$119+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MDW
Oct 1 — Oct 81
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
Cheapest flights from Oakland to MidwayExplore 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 September 1, 2026.
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 September 1, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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.
Thu 9/242:30 pm -
1 stop7h 20m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/30. 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.
Tue 9/2211:55 pm -
Nonstop4h 00m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/30![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 10/176:50 pm -
1 stop7h 40m
Wed 10/218:35 pm -
Nonstop4h 45m
Deal found 8/31![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 10/173:40 pm -
1 stop6h 35m
Thu 10/225:25 am -
1 stop8h 10m
Deal found 8/31![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 9/2811:55 pm -
Nonstop4h 00m
Sat 10/37:30 pm -
Nonstop4h 40m
Deal found 8/27![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 9/2611:55 pm -
Nonstop4h 00m
Tue 10/68:35 pm -
Nonstop4h 45m
Deal found 8/31![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/29. 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.
Tue 10/137:15 am -
2 stops7h 30m
Tue 10/201:05 pm -
2 stops7h 50m
Deal found 8/29![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/27. 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.
Thu 9/178:10 pm -
1 stop7h 15m
Mon 9/218:35 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 8/27. 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.
Thu 10/13:20 pm -
2 stops7h 35m
Mon 10/59:30 pm -
Nonstop4h 45m
Deal found 8/27![Southwest logo]()
$293
Best flights from Oakland to MidwayDiscover carefully curated flight deals from Oakland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
Discover carefully curated flight deals from Oakland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sat 9/2611:55 pm -
Nonstop4h 00m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/28![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 9/2611:55 pm -
Nonstop4h 00m
Tue 10/61:05 pm -
2 stops7h 50m
Deal found 8/31![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 8/31. 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.
Mon 9/285:20 am -
2 stops7h 15m
Mon 10/55:25 am -
1 stop8h 10m
Deal found 8/31![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/29. 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.
Thu 10/13:20 pm -
2 stops7h 35m
Tue 10/65:45 pm -
1 stop6h 25m
Deal found 8/29![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/28. 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.
Mon 10/58:10 pm -
2 stops7h 35m
Tue 10/61:05 pm -
2 stops7h 50m
Deal found 8/28![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/27. 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 10/188:55 pm -
1 stop6h 45m
Wed 10/215:45 am -
1 stop6h 40m
Deal found 8/27![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 8/28. 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.
Fri 10/28:40 pm -
1 stop7h 00m
Thu 10/89:30 pm -
Nonstop4h 45m
Deal found 8/28![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 8/27. 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.
Fri 10/28:10 pm -
2 stops7h 35m
Mon 10/55:25 am -
1 stop8h 10m
Deal found 8/27![Southwest logo]()
$345
Last-minute flights from Oakland to MidwayDiscover last-minute flight deals from Oakland to Midway. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Midway. Data last updated September 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/27. 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.
Thu 9/178:10 pm -
1 stop7h 15m
Mon 9/218:35 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 8/28. 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.
Tue 9/2211:55 pm -
Nonstop4h 00m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/28![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 8/31. 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.
Wed 9/238:30 pm -
1 stop7h 15m
Mon 9/286:15 am -
1 stop7h 20m
Deal found 8/31![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 8/27. 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.
Thu 9/242:30 pm -
1 stop7h 20m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 9/2611:55 pm -
Nonstop4h 00m
Tue 10/68:35 pm -
Nonstop4h 45m
Deal found 8/31![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 8/27. 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 9/275:25 am -
Nonstop4h 05m
Wed 9/308:35 pm -
Nonstop4h 35m
Deal found 8/27![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 9/2811:55 pm -
Nonstop4h 00m
Sat 10/37:30 pm -
Nonstop4h 40m
Deal found 8/27![Southwest logo]()
$278
One-way flights from Oakland to MidwaySearch for one-way flight options from Oakland to Midway. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
Search for one-way flight options from Oakland to Midway. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 10/265:50 am -
Nonstop4h 00m
Deal found 8/27![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 9/1. 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.
Mon 9/2811:55 pm -
Nonstop4h 00m
Deal found 9/1![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 8/27. 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.
Tue 10/137:15 am -
2 stops7h 30m
Deal found 8/27![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 8/31. 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.
Wed 9/308:55 am -
1 stop8h 15m
Deal found 8/31![Southwest logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:48 pm -
2 stops26h 59m
Deal found 8/27![Frontier logo]()
$158
This Southwest deal was found by Cheapflights users on 8/27. 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.
Mon 11/2311:50 pm -
Nonstop4h 05m
Deal found 8/27![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 8/31. 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.
Thu 10/16:55 pm -
1 stop7h 35m
Deal found 8/31![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:48 pm -
2 stops26h 59m
Deal found 8/27![Frontier logo]()
$165
This Southwest deal was found by Cheapflights users on 8/30. 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 9/2711:55 pm -
Nonstop4h 00m
Deal found 8/30![Southwest logo]()
$169
Find 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 September 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | July |
Cheapest in | February |
Average price | $386 |
Good round-trip deal | $418 or less |
Good one-way deal | $270 or less |
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 7,457,451 searches. Data last updated September 1, 2026.
Use the filters below to find and compare flights from Oakland to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 9/26
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Tue 9/29
8:35 pm-11:10 pm
Nonstop4h 35m
$257
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 9/26
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Tue 10/6
1:05 pm-6:55 pm
2 stops7h 50m
$272
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 9/28
5:20 am-2:35 pm
2 stops7h 15m
Chicago Midway
Mon 10/5
5:25 am-11:35 am
1 stop8h 10m
$282
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Thu 10/1
3:20 pm-12:55 am
2 stops7h 35m
Chicago Midway
Tue 10/6
5:45 pm-10:10 pm
1 stop6h 25m
$282
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 10/5
8:10 pm-5:45 am
2 stops7h 35m
Chicago Midway
Tue 10/6
1:05 pm-6:55 pm
2 stops7h 50m
$287
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sun 10/18
8:55 pm-5:40 am
1 stop6h 45m
Chicago Midway
Wed 10/21
5:45 am-10:25 am
1 stop6h 40m
$317
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 10/2
8:40 pm-5:40 am
1 stop7h 00m
Chicago Midway
Thu 10/8
9:30 pm-12:15 am
Nonstop4h 45m
$318
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 10/2
8:10 pm-5:45 am
2 stops7h 35m
Chicago Midway
Mon 10/5
5:25 am-11:35 am
1 stop8h 10m
$345
Cheapest one-way
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 10/26
8:40 pm-5:40 am
1 stop7h 00m
$129
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 11/23
3:35 pm-12:10 am
1 stop6h 35m
$129
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Oakland to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Midway in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Oakland, California-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Oakland, California-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
OAK-MDW
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
Prices
Airlines
What is the cheapest month to book a flight from Oakland, California to Chicago Midway Airport?
Currently, February is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $288). Flying from Oakland, California to Chicago Midway Airport in July is currently the most expensive (average of $579). 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 September 1, 2026.
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 evening, which can drop the price by up to 60% versus a flight in the afternoon.
The best insider tips for Oakland to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Oakland to Chicago Midway Airport trip
Our travel experts
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 September 1, 2026.
Peruse reviews from past customers who have flown with Southwest 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.
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
Oakland and Midway flights
Browse other Oakland and Midway flight options. Last updated on September 1, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$311 | Average$472 | FlexibilityNo cancel fee | On-time63% |