MDW - OAK

$100 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 7/4. 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 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
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Midway to Oakland

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Oakland.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
8:35 am - 1:00 pmMDW-OAK
6h 25m1 stop
Southwest Logo
4:25 pm - 12:50 amOAK-MDW
6h 25m1 stop
$247Southwest
Find Deal
Wed, Jun 4 - Tue, Jun 10
Southwest Logo
6:45 pm - 11:15 pmMDW-OAK
6h 30m1 stop
Southwest Logo
6:50 am - 4:55 pmOAK-MDW
8h 05m2 stops
$252Southwest
Find Deal
Tue, Jun 3 - Wed, Jun 11
Southwest Logo
5:35 am - 9:35 amMDW-OAK
6h 00m1 stop
Southwest Logo
2:45 pm - 10:50 pmOAK-MDW
6h 05m1 stop
$263Southwest
Find Deal
Fri, Jul 4 - Fri, Jul 4
Delta Logo
1:55 pm - 11:49 pmMDW-OAK
11h 54m2 stops
Delta Logo
6:00 am - 5:45 pmOAK-MDW
9h 45m2 stops
$267Delta
Find Deal
Fri, May 30 - Mon, Jun 2
Southwest Logo
12:45 pm - 5:55 pmMDW-OAK
7h 10m1 stop
Southwest Logo
7:55 pm - 5:00 amOAK-MDW
7h 05m1 stop
$273Southwest
Find Deal
Thu, Jun 26 - Mon, Jun 30
Southwest Logo
9:05 am - 1:35 pmMDW-OAK
6h 30m1 stop
Southwest Logo
5:50 am - 12:00 pmOAK-MDW
4h 10mnonstop
$277Southwest
Find Deal
Fri, May 30 - Tue, Jun 3
Southwest Logo
8:35 am - 1:00 pmMDW-OAK
6h 25m1 stop
Southwest Logo
6:50 am - 4:55 pmOAK-MDW
8h 05m2 stops
$282Southwest
Find Deal
Wed, Jun 4 - Wed, Jun 11
Southwest Logo
8:05 am - 1:35 pmMDW-OAK
7h 30m1 stop
Southwest Logo
2:55 pm - 11:55 pmOAK-MDW
7h 00m1 stop
$287Southwest
Find Deal
Fri, May 30 - Tue, Jun 3
Southwest Logo
9:10 pm - 11:45 pmMDW-OAK
4h 35mnonstop
Southwest Logo
5:50 am - 12:00 pmOAK-MDW
4h 10mnonstop
$289Southwest
Find Deal
Fri, May 30 - Tue, Jun 3
Delta Logo
1:55 pm - 11:49 pmMDW-OAK
11h 54m2 stops
Delta Logo
6:00 am - 5:40 pmOAK-MDW
9h 40m2 stops
$313Delta
Find Deal
Tue, Jun 3 - Wed, Jun 11
Useful Info

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 Thursday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Sunday, and avoid Mondays 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 November, where tickets cost $286 (return) on average. On the other hand, the most expensive months are July and September, where the average cost of round-trip tickets is $673 and $480 respectively.

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Good to know

Low seasonApril
High seasonNovember
Cheapest flight$100
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 29% 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 3 days, the lowest price for a flight from Chicago Midway Airport to Oakland was $100 for a one-way ticket and $247 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, Alaska Airlines, and Hawaiian Airlines 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 $166 or less one-way and $287 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
See more direct flights

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

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

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

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

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 Midway to Oakland

Information on your arrival and departure airports

Oakland (OAK)
Chicago Midway Airport (MDW)

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