$157+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Jul 11 — Jul 181
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 June 11, 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 June 11, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 7/15:30 am
MDW
- SNA
1 stop6h 00m
Southwest
Wed 7/81:45 pm
SNA
- MDW
1 stop5h 35m
Southwest
Deal found 6/10![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 11/410:05 am
MDW
- SNA
2 stops8h 15m
Southwest
Sat 11/146:45 am
SNA
- MDW
2 stops8h 20m
Southwest
Deal found 6/8![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 6/10. 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 9/36:15 am
MDW
- SNA
2 stops9h 10m
Southwest
Mon 9/78:30 pm
SNA
- MDW
1 stop7h 15m
Southwest
Deal found 6/10![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 8/410:10 am
MDW
- SNA
2 stops6h 50m
Southwest
Sat 8/86:25 pm
SNA
- MDW
1 stop8h 35m
Southwest
Deal found 6/9![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 8/2812:15 pm
MDW
- SNA
1 stop6h 10m
Southwest
Sun 8/304:35 pm
SNA
- MDW
1 stop6h 20m
Southwest
Deal found 6/9![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 6/9. 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 8/298:00 am
MDW
- SNA
2 stops9h 45m
Southwest
Mon 9/146:45 am
SNA
- MDW
2 stops8h 15m
Southwest
Deal found 6/9![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 6/10. 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 7/25:15 am
MDW
- SNA
1 stop6h 00m
Southwest
Wed 7/83:35 pm
SNA
- MDW
1 stop6h 35m
Southwest
Deal found 6/10![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:49 pm
MDW
- SNA
1 stop8h 35m
Delta
Tue 7/76:45 pm
SNA
- MDW
2 stops11h 52m
Delta
Deal found 6/10![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 6/7. 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 8/15:10 am
MDW
- SNA
1 stop6h 05m
Southwest
Thu 8/68:50 pm
SNA
- MDW
1 stop6h 50m
Southwest
Deal found 6/7![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:51 pm
MDW
- SNA
1 stop8h 16m
Delta
Tue 9/88:00 am
SNA
- MDW
1 stop8h 05m
Delta
Deal found 6/10![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:54 am
MDW
- SNA
1 stop9h 43m
Delta
Mon 8/316:02 pm
SNA
- MDW
2 stops12h 37m
Delta
Deal found 6/10![Delta logo]()
$354
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 June 11, 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 June 11, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 8/410:10 am
MDW
- SNA
2 stops6h 50m
Southwest
Sat 8/86:25 pm
SNA
- MDW
1 stop8h 35m
Southwest
Deal found 6/9![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 6/5. 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 7/31:49 pm
MDW
- SNA
2 stops10h 39m
Delta
Tue 7/76:45 pm
SNA
- MDW
2 stops11h 52m
Delta
Deal found 6/5![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 6/9. 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 8/298:00 am
MDW
- SNA
2 stops9h 45m
Southwest
Mon 9/146:45 am
SNA
- MDW
2 stops8h 15m
Southwest
Deal found 6/9![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 6/5. 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.
Mon 6/297:30 am
MDW
- SNA
1 stop6h 15m
Southwest
Mon 7/68:30 pm
SNA
- MDW
1 stop7h 30m
Southwest
Deal found 6/5![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 6/271:49 pm
MDW
- SNA
1 stop8h 35m
Delta
Mon 6/298:00 am
SNA
- MDW
1 stop8h 18m
Delta
Deal found 6/8![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 6/8. 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.
Sat 7/113:40 pm
MDW
- SNA
1 stop6h 25m
Southwest
Mon 7/135:15 pm
SNA
- MDW
1 stop5h 25m
Southwest
Deal found 6/8![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 8/66:15 pm
MDW
- SNA
1 stop5h 55m
Southwest
Tue 8/116:45 am
SNA
- MDW
2 stops7h 15m
Southwest
Deal found 6/7![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 7/244:35 pm
MDW
- SNA
1 stop7h 50m
Southwest
Fri 7/315:15 pm
SNA
- MDW
1 stop5h 25m
Southwest
Deal found 6/9![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 6/5. 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.
Mon 8/35:20 am
MDW
- SNA
1 stop6h 10m
Southwest
Thu 8/66:45 am
SNA
- MDW
2 stops8h 15m
Southwest
Deal found 6/5![Southwest logo]()
$438
This Southwest deal was found by Cheapflights users on 6/6. 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 7/176:40 pm
MDW
- SNA
1 stop5h 45m
Southwest
Sun 7/269:10 pm
SNA
- MDW
1 stop6h 35m
Southwest
Deal found 6/6![Southwest logo]()
$441
Last-minute flights from Midway to AnaheimDiscover last-minute flight deals from Midway to Anaheim. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Anaheim. Data last updated June 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 6/306:20 am
MDW
- SNA
1 stop6h 10m
Southwest
Sun 7/59:10 pm
SNA
- MDW
1 stop6h 35m
Southwest
Deal found 6/9![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 7/15:35 pm
MDW
- SNA
1 stop6h 35m
Southwest
Sat 7/41:30 pm
SNA
- MDW
1 stop5h 35m
Southwest
Deal found 6/8![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 6/5. 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 7/21:49 pm
MDW
- SNA
1 stop8h 35m
Delta
Tue 7/76:45 pm
SNA
- MDW
2 stops11h 52m
Delta
Deal found 6/5![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 6/10. 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 7/37:30 am
MDW
- SNA
1 stop6h 15m
Southwest
Tue 7/76:55 pm
SNA
- MDW
1 stop8h 05m
Southwest
Deal found 6/10![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:49 pm
MDW
- SNA
1 stop8h 35m
Delta
Tue 7/76:45 pm
SNA
- MDW
2 stops11h 52m
Delta
Deal found 6/10![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 7/711:20 am
MDW
- SNA
2 stops9h 00m
Southwest
Tue 7/141:45 pm
SNA
- MDW
1 stop8h 00m
Southwest
Deal found 6/9![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 6/6. 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.
Sat 7/115:10 pm
MDW
- SNA
1 stop6h 35m
Southwest
Sat 7/185:50 pm
SNA
- MDW
2 stops9h 30m
Southwest
Deal found 6/6![Southwest logo]()
$365
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 June 11, 2026.
Search for one-way flight options from Midway to Anaheim. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/68:20 pm
MDW
- SNA
1 stop17h 52m
Allegiant Air
Deal found 6/5![Allegiant Air logo]()
$157
This Southwest deal was found by Cheapflights users on 6/9. 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 8/65:40 am
MDW
- SNA
1 stop5h 40m
Southwest
Deal found 6/9![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 6/8. 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.
Wed 7/85:30 am
MDW
- SNA
1 stop6h 00m
Southwest
Deal found 6/8![Southwest logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 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 stop18h 20m
Allegiant Air
Deal found 6/10![Allegiant Air logo]()
$173
This Southwest deal was found by Cheapflights users on 6/6. 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 7/16:45 am
MDW
- SNA
1 stop8h 00m
Southwest
Deal found 6/6![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Sun 8/168:20 pm
MDW
- SNA
2 stops18h 11m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 6/10. 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.
Sat 7/45:25 am
MDW
- SNA
2 stops7h 05m
Southwest
Deal found 6/10![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 6/6. 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 7/76:20 am
MDW
- SNA
1 stop6h 10m
Southwest
Deal found 6/6![Southwest logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:27 pm
MDW
- SNA
3 stops31h 18m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 6/7. 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 8/77:10 am
MDW
- SNA
1 stop5h 40m
Southwest
Deal found 6/7![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 6/9. 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.
Wed 8/510:30 am
MDW
- SNA
2 stops8h 15m
Southwest
Deal found 6/9![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
Sun 7/128:11 pm
MDW
- SNA
1 stop18h 04m
Allegiant Air
Deal found 6/6![Allegiant Air logo]()
$192
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 June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (Southwest) |
One-way from | $157 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $505 |
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 June 11, 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
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Tue 8/4
10:10 am-3:00 pm
2 stops6h 50m
Santa Ana J. Wayne/Orange Cnty
Sat 8/8
6:25 pm-5:00 am
1 stop8h 35m
$332
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Sat 8/29
8:00 am-3:45 pm
2 stops9h 45m
Santa Ana J. Wayne/Orange Cnty
Mon 9/14
6:45 am-5:00 pm
2 stops8h 15m
$337
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Mon 6/29
7:30 am-11:45 am
1 stop6h 15m
Santa Ana J. Wayne/Orange Cnty
Mon 7/6
8:30 pm-6:00 am
1 stop7h 30m
$349
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 7/3
1:49 pm-10:28 pm
2 stops10h 39m
Santa Ana J. Wayne/Orange Cnty
Tue 7/7
6:45 pm-8:37 am
2 stops11h 52m
$354
Quickest round-trip
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Sat 7/11
3:40 pm-8:05 pm
1 stop6h 25m
Santa Ana J. Wayne/Orange Cnty
Mon 7/13
5:15 pm-12:40 am
1 stop5h 25m
$359
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Thu 8/6
6:15 pm-10:10 pm
1 stop5h 55m
Santa Ana J. Wayne/Orange Cnty
Tue 8/11
6:45 am-4:00 pm
2 stops7h 15m
$379
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 7/24
4:35 pm-10:25 pm
1 stop7h 50m
Santa Ana J. Wayne/Orange Cnty
Fri 7/31
5:15 pm-12:40 am
1 stop5h 25m
$383
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Sat 6/27
1:49 pm-8:24 pm
1 stop8h 35m
Santa Ana J. Wayne/Orange Cnty
Mon 6/29
8:00 am-6:18 pm
1 stop8h 18m
$394
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Mon 8/3
5:20 am-9:30 am
1 stop6h 10m
Santa Ana J. Wayne/Orange Cnty
Thu 8/6
6:45 am-5:00 pm
2 stops8h 15m
$438
ChicagoSanta Ana
MDW - SNA
MDWSNA
Chicago Midway
Fri 7/17
6:40 pm-10:25 pm
1 stop5h 45m
Santa Ana J. Wayne/Orange Cnty
Sun 7/26
9:10 pm-5:45 am
1 stop6h 35m
$441
Showing 1-10 of 18 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 June 11, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Anaheim in the afternoon. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight in the morning.
How much does it cost to fly round-trip from Chicago Midway Airport to Anaheim?
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 June 8, 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 June 11, 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$291 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$183 | Average$316 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$435 | FlexibilityNo cancel fee | On-time63% |