HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$90+ Cheap flights from Oakland, CA (OAK) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Oakland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 3, 2025.

Round-trip from

$207
(Southwest)

One-way from

$90
(Southwest)

Popular in

January

Cheapest in

October

Average price

$389

Good round-trip deal

$417 or less

Good one-way deal

$228 or less
From Oakland to Chicago Midway
Search Deals
One-way flight from Oakland to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Oakland to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Oakland to Chicago Midway.
Search Deals

Find flight deals from Oakland to Midway

Cheapest flights from Oakland to Midway
Explore the most affordable flight options available from Oakland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/105:50 amOAK - MDW
Nonstop4h 05mSouthwest
Sat 8/163:25 pmMDW - OAK
Nonstop4h 30mSouthwest
Deal found 7/3$207
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:05 pmOAK - MDW
2 stops14h 35mDelta
Sat 10/41:43 pmMDW - OAK
2 stops11h 05mDelta
Deal found 7/3$267

Cheapflights Fare Finder

Customize your flight search to find flights from Oakland to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
Use the filters below to find and compare flights from Oakland to Chicago Midway Airport that are best for you.

Fly from

Oakland

Fly to

Midway

Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 8/10

5:50 am-11:55 am

Nonstop4h 05m

Chicago Midway

Sat 8/16

3:25 pm-5:55 pm

Nonstop4h 30m

$207

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 9/30

5:05 pm-9:40 am

2 stops14h 35m

Chicago Midway

Sat 10/4

1:43 pm-10:48 pm

2 stops11h 05m

$267

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sun 8/31

8:15 am-2:20 pm

Nonstop4h 05m

$90

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 9/26

6:00 am-8:52 pm

1 stop12h 52m

$97

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 9/8

4:58 pm-9:34 am

2 stops14h 36m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Best time to book a flight from Oakland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Chicago Midway Airport

What is the cheapest month to book a flight from Oakland, California to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $160). Flying from Oakland, California to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAK to MDW?

Find hourly flight availability from Oakland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

When flying from Oakland, California to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 14% versus a flight in the afternoon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 3, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from Oakland to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oakland to Chicago Midway?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Chicago Midway from Oakland. Booking flights from Oakland (OAK) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 1 airline.

  • What are the cheapest airlines flying from Oakland, California to Chicago Midway Airport round-trip?

    Southwest, at $207, was found to be the cheapest airline from Oakland, California to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. Southwest is 50% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from Oakland, California to Chicago Midway Airport?

    Looking for the cheapest flight from Oakland, California to Chicago Midway Airport? While on average our users pay $386, our data indicates the cheapest price to be $98. The most popular route (Oakland - Chicago Midway), is priced around $207.

  • Can I find deals for flights from Oakland to Midway that include hotel bookings?

    Yes. In addition to deals on Oakland to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Midway.

  • Can I find deals for business class flights from Oakland to Midway?

    Yes. Cheapflights offers flight deals from Oakland to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $160). Flying from Oakland, California to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Oakland?

Book flights to Oakland if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Burbank to O'Hare Intl flights
Los Angeles to Midway flights
San Diego to O'Hare Intl flights
San Francisco to Midway flights
San Jose to O'Hare Intl flights
Oakland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
San Diego to Midway flights
San Jose to Midway flights
Santa Ana to Midway flights
Sacramento to Midway flights
Ontario to Midway flights
Long Beach to O'Hare Intl flights
Las Vegas to Midway flights
Fresno to O'Hare Intl flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Reno to O'Hare Intl flights
Fresno to Midway flights
Palm Springs to Midway flights
San Luis Obispo to O'Hare Intl flights
Medford to O'Hare Intl flights
Long Beach to Midway flights
Monterey to O'Hare Intl flights
Santa Barbara to O'Hare Intl flights
Bakersfield to O'Hare Intl flights
Reno to Midway flights
Medford to Midway flights
Santa Rosa to O'Hare Intl flights
Los Angeles to Rockford flights
Sacramento to Rockford flights
Oakland to Rockford flights
Las Vegas to Rockford flights
Redding to O'Hare Intl flights
Arcata to O'Hare Intl flights
San Diego to Rockford flights
Yuma to O'Hare Intl flights
San Jose to Rockford flights
Tijuana to O'Hare Intl flights
Bakersfield to Midway flights
Tijuana to Midway flights
San Francisco to Rockford flights
Ontario to Rockford flights

Top airline flying from Oakland to Midway

Discover the top airline that operate flights from Oakland to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$271Average$415FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.