Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights

MDW - OAK

$172 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 10/6. 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
Thu 7/11
Thu 7/18

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 44,212,782 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Oakland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:47 pm - 9:41 pmMDW-OAK
7h 54m1 stop
6:00 am - 6:38 pmOAK-MDW
10h 38m2 stops
$302Delta
Find Deal
Thu, Aug 15 - Mon, Aug 19
12:47 pm - 9:20 pmMDW-OAK
10h 33m1 stop
10:30 pm - 1:27 pmOAK-MDW
12h 57m2 stops
$332Delta
Find Deal
Fri, Sep 20 - Mon, Sep 23
9:29 am - 9:44 pmMDW-OAK
14h 15m2 stops
6:00 am - 6:39 pmOAK-MDW
10h 39m2 stops
$333Delta
Find Deal
Thu, Jul 4 - Tue, Jul 9
3:45 pm - 9:44 pmMDW-OAK
7h 59m1 stop
6:00 am - 6:39 pmOAK-MDW
10h 39m2 stops
$363Delta
Find Deal
Thu, Jul 4 - Tue, Jul 9
3:45 pm - 9:44 pmMDW-OAK
7h 59m1 stop
10:55 pm - 9:51 amOAK-MDW
8h 56m1 stop
$373Delta
Find Deal
Mon, Jul 1 - Thu, Jul 4
9:29 am - 9:44 pmMDW-OAK
14h 15m2 stops
10:55 pm - 9:51 amOAK-MDW
8h 56m1 stop
$378Delta
Find Deal
Mon, Jul 1 - Thu, Jul 4
6:00 am - 9:30 pmMDW-OAK
17h 30m2 stops
11:30 pm - 12:51 pmOAK-MDW
11h 21m1 stop
$614Frontier
Find Deal
Wed, Oct 2 - Sun, Oct 6
12:03 pm - 11:12 amMDW-OAK
25h 09m2 stops
5:39 pm - 9:37 pmOAK-MDW
25h 58m3 stops
$696
Find Deal
Mon, Jun 24 - Tue, Jul 2
5:55 am - 9:30 pmMDW-OAK
17h 35m2 stops
11:59 pm - 7:28 pmOAK-MDW
17h 29m2 stops
$874Frontier
Find Deal
Wed, Jun 26 - Wed, Jun 26
5:55 am - 9:30 pmMDW-OAK
17h 35m2 stops
11:59 pm - 5:10 pmOAK-MDW
15h 11m2 stops
$906Frontier
Find Deal
Mon, Jun 24 - Mon, Jun 24

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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Oakland, 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 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 $356 respectively.

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 ($184) and Frontier ($457). The cheapest round-trip tickets were found on Delta ($302) and Frontier ($614).

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

Each day, there are between 2 and 6 nonstop flights that take off from Chicago Midway Airport and land in Oakland, with an average flight time of 4h 28m. The most common departure time is 5:00 am and most flights take off in the afternoon. Each week, there are 29 flights. The most frequent day of departure is Friday, when 21% 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?

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 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 jets off at 10:40 pm and lands at 1:10 am.

Good to know

Cheapest flight

$172
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?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Oakland was $172 for a one-way ticket and $302 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.
10/6Sun
2 stops
19h 19mMDW-OAK
$172
8/2Fri
2 stopsDelta
11h 02mMDW-OAK
$184
8/3Sat
2 stopsDelta
13h 42mMDW-OAK
$198
10/6Sun
3 stops
28h 03mMDW-OAK
$207
9/30Mon
1 stopDelta
7h 32mMDW-OAK
$209
8/27Tue
2 stopsDelta
8h 34mMDW-OAK
$214
6/17Mon
3 stops
26h 17mMDW-OAK
$265
9/19Thu
2 stopsFrontier
17h 30mMDW-OAK
$457
7/14Sun
2 stopsVolaris
25h 41mMDW-OAK
$678
7/6Sat
1 stopVolaris
15h 33mMDW-OAK
$771

Search by stops

Search by airline

Search by price

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.
6/15Sat
multi-stopDelta
8h 00mMDW-OAK
6/24Mon
multi-stopDelta
11h 48mOAK-MDW
$663
6/15Sat
multi-stopDelta
8h 40mMDW-OAK
6/24Mon
multi-stopDelta
11h 48mOAK-MDW
$706
6/15Sat
multi-stopDelta
8h 00mMDW-OAK
6/24Mon
multi-stopDelta
8h 56mOAK-MDW
$829
6/13Thu
multi-stopDelta
8h 00mMDW-OAK
6/16Sun
multi-stopDelta
13h 56mOAK-MDW
$873
6/13Thu
multi-stopDelta
13h 10mMDW-OAK
6/16Sun
multi-stopDelta
13h 56mOAK-MDW
$878
6/13Thu
multi-stopDelta
8h 00mMDW-OAK
6/16Sun
multi-stopDelta
13h 56mOAK-MDW
$893
6/13Thu
multi-stopDelta
14h 11mMDW-OAK
6/16Sun
multi-stopDelta
13h 56mOAK-MDW
$898
6/12Wed
multi-stopDelta
10h 21mMDW-OAK
6/18Tue
multi-stopDelta
8h 56mOAK-MDW
$913
6/12Wed
multi-stopDelta
10h 21mMDW-OAK
6/18Tue
multi-stopDelta
11h 48mOAK-MDW
$979
6/12Wed
multi-stopDelta
8h 00mMDW-OAK
6/18Tue
multi-stopDelta
8h 56mOAK-MDW
$1,067

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Oakland Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Oakland (OAK)United States

Return flight deals:

Oakland - Chicago Midway Airport

Cabin classes:

Browse origins:

Browse destinations: