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 6/3. 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

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 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.

Recent round-trip flight deals from Oakland to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Oakland to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
9:15 pm - 5:00 amOAK-MDW
5h 45m1 stop
Southwest Logo
7:50 am - 12:05 pmMDW-OAK
6h 15m1 stop
$227Southwest
Find Deal
Mon, Jun 30 - Sat, Jul 12
Southwest Logo
8:00 pm - 5:20 amOAK-MDW
7h 20m1 stop
Southwest Logo
6:45 pm - 11:15 pmMDW-OAK
6h 30m1 stop
$247Southwest
Find Deal
Thu, May 29 - Tue, Jun 3
Delta Logo
6:00 am - 5:45 pmOAK-MDW
9h 45m2 stops
Delta Logo
9:21 am - 4:16 pmMDW-OAK
8h 55m2 stops
$267Delta
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Tue, Jun 3 - Wed, Jun 11
Southwest Logo
5:05 am - 11:15 amOAK-MDW
4h 10mnonstop
Southwest Logo
5:20 am - 12:10 pmMDW-OAK
8h 50m2 stops
$272Southwest
Find Deal
Mon, May 26 - Sat, May 31
Southwest Logo
8:55 pm - 5:15 amOAK-MDW
6h 20m1 stop
Southwest Logo
8:00 pm - 12:05 amMDW-OAK
6h 05m1 stop
$277Southwest
Find Deal
Mon, Jun 2 - Fri, Jun 6
Southwest Logo
10:30 am - 9:20 pmOAK-MDW
8h 50m1 stop
Southwest Logo
8:40 am - 2:10 pmMDW-OAK
7h 30m1 stop
$285Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
Southwest Logo
10:30 am - 9:20 pmOAK-MDW
8h 50m1 stop
Southwest Logo
4:00 pm - 9:40 pmMDW-OAK
7h 40m2 stops
$290Southwest
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Sat, Aug 30 - Tue, Sep 2
Delta Logo
6:00 am - 5:12 pmOAK-MDW
9h 12m2 stops
Delta Logo
6:00 am - 4:16 pmMDW-OAK
12h 16m2 stops
$318Delta
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Sat, Jun 14 - Sat, Jun 21
Delta Logo
6:00 am - 5:39 pmOAK-MDW
9h 39m2 stops
Delta Logo
9:19 am - 4:14 pmMDW-OAK
8h 55m2 stops
$353Delta
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Wed, Jul 16 - Fri, Jul 18
Logo
5:30 am - 9:44 amOAK-MDW
26h 14m2 stops
Logo
8:09 pm - 4:26 pmMDW-OAK
22h 17m2 stops
$574
Find Deal
Thu, Jun 26 - Sun, Jun 29
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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 Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Oakland to Chicago Midway Airport. For your return ticket, we recommend flying on a Thursday 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 September, where the average cost of round-trip tickets is $571 and $490 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 $258, prices are generally cheapest when you fly direct.

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Good to know

Low seasonAugust
High seasonSeptember
Cheapest flight$99
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 17% 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 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 $227 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?

    American Airlines, JetBlue, Alaska Airlines, 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 $208 or less one-way and $387 or less round-trip.

Prefer to fly direct from Oakland to Chicago Midway Airport?

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
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 4294 reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

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.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

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

Information on your arrival and departure airports

Midway (MDW)
Oakland (OAK)

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