$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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Apr 9 — Apr 161
Round-trip
1 adult, Economy
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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 March 10, 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 March 10, 2026.
This eDestinos deal was found by Cheapflights users on 3/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:30 pm
MDW
- SNA
1 stop26h 14m
Frontier
Fri 5/17:56 pm
SNA
- MDW
2 stops20h 41m
Frontier
Deal found 3/9![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/236:20 am
MDW
- SNA
2 stops13h 41m
Multiple Airlines
Sun 4/266:48 pm
SNA
- MDW
1 stop25h 07m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 3/8. 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 5/11:24 pm
MDW
- SNA
2 stops11h 04m
Delta
Mon 5/46:58 pm
SNA
- MDW
2 stops11h 49m
Delta
Deal found 3/8![Delta logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/236:20 am
MDW
- SNA
1 stop28h 30m
Frontier
Sun 4/265:33 pm
SNA
- MDW
1 stop26h 22m
Frontier
Deal found 3/8![Frontier logo]()
$298
This Southwest deal was found by Cheapflights users on 3/8. 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 5/110:10 am
MDW
- SNA
1 stop6h 30m
Southwest
Mon 5/48:10 pm
SNA
- MDW
1 stop7h 50m
Southwest
Deal found 3/8![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 3/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:10 am
MDW
- SNA
1 stop7h 20m
Southwest
Tue 4/147:50 am
SNA
- MDW
1 stop7h 05m
Southwest
Deal found 3/5![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 3/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/310:45 am
MDW
- SNA
2 stops8h 35m
Southwest
Fri 4/109:10 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 3/6![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 3/9. 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 4/1810:15 am
MDW
- SNA
1 stop9h 55m
Southwest
Tue 4/217:40 pm
SNA
- MDW
1 stop7h 45m
Southwest
Deal found 3/9![Southwest logo]()
$319
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2710:36 pm
MDW
- SNA
1 stop12h 19m
Frontier
Mon 3/302:23 pm
SNA
- MDW
1 stop7h 16m
Frontier
Deal found 3/9![Frontier logo]()
$320
This Delta deal was found by Cheapflights users on 3/7. 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 4/219:27 am
MDW
- SNA
2 stops10h 26m
Delta
Tue 4/288:00 am
SNA
- MDW
1 stop8h 36m
Delta
Deal found 3/7![Delta logo]()
$322
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 March 10, 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 March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:40 pm
MDW
- SNA
1 stop5h 45m
Southwest
Mon 6/158:45 pm
SNA
- MDW
1 stop7h 00m
Southwest
Deal found 3/6![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/33:30 pm
MDW
- SNA
1 stop7h 40m
Southwest
Sun 4/128:40 pm
SNA
- MDW
1 stop7h 05m
Southwest
Deal found 3/7![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 3/9. 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 4/96:55 am
MDW
- SNA
1 stop7h 00m
Southwest
Mon 4/133:50 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 3/9![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 3/9. 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 4/910:00 am
MDW
- SNA
1 stop7h 05m
Southwest
Sun 4/128:40 pm
SNA
- MDW
1 stop7h 05m
Southwest
Deal found 3/9![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:15 pm
MDW
- SNA
2 stops9h 25m
Southwest
Sat 7/187:45 pm
SNA
- MDW
1 stop7h 25m
Southwest
Deal found 3/7![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 3/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:10 am
MDW
- SNA
1 stop6h 55m
Southwest
Sat 4/116:45 am
SNA
- MDW
2 stops8h 05m
Southwest
Deal found 3/6![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 3/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/52:15 pm
MDW
- SNA
2 stops8h 05m
Southwest
Sun 4/128:40 pm
SNA
- MDW
1 stop7h 05m
Southwest
Deal found 3/6![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:20 pm
MDW
- SNA
2 stops8h 50m
Southwest
Wed 7/152:15 pm
SNA
- MDW
1 stop5h 30m
Southwest
Deal found 3/7![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 3/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:05 pm
MDW
- SNA
2 stops8h 35m
Southwest
Fri 3/278:30 pm
SNA
- MDW
1 stop7h 25m
Southwest
Deal found 3/6![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 3/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:15 pm
MDW
- SNA
2 stops7h 45m
Southwest
Wed 6/178:15 pm
SNA
- MDW
1 stop6h 45m
Southwest
Deal found 3/5![Southwest logo]()
$443
This Southwest deal was found by Cheapflights users on 3/8. 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 4/71:05 pm
MDW
- SNA
2 stops8h 00m
Southwest
Tue 4/149:00 am
SNA
- MDW
2 stops8h 30m
Southwest
Deal found 3/8![Southwest logo]()
$455
Last-minute flights from Midway to AnaheimDiscover last-minute flight deals from Midway to Anaheim. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Anaheim. Data last updated March 10, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2710:36 pm
MDW
- SNA
1 stop12h 19m
Frontier
Mon 3/302:23 pm
SNA
- MDW
1 stop7h 16m
Frontier
Deal found 3/9![Frontier logo]()
$320
This Southwest deal was found by Cheapflights users on 3/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/310:45 am
MDW
- SNA
2 stops8h 35m
Southwest
Fri 4/109:10 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 3/6![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 3/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:10 am
MDW
- SNA
1 stop7h 20m
Southwest
Tue 4/147:50 am
SNA
- MDW
1 stop7h 05m
Southwest
Deal found 3/5![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 3/9. 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 4/1810:15 am
MDW
- SNA
1 stop9h 55m
Southwest
Tue 4/217:40 pm
SNA
- MDW
1 stop7h 45m
Southwest
Deal found 3/9![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 3/7. 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 4/219:27 am
MDW
- SNA
2 stops10h 26m
Delta
Tue 4/288:00 am
SNA
- MDW
1 stop8h 36m
Delta
Deal found 3/7![Delta logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/236:20 am
MDW
- SNA
2 stops13h 41m
Multiple Airlines
Sun 4/266:48 pm
SNA
- MDW
1 stop25h 07m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/236:20 am
MDW
- SNA
1 stop28h 30m
Frontier
Sun 4/265:33 pm
SNA
- MDW
1 stop26h 22m
Frontier
Deal found 3/8![Frontier logo]()
$298
This eDestinos deal was found by Cheapflights users on 3/9. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:30 pm
MDW
- SNA
1 stop26h 14m
Frontier
Fri 5/17:56 pm
SNA
- MDW
2 stops20h 41m
Frontier
Deal found 3/9![Frontier logo]()
$285
This Southwest deal was found by Cheapflights users on 3/10. 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 4/244:10 pm
MDW
- SNA
1 stop7h 25m
Southwest
Fri 5/19:10 pm
SNA
- MDW
1 stop5h 50m
Southwest
Deal found 3/10![Southwest logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/257:34 pm
MDW
- SNA
2 stops44h 10m
Frontier
Sat 5/92:39 pm
SNA
- MDW
1 stop22h 10m
Frontier
Deal found 3/9![Frontier logo]()
$330
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 March 10, 2026.
Search for one-way flight options from Midway to Anaheim. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 3/294:02 pm
MDW
- SNA
1 stop18h 48m
Frontier
Deal found 3/8![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:30 pm
MDW
- SNA
1 stop26h 14m
Frontier
Deal found 3/6![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 6/48:03 pm
MDW
- SNA
1 stop14h 02m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/272:15 pm
MDW
- SNA
3 stops33h 30m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 3/8. 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 6/168:00 am
MDW
- SNA
1 stop6h 45m
Southwest
Deal found 3/8![Southwest logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/135:11 pm
MDW
- SNA
2 stops18h 42m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:15 pm
MDW
- SNA
2 stops25h 29m
Frontier
Deal found 3/6![Frontier logo]()
$158
This Southwest deal was found by Cheapflights users on 3/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:55 am
MDW
- SNA
2 stops8h 15m
Southwest
Deal found 3/7![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 3/10. 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 4/25:00 am
MDW
- SNA
1 stop6h 50m
Southwest
Deal found 3/10![Southwest logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 4/116:40 am
MDW
- SNA
3 stops16h 33m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:56 pm
MDW
- SNA
3 stops44h 57m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$175
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 March 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $285 (eDestinos) |
One-way from | $145 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $402 |
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 March 10, 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
Fri 6/12
6:40 pm-10:25 pm
1 stop5h 45m
Santa Ana J. Wayne/Orange Cnty
Mon 6/15
8:45 pm-5:45 am
1 stop7h 00m
$309
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 4/3
3:30 pm-9:10 pm
1 stop7h 40m
Santa Ana J. Wayne/Orange Cnty
Sun 4/12
8:40 pm-5:45 am
1 stop7h 05m
$309
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 4/9
6:55 am-11:55 am
1 stop7h 00m
Santa Ana J. Wayne/Orange Cnty
Mon 4/13
3:50 pm-11:40 pm
1 stop5h 50m
$331
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 4/9
10:00 am-3:05 pm
1 stop7h 05m
Santa Ana J. Wayne/Orange Cnty
Sun 4/12
8:40 pm-5:45 am
1 stop7h 05m
$375
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Sat 7/11
12:15 pm-7:40 pm
2 stops9h 25m
Santa Ana J. Wayne/Orange Cnty
Sat 7/18
7:45 pm-5:10 am
1 stop7h 25m
$382
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Wed 4/8
6:10 am-11:05 am
1 stop6h 55m
Santa Ana J. Wayne/Orange Cnty
Sat 4/11
6:45 am-4:50 pm
2 stops8h 05m
$382
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Sun 4/5
2:15 pm-8:20 pm
2 stops8h 05m
Santa Ana J. Wayne/Orange Cnty
Sun 4/12
8:40 pm-5:45 am
1 stop7h 05m
$393
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Wed 7/8
12:20 pm-7:10 pm
2 stops8h 50m
Santa Ana J. Wayne/Orange Cnty
Wed 7/15
2:15 pm-9:45 pm
1 stop5h 30m
$416
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 3/24
1:05 pm-7:40 pm
2 stops8h 35m
Santa Ana J. Wayne/Orange Cnty
Fri 3/27
8:30 pm-5:55 am
1 stop7h 25m
$428
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 6/11
12:15 pm-6:00 pm
2 stops7h 45m
Santa Ana J. Wayne/Orange Cnty
Wed 6/17
8:15 pm-5:00 am
1 stop6h 45m
$443
Showing 1-10 of 21 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 month to book a flight from Chicago Midway Airport to Anaheim?
Currently, June is the cheapest month in which you can book a flight from Chicago Midway Airport to Anaheim (average of $133). Flying from Chicago Midway Airport to Anaheim in December is currently the most expensive (average of $256). 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 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 March 10, 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 13% 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 February 21, 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.
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 March 10, 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
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentWalter,Aug 2025
OAK - SAN
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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Midway and Anaheim flights
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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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$164 | 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% |