$114 Cheap Flights from Oakland (OAK) to Chicago (MDW)

View $114 flight on Wed, Dec 3, 2025Opens in a new window

Popular airlines from Oakland Intl. Airport (OAK) to Chicago Midway Airport (MDW)

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Cheap Flights from Oakland to Chicago (OAK-MDW)

Prices were available within the past 7 days and start at $114 for one-way flights and $252 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Dec 7 - Wed, Dec 10
OAK
Oakland
MDW
Chicago
$252 Roundtrip, found 6 days ago
$252
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Dec 7 from Oakland to Chicago, returning Wed, Dec 10, priced at $252 found 6 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
OAK
Oakland
MDW
Chicago
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Oakland to Chicago, returning Sat, Dec 6, priced at $258 found 1 day ago
Southwest Airlines
Sat, Dec 6 - Wed, Dec 10
OAK
Oakland
MDW
Chicago
$260 Roundtrip, found 6 days ago
$260
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Oakland to Chicago, returning Wed, Dec 10, priced at $260 found 6 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
OAK
Oakland
MDW
Chicago
$264 Roundtrip, found 4 days ago
$264
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Oakland to Chicago, returning Sat, Dec 6, priced at $264 found 4 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
OAK
Oakland
MDW
Chicago
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Oakland to Chicago, returning Sat, Dec 6, priced at $268 found 1 day ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
OAK
Oakland
MDW
Chicago
$273 Roundtrip, found 5 days ago
$273
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Oakland to Chicago, returning Wed, Nov 19, priced at $273 found 5 days ago
Southwest Airlines
Thu, Nov 27 - Sat, Dec 6
OAK
Oakland
MDW
Chicago
$276 Roundtrip, found 5 days ago
$276
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Nov 27 from Oakland to Chicago, returning Sat, Dec 6, priced at $276 found 5 days ago
Southwest Airlines
Tue, Nov 18 - Wed, Nov 19
OAK
Oakland
MDW
Chicago
$278 Roundtrip, found 5 days ago
$278
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Oakland to Chicago, returning Wed, Nov 19, priced at $278 found 5 days ago
Southwest Airlines
Thu, Jan 29 - Mon, Feb 2
OAK
Oakland
MDW
Chicago
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Jan 29 from Oakland to Chicago, returning Mon, Feb 2, priced at $279 found 3 days ago
Southwest Airlines
Wed, Dec 3 - Sat, Dec 6
OAK
Oakland
MDW
Chicago
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Oakland to Chicago, returning Sat, Dec 6, priced at $280 found 2 days ago

Find the cheapest month to fly from Oakland (OAK) to Chicago (MDW)

September is typically the cheapest month to fly

From $161 - $617 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $498
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $498
Flights from Oakland (OAK) to Chicago (MDW)
Origin airport
Oakland Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$252
Distance
1840 mi
Average flight time
6 hours 55 mins

Oakland to Chicago Flights

The cheapest times to fly from Oakland to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Oakland to Chicago are during the month of December. You can find some of the cheapest flights from Oakland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Oakland to Chicago

Sunday is one of the best days to book for cheap flights from Oakland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Oakland to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Oakland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $114 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Oakland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Oakland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $114 or cheap return flight from $252 from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
December is the least expensive month to fly from OAK to MDW. Traveling during an off-peak travel window is often the key to finding better deals on flights.
Which airlines fly direct from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
You can fly directly from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest OAK to MDW flight.
How many flights per day from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
On average, there's only 1 nonstop flight operating from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW) each day. If this doesn't work with your itinerary, check out flights with a layover. Simply filter your search results on Expedia to include one stop or more to find the next best option.
What are the most popular departure times for flights from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
More passengers fly between OAK and MDW at 11 AM than at any other point in the day. Looking to skip the crowds? Travel outside of rush hours and you're likely to save on your fare as well.
What day of the week has the most flights from OAK to MDW?
If you depart on a Friday, you'll get the biggest range of choices for flights from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW).
What is the earliest flight from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
Oakland Intl. Airport (OAK)'s first flight to Midway Intl. Airport (MDW) leaves at approximately 7:40AM UTC-8. With a flight time of 4h 5m, you'll touch down at around 1:45PM UTC-6.
How long does it take to fly from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
The average flight duration from OAK to MDW is 4 hours and 5 minutes, covering a total distance of 1,850 mi.
What airline has the least delays from OAK to MDW?
Consider booking with United Airlines if you'd like to fly straight from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW) without any delays. This carrier has the best track record for punctuality, with an on-time performance of 100%. Want to be notified if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on time, select a flight that takes off from Oakland Intl. Airport (OAK) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Oakland Intl. Airport (OAK)?
If you're taking a direct flight from Oakland Intl. Airport (OAK) to Chicago, Midway Intl. Airport (MDW) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your trip to book your flight from OAK to MDW often results in higher prices. Although you may find some last-minute discounts, there's no guarantee. Keep your travel plans flexible to boost your chances of landing a bargain.
Is it cheaper to book an OAK to MDW flight and hotel package?
You'll generally save money by booking an OAK to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your ideal accommodations and flights, you can add extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from Oakland Intl. Airport (OAK) to Midway Intl. Airport (MDW)?
Generally, it's possible to reschedule or cancel your OAK to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.