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Cheap flights from Oakland (OAK) to Midway (MDW) from $123

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 9/23. 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. 11 — jun. 181
From?
To?
mar. 6/11
mar. 6/18
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 junio 6, 2024.

Popular in

July

Cheapest in

September

Average price

$344

Round-trip from

$223
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 3,050,429 searches. Prices were last updated on junio 6, 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.
mar. 7/95:00 pmOAK - MDW
2 stops13h 53mDelta
vie. 7/262:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$371
lun. 7/85:00 pmOAK - MDW
2 stops23h 39mDelta
vie. 7/262:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$396
lun. 7/2910:52 pmOAK - MDW
2 stops13h 17mDelta
vie. 8/22:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$398
mié. 7/106:00 amOAK - MDW
2 stops10h 39mDelta
mié. 7/171:25 pmMDW - OAK
2 stops12h 26mDelta
Deal found 6/5$428
jue. 7/115:00 pmOAK - MDW
2 stops23h 39mDelta
vie. 7/262:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$440
mar. 7/95:00 pmOAK - MDW
2 stops13h 53mDelta
mar. 7/239:18 amMDW - OAK
2 stops16h 33mDelta
Deal found 6/5$445
mié. 7/105:00 pmOAK - MDW
2 stops13h 53mDelta
vie. 7/262:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$455
lun. 7/85:00 pmOAK - MDW
2 stops23h 39mDelta
mar. 7/239:18 amMDW - OAK
2 stops16h 33mDelta
Deal found 6/5$470
mar. 7/95:00 pmOAK - MDW
2 stops13h 53mDelta
jue. 7/259:18 amMDW - OAK
2 stops16h 33mDelta
Deal found 6/5$492

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 3,050,429 searches. Data last updated junio 6, 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.
sáb. 9/2810:30 pmOAK - MDW
2 stops11h 58mDelta
lun. 9/3012:47 pmMDW - OAK
1 stop10h 33mDelta
Deal found 6/5$332
vie. 8/166:00 amOAK - MDW
2 stops10h 38mDelta
mar. 8/201:24 pmMDW - OAK
2 stops12h 27mDelta
Deal found 6/5$337
lun. 10/1410:45 pmOAK - MDW
1 stop8h 32mDelta
vie. 10/181:05 pmMDW - OAK
1 stop10h 30mDelta
Deal found 6/4$338
mar. 7/95:00 pmOAK - MDW
2 stops13h 53mDelta
vie. 7/262:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$371
vie. 9/2010:30 pmOAK - MDW
1 stop9h 18mDelta
sáb. 9/282:10 pmMDW - OAK
1 stop9h 10mDelta
Deal found 6/5$378
sáb. 10/126:00 amOAK - MDW
2 stops10h 05mDelta
sáb. 10/192:05 pmMDW - OAK
1 stop9h 30mDelta
Deal found 6/6$383
lun. 7/85:00 pmOAK - MDW
2 stops23h 39mDelta
vie. 7/262:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$396
lun. 7/2910:52 pmOAK - MDW
2 stops13h 17mDelta
vie. 8/22:49 pmMDW - OAK
2 stops11h 02mDelta
Deal found 6/5$398
vie. 10/1110:45 pmOAK - MDW
1 stop8h 32mDelta
vie. 10/181:05 pmMDW - OAK
1 stop10h 30mDelta
Deal found 6/4$408

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 3,050,429 searches. Data last updated junio 6, 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.
mié. 6/125:50 amOAK - MDW
2 stops9h 14mDelta
mié. 6/191:24 pmMDW - OAK
2 stops12h 31mDelta
Deal found 6/5$622
mar. 6/1110:55 pmOAK - MDW
2 stops11h 48mDelta
mié. 6/269:34 amMDW - OAK
2 stops14h 11mDelta
Deal found 6/6$728
mié. 6/125:50 amOAK - MDW
2 stops9h 14mDelta
mié. 6/193:45 pmMDW - OAK
1 stop8h 00mDelta
Deal found 6/5$737
mié. 6/125:15 amOAK - MDW
3 stops36h 18mMultiple Airlines
mié. 6/1910:41 pmMDW - OAK
2 stops22h 39mMultiple Airlines
Deal found 6/5$741
sáb. 6/1510:55 pmOAK - MDW
1 stop8h 56mDelta
jue. 6/201:24 pmMDW - OAK
2 stops10h 21mDelta
Deal found 6/5$781
mar. 6/1110:55 pmOAK - MDW
1 stop8h 56mDelta
mié. 6/269:34 amMDW - OAK
2 stops14h 11mDelta
Deal found 6/6$782
sáb. 6/155:50 amOAK - MDW
2 stops10h 40mDelta
jue. 6/201:24 pmMDW - OAK
2 stops10h 21mDelta
Deal found 6/5$786
mié. 6/125:15 amOAK - MDW
3 stops36h 18mMultiple Airlines
mié. 6/1910:41 pmMDW - OAK
3 stops26h 22mMultiple Airlines
Deal found 6/5$795
sáb. 6/156:39 pmOAK - MDW
1 stop13h 08mFrontier
vie. 6/215:55 amMDW - OAK
2 stops17h 35mFrontier
Deal found 6/5$810

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 3,050,429 searches. Data last updated junio 6, 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.
lun. 9/2310:30 pmOAK - MDW
2 stops12h 57mDelta
Deal found 6/5$123
lun. 9/2310:30 pmOAK - MDW
1 stop9h 18mDelta
Deal found 6/5$169
sáb. 7/205:00 pmOAK - MDW
2 stops13h 38mDelta
Deal found 6/5$184
lun. 7/295:00 pmOAK - MDW
2 stops23h 39mDelta
Deal found 6/5$188
jue. 7/41:00 pmOAK - MDW
2 stops19h 04mMultiple Airlines
Deal found 6/5$193
vie. 8/2310:52 pmOAK - MDW
1 stop8h 46mDelta
Deal found 6/6$209
mar. 8/276:00 amOAK - MDW
2 stops10h 38mDelta
Deal found 6/5$214
lun. 6/245:00 pmOAK - MDW
2 stops23h 36mDelta
Deal found 6/5$223
jue. 7/410:55 pmOAK - MDW
1 stop8h 56mDelta
Deal found 6/4$228

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 3,050,429 searches. Data last updated junio 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$332 - $751

Route

Depart

Return

Price

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

sáb. 9/28

2 stops11h 58m

Chicago Midway

lun. 9/30

1 stop10h 33m

$332

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

vie. 8/16

2 stops10h 38m

Chicago Midway

mar. 8/20

2 stops12h 27m

$337

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

lun. 10/14

1 stop8h 32m

Chicago Midway

vie. 10/18

1 stop10h 30m

$338

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

mar. 7/9

2 stops13h 53m

Chicago Midway

vie. 7/26

2 stops11h 02m

$371

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

vie. 9/20

1 stop9h 18m

Chicago Midway

sáb. 9/28

1 stop9h 10m

$378

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

sáb. 10/12

2 stops10h 05m

Chicago Midway

sáb. 10/19

1 stop9h 30m

$383

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

mié. 6/19

3 stops35h 35m

Chicago Midway

mar. 6/25

3 stops28h 04m

$643

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

vie. 8/30

1 stop13h 08m

Chicago Midway

lun. 9/2

2 stops17h 25m

$689

OaklandChicago Midway

OAK - MDW

OAKMDW

Oakland

vie. 8/30

1 stop13h 08m

Chicago Midway

lun. 9/2

1 stop19h 18m

$751

Flights are sorted by cheapest first

Deals found on 6/5

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 2, 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 junio 6, 2024.
Read reviews from past customers who have flown Delta, Frontier and Volaris 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.
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Delta
8.0
Very good
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Volaris
6.6
Okay
1,462 reviews
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Frontier
6.2
Okay
3,985 reviews
Delta
8.0
Very good
10,368 reviews

Entertainment

8.0

Overall

8.0

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.4

Reviews

1 / 10

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

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 $400 on Cheapflights?

    Yes, there are multiple flights from Oakland, California to Chicago Midway Airport for under $400. The cheapest flight booked recently is on Delta for just $332, but on average you can expect to pay $413.

  • Are there last-minute flights available from Oakland, California to Chicago Midway Airport for under $700?

    There are currently 20+ open flights from Oakland, California to Chicago Midway Airport within the next 7 days for less than $700.

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

    Delta, at $332, was found to be the cheapest airline from Oakland, California to Chicago Midway Airport.. Delta is 7% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 6/6.

  • 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 3,050,429 searches. Data last updated junio 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$167FlexibilityNo cancel feeOn-time62%
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Hartford to Orlando flights
Los Angeles to Paris flights
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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 junio 6, 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 junio 6, 2024.
Sunday4daily flights
Monday8daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday8daily flights
Friday8daily flights
Saturday4daily flights

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