OAK - MDW

$99 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 9/20. 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

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
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Flights 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

Thu, Jul 31 - Tue, Aug 12
Southwest Logo
6:00 am - 2:40 pmOAK-MDW
6h 40m1 stop
Southwest Logo
3:10 pm - 5:40 pmMDW-OAK
4h 30mnonstop
$253Southwest
Find Deal
Thu, Jul 31 - Tue, Aug 12
Southwest Logo
9:15 pm - 5:00 amOAK-MDW
5h 45m1 stop
Southwest Logo
1:35 pm - 7:40 pmMDW-OAK
8h 05m1 stop
$254Southwest
Find Deal
Fri, Jul 25 - Tue, Jul 29
Southwest Logo
6:00 am - 2:40 pmOAK-MDW
6h 40m1 stop
Southwest Logo
6:50 pm - 11:15 pmMDW-OAK
6h 25m1 stop
$267Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
7:15 am - 4:25 pmOAK-MDW
7h 10m1 stop
Southwest Logo
7:40 am - 12:20 pmMDW-OAK
6h 40m1 stop
$273Southwest
Find Deal
Mon, Sep 22 - Sat, Sep 27
Delta Logo
5:05 pm - 9:51 amOAK-MDW
14h 46m2 stops
Delta Logo
1:00 pm - 10:53 pmMDW-OAK
11h 53m2 stops
$277Delta
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Wed, Aug 13 - Tue, Aug 19
Southwest Logo
1:10 pm - 9:50 pmOAK-MDW
6h 40m1 stop
Southwest Logo
6:10 am - 10:25 amMDW-OAK
6h 15m1 stop
$279Southwest
Find Deal
Mon, Jul 28 - Thu, Jul 31
Southwest Logo
11:35 am - 7:10 pmOAK-MDW
5h 35m1 stop
Southwest Logo
5:50 am - 10:10 amMDW-OAK
6h 20m1 stop
$282Southwest
Find Deal
Wed, Sep 3 - Tue, Sep 16
Delta Logo
4:58 pm - 9:16 amOAK-MDW
14h 18m2 stops
Delta Logo
6:00 am - 4:31 pmMDW-OAK
12h 31m2 stops
$293Delta
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Tue, Sep 30 - Sat, Oct 4
Delta Logo
5:55 am - 6:36 pmOAK-MDW
10h 41m2 stops
Delta Logo
1:00 pm - 10:53 pmMDW-OAK
11h 53m2 stops
$332Delta
Find Deal
Thu, Jun 26 - Mon, Jul 7
Logo
10:31 am - 2:56 pmOAK-MDW
26h 25m2 stops
Logo
12:35 pm - 7:33 pmMDW-OAK
32h 58m2 stops
$371
Find Deal
Expert advice

Expert advice for your flight from Oakland to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
OAK

OAK's compact size makes it easy to navigate, with short distances to gates and efficient parking options.

Read more about OAKby Gabriel Leigh
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes, avoiding traffic delays.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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 Leigh

Gabriel Leigh

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
Useful Info

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 Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday 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 Sundays 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 October, where tickets cost $308 (return) on average. On the other hand, the most expensive months are January and November, where the average cost of round-trip tickets is $571 and $503 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.

No, with an average price for the route of $432, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJanuary
High seasonJune
Cheapest flight$99
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 4% 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 $99 for a one-way ticket and $253 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?

    Alaska Airlines, American Airlines, JetBlue, Hawaiian Airlines, and Delta 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 $229 or less one-way and $407 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

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 4278 reviews
8.6Crew
7.6Entertainment
8.2Boarding
7.1Food
8.0Comfort
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

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

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

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

Information on your arrival and departure airports

Oakland (OAK)
Midway (MDW)

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