OAK - MDW

$109 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 5/5. 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 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
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
$217
Overall average: $422
Southwest
Wed 3/4Tue 3/10
OAK - MDW • Non-stop
Cheapest one-way
$109
Typical prices: $186-$243
Southwest
Tue 5/5
OAK - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
OAK's compact size ensures quick navigation.
The CTA Orange Line from MDW reaches downtown in 25-30 mins.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $217 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 19% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

Recent round-trip flight deals from Oakland to Midway

Wed, Mar 4 - Tue, Mar 10
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$217Southwest
Wed, Mar 4 - Tue, Mar 10
Southwest Logo
6:55 pm - 4:55 am
OAK
-
MDW
8h 00m
1 stop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$227Southwest
Wed, Mar 4 - Tue, Mar 10
Southwest Logo
6:55 pm - 4:55 am
OAK
-
MDW
8h 00m
1 stop
Southwest Logo
4:00 pm - 9:35 pm
MDW
-
OAK
7h 35m
1 stop
$237Southwest
Tue, Mar 10 - Fri, Mar 13
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
9:30 pm - 12:10 am
MDW
-
OAK
4h 40mnonstop
$250Southwest
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$255Southwest
Tue, Feb 24 - Thu, Feb 26
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:00 am - 10:10 am
MDW
-
OAK
7h 10m
1 stop
$260Southwest
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
2:10 pm - 7:50 pm
MDW
-
OAK
7h 40m
1 stop
$263Southwest
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:10 pm - 10:05 pm
MDW
-
OAK
6h 55m
1 stop
$265Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$267Southwest
Tue, Feb 24 - Thu, Feb 26
Southwest Logo
8:30 pm - 5:05 am
OAK
-
MDW
6h 35m
1 stop
Southwest Logo
6:10 am - 12:05 pm
MDW
-
OAK
7h 55m
1 stop
$270Southwest
Booking Insights

KAYAK's insights & trends for Oakland to Midway flights

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

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

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Oakland to Chicago Midway Airport. For your return ticket, we recommend flying on a Monday and avoiding Tuesdays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland 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 to Chicago Midway Airport is September, where tickets cost $377 (return) on average. On the other hand, the most expensive months are November and July, where the average cost of round-trip tickets is $647 and $558 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $374 on average.

Find deals
Expert advice

Expert advice for your flight from Oakland to Midway

 
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 seasonDecember
Cheapest flight$109
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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 to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Oakland to Chicago Midway Airport was $109 for a one-way ticket and $217 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 airlines offer Wi-Fi service onboard planes from Oakland to Chicago Midway Airport?

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

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

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

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $141 or less one-way and $358 or less round-trip.

Prefer to fly direct from Oakland to Chicago Midway Airport?

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

Direct 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

Direct 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

Reviews of the 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.
8.0
SouthwestOverall score based on 4268 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

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

We got exit row seats both flights. Everything was running on time

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.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

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

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

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

Information on your arrival and departure airports

Oakland (OAK)
Midway (MDW)