MDW - OAK

$107 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 4/29. 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

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$237
Southwest
Wed 4/15Tue 4/21
MDW - OAK • Non-stop
Cheapest one-way
$107
Typical prices: $193-$309
Southwest
Wed 4/29
MDW - OAK • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's user-friendly terminal eases pre-flight stress.
Use BART from Oakland for a quick Bay crossing.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $237 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 4h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Southwest
Most punctual • 73% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Las Vegas (LAS)
Cheapest • Avg $241 (round-trip)
Denver (DEN)
Shortest trip • 6h 00m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Oakland!
Flight Deals
Booking Insights
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

Wed, Apr 15 - Tue, Apr 21
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
$237Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
$243Southwest
Tue, Apr 14 - Wed, Apr 15
Southwest Logo
4:30 pm - 8:45 pm
MDW
-
OAK
6h 15m
1 stop
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
$247Southwest
Mon, Apr 20 - Tue, Apr 21
Southwest Logo
9:50 pm - 12:25 am
MDW
-
OAK
4h 35mnonstop
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
$251Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
Southwest Logo
5:45 am - 3:05 pm
OAK
-
MDW
7h 20m
2 stops
$252Southwest
Tue, Apr 14 - Wed, Apr 15
Southwest Logo
12:35 pm - 6:50 pm
MDW
-
OAK
8h 15m
1 stop
Southwest Logo
6:00 am - 2:00 pm
OAK
-
MDW
6h 00m
1 stop
$257Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
Southwest Logo
5:45 am - 3:05 pm
OAK
-
MDW
7h 20m
2 stops
$258Southwest
Sat, Apr 18 - Tue, May 5
Southwest Logo
3:15 pm - 9:00 pm
MDW
-
OAK
7h 45m
1 stop
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
$261Southwest
Tue, Apr 14 - Wed, Apr 15
Southwest Logo
4:30 pm - 8:45 pm
MDW
-
OAK
6h 15m
1 stop
Southwest Logo
5:45 am - 3:05 pm
OAK
-
MDW
7h 20m
2 stops
$262Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
9:50 pm - 12:25 am
MDW
-
OAK
4h 35mnonstop
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
$265Southwest
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 Tuesday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Monday, and avoid Saturdays for better deals.

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 $421, 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 seasonSeptember
Cheapest flight$107
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly with an average 11% increase in price.
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 $107 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?

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

  • 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 $126 or less one-way and $365 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 4324 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The charges were ridiculous for an hour flight and the turbulence was very scary.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

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)