225:50 pmOAK - MDW
Nonstop4h 05mSouthwest
Deal found 5/2$450
Mon 5/203:10 pmMDW - OAK
2 stops7h 50mSouthwest
Wed 5/2211:00 amOAK - MDW
1 stop7h 40mSouthwest
Deal found 5/2$469

Cheap Volaris flights from Midway to Oakland

Explore cheap flight options specifically provided by Volaris for the route between Midway and Oakland. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 3, 2024.
Some of the lowest-priced Volaris flights we've found at this time heading from Chicago to Oakland. Deals frequently update to provide users with more options.
Fri 5/2410:41 pmMDW - OAK
1 stop19h 18mVolaris
Mon 5/276:39 pmOAK - MDW
1 stop13h 08mVolaris
Deal found 5/2$815
Wed 9/258:50 pmMDW - OAK
2 stops25h 36mVolaris
Sun 9/2910:08 pmOAK - MDW
2 stops12h 43mVolaris
Deal found 5/2$937
Sun 5/128:45 pmMDW - OAK
2 stops25h 41mVolaris
Wed 5/156:39 pmOAK - MDW
1 stop13h 08mVolaris
Deal found 5/2$971
Tue 5/710:41 pmMDW - OAK
1 stop15h 33mVolaris
Sat 5/112:51 pmOAK - MDW
1 stop16h 15mVolaris
Deal found 5/2$1,028
Tue 5/78:45 pmMDW - OAK
2 stops25h 41mVolaris
Sat 5/116:39 pmOAK - MDW
1 stop13h 08mVolaris
Deal found 5/2$1,227

Cheap Midway to Oakland flights in May & June 2024

Find cheap flight options from Midway to Oakland specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,899,487 searches. Prices were last updated on May 3, 2024.
Check out some of the best flight deals from Chicago to Oakland in 2024. For more flight deals, be sure to check back very soon.
Mon 5/207:00 pmMDW - OAK
1 stop6h 25mSouthwest
Wed 5/223:05 pmOAK - MDW
1 stop6h 15mSouthwest
Deal found 5/2$391
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/223:05 pmOAK - MDW
1 stop6h 15mSouthwest
Deal found 5/2$421
Tue 5/72:15 pmMDW - OAK
2 stops11h 36mDelta
Sat 5/115:50 amOAK - MDW
2 stops9h 05mDelta
Deal found 5/2$423
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/225:50 pmOAK - MDW
Nonstop4h 05mSouthwest
Deal found 5/2$450
Mon 5/203:10 pmMDW - OAK
2 stops7h 50mSouthwest
Wed 5/2211:00 amOAK - MDW
1 stop7h 40mSouthwest
Deal found 5/2$469
Thu 6/131:24 pmMDW - OAK
2 stops12h 31mDelta
Sun 6/165:50 amOAK - MDW
2 stops10h 46mDelta
Deal found 5/2$538
Tue 6/111:24 pmMDW - OAK
2 stops12h 31mDelta
Tue 6/2510:55 pmOAK - MDW
1 stop8h 56mDelta
Deal found 5/2$567
Tue 6/111:24 pmMDW - OAK
2 stops12h 31mDelta
Tue 6/255:00 pmOAK - MDW
2 stops14h 51mDelta
Deal found 5/2$572
Fri 6/141:24 pmMDW - OAK
2 stops12h 31mDelta
Tue 6/185:00 pmOAK - MDW
2 stops13h 48mDelta
Deal found 5/2$598

Midway to Oakland 2024 flight deals

Discover exclusive flight deals for travel between Midway and Oakland in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 3, 2024.
Check out some of the best flight deals from Chicago to Oakland in 2024. For more flight deals, be sure to check back very soon.
Fri 7/191:05 pmMDW - OAK
1 stop10h 40mDelta
Tue 7/235:00 pmOAK - MDW
2 stops13h 40mDelta
Deal found 5/2$348
Mon 5/207:00 pmMDW - OAK
1 stop6h 25mSouthwest
Wed 5/223:05 pmOAK - MDW
1 stop6h 15mSouthwest
Deal found 5/2$391
Fri 7/191:24 pmMDW - OAK
2 stops12h 30mDelta
Tue 7/235:00 pmOAK - MDW
2 stops13h 40mDelta
Deal found 5/2$413
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/223:05 pmOAK - MDW
1 stop6h 15mSouthwest
Deal found 5/2$421
Tue 5/72:15 pmMDW - OAK
2 stops11h 36mDelta
Sat 5/115:50 amOAK - MDW
2 stops9h 05mDelta
Deal found 5/2$423
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/225:50 pmOAK - MDW
Nonstop4h 05mSouthwest
Deal found 5/2$450
Mon 5/203:10 pmMDW - OAK
2 stops7h 50mSouthwest
Wed 5/2211:00 amOAK - MDW
1 stop7h 40mSouthwest
Deal found 5/2$469
Thu 6/131:24 pmMDW - OAK
2 stops12h 31mDelta
Sun 6/165:50 amOAK - MDW
2 stops10h 46mDelta
Deal found 5/2$538
Tue 6/111:24 pmMDW - OAK
2 stops12h 31mDelta
Tue 6/2510:55 pmOAK - MDW
1 stop8h 56mDelta
Deal found 5/2$567

Non-stop flights to Oakland from Midway

Discover non-stop flight options from Midway to Oakland. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 3, 2024.
Take a look at some of the direct flights traveling from Chicago to Oakland in the near future. Search for alternative flights from Chicago to Oakland by utilizing the search form above.
Mon 5/206:30 amMDW - OAK
Nonstop4h 40mSouthwest
Wed 5/225:50 pmOAK - MDW
Nonstop4h 05mSouthwest
Deal found 5/2$450

Midway to Oakland flights leaving soon

Find last-minute flight options from Midway to Oakland for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 3, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to Oakland. To prevent any unwanted surprises, users should verify their flight info before booking.
Tue 5/72:15 pmMDW - OAK
2 stops11h 36mDelta
Sat 5/115:50 amOAK - MDW
2 stops9h 05mDelta
Deal found 5/2$423
Fri 5/105:47 pmMDW - OAK
2 stops8h 04mDelta
Wed 5/155:50 amOAK - MDW
2 stops10h 17mDelta
Deal found 5/2$813
Tue 5/78:45 pmMDW - OAK
3 stops26h 55mMultiple Airlines
Sat 5/113:52 pmOAK - MDW
3 stops23h 30mMultiple Airlines
Deal found 5/2$823
Sun 5/128:45 pmMDW - OAK
2 stops25h 41mVolaris
Wed 5/156:39 pmOAK - MDW
1 stop13h 08mVolaris
Deal found 5/2$971
Sun 5/122:15 pmMDW - OAK
2 stops11h 36mDelta
Wed 5/155:50 amOAK - MDW
2 stops9h 16mDelta
Deal found 5/2$972
Tue 5/710:41 pmMDW - OAK
1 stop15h 33mVolaris
Sat 5/112:51 pmOAK - MDW
1 stop16h 15mVolaris
Deal found 5/2$1,028
Tue 5/78:45 pmMDW - OAK
2 stops25h 41mVolaris
Sat 5/116:39 pmOAK - MDW
1 stop13h 08mVolaris
Deal found 5/2$1,227
Thu 5/93:45 pmMDW - OAK
2 stops10h 06mDelta
Thu 5/165:50 amOAK - MDW
2 stops9h 16mDelta
Deal found 5/2$1,347

One-way flights to Oakland from Midway

Search for one-way flight options from Midway to Oakland. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,899,487 searches. Data last updated May 3, 2024.
If you're seeking multiple options on one-way flights from Chicago to Oakland, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Chicago to Oakland should utilize the search form at the the top of the page.
Wed 5/1510:12 amMDW - OAK
2 stops13h 28mMultiple Airlines
Deal found 5/2$122
Tue 5/212:15 pmMDW - OAK
2 stops11h 36mDelta
Deal found 5/2$123
Mon 6/38:33 pmMDW - OAK
3 stops40h 39mMultiple Airlines
Deal found 5/2$194
Wed 5/156:08 pmMDW - OAK
3 stops30h 51mMultiple Airlines
Deal found 5/2$221
Mon 6/312:08 pmMDW - OAK
2 stops25h 04mMultiple Airlines
Deal found 5/2$259
Thu 5/305:47 pmMDW - OAK
2 stops8h 04mDelta
Deal found 5/2$264
Tue 5/72:15 pmMDW - OAK
2 stops11h 36mDelta
Deal found 5/2$265
Fri 6/282:24 pmMDW - OAK
2 stops11h 31mDelta
Deal found 5/2$269
Sat 6/83:45 pmMDW - OAK
1 stop8h 00mDelta
Deal found 5/2$399

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 2,899,487 searches. Data last updated May 3, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$348 - $828

Route

Depart

Return

Price

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 7/19

1 stop10h 40m

Oakland

Tue 7/23

2 stops13h 40m

$348

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 5/20

1 stop6h 25m

Oakland

Wed 5/22

1 stop6h 15m

$391

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 7/19

2 stops12h 30m

Oakland

Tue 7/23

2 stops13h 40m

$413

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 5/20

Nonstop4h 40m

Oakland

Wed 5/22

1 stop6h 15m

$421

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 5/20

Nonstop4h 40m

Oakland

Wed 5/22

Nonstop4h 05m

$450

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Mon 5/20

2 stops7h 50m

Oakland

Wed 5/22

1 stop7h 40m

$469

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 6/13

2 stops12h 31m

Oakland

Sun 6/16

2 stops10h 46m

$538

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 5/24

1 stop19h 18m

Oakland

Mon 5/27

1 stop13h 08m

$815

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 5/24

1 stop19h 18m

Oakland

Mon 5/27

2 stops19h 53m

$828

Flights are sorted by cheapest first

Deals found on 5/2

No data available for this route at this time. Please check back soon.

Average price of flights to Oakland by month

Plan your trip from Midway to Oakland by taking into account the cheapest months to travel. The average price of a one-way flight from Midway to Oakland is currently $235 while a round-trip flight costs $519. Price data was last updated on April 28, 2024.

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $169). Flying from Chicago Midway Airport to Oakland, California in June is currently the most expensive (average of $236). 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.

January

$201

February

$218

March

$218

April

$191

May

$208

June

$236

July

$210

August

$178

September

$181

October

$169

November

$202

December

$208

Temperature and rainfall in Oakland by month

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

SFO

Temperature

51.8 - 62.6 °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 May 3, 2024.
Read through reviews of airlines operating flights from Chicago to Oakland, such as Southwest, Volaris and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
6,108 reviews
Check prices

Boarding

8.3

Overall

8.2

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Southwest
8.2
Very good
6,108 reviews
Southwest
8.2
Very good
6,108 reviews
Check prices

Boarding

8.3

Overall

8.2

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Delta
8.1
Very good
10,858 reviews
Southwest
8.2
Very good
6,108 reviews
Check prices

Boarding

8.3

Overall

8.2

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Volaris
6.7
Okay
1,525 reviews
Southwest
8.2
Very good
6,108 reviews
Check prices

Boarding

8.3

Overall

8.2

Entertainment

7.8

Crew

8.7

Food

7.3

Comfort

8.1

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

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. 0 airlines 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 2 inbound flights from Chicago Midway per day.

  • Can I find flights from Chicago Midway Airport to Oakland, California for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Oakland, California for under $400. The cheapest flight booked recently is on Delta for just $348, but on average you can expect to pay $597.

  • Are there nonstop flights from Chicago Midway Airport to Oakland, California for under $500 on Cheapflights?

    Cheapflights has at least 1 direct flight from Chicago Midway Airport to Oakland, California under $500. A good price for a nonstop flight from Chicago Midway Airport to Oakland, California is less than $450.

  • Are there last-minute flights available from Chicago Midway Airport to Oakland, California for under $500?

    There are currently 8+ open flights from Chicago Midway Airport to Oakland, California within the next 7 days for less than $500.

  • 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 $348. Other airlines that can offer you cheap pricing are Southwest, from $391, and Volaris, from $815.

  • What does MDW to OAK mean?

    MDW and OAK are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. MDW to OAK refers to a flight route from Chicago Midway Airport to Oakland Airport.

  • Can I find deals for flights from Midway to Oakland that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Oakland flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Oakland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Oakland flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to Oakland that allow pets onboard?

    Many airlines flying from Midway to Oakland offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Oakland?

    Yes, you can often find last-minute deals on Midway to Oakland flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Oakland, California flight deals updated?

    The Chicago Midway Airport to Oakland, California flight deals you see on this page were last updated on 5/2.

See more FAQs

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Alternative routes for Midway to Oakland
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Search flights from Midway to Oakland by cabin class

Find flights from Midway to Oakland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Midway to Oakland

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 May 3, 2024.
15%of flight departuresEarly morningMidnight to 6 am
19%of flight departuresMorning6 am to noon
52%of flight departuresAfternoonNoon to 6 pm
14%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Midway to Oakland

Explore weekly flight availability from Midway to Oakland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 3, 2024.
Sunday1daily flight
Monday3daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday3daily flights
Friday3daily flights
Saturday3daily flights

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Can Cheapflights find flights from Midway to Oakland with no change fees?

Need flexible booking options for your flight to Oakland from Midway? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Midway to Oakland become cheaper?

Of course! You can now track prices for flights from Midway to Oakland and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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