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OAK - MDW

$158 Find cheap flights from Oakland to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Midway departing on 5/11. 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 6/1
Sat 6/8

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Chicago, 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 Oakland to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Midway 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
5:00 pm - 8:48 amOAK-MDW
13h 48m2 stops
1:24 pm - 11:55 pmMDW-OAK
12h 31m2 stops
$277Delta
Find Deal
Fri, Jun 7 - Tue, Jun 11
5:50 am - 4:55 pmOAK-MDW
9h 05m2 stops
5:47 pm - 11:51 pmMDW-OAK
8h 04m2 stops
$298Delta
Find Deal
Sun, May 26 - Wed, May 29
10:55 pm - 9:14 amOAK-MDW
8h 19m1 stop
3:45 pm - 9:35 pmMDW-OAK
7h 50m1 stop
$318Delta
Find Deal
Mon, Jul 29 - Thu, Aug 8
10:55 pm - 9:14 amOAK-MDW
8h 19m1 stop
3:45 pm - 9:35 pmMDW-OAK
7h 50m1 stop
$347Delta
Find Deal
Fri, Aug 2 - Thu, Aug 8
5:40 am - 6:40 pmOAK-MDW
11h 00m1 stop
10:15 pm - 3:20 pmMDW-OAK
19h 05m1 stop
$423Southwest
Find Deal
Tue, May 14 - Fri, May 17
8:45 am - 6:10 pmOAK-MDW
7h 25m2 stops
10:15 pm - 6:10 pmMDW-OAK
21h 55m1 stop
$428Southwest
Find Deal
Tue, May 14 - Fri, May 17
1:51 pm - 11:23 amOAK-MDW
19h 32m1 stop
8:50 pm - 11:51 pmMDW-OAK
29h 01m2 stops
$670
Find Deal
Sun, May 19 - Wed, May 22
1:51 pm - 11:23 amOAK-MDW
19h 32m1 stop
10:41 pm - 12:14 pmMDW-OAK
15h 33m1 stop
$678Volaris
Find Deal
Sun, May 19 - Thu, May 23
5:50 am - 9:47 amOAK-MDW
25h 57m2 stops
7:35 pm - 8:50 pmMDW-OAK
27h 15m3 stops
$681
Find Deal
Fri, May 31 - Fri, Jun 7
6:39 pm - 9:47 amOAK-MDW
13h 08m1 stop
8:45 pm - 8:26 pmMDW-OAK
25h 41m2 stops
$700Volaris
Find Deal
Thu, May 16 - Mon, May 20

Flights from Oakland to Midway - Travel Insights & Trends

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Oakland, California to Chicago Midway Airport, 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 Oakland, California to Chicago Midway Airport is November, where tickets cost $163 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $389 and $345 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Oakland, California to Chicago Midway Airport, 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 Oakland, California to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 32 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Oakland to Chicago Midway Airport found on KAYAK was with Delta for $158. Delta proposed a round-trip connection from $277 and Southwest from $423.

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

Each day, there are between 1 and 2 nonstop flights that take off from Oakland, California and land in Chicago Midway Airport, with an average flight time of 4h 07m. The most common departure time is 5:00 am and most flights take off at night. Each week, there are 12 flights. The most frequent day of departure is Friday, when 17% of all weekly flights depart. The fewest flights depart on a Sunday.

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

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.

How long does a flight from Oakland to Chicago Midway Airport take?

The average nonstop flight takes 4h 05m, covering a distance of 1,839 miles.

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

Early birds can take the earliest flight from Oakland, California at 5:05 am and will be landing in Chicago Midway Airport at 11:10 am.

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

If you prefer to fly at night, the latest flight from Oakland, California to Chicago Midway Airport jets off at 6:55 pm and lands at 12:55 am.

Good to know

Low season

April

High season

May

Cheapest flight

$158
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Oakland to Chicago Midway Airport

When to book flights from Oakland to Midway

Are your dates flexible? Find out the best times to travel from Oakland to Midway 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 Oakland to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Oakland, California to Chicago Midway Airport was $158 for a one-way ticket and $277 for a round-trip.

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

    A passport is not required to fly from Oakland to Chicago Midway Airport.

  • Which airports will I be using when flying from Oakland to Chicago Midway Airport?

    Oakland airport is called Oakland and the only airport in Chicago Midway Airport is Chicago Midway.

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

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

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

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

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

    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 Oakland to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Oakland 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 Oakland to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Oakland with another airline. Booking your flights between Oakland and MDW 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 Oakland to Chicago Midway Airport?

    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 Chicago Midway Airport from Oakland 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 Oakland to Chicago Midway Airport?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top airline flying from Oakland to Midway

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Oakland to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.2
FrontierOverall score based on 4108 reviews
5.8Comfort
7.1Crew
4.9Entertainment
6.6Boarding
5.2Food
Airline reviews

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

2.0 MediocreJanay, Apr 2024LAX - PHX
Read more about Frontier reviews

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

Book cheap flights from Oakland to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Oakland to Chicago found on KAYAK in the last 72 hours.
5/11Sat
2 stopsDelta
9h 05mOAK-MDW
$158
8/6Tue
1 stopDelta
8h 27mOAK-MDW
$174
7/20Sat
2 stopsDelta
13h 40mOAK-MDW
$179
8/3Sat
1 stopDelta
8h 19mOAK-MDW
$203
5/20Mon
2 stopsDelta
23h 17mOAK-MDW
$248
5/22Wed
2 stopsDelta
9h 16mOAK-MDW
$264
5/15Wed
2 stops
21h 47mOAK-MDW
$336
5/15Wed
1 stopVolaris
13h 08mOAK-MDW
$353
10/13Sun
1 stopVolaris
13h 08mOAK-MDW
$364
6/30Sun
1 stopVolaris
13h 08mOAK-MDW
$385

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Last minute flights from Oakland to Midway

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 Oakland to Chicago that are departing in the next 10 days.
5/4Sat
multi-stopDelta
8h 28mOAK-MDW
5/7Tue
multi-stopDelta
11h 36mMDW-OAK
$527
5/5Sun
nonstopSouthwest
4h 10mOAK-MDW
5/8Wed
multi-stopSouthwest
6h 35mMDW-OAK
$605
5/5Sun
multi-stopSouthwest
5h 50mOAK-MDW
5/8Wed
multi-stopSouthwest
6h 35mMDW-OAK
$615
5/6Mon
multi-stop
13h 08mOAK-MDW
5/8Wed
multi-stop
22h 37mMDW-OAK
$660
5/6Mon
multi-stop
25h 47mOAK-MDW
5/8Wed
multi-stop
22h 37mMDW-OAK
$695
5/5Sun
multi-stop
13h 08mOAK-MDW
5/7Tue
multi-stop
26h 55mMDW-OAK
$701
5/5Sun
nonstopSouthwest
4h 10mOAK-MDW
5/8Wed
nonstopSouthwest
4h 35mMDW-OAK
$717
5/5Sun
multi-stop
13h 08mOAK-MDW
5/7Tue
multi-stop
26h 55mMDW-OAK
$720
5/6Mon
multi-stopVolaris
13h 08mOAK-MDW
5/8Wed
multi-stopVolaris
25h 36mMDW-OAK
$746
5/5Sun
multi-stopVolaris
13h 08mOAK-MDW
5/7Tue
multi-stopVolaris
15h 33mMDW-OAK
$823

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Oakland - Chicago Midway Airport Flights

Departure:

Oakland (OAK)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Oakland

Cabin classes:

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