$389+ Cheap flights from Oakland, CA to Madison (OAK - MSN)
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MSN
Aug 6 — Aug 131
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oakland to Madison 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 Madison
Cheapest
Best
Last-minute
One-way
Cheapest flights from Oakland to MadisonExplore the most affordable flight options available from Oakland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 7, 2026.
Explore the most affordable flight options available from Oakland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 7, 2026.
This Delta deal was found by Cheapflights users on 7/2. 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 8/255:00 pm
OAK
- MSN
2 stops16h 26m
Delta
Sat 11/2111:00 am
MSN
- OAK
2 stops14h 56m
Delta
Deal found 7/2![Delta logo]()
$583
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/65:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Tue 8/116:05 am
MSN
- OAK
2 stops7h 47m
Delta
Deal found 7/5![Delta logo]()
$587
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/135:00 pm
OAK
- MSN
2 stops13h 16m
Delta
Mon 8/176:16 pm
MSN
- OAK
2 stops7h 40m
Delta
Deal found 7/5![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 7/6. 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.
Mon 8/2412:33 pm
OAK
- MSN
2 stops20h 53m
Delta
Sat 11/216:15 am
MSN
- OAK
2 stops19h 41m
Delta
Deal found 7/6![Delta logo]()
$607
This Delta deal was found by Cheapflights users on 7/5. 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.
Fri 8/75:00 pm
OAK
- MSN
2 stops16h 26m
Delta
Tue 8/116:16 pm
MSN
- OAK
2 stops7h 40m
Delta
Deal found 7/5![Delta logo]()
$626
This Delta deal was found by Cheapflights users on 7/5. 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 9/2212:39 pm
OAK
- MSN
2 stops22h 05m
Delta
Wed 9/302:47 pm
MSN
- OAK
2 stops11h 12m
Delta
Deal found 7/5![Delta logo]()
$632
This Delta deal was found by Cheapflights users on 7/6. 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.
Wed 8/512:33 pm
OAK
- MSN
2 stops8h 27m
Delta
Wed 8/126:05 am
MSN
- OAK
2 stops7h 47m
Delta
Deal found 7/6![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 7/5. 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.
Mon 9/215:00 pm
OAK
- MSN
2 stops21h 23m
Delta
Tue 9/299:02 am
MSN
- OAK
2 stops9h 18m
Delta
Deal found 7/5![Delta logo]()
$652
This Delta deal was found by Cheapflights users on 7/5. 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.
Sat 9/1912:39 pm
OAK
- MSN
2 stops26h 38m
Delta
Tue 9/292:47 pm
MSN
- OAK
2 stops11h 12m
Delta
Deal found 7/5![Delta logo]()
$667
This Delta deal was found by Cheapflights users on 7/5. 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.
Sun 9/205:00 pm
OAK
- MSN
2 stops21h 23m
Delta
Wed 9/302:47 pm
MSN
- OAK
2 stops11h 12m
Delta
Deal found 7/5![Delta logo]()
$696
This Delta deal was found by Cheapflights users on 7/5. 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 9/2212:39 pm
OAK
- MSN
2 stops8h 22m
Delta
Sat 9/266:00 am
MSN
- OAK
2 stops12h 20m
Delta
Deal found 7/5![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/65:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Mon 8/106:16 pm
MSN
- OAK
2 stops19h 36m
Delta
Deal found 7/5![Delta logo]()
$736
Best flights from Oakland to MadisonDiscover carefully curated flight deals from Oakland to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 7, 2026.
Discover carefully curated flight deals from Oakland to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 7, 2026.
This Delta deal was found by Cheapflights users on 7/2. 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 8/255:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Sun 11/227:55 pm
MSN
- OAK
2 stops22h 37m
Delta
Deal found 7/2![Delta logo]()
$583
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 8/265:00 pm
OAK
- MSN
2 stops13h 16m
Delta
Sun 11/227:55 pm
MSN
- OAK
2 stops22h 37m
Delta
Deal found 7/2![Delta logo]()
$583
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 8/265:00 pm
OAK
- MSN
2 stops16h 26m
Delta
Sat 11/216:15 am
MSN
- OAK
2 stops19h 41m
Delta
Deal found 7/2![Delta logo]()
$583
This Delta deal was found by Cheapflights users on 7/7. 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 8/255:00 pm
OAK
- MSN
2 stops16h 26m
Delta
Sat 11/2111:00 am
MSN
- OAK
2 stops14h 56m
Delta
Deal found 7/7![Delta logo]()
$607
This Delta deal was found by Cheapflights users on 7/7. 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.
Mon 8/245:00 pm
OAK
- MSN
2 stops13h 16m
Delta
Tue 8/252:51 pm
MSN
- OAK
2 stops11h 05m
Delta
Deal found 7/7![Delta logo]()
$765
This Delta deal was found by Cheapflights users on 7/5. 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.
Sat 9/196:00 am
OAK
- MSN
2 stops13h 30m
Delta
Fri 10/212:00 pm
MSN
- OAK
2 stops30h 20m
Delta
Deal found 7/5![Delta logo]()
$768
This Delta deal was found by Cheapflights users on 7/5. 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.
Mon 8/2412:33 pm
OAK
- MSN
2 stops8h 27m
Delta
Fri 11/201:45 pm
MSN
- OAK
2 stops12h 11m
Delta
Deal found 7/5![Delta logo]()
$798
This Delta deal was found by Cheapflights users on 7/5. 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 8/2512:33 pm
OAK
- MSN
2 stops8h 27m
Delta
Fri 11/201:45 pm
MSN
- OAK
2 stops12h 11m
Delta
Deal found 7/5![Delta logo]()
$798
This Delta deal was found by Cheapflights users on 7/7. 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.
Mon 8/2412:33 pm
OAK
- MSN
2 stops8h 27m
Delta
Sun 11/226:15 am
MSN
- OAK
2 stops8h 10m
Delta
Deal found 7/7![Delta logo]()
$847
This Delta deal was found by Cheapflights users on 7/6. 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 7/2112:30 pm
OAK
- MSN
2 stops8h 30m
Delta
Fri 7/246:13 pm
MSN
- OAK
2 stops7h 37m
Delta
Deal found 7/6![Delta logo]()
$925
Last-minute flights from Oakland to MadisonDiscover last-minute flight deals from Oakland to Madison. Data last updated July 7, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Madison. Data last updated July 7, 2026 and is based on user searches.
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.
Fri 7/105:05 pm
OAK
- MSN
2 stops13h 47m
Delta
Tue 7/146:13 pm
MSN
- OAK
2 stops7h 37m
Delta
Deal found 7/3![Delta logo]()
$737
This Delta deal was found by Cheapflights users on 7/6. 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.
Wed 8/512:33 pm
OAK
- MSN
2 stops8h 27m
Delta
Wed 8/126:05 am
MSN
- OAK
2 stops7h 47m
Delta
Deal found 7/6![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/65:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Tue 8/116:05 am
MSN
- OAK
2 stops7h 47m
Delta
Deal found 7/5![Delta logo]()
$587
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/65:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Mon 8/106:16 pm
MSN
- OAK
2 stops19h 36m
Delta
Deal found 7/5![Delta logo]()
$736
This Delta deal was found by Cheapflights users on 7/5. 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.
Fri 8/75:00 pm
OAK
- MSN
2 stops16h 26m
Delta
Tue 8/116:16 pm
MSN
- OAK
2 stops7h 40m
Delta
Deal found 7/5![Delta logo]()
$626
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/135:00 pm
OAK
- MSN
2 stops13h 16m
Delta
Mon 8/176:16 pm
MSN
- OAK
2 stops7h 40m
Delta
Deal found 7/5![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/135:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Tue 8/186:05 am
MSN
- OAK
2 stops12h 09m
Delta
Deal found 7/5![Delta logo]()
$632
This Delta deal was found by Cheapflights users on 7/5. 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.
Fri 8/1412:33 pm
OAK
- MSN
2 stops8h 27m
Delta
Mon 8/176:16 pm
MSN
- OAK
2 stops7h 40m
Delta
Deal found 7/5![Delta logo]()
$783
This Delta deal was found by Cheapflights users on 7/7. 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.
Sun 8/235:00 pm
OAK
- MSN
2 stops28h 00m
Delta
Sat 11/216:15 am
MSN
- OAK
2 stops19h 41m
Delta
Deal found 7/7![Delta logo]()
$784
This Delta deal was found by Cheapflights users on 7/6. 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.
Mon 8/2412:33 pm
OAK
- MSN
2 stops20h 53m
Delta
Sat 11/216:15 am
MSN
- OAK
2 stops19h 41m
Delta
Deal found 7/6![Delta logo]()
$607
This Delta deal was found by Cheapflights users on 7/7. 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.
Mon 8/245:00 pm
OAK
- MSN
2 stops13h 16m
Delta
Tue 8/252:51 pm
MSN
- OAK
2 stops11h 05m
Delta
Deal found 7/7![Delta logo]()
$765
This Delta deal was found by Cheapflights users on 7/2. 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 8/255:00 pm
OAK
- MSN
2 stops16h 26m
Delta
Sat 11/2111:00 am
MSN
- OAK
2 stops14h 56m
Delta
Deal found 7/2![Delta logo]()
$583
One-way flights from Oakland to MadisonSearch for one-way flight options from Oakland to Madison. Find affordable one-way fares based on user searches. Data last updated July 7, 2026.
Search for one-way flight options from Oakland to Madison. Find affordable one-way fares based on user searches. Data last updated July 7, 2026.
This Delta deal was found by Cheapflights users on 7/6. 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.
Mon 8/245:00 pm
OAK
- MSN
2 stops19h 11m
Delta
Deal found 7/6![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 7/6. 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.
Mon 7/1312:30 pm
OAK
- MSN
2 stops8h 30m
Delta
Deal found 7/6![Delta logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 7/5. 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.
Thu 8/137:13 pm
OAK
- MSN
3 stops25h 47m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 7/2. 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.
Wed 7/156:00 am
OAK
- MSN
2 stops24h 52m
Delta
Deal found 7/2![Delta logo]()
$609
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 7/1511:30 pm
OAK
- MSN
3 stops40h 40m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$617
This Delta deal was found by Cheapflights users on 7/5. 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.
Thu 8/136:00 am
OAK
- MSN
2 stops9h 35m
Delta
Deal found 7/5![Delta logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Sun 7/198:30 pm
OAK
- MSN
3 stops43h 29m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$683
This Delta deal was found by Cheapflights users on 7/6. 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.
Mon 7/2012:30 pm
OAK
- MSN
2 stops8h 30m
Delta
Deal found 7/6![Delta logo]()
$745
This Delta deal was found by Cheapflights users on 7/2. 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.
Sun 7/1912:30 pm
OAK
- MSN
2 stops8h 30m
Delta
Deal found 7/2![Delta logo]()
$1,025
Find flight deals from Oakland to Madison
Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Madison (MSN). 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 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $583 (Delta) |
One-way from | $389 (Delta) |
Popular in | June |
Cheapest in | August |
Average price | $503 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Madison 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 7, 2026.
Use the filters below to find and compare flights from Oakland to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Tue 8/25
5:00 pm-11:00 pm
2 stops28h 00m
Madison Truax Field
Sun 11/22
7:55 pm-4:32 pm
2 stops22h 37m
$583
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Wed 8/26
5:00 pm-8:16 am
2 stops13h 16m
Madison Truax Field
Sun 11/22
7:55 pm-4:32 pm
2 stops22h 37m
$583
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Wed 8/26
5:00 pm-11:26 am
2 stops16h 26m
Madison Truax Field
Sat 11/21
6:15 am-11:56 pm
2 stops19h 41m
$583
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Tue 8/25
5:00 pm-11:26 am
2 stops16h 26m
Madison Truax Field
Sat 11/21
11:00 am-11:56 pm
2 stops14h 56m
$607
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Mon 8/24
5:00 pm-8:16 am
2 stops13h 16m
Madison Truax Field
Tue 8/25
2:51 pm-11:56 pm
2 stops11h 05m
$765
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Sat 9/19
6:00 am-9:30 pm
2 stops13h 30m
Madison Truax Field
Fri 10/2
12:00 pm-4:20 pm
2 stops30h 20m
$768
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Mon 8/24
12:33 pm-11:00 pm
2 stops8h 27m
Madison Truax Field
Fri 11/20
1:45 pm-11:56 pm
2 stops12h 11m
$798
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Tue 8/25
12:33 pm-11:00 pm
2 stops8h 27m
Madison Truax Field
Fri 11/20
1:45 pm-11:56 pm
2 stops12h 11m
$798
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Mon 8/24
12:33 pm-11:00 pm
2 stops8h 27m
Madison Truax Field
Sun 11/22
6:15 am-12:25 pm
2 stops8h 10m
$847
Quickest round-trip
OaklandMadison
OAK - MSN
OAKMSN
Oakland
Tue 7/21
12:30 pm-11:00 pm
2 stops8h 30m
Madison Truax Field
Fri 7/24
6:13 pm-11:50 pm
2 stops7h 37m
$925
Showing 1-10 of 16 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Oakland, California-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Oakland, California-Madison 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-Madison 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 Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Oakland with our price prediction graph.
OAK-MSN
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.
Reviews of airlines servicing Madison
Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated July 7, 2026.
Read through reviews of airlines operating flights from Oakland to Madison, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Comfort
7.8
Overall
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentMichael,Sep 2023
SMF - ATL
Crew
8.5
Comfort
7.8
Overall
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentMichael,Sep 2023
SMF - ATL
Related info for your journey
Find useful and relevant information for your journey from Oakland to Madison. 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 Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Baraboo
Fitchburg
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
Complete your trip
Flights by cabin class
Madison flight routes
Other flight options
Other flights from Oakland
Popular flights
Alternative routes for Oakland to Madison
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Madison by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Madison by cabin class
Find flights from Oakland to Madison, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Madison
Explore flights to Madison departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 7, 2026.
Oakland and Madison flights
Browse other Oakland and Madison flight options. Last updated on July 7, 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 July 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Oakland to Madison
Discover the top airline that operate flights from Oakland to Madison. 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 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$279 | Average$519 | FlexibilityNo cancel fee | On-timeN/A |