$146+ Cheap flights from Midway (MDW) to Oakland, CA (OAK)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OAK
Oct 25 — Nov 11
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Oakland 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 Midway to Oakland
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Cheapest flights from Midway to OaklandExplore the most affordable flight options available from Midway to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
Explore the most affordable flight options available from Midway to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
This Southwest deal was found by Cheapflights users on 9/23. 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 10/159:30 pm -
Nonstop4h 45m
Sat 10/2411:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/21. 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 10/199:30 pm -
Nonstop4h 45m
Wed 10/2111:55 pm -
Nonstop4h 00m
Deal found 9/21![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/21. 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 11/55:20 am -
2 stops8h 15m
Mon 11/911:50 pm -
Nonstop4h 05m
Deal found 9/21![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 9/23. 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 10/169:30 pm -
Nonstop4h 45m
Sat 10/2411:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 9/23. 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 10/218:35 pm -
Nonstop4h 45m
Mon 10/268:00 am -
2 stops7h 25m
Deal found 9/23![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/24. 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 12/18:45 pm -
Nonstop4h 50m
Mon 12/77:45 am -
1 stop7h 00m
Deal found 9/24![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 9/23. 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 10/306:15 pm -
1 stop6h 25m
Tue 11/36:30 am -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 9/22. 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 10/136:05 am -
1 stop6h 30m
Thu 10/226:55 pm -
1 stop7h 35m
Deal found 9/22![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/23. 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 10/169:30 pm -
Nonstop4h 45m
Mon 10/268:15 pm -
1 stop7h 30m
Deal found 9/23![Southwest logo]()
$360
Best flights from Midway to OaklandDiscover carefully curated flight deals from Midway to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from Midway to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
This Southwest deal was found by Cheapflights users on 9/24. 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 12/18:45 pm -
Nonstop4h 50m
Mon 12/76:30 am -
Nonstop4h 00m
Deal found 9/24![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/24. 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 10/159:30 pm -
Nonstop4h 45m
Sat 10/245:30 am -
2 stops7h 50m
Deal found 9/24![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 9/23. 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 10/148:35 pm -
Nonstop4h 45m
Fri 10/2311:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 9/21. 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 11/59:55 pm -
Nonstop4h 45m
Sun 11/85:35 am -
Nonstop4h 00m
Deal found 9/21![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/21. 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 11/65:20 pm -
2 stops7h 20m
Sun 11/811:50 pm -
Nonstop4h 05m
Deal found 9/21![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 9/20. 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 11/239:55 pm -
Nonstop4h 45m
Mon 11/3011:50 pm -
Nonstop4h 05m
Deal found 9/20![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 9/21. 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 11/1910:10 am -
2 stops8h 10m
Mon 11/3011:50 pm -
Nonstop4h 05m
Deal found 9/21![Southwest logo]()
$442
This Southwest deal was found by Cheapflights users on 9/22. 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 10/267:15 pm -
1 stop7h 25m
Tue 10/278:05 pm -
1 stop7h 40m
Deal found 9/22![Southwest logo]()
$457
Last-minute flights from Midway to OaklandDiscover last-minute flight deals from Midway to Oakland. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Oakland. Data last updated September 25, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/22. 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 10/136:05 am -
1 stop6h 30m
Thu 10/226:55 pm -
1 stop7h 35m
Deal found 9/22![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/23. 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 10/159:30 pm -
Nonstop4h 45m
Sat 10/2411:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/21. 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 10/159:30 pm -
Nonstop4h 45m
Wed 10/216:35 am -
2 stops7h 30m
Deal found 9/21![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 9/23. 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 10/169:30 pm -
Nonstop4h 45m
Mon 10/2611:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 9/21. 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 10/199:30 pm -
Nonstop4h 45m
Wed 10/2111:55 pm -
Nonstop4h 00m
Deal found 9/21![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/23. 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 10/218:35 pm -
Nonstop4h 45m
Wed 10/287:15 am -
2 stops7h 30m
Deal found 9/23![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/23. 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 10/216:05 am -
1 stop6h 30m
Mon 10/268:10 pm -
2 stops7h 35m
Deal found 9/23![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 9/23. 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 10/306:15 pm -
1 stop6h 25m
Tue 11/36:30 am -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$356
One-way flights from Midway to OaklandSearch for one-way flight options from Midway to Oakland. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from Midway to Oakland. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 11/176:16 am -
2 stops31h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/203:30 pm -
2 stops22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Mon 10/261:12 pm -
2 stops24h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Mon 11/212:20 pm -
2 stops25h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/213:30 pm -
2 stops26h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 9/23. 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 10/199:30 pm -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 9/22. 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 12/1010:00 am -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 9/24. 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 10/239:30 pm -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$182
Find flight deals from Midway to Oakland
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Oakland (OAK). 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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (Southwest) |
One-way from | $146 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $397 |
Good round-trip deal | $345 or less |
Good one-way deal | $181 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Oakland 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 25, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Oakland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sat 11/21
9:30 pm-12:15 am
Nonstop4h 45m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$169
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 3/23
2:05 pm-6:55 pm
1 stop6h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$193
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Mon 12/21
9:25 pm-12:15 am
Nonstop4h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$202
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 12/22
5:10 am-10:55 am
1 stop7h 45m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$212
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Mon 10/26
9:30 pm-12:15 am
Nonstop4h 45m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$217
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sun 11/22
5:10 am-10:25 am
1 stop7h 15m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$229
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Fri 3/19
3:45 pm-8:35 pm
1 stop6h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$232
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 12/1
3:45 pm-9:40 pm
1 stop7h 55m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$249
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sun 3/21
5:00 am-9:35 am
1 stop6h 35m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$254
Quickest round-trip
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Fri 11/20
10:00 am-12:40 pm
Nonstop4h 40m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$258
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Midway to Oakland
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 Midway to Oakland in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Oakland, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Oakland, California 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 Chicago Midway Airport-Oakland, California 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 Midway to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Midway with our price prediction graph.
MDW-OAK
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 Chicago Midway Airport to Oakland
Prices
Delays
What is the cheapest month to book a flight from Chicago Midway Airport to Oakland, California?
Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $256). Flying from Chicago Midway Airport to Oakland, California in November is currently the most expensive (average of $612). 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 MDW to OAK?
Find hourly flight availability from Midway to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 2026.
It’s typically best to fly out from Chicago Midway Airport to Oakland, California in the afternoon. Doing so could potentially save you 49% on the flight price compared to flying in the morning, which is usually more expensive.
How often are flights from Chicago to Oakland delayed?
About 32% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 135 minutes.
What is the most punctual flight time for Chicago to Oakland flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Oakland flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 32% of flights being delayed.
The best insider tips for Chicago Midway Airport to Oakland 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 Chicago Midway Airport to Oakland trip
Our travel experts
Reviews of airlines servicing Oakland
Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated September 25, 2026.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Oakland
Explore flights to Oakland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Midway and Oakland flights
Browse other Midway and Oakland flight options. Last updated on September 25, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Oakland
Discover the top airline that operate flights from Midway to Oakland. 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$274 | Average$397 | FlexibilityNo cancel fee | On-time63% |