$145+ Cheap flights from Midway (MDW) to Anaheim, CA
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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
May 23 — May 301
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Anaheim with Cheapflights
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Cheapest flights from Midway to AnaheimExplore the most affordable flight options available from Midway to Anaheim. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.
Explore the most affordable flight options available from Midway to Anaheim. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 8/225:40 am
MDW
- SNA
1 stop7h 40m
Southwest
Tue 8/256:35 pm
SNA
- MDW
1 stop8h 25m
Southwest
Deal found 4/21![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 8/157:45 am
MDW
- SNA
2 stops8h 25m
Southwest
Wed 8/197:55 pm
SNA
- MDW
1 stop7h 50m
Southwest
Deal found 4/21![Southwest logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/317:49 pm
MDW
- SNA
1 stop15h 59m
Multiple Airlines
Sat 6/64:33 pm
SNA
- MDW
2 stops19h 39m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 4/19. 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 5/196:30 am
MDW
- SNA
1 stop5h 55m
Southwest
Sat 5/236:10 pm
SNA
- MDW
1 stop9h 30m
Southwest
Deal found 4/19![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 4/19. 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 9/161:40 pm
MDW
- SNA
1 stop6h 25m
Southwest
Sat 9/196:25 pm
SNA
- MDW
1 stop8h 35m
Southwest
Deal found 4/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 5/294:10 pm
MDW
- SNA
1 stop6h 10m
Southwest
Mon 6/13:50 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 4/22![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sat 5/235:30 pm
MDW
- SNA
1 stop5h 50m
Southwest
Tue 5/267:30 pm
SNA
- MDW
1 stop8h 30m
Southwest
Deal found 4/22![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 4/19. 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 8/1310:10 am
MDW
- SNA
1 stop7h 50m
Southwest
Sat 8/226:25 pm
SNA
- MDW
1 stop8h 35m
Southwest
Deal found 4/19![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 4/20. 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.
Fri 6/55:20 am
MDW
- SNA
1 stop6h 10m
Southwest
Mon 6/88:45 pm
SNA
- MDW
1 stop6h 25m
Southwest
Deal found 4/20![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/910:05 am
MDW
- SNA
2 stops7h 15m
Southwest
Tue 5/127:50 pm
SNA
- MDW
1 stop7h 10m
Southwest
Deal found 4/21![Southwest logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
MDW
- SNA
2 stops32h 19m
Multiple Airlines
Wed 5/272:30 pm
SNA
- MDW
1 stop26h 29m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/317:49 pm
MDW
- SNA
1 stop15h 59m
Multiple Airlines
Mon 6/84:20 pm
SNA
- MDW
2 stops16h 52m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$338
Best flights from Midway to AnaheimDiscover carefully curated flight deals from Midway to Anaheim that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 23, 2026.
Discover carefully curated flight deals from Midway to Anaheim that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 23, 2026.
This Southwest deal was found by Cheapflights users on 4/22. 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 6/44:55 pm
MDW
- SNA
1 stop6h 30m
Southwest
Mon 6/88:45 pm
SNA
- MDW
1 stop6h 25m
Southwest
Deal found 4/22![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 4/18. 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 5/121:59 pm
MDW
- SNA
1 stop9h 18m
Delta
Sat 5/168:00 am
SNA
- MDW
1 stop7h 56m
Delta
Deal found 4/18![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 4/22. 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.
Wed 6/105:25 am
MDW
- SNA
1 stop6h 00m
Southwest
Wed 6/177:45 pm
SNA
- MDW
1 stop7h 40m
Southwest
Deal found 4/22![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 4/21. 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.
Tue 6/167:00 am
MDW
- SNA
1 stop8h 10m
Southwest
Tue 6/233:35 pm
SNA
- MDW
1 stop6h 30m
Southwest
Deal found 4/21![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 4/19. 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 7/2811:45 am
MDW
- SNA
2 stops7h 00m
Southwest
Sat 8/17:05 pm
SNA
- MDW
1 stop8h 40m
Southwest
Deal found 4/19![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 4/18. 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 5/76:55 am
MDW
- SNA
1 stop7h 00m
Southwest
Mon 5/112:20 pm
SNA
- MDW
2 stops7h 35m
Southwest
Deal found 4/18![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 4/19. 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 6/175:30 am
MDW
- SNA
1 stop6h 00m
Southwest
Sun 6/218:50 pm
SNA
- MDW
1 stop7h 10m
Southwest
Deal found 4/19![Southwest logo]()
$433
This Southwest deal was found by Cheapflights users on 4/18. 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 7/105:15 am
MDW
- SNA
1 stop6h 00m
Southwest
Sat 7/257:05 pm
SNA
- MDW
1 stop8h 40m
Southwest
Deal found 4/18![Southwest logo]()
$441
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 5/156:25 pm
MDW
- SNA
1 stop5h 55m
Southwest
Sun 5/178:05 pm
SNA
- MDW
1 stop7h 20m
Southwest
Deal found 4/22![Southwest logo]()
$444
Last-minute flights from Midway to AnaheimDiscover last-minute flight deals from Midway to Anaheim. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Anaheim. Data last updated April 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Thu 4/303:27 pm
MDW
- SNA
1 stop19h 23m
Multiple Airlines
Tue 5/127:30 am
SNA
- MDW
2 stops25h 39m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/910:05 am
MDW
- SNA
2 stops7h 15m
Southwest
Tue 5/127:50 pm
SNA
- MDW
1 stop7h 10m
Southwest
Deal found 4/21![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
MDW
- SNA
1 stop9h 18m
Delta
Sat 5/168:00 am
SNA
- MDW
1 stop7h 56m
Delta
Deal found 4/20![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 4/19. 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 5/196:30 am
MDW
- SNA
1 stop5h 55m
Southwest
Sat 5/236:10 pm
SNA
- MDW
1 stop9h 30m
Southwest
Deal found 4/19![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
MDW
- SNA
2 stops32h 19m
Multiple Airlines
Wed 5/272:30 pm
SNA
- MDW
1 stop26h 29m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 4/22. 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.
Sat 5/235:30 pm
MDW
- SNA
1 stop5h 50m
Southwest
Tue 5/267:30 pm
SNA
- MDW
1 stop8h 30m
Southwest
Deal found 4/22![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 4/22. 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 5/285:25 am
MDW
- SNA
1 stop6h 10m
Southwest
Sun 5/319:05 pm
SNA
- MDW
1 stop6h 55m
Southwest
Deal found 4/22![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 5/294:10 pm
MDW
- SNA
1 stop6h 10m
Southwest
Mon 6/13:50 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 4/22![Southwest logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/317:49 pm
MDW
- SNA
1 stop15h 59m
Multiple Airlines
Sat 6/64:33 pm
SNA
- MDW
2 stops19h 39m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/317:49 pm
MDW
- SNA
1 stop15h 59m
Multiple Airlines
Mon 6/84:20 pm
SNA
- MDW
2 stops16h 52m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/317:49 pm
MDW
- SNA
1 stop15h 59m
Multiple Airlines
Sun 6/74:20 pm
SNA
- MDW
2 stops16h 49m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/317:49 pm
MDW
- SNA
1 stop15h 59m
Multiple Airlines
Fri 6/54:33 pm
SNA
- MDW
2 stops19h 39m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$345
One-way flights from Midway to AnaheimSearch for one-way flight options from Midway to Anaheim. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
Search for one-way flight options from Midway to Anaheim. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 7/98:11 pm
MDW
- SNA
1 stop18h 04m
Allegiant Air
Deal found 4/19![Allegiant Air logo]()
$145
This Super.com deal was found by Cheapflights users on 4/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:20 am
MDW
- SNA
1 stop9h 24m
Frontier
Deal found 4/18![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Wed 5/612:04 pm
MDW
- SNA
2 stops25h 24m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/288:03 pm
MDW
- SNA
1 stop15h 45m
Allegiant Air
Deal found 4/22![Allegiant Air logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Sat 5/911:59 am
MDW
- SNA
2 stops25h 29m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 4/20. 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 6/16:25 pm
MDW
- SNA
1 stop5h 55m
Southwest
Deal found 4/20![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/1912:24 pm
MDW
- SNA
2 stops49h 55m
Frontier
Deal found 4/18![Frontier logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:03 pm
MDW
- SNA
1 stop19h 18m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Sat 5/2311:59 am
MDW
- SNA
2 stops24h 29m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$169
Find flight deals from Midway to Anaheim
Keep the following information in mind while searching for Midway to Anaheim flight deals. Data was last updated April 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Southwest) |
One-way from | $145 (Kiwi.com) |
Popular in | June |
Cheapest in | August |
Average price | $388 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Anaheim 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 April 23, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Anaheim that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 6/4
4:55 pm-9:25 pm
1 stop6h 30m
Santa Ana J. Wayne/Orange Cnty
Mon 6/8
8:45 pm-5:10 am
1 stop6h 25m
$312
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Wed 6/10
5:25 am-9:25 am
1 stop6h 00m
Santa Ana J. Wayne/Orange Cnty
Wed 6/17
7:45 pm-5:25 am
1 stop7h 40m
$344
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 5/12
1:59 pm-9:17 pm
1 stop9h 18m
Santa Ana J. Wayne/Orange Cnty
Sat 5/16
8:00 am-5:56 pm
1 stop7h 56m
$349
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 6/16
7:00 am-1:10 pm
1 stop8h 10m
Santa Ana J. Wayne/Orange Cnty
Tue 6/23
3:35 pm-12:05 am
1 stop6h 30m
$349
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 7/28
11:45 am-4:45 pm
2 stops7h 00m
Santa Ana J. Wayne/Orange Cnty
Sat 8/1
7:05 pm-5:45 am
1 stop8h 40m
$388
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 5/7
6:55 am-11:55 am
1 stop7h 00m
Santa Ana J. Wayne/Orange Cnty
Mon 5/11
2:20 pm-11:55 pm
2 stops7h 35m
$389
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Wed 6/17
5:30 am-9:30 am
1 stop6h 00m
Santa Ana J. Wayne/Orange Cnty
Sun 6/21
8:50 pm-6:00 am
1 stop7h 10m
$433
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 7/10
5:15 am-9:15 am
1 stop6h 00m
Santa Ana J. Wayne/Orange Cnty
Sat 7/25
7:05 pm-5:45 am
1 stop8h 40m
$441
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 5/15
6:25 pm-10:20 pm
1 stop5h 55m
Santa Ana J. Wayne/Orange Cnty
Sun 5/17
8:05 pm-5:25 am
1 stop7h 20m
$444
Cheapest one-way
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 6/23
4:40 pm-9:55 pm
1 stop7h 15m
$175
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Midway to Anaheim
Have a flexible travel schedule? Discover the best time to fly to Anaheim from Midway with our price prediction graph.
MDW-SNA
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 Anaheim
MDW-AN4
MDW-SNA
What is the cheapest time of day to fly from MDW to AN4?
Find hourly flight availability from Midway to Anaheim. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Anaheim in the evening. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Chicago Midway Airport to Anaheim?
Use this chart to determine the cheapest time to fly round-trip from Midway to Anaheim. Price data was last updated on April 18, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Anaheim flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Chicago Midway Airport to Anaheim?
Reviews of airlines servicing Anaheim
Get insights into the airlines that provide service to Anaheim. 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 Anaheim. Reviews last updated April 23, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Anaheim, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Anaheim. 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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Alternative routes for Midway to Anaheim
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Complete your trip
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Midway and Anaheim flights
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Other flights from Midway
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Top 3 airlines flying from Midway to Anaheim
Discover the top 3 airlines that operate flights from Midway to Anaheim. 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 April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$272 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$183 | Average$316 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$430 | FlexibilityNo cancel fee | On-time63% |