MDW - OAK

$119 Find Cheap Flights from Chicago Midway Airport to Oakland - Compare and Save

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 8/12. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$237
Typical prices: $280-$333
Southwest
Sat 8/29Sat 9/5
MDW - OAK • Non-stop
Cheapest one-way
$119
Typical prices: $250-$368
Southwest
Wed 8/12
MDW - OAK • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 4h 30m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 70% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 40% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Oakland

Sat, Aug 29 - Sat, Sep 5
Southwest Logo
1:55 pm - 4:20 pm
MDW
-
OAK
4h 25mnonstop
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
$237Southwest
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
6:55 am - 12:55 pm
MDW
-
OAK
8h 00m
1 stop
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
$247Southwest
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
1:55 pm - 4:20 pm
MDW
-
OAK
4h 25mnonstop
Southwest Logo
7:50 am - 5:00 pm
OAK
-
MDW
7h 10m
2 stops
$248Southwest
Tue, Aug 18 - Thu, Aug 20
Southwest Logo
8:35 pm - 11:05 pm
MDW
-
OAK
4h 30mnonstop
Southwest Logo
5:20 am - 2:35 pm
OAK
-
MDW
7h 15m
2 stops
$252Southwest
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
5:55 pm - 10:10 pm
MDW
-
OAK
6h 15m
1 stop
Southwest Logo
5:20 am - 1:20 pm
OAK
-
MDW
6h 00m
1 stop
$257Southwest
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
2:05 pm - 6:25 pm
MDW
-
OAK
6h 20m
1 stop
Southwest Logo
7:50 am - 5:00 pm
OAK
-
MDW
7h 10m
2 stops
$258Southwest
Thu, Aug 13 - Thu, Aug 20
Southwest Logo
4:55 pm - 10:45 pm
MDW
-
OAK
7h 50m
1 stop
Southwest Logo
5:20 am - 2:35 pm
OAK
-
MDW
7h 15m
2 stops
$262Southwest
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
2:05 pm - 7:45 pm
MDW
-
OAK
7h 40m
2 stops
Southwest Logo
7:50 am - 5:00 pm
OAK
-
MDW
7h 10m
2 stops
$263Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
8:45 pm - 11:25 pm
MDW
-
OAK
4h 40mnonstop
Southwest Logo
11:50 pm - 5:55 am
OAK
-
MDW
4h 05mnonstop
$269Southwest
Wed, Aug 12 - Tue, Aug 18
Southwest Logo
8:35 pm - 11:05 pm
MDW
-
OAK
4h 30mnonstop
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
$277Southwest
Booking Insights

KAYAK's insights & trends for Midway to Oakland flights

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’s the cheapest day of the week to fly from Chicago Midway Airport to Oakland?

The average price of all round-trip flights from Chicago Midway Airport to Oakland clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Oakland on a Wednesday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

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 round-trip 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 September, where tickets cost $236 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $612 and $531 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Oakland?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $478, prices are generally cheapest when you fly direct.

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Expert advice

Expert advice for your flight from Midway to Oakland

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on OAK

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more

Good to know

Low season

August

Cheapest flight

$119
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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 5 days, the lowest price for a flight from Chicago Midway Airport to Oakland was $119 for a one-way ticket and $237 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 airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Oakland?

    All the following airlines offer inflight Wi-Fi service on the Chicago Midway Airport to Oakland flight route: American Airlines, United Airlines, Air Canada, Alaska Airlines, JetBlue, and Hawaiian Airlines.

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to Oakland flight 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Oakland

  • Looking for a cheap flight? 25% of our users found flights on this route for $267 or less one-way and $485 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Oakland?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Oakland.
Find which airlines fly direct from Chicago Midway Airport to Oakland Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the top airline flying from Midway to Oakland

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Oakland. 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 Midway to Oakland? 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.
8.0
SouthwestOverall score based on 4242 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

Boarding was easy. The seats are small and fairly uncomfortable

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day

no entertainment options available on a 4+ hour flight. packed in like sardines. one bathroom. late flight.

Everything you need to know for your flight from Midway to Oakland

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Oakland (OAK)