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MDW - OAK

$169 Find cheap flights from Chicago Midway Airport to Oakland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Oakland departing on 6/13. 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.
1 adult
0 bags
Sat 6/15
Sat 6/22

Search hundreds of travel sites at once for deals on flights to Oakland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Oakland, as well as popular online travel agencies
In the last 7 days travelers have searched 42,211,976 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Oakland (MDW-OAK)

 
These are the cheapest deals for flights from Midway to Oakland currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Oakland

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Oakland.

Recent one-way flight deals from Midway to Oakland

Only flying one-way? Below are some of the best one-way flight deals from Midway to Oakland found on KAYAK recently.

Recent last minute flight deals from Midway to Oakland

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Oakland.

Recent direct flight deals from Midway to Oakland

The latest deals for direct flights from Midway to Oakland so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Oakland

Find recent round-trip train or bus tickets from Midway to Oakland.

All round-trip flight deals to Oakland

The cheapest plane tickets to Oakland found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
2:05 pm - 9:35 pmMDW-OAK
9h 30m1 stop
10:45 pm - 9:17 amOAK-MDW
8h 32m1 stop
$236Delta
Find Deal
Sat, Oct 26 - Tue, Oct 29
2:24 pm - 11:51 pmMDW-OAK
11h 27m2 stops
10:45 pm - 12:31 pmOAK-MDW
11h 46m2 stops
$272Delta
Find Deal
Fri, Jul 19 - Mon, Aug 19
3:47 pm - 9:31 pmMDW-OAK
7h 44m1 stop
10:45 pm - 12:31 pmOAK-MDW
11h 46m2 stops
$292Delta
Find Deal
Fri, Jul 19 - Mon, Aug 19
1:05 pm - 9:35 pmMDW-OAK
10h 30m1 stop
10:45 pm - 9:17 amOAK-MDW
8h 32m1 stop
$313Delta
Find Deal
Fri, Sep 13 - Mon, Sep 16
3:47 pm - 9:31 pmMDW-OAK
7h 44m1 stop
10:45 pm - 9:12 amOAK-MDW
8h 27m1 stop
$338Delta
Find Deal
Fri, Jul 19 - Mon, Aug 19
3:45 pm - 9:35 pmMDW-OAK
7h 50m1 stop
10:45 pm - 9:17 amOAK-MDW
8h 32m1 stop
$368Delta
Find Deal
Thu, Sep 19 - Fri, Sep 27
6:05 am - 9:30 pmMDW-OAK
17h 25m2 stops
6:39 pm - 9:52 amOAK-MDW
13h 13m1 stop
$597Frontier
Find Deal
Wed, Aug 21 - Tue, Aug 27
6:35 am - 9:30 pmMDW-OAK
16h 55m2 stops
6:39 pm - 9:52 amOAK-MDW
13h 13m1 stop
$679Frontier
Find Deal
Thu, Jun 6 - Tue, Jun 11
5:05 am - 9:30 pmMDW-OAK
18h 25m2 stops
6:39 pm - 5:10 pmOAK-MDW
20h 31m2 stops
$701Frontier
Find Deal
Sun, Jun 23 - Mon, Jun 24
8:50 pm - 8:26 pmMDW-OAK
25h 36m2 stops
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
$1,012Volaris
Find Deal
Wed, Jun 26 - Thu, Jul 11
3:45 pm - 9:45 pmMDW-OAK
8h 00m1 stop
$169Delta
Find Deal
Thu, Jun 13
9:28 am - 9:45 pmMDW-OAK
14h 17m2 stops
$174Delta
Find Deal
Sat, Jun 8
3:45 pm - 9:45 pmMDW-OAK
8h 00m1 stop
$199Delta
Find Deal
Sat, Jun 8
2:24 pm - 11:55 pmMDW-OAK
11h 31m2 stops
$203Delta
Find Deal
Tue, Jun 18
8:50 pm - 3:59 pmMDW-OAK
21h 09m1 stop
$398Frontier
Find Deal
Wed, Nov 6
9:30 pm - 1:21 pmMDW-OAK
17h 51m1 stop
$412Volaris
Find Deal
Tue, Sep 24
8:45 pm - 11:43 pmMDW-OAK
28h 58m3 stops
$426
Find Deal
Sun, Jun 2
6:05 am - 8:30 pmMDW-OAK
16h 25m2 stops
$434Frontier
Find Deal
Wed, Nov 6
8:45 pm - 12:11 pmMDW-OAK
17h 26m2 stops
$443
Find Deal
Sun, Jun 2
10:41 pm - 12:14 pmMDW-OAK
15h 33m1 stop
$533Volaris
Find Deal
Sun, May 26
9:32 am - 4:07 pmMDW-OAK
8h 35m2 stops
5:50 am - 5:06 pmOAK-MDW
9h 16m2 stops
$928Delta
Find Deal
Sat, May 18 - Sun, May 19
8:45 pm - 12:11 pmMDW-OAK
17h 26m2 stops
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
$932
Find Deal
Sun, May 19 - Wed, May 22
8:45 pm - 12:17 pmMDW-OAK
17h 32m2 stops
6:39 pm - 9:52 amOAK-MDW
13h 13m1 stop
$941
Find Deal
Fri, May 17 - Tue, May 21
6:00 am - 9:30 pmMDW-OAK
17h 30m2 stops
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
$944Frontier
Find Deal
Tue, May 21 - Thu, May 23
8:45 pm - 12:11 pmMDW-OAK
17h 26m2 stops
10:00 am - 9:47 amOAK-MDW
21h 47m2 stops
$948
Find Deal
Sun, May 19 - Wed, May 22
10:41 pm - 12:14 pmMDW-OAK
15h 33m1 stop
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
$954Volaris
Find Deal
Sun, May 19 - Wed, May 22
10:41 pm - 3:59 pmMDW-OAK
19h 18m1 stop
5:39 pm - 11:23 amOAK-MDW
15h 44m1 stop
$955Volaris
Find Deal
Fri, May 17 - Tue, May 21
6:49 pm - 10:24 amMDW-OAK
41h 35m3 stops
10:00 am - 9:47 amOAK-MDW
21h 47m2 stops
$1,026
Find Deal
Sun, May 19 - Wed, May 22
9:46 am - 11:51 pmMDW-OAK
16h 05m2 stops
5:50 am - 6:07 pmOAK-MDW
10h 17m2 stops
$1,117Delta
Find Deal
Tue, May 21 - Wed, May 22
9:46 am - 11:51 pmMDW-OAK
16h 05m2 stops
5:50 am - 6:07 pmOAK-MDW
10h 17m2 stops
$1,270Delta
Find Deal
Tue, May 21 - Wed, May 22

Flights from Midway to Oakland - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Oakland to help you find the cheapest flights, the best time to fly and much more.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Oakland, California, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Oakland, California is February, where tickets cost $154 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $439 and $365 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Oakland, California, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Oakland, California, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 21 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Oakland?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Delta ($169) and Frontier ($398). The cheapest round-trip tickets were found on Delta ($236) and Frontier ($597).

How many flights are there between Chicago Midway Airport and Oakland, California per day?

Each day, there are between 3 and 5 nonstop flights that take off from Chicago Midway Airport and land in Oakland, California, with an average flight time of 4h 30m. The most common departure time is 5:00 am and most flights take off in the afternoon. Each week, there are 32 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

Which cabin class options are there for flights between Chicago Midway Airport and Oakland, California?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Chicago Midway Airport to Oakland?

Early birds can take the earliest flight from Chicago Midway Airport at 5:35 am and will be landing in Oakland, California at 8:00 am.

What’s the latest departure time from Chicago Midway Airport to Oakland?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Oakland, California jets off at 10:40 pm and lands at 1:10 am.

Good to know

Cheapest flight

$169
Flight from Chicago Midway Airport to Oakland

When to book flights from Midway to Oakland

Are your dates flexible? Find out the best times to travel from Midway to Oakland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Oakland flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Oakland, California was $169 for a one-way ticket and $236 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Oakland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Oakland?

    We unfortunately don’t have that data for this specific route.

  • On which days can I fly direct from Chicago Midway Airport to Oakland?

    There are nonstop flights from Chicago Midway Airport to Oakland on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Oakland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Oakland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Oakland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Oakland from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Oakland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Oakland with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and OAK can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Oakland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Oakland from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to Oakland?

Find which airlines fly direct from Midway to Oakland, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Oakland

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Oakland to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Book cheap flights from Chicago to Oakland

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Oakland found on KAYAK in the last 72 hours.
6/13Thu
1 stopDelta
8h 00mMDW-OAK
$169
6/8Sat
2 stopsDelta
14h 17mMDW-OAK
$174
6/8Sat
1 stopDelta
8h 00mMDW-OAK
$199
6/18Tue
2 stopsDelta
11h 31mMDW-OAK
$203
11/6Wed
1 stopFrontier
21h 09mMDW-OAK
$398
9/24Tue
1 stopVolaris
17h 51mMDW-OAK
$412
6/2Sun
3 stops
28h 58mMDW-OAK
$426
11/6Wed
2 stopsFrontier
16h 25mMDW-OAK
$434
6/2Sun
2 stops
17h 26mMDW-OAK
$443
5/26Sun
1 stopVolaris
15h 33mMDW-OAK
$533

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Last minute flights from Midway to Oakland

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Oakland that are departing in the next 10 days.
5/18Sat
multi-stopDelta
8h 35mMDW-OAK
5/19Sun
multi-stopDelta
9h 16mOAK-MDW
$928
5/19Sun
multi-stop
17h 26mMDW-OAK
5/22Wed
multi-stop
13h 08mOAK-MDW
$932
5/17Fri
multi-stop
17h 32mMDW-OAK
5/21Tue
multi-stop
13h 13mOAK-MDW
$941
5/21Tue
multi-stopFrontier
17h 30mMDW-OAK
5/23Thu
multi-stopFrontier
13h 08mOAK-MDW
$944
5/19Sun
multi-stop
17h 26mMDW-OAK
5/22Wed
multi-stop
21h 47mOAK-MDW
$948
5/19Sun
multi-stopVolaris
15h 33mMDW-OAK
5/22Wed
multi-stopVolaris
13h 08mOAK-MDW
$954
5/17Fri
multi-stopVolaris
19h 18mMDW-OAK
5/21Tue
multi-stopVolaris
15h 44mOAK-MDW
$955
5/19Sun
multi-stop
41h 35mMDW-OAK
5/22Wed
multi-stop
21h 47mOAK-MDW
$1,026
5/21Tue
multi-stopDelta
16h 05mMDW-OAK
5/22Wed
multi-stopDelta
10h 17mOAK-MDW
$1,117
5/21Tue
multi-stopDelta
16h 05mMDW-OAK
5/22Wed
multi-stopDelta
10h 17mOAK-MDW
$1,270

Search by stops

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Search by price

Chicago Midway Airport - Oakland Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

Oakland (OAK)United States

Return flight deals:

Oakland - Chicago Midway Airport

Cabin classes:

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