How long is the flight from Chicago Midway Airport to Oakland, California?

A quick flight from Chicago Midway Airport to Oakland, California can take about 6h 30m. Southwest provides one of the quickest options available for as low as $297. The distance between Chicago Midway Airport and Oakland, California is about 1839 mi.

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

Cheapflights users have booked flights from Chicago Midway Airport to Oakland, California round-trip from $247. This flight start at 36% lower than the current average price 3 months from now.

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 Thursday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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.

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).

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

Looking at all options, your cheapest flight can be booked for $127. While the most popular route (Chicago Midway - Oakland) can be booked for $200 on average, our data indicates $441 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 Sunday can be a cost-effective option. It’s possible to save up to 59% 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 49 days early can save you up to 121% on average compared to booking a flight this week. If booking 49 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 $370 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 $579 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 July tends to be the cheapest month to fly to Oakland, California from Chicago Midway Airport. Users have commonly found prices around $316 for the month, but tickets can be as low as $172. Due to multiple factors, prepare for potentially higher prices in December.

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 2 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.

$136+ Flights from Chicago Midway Airport to Oakland, CA

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Cheap flight deals from Midway to Oakland

Round-trip from	$297 (Southwest)
One-way from	$136 (Kiwi.com)
Popular in	November
Cheapest in	May
Average price	$348
Good round-trip deal	$464 or less
Good one-way deal	$234 or less

From Chicago Midway to Oakland

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One-way flight from Chicago Midway to Oakland

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Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Price to beat on a round-trip flight from Chicago Midway to Oakland.

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Price to beat on a one-way flight from Chicago Midway to Oakland.

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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 September 15, 2025.

Wed 10/157:10 amMDW - OAK

1 stop7h 40mSouthwest

Wed 10/223:10 pmOAK - MDW

1 stop7h 15mSouthwest

Deal found 9/15

$297

Tue 10/289:20 amMDW - OAK

2 stops7h 55mSouthwest

Tue 11/47:50 amOAK - MDW

1 stop7h 05mSouthwest

Deal found 9/15

$302

Thu 10/2310:35 amMDW - OAK

1 stop7h 10mSouthwest

Mon 10/275:50 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/14

$307

Fri 11/147:45 amMDW - OAK

Nonstop4h 40mSouthwest

Tue 11/187:35 amOAK - MDW

1 stop7h 20mSouthwest

Deal found 9/15

$310

Sat 10/118:25 amMDW - OAK

1 stop7h 55mSouthwest

Tue 10/215:50 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/15

$320

Tue 10/289:20 amMDW - OAK

2 stops8h 51mDelta

Tue 11/45:55 amOAK - MDW

2 stops9h 48mDelta

Deal found 9/15

$322

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 September 15, 2025.

Tue 10/281:15 pmMDW - OAK

1 stop6h 30mSouthwest

Tue 11/47:50 amOAK - MDW

1 stop7h 05mSouthwest

Deal found 9/15

$297

Fri 11/141:14 pmMDW - OAK

2 stops12h 49mDelta

Sat 11/155:45 amOAK - MDW

2 stops10h 23mDelta

Deal found 9/15

$408

Thu 10/2310:35 amMDW - OAK

1 stop7h 10mSouthwest

Mon 10/275:50 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/14

$307

Sat 10/185:15 amMDW - OAK

2 stops8h 50mSouthwest

Sun 10/196:40 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/15

$338

Fri 10/173:30 pmMDW - OAK

1 stop8h 10mSouthwest

Sun 10/196:40 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/13

$361

Thu 12/2512:00 pmMDW - OAK

1 stop7h 15mSouthwest

Mon 12/298:00 pmOAK - MDW

1 stop7h 15mSouthwest

Deal found 9/14

$362

Fri 10/173:30 pmMDW - OAK

1 stop7h 05mSouthwest

Sat 10/259:05 amOAK - MDW

Nonstop4h 10mSouthwest

Deal found 9/15

$389

Thu 10/1610:35 amMDW - OAK

1 stop7h 10mSouthwest

Tue 10/2110:20 amOAK - MDW

1 stop7h 05mSouthwest

Deal found 9/15

$447

Last-minute flights from Midway to Oakland
Discover last-minute flight deals from Midway to Oakland. Data last updated September 15, 2025 and is based on user searches.

Wed 10/85:20 pmMDW - OAK

1 stop6h 25mSouthwest

Mon 10/133:55 pmOAK - MDW

1 stop6h 15mSouthwest

Deal found 9/14

$358

Sat 10/118:25 amMDW - OAK

1 stop7h 55mSouthwest

Tue 10/215:50 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/15

$320

Wed 10/157:10 amMDW - OAK

1 stop7h 40mSouthwest

Wed 10/223:10 pmOAK - MDW

1 stop7h 15mSouthwest

Deal found 9/15

$297

Wed 10/157:10 amMDW - OAK

1 stop7h 40mSouthwest

Sat 10/187:05 pmOAK - MDW

1 stop7h 55mSouthwest

Deal found 9/15

$348

Sat 10/185:15 amMDW - OAK

2 stops8h 50mSouthwest

Sun 10/196:40 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/15

$338

Thu 10/2310:35 amMDW - OAK

1 stop7h 10mSouthwest

Mon 10/275:50 amOAK - MDW

Nonstop4h 05mSouthwest

Deal found 9/14

$307

Tue 10/289:20 amMDW - OAK

2 stops7h 55mSouthwest

Tue 11/47:50 amOAK - MDW

1 stop7h 05mSouthwest

Deal found 9/15

$302

Tue 10/289:20 amMDW - OAK

2 stops8h 51mDelta

Tue 11/45:55 amOAK - MDW

2 stops9h 48mDelta

Deal found 9/15

$322

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 September 15, 2025.

Sun 9/2810:13 amMDW - OAK

2 stops39h 19mMultiple Airlines

Deal found 9/15

$136

Wed 11/54:05 pmMDW - OAK

Nonstop4h 35mSouthwest

Deal found 9/15

$139

Sat 10/189:20 amMDW - OAK

2 stops14h 12mDelta

Deal found 9/14

$144

Thu 10/307:45 amMDW - OAK

Nonstop4h 30mSouthwest

Deal found 9/15

$149

Wed 10/299:20 amMDW - OAK

2 stops7h 55mSouthwest

Deal found 9/15

$154

Mon 12/229:50 amMDW - OAK

1 stop6h 55mSouthwest

Deal found 9/15

$159

Wed 10/224:15 pmMDW - OAK

Nonstop4h 35mSouthwest

Deal found 9/14

$162

Sat 1/247:40 pmMDW - OAK

Nonstop4h 55mSouthwest

Deal found 9/15

$164

Fri 10/314:10 pmMDW - OAK

1 stop6h 30mSouthwest

Deal found 9/15

$169

Sat 12/2010:50 pmMDW - OAK

Nonstop4h 40mSouthwest

Deal found 9/15

$170

Fri 10/244:30 pmMDW - OAK

1 stop7h 20mSouthwest

Deal found 9/15

$172

Fri 12/52:35 pmMDW - OAK

1 stop7h 15mSouthwest

Deal found 9/15

$174

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Oakland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 10/28

1:15 pm-5:45 pm

1 stop6h 30m

Oakland

Tue 11/4

7:50 am-4:55 pm

1 stop7h 05m

$297

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 10/23

10:35 am-3:45 pm

1 stop7h 10m

Oakland

Mon 10/27

5:50 am-11:55 am

Nonstop4h 05m

$307

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 10/18

5:15 am-12:05 pm

2 stops8h 50m

Oakland

Sun 10/19

6:40 am-12:45 pm

Nonstop4h 05m

$338

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 10/17

3:30 pm-9:40 pm

1 stop8h 10m

Oakland

Sun 10/19

6:40 am-12:45 pm

Nonstop4h 05m

$361

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 12/25

12:00 pm-5:15 pm

1 stop7h 15m

Oakland

Mon 12/29

8:00 pm-5:15 am

1 stop7h 15m

$362

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 10/17

3:30 pm-8:35 pm

1 stop7h 05m

Oakland

Sat 10/25

9:05 am-3:15 pm

Nonstop4h 10m

$389

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 11/14

1:14 pm-12:03 am

2 stops12h 49m

Oakland

Sat 11/15

5:45 am-6:08 pm

2 stops10h 23m

$408

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 10/16

10:35 am-3:45 pm

1 stop7h 10m

Oakland

Tue 10/21

10:20 am-7:25 pm

1 stop7h 05m

$447

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Sat 10/18

9:20 am-9:32 pm

2 stops14h 12m

$144

ChicagoOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 12/10

1:14 pm-12:08 am

2 stops12h 54m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 18 results

The best insider tips for Chicago Midway Airport to Oakland flights

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.

OAK

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

Our travel experts

Ramsey Qubein

Expert on MDW

Bill Fink

Expert on OAK

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?

It’s typically best to fly out from Chicago Midway Airport to Oakland, California at noon. Doing so could potentially save you 39% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Oakland

Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

8.0

Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Southwest

8.0

Very good

4,242 reviews

Southwest

8.0

Very good

4,242 reviews

Reviews

1 / 20

8.0

Excellent

Walter,Aug 2025

OAK - SAN

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 2 inbound flights from Chicago Midway per day.
How long is the flight from Chicago Midway Airport to Oakland, California?
A quick flight from Chicago Midway Airport to Oakland, California can take about 6h 30m. Southwest provides one of the quickest options available for as low as $297. The distance between Chicago Midway Airport and Oakland, California is about 1839 mi.
What is the cheapest airline to fly from Chicago Midway Airport to Oakland, California round-trip?
Cheapflights users have booked flights from Chicago Midway Airport to Oakland, California round-trip from $247. This flight start at 36% 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 $127. While the most popular route (Chicago Midway - Oakland) can be booked for $200 on average, our data indicates $441 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

Top airline flying from Midway to Oakland

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$247	Average$372	FlexibilityNo cancel fee	On-time63%

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$136+ 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 9/28. 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

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Cheap flight deals from Midway to Oakland

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Good one-way deal

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 September 15, 2025.

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 September 15, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Oakland that are best for you.

The best insider tips for Chicago Midway Airport to Oakland flights

Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Oakland trip

Airports

MDW

OAK

Our travel experts

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.

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?

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

Reviews of airlines servicing Oakland

Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Oakland by reading reviews from past customers. 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?

How long is the flight from Chicago Midway Airport to Oakland, California?

What is the cheapest airline to fly 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 September 15, 2025.