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Cheap flights from Oakland (OAK) to Midway (MDW) from $118

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. Click the price to replicate the search for this deal.
OAK — MDW
Jun 15 — Jun 221
From?
To?
Sat 6/15
Sat 6/22
1 adult, Economy
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Cheap flight deals from Oakland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Midway (MDW). 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 June 10, 2024.

Popular in

July

Cheapest in

September

Average price

$344

Round-trip from

$222
High demand for flights, 50% potential price rise
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Best time to find cheap flights, 59% potential price drop
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Average for round-trip flights in June 2024
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From Oakland to Chicago Midway
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What is the cheapest day to fly round-trip from Oakland, California to Chicago Midway Airport?

It’s generally more expensive to depart on a Friday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

To save on the cost of your flight from Oakland, California to Chicago Midway Airport, book at least 47 days before your planned departure. Booking around this time can save you about 40% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $308 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $448.

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

Our data shows that October tends to be the cheapest month to fly to Chicago Midway Airport from Oakland, California. Users have commonly found prices around $320 for the month, but tickets can be as low as $88. Due to multiple factors, prepare for potentially higher prices in March.

What is the cheapest time of day to fly from OAK to MDW?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Chicago Midway Airport as you normally would.

Cheap Oakland to Midway flights in June & July 2024

Find cheap flight options from Oakland to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Prices were last updated on June 10, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
Wed 7/106:15 pmOAK - MDW
Nonstop4h 00mSouthwest
Thu 7/1110:40 pmMDW - OAK
Nonstop4h 30mSouthwest
Deal found 6/10$322
Wed 7/106:20 amOAK - MDW
1 stop11h 15mSouthwest
Thu 7/115:35 amMDW - OAK
Nonstop4h 25mSouthwest
Deal found 6/10$331
Sat 7/136:00 amOAK - MDW
2 stops10h 39mDelta
Wed 7/171:25 pmMDW - OAK
2 stops12h 26mDelta
Deal found 6/9$343
Wed 7/106:20 amOAK - MDW
1 stop9h 50mSouthwest
Thu 7/112:05 pmMDW - OAK
1 stop5h 55mSouthwest
Deal found 6/10$355
Tue 6/185:15 amOAK - MDW
1 stop21h 18mMultiple Airlines
Fri 6/2111:26 amMDW - OAK
2 stops14h 02mMultiple Airlines
Deal found 6/10$363
Wed 6/195:15 amOAK - MDW
3 stops35h 35mMultiple Airlines
Fri 7/1212:08 pmMDW - OAK
2 stops25h 11mMultiple Airlines
Deal found 6/10$464
Wed 6/195:15 amOAK - MDW
3 stops35h 35mMultiple Airlines
Fri 7/1212:08 pmMDW - OAK
3 stops26h 05mMultiple Airlines
Deal found 6/10$486
Thu 7/41:00 pmOAK - MDW
2 stops19h 04mMultiple Airlines
Mon 7/812:08 pmMDW - OAK
2 stops25h 04mMultiple Airlines
Deal found 6/9$490
Thu 7/410:55 pmOAK - MDW
1 stop8h 56mDelta
Mon 7/83:47 pmMDW - OAK
1 stop7h 44mDelta
Deal found 6/9$507

Oakland to Midway 2024 flight deals

Discover exclusive flight deals for travel between Oakland and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,020,828 searches. Data last updated June 10, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 8/1210:52 pmOAK - MDW
2 stops12h 51mDelta
Thu 8/153:47 pmMDW - OAK
1 stop7h 54mDelta
Deal found 6/9$241
Fri 9/2010:30 pmOAK - MDW
1 stop9h 18mDelta
Sat 9/282:10 pmMDW - OAK
1 stop9h 10mDelta
Deal found 6/10$307
Wed 7/106:15 pmOAK - MDW
Nonstop4h 00mSouthwest
Thu 7/1110:40 pmMDW - OAK
Nonstop4h 30mSouthwest
Deal found 6/10$322
Wed 7/106:20 amOAK - MDW
1 stop11h 15mSouthwest
Thu 7/115:35 amMDW - OAK
Nonstop4h 25mSouthwest
Deal found 6/10$331
Mon 8/1210:52 pmOAK - MDW
2 stops11h 50mDelta
Thu 8/151:24 pmMDW - OAK
2 stops12h 27mDelta
Deal found 6/9$337
Sat 7/136:00 amOAK - MDW
2 stops10h 39mDelta
Wed 7/171:25 pmMDW - OAK
2 stops12h 26mDelta
Deal found 6/9$343
Wed 9/183:10 pmOAK - MDW
3 stops25h 42mMultiple Airlines
Sun 9/227:42 pmMDW - OAK
2 stops19h 30mMultiple Airlines
Deal found 6/9$352
Wed 7/106:20 amOAK - MDW
1 stop9h 50mSouthwest
Thu 7/112:05 pmMDW - OAK
1 stop5h 55mSouthwest
Deal found 6/10$355
Thu 8/86:20 pmOAK - MDW
2 stops23h 20mMultiple Airlines
Mon 8/1212:08 pmMDW - OAK
2 stops24h 15mMultiple Airlines
Deal found 6/9$357

Oakland to Midway flights leaving soon

Find last-minute flight options from Oakland to Midway 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 3,020,828 searches. Data last updated June 10, 2024.
Users seeking a last-minute flight from Oakland to Chicago should consider booking one of these fares. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Tue 6/185:15 amOAK - MDW
1 stop21h 18mMultiple Airlines
Fri 6/2111:26 amMDW - OAK
2 stops14h 02mMultiple Airlines
Deal found 6/10$363
Wed 6/195:15 amOAK - MDW
3 stops35h 35mMultiple Airlines
Fri 7/1212:08 pmMDW - OAK
2 stops25h 11mMultiple Airlines
Deal found 6/10$464
Wed 6/195:15 amOAK - MDW
3 stops35h 35mMultiple Airlines
Fri 7/1212:08 pmMDW - OAK
3 stops26h 05mMultiple Airlines
Deal found 6/10$486
Sun 6/1611:59 pmOAK - MDW
2 stops18h 19mMultiple Airlines
Sun 6/235:54 pmMDW - OAK
3 stops40h 37mMultiple Airlines
Deal found 6/9$647
Thu 6/205:00 pmOAK - MDW
2 stops13h 48mDelta
Tue 6/252:24 pmMDW - OAK
2 stops11h 31mDelta
Deal found 6/9$688
Wed 6/196:39 pmOAK - MDW
1 stop13h 08mMultiple Airlines
Fri 7/1212:08 pmMDW - OAK
2 stops25h 11mMultiple Airlines
Deal found 6/10$733
Sat 6/1510:55 pmOAK - MDW
1 stop8h 56mDelta
Wed 6/193:45 pmMDW - OAK
1 stop8h 00mDelta
Deal found 6/10$734
Sun 6/165:15 amOAK - MDW
3 stops37h 03mMultiple Airlines
Sun 6/235:54 pmMDW - OAK
3 stops40h 37mMultiple Airlines
Deal found 6/9$756
Tue 6/1810:55 pmOAK - MDW
2 stops11h 48mDelta
Tue 7/231:25 pmMDW - OAK
2 stops10h 06mDelta
Deal found 6/9$782

One-way flights to Midway from Oakland

Search for one-way flight options from Oakland to Midway. 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 3,020,828 searches. Data last updated June 10, 2024.
Users traveling one-way from Oakland to Chicago can select one of these great deals. For those needing a return trip from Oakland, there is a search form available above.
Thu 7/410:55 pmOAK - MDW
1 stop8h 56mDelta
Deal found 6/10$118
Sat 7/276:00 amOAK - MDW
2 stops10h 39mDelta
Deal found 6/10$149
Fri 9/2010:30 pmOAK - MDW
1 stop9h 18mDelta
Deal found 6/9$169
Thu 7/111:15 pmOAK - MDW
2 stops18h 49mMultiple Airlines
Deal found 6/10$184
Sat 7/205:00 pmOAK - MDW
2 stops13h 38mDelta
Deal found 6/9$188
Thu 7/1111:59 amOAK - MDW
3 stops30h 18mMultiple Airlines
Deal found 6/10$205
Fri 7/1910:52 pmOAK - MDW
1 stop8h 34mDelta
Deal found 6/10$209
Fri 9/135:30 amOAK - MDW
2 stops11h 56mMultiple Airlines
Deal found 6/9$213
Thu 8/295:30 amOAK - MDW
3 stops29h 30mMultiple Airlines
Deal found 6/9$326

Find flights from Oakland to Midway within your budget

Customize your flight search to find flights from Oakland to Midway 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 3,020,828 searches. Data last updated June 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$241 - $689

Route

Depart

Return

Price

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Mon 8/12

2 stops12h 51m

Chicago Midway

Thu 8/15

1 stop7h 54m

$241

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Fri 9/20

1 stop9h 18m

Chicago Midway

Sat 9/28

1 stop9h 10m

$307

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Wed 7/10

Nonstop4h 00m

Chicago Midway

Thu 7/11

Nonstop4h 30m

$322

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Wed 7/10

1 stop11h 15m

Chicago Midway

Thu 7/11

Nonstop4h 25m

$331

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Mon 8/12

2 stops11h 50m

Chicago Midway

Thu 8/15

2 stops12h 27m

$337

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Wed 9/18

3 stops25h 42m

Chicago Midway

Sun 9/22

2 stops19h 30m

$352

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Wed 7/10

1 stop9h 50m

Chicago Midway

Thu 7/11

1 stop5h 55m

$355

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Thu 8/8

2 stops23h 20m

Chicago Midway

Mon 8/12

2 stops24h 15m

$357

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

Fri 8/30

1 stop13h 08m

Chicago Midway

Mon 9/2

2 stops17h 25m

$689

Flights are sorted by cheapest first

Deals found on 6/9

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

Use this chart to determine the cheapest time to fly round-trip from Oakland to Midway. Price data was last updated on June 9, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Oakland, California to Chicago Midway Airport flight should consider departing on Saturday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Oakland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oakland 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.

Temperature and rainfall in Midway by month

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

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 10, 2024.
Read reviews from past customers who have flown Frontier, Delta and Southwest from Oakland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,889 reviews

Boarding

8.3

Entertainment

7.8

Crew

8.7

Comfort

8.1

Food

7.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.2
Very good
5,889 reviews
Southwest
8.2
Very good
5,889 reviews

Boarding

8.3

Entertainment

7.8

Crew

8.7

Comfort

8.1

Food

7.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
10,295 reviews
Southwest
8.2
Very good
5,889 reviews

Boarding

8.3

Entertainment

7.8

Crew

8.7

Comfort

8.1

Food

7.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Volaris
6.6
Okay
1,455 reviews
Southwest
8.2
Very good
5,889 reviews

Boarding

8.3

Entertainment

7.8

Crew

8.7

Comfort

8.1

Food

7.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Frontier
6.2
Okay
3,969 reviews
Southwest
8.2
Very good
5,889 reviews

Boarding

8.3

Entertainment

7.8

Crew

8.7

Comfort

8.1

Food

7.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Related info for your journey

Find useful and relevant information for your journey from Oakland to Midway. 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 from for flights from Oakland to Chicago Midway?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Chicago Midway from Oakland. Booking flights from Oakland (OAK) to Chicago Midway should be relatively easy as there are 6 daily outbound flights to Chicago Midway from 1 airline.

  • Can I find flights from Oakland, California to Chicago Midway Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from Oakland, California to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Delta for just $241, but on average you can expect to pay $376.

  • Are there nonstop flights from Oakland, California to Chicago Midway Airport for under $400 on Cheapflights?

    Cheapflights has at least 1 direct flight from Oakland, California to Chicago Midway Airport under $400. A good price for a nonstop flight from Oakland, California to Chicago Midway Airport is less than $322.

  • Are there last-minute flights available from Oakland, California to Chicago Midway Airport for under $400?

    There are currently 20+ open flights from Oakland, California to Chicago Midway Airport within the next 7 days for less than $400.

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

    Delta, at $241, was found to be the cheapest airline from Oakland, California to Chicago Midway Airport. An alternate airline flying to your destination would be Southwest. Delta is 33% cheaper than the average price of flights available within the next 90 days to this destination.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $118. Users have also found prices from $429 and $442 on Volaris and Frontier, respectively.

  • What does OAK to MDW mean?

    OAK and MDW 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. OAK to MDW refers to a flight route from Oakland Airport to Chicago Midway Airport.

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

    The amount of baggage you can bring on your Oakland to Midway 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 Oakland to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Oakland to Midway 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 Oakland to Midway that include hotel bookings?

    Yes. In addition to deals on Oakland to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Midway.

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

    Yes. Cheapflights offers flight deals from Oakland to Midway 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 Oakland to Midway that allow pets onboard?

    Many airlines flying from Oakland to Midway 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 Oakland to Midway?

    Yes, you can often find last-minute deals on Oakland to Midway 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 Oakland, California to Chicago Midway Airport flight deals updated?

    The Oakland, California to Chicago Midway Airport flight deals you see on this page were last updated on 6/10.

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

    Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $141). Flying from Oakland, California to Chicago Midway Airport in July is currently the most expensive (average of $249). 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 Oakland to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Top airline flying from Oakland to Midway

Discover the top airline that operate flights from Oakland to Midway. 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 3,020,828 searches. Data last updated June 10, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$167FlexibilityNo cancel feeOn-time62%
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Nashville to Denver flights
Hartford to Orlando flights
Los Angeles to Paris flights
New York to Dubai flights
Boston to Dublin flights
New York to Lisbon flights
Oakland, California to Mendoza flights

Search flights from Oakland to Midway by cabin class

Find flights from Oakland to Midway, 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 Oakland to Midway

Find hourly flight availability from Oakland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 10, 2024.
46%of flight departuresEarly morningMidnight to 6 am
18%of flight departuresMorning6 am to noon
36%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Oakland to Midway

Explore weekly flight availability from Oakland to Midway. 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 June 10, 2024.
Sunday4daily flights
Monday8daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday8daily flights
Friday8daily flights
Saturday4daily flights

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