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$173+ 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Feb 23 — Mar 21
Mon 2/23
Mon 3/2
1 adult, Economy
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Cheap flight deals from Midway to Anaheim

Cheapest flights from Midway to Anaheim
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 January 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 am
MDW
-
SNA
2 stops11h 25m
Frontier
Thu 2/2612:46 pm
SNA
-
MDW
1 stop8h 55m
Frontier
Deal found 1/23$272
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/87:30 am
MDW
-
SNA
1 stop27h 42m
Frontier
Thu 2/127:25 pm
SNA
-
MDW
1 stop26h 16m
Frontier
Deal found 1/23$273
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
-
SNA
2 stops14h 22m
Frontier
Mon 3/212:36 pm
SNA
-
MDW
1 stop9h 18m
Frontier
Deal found 1/23$274
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:25 am
MDW
-
SNA
2 stops14h 15m
Frontier
Sun 3/17:10 pm
SNA
-
MDW
1 stop26h 44m
Frontier
Deal found 1/23$275
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/203:00 pm
MDW
-
SNA
2 stops23h 25m
Multiple Airlines
Fri 2/2712:36 pm
SNA
-
MDW
1 stop9h 05m
Multiple Airlines
Deal found 1/23$276
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/1111:25 am
MDW
-
SNA
2 stops11h 32m
Multiple Airlines
Fri 3/205:54 pm
SNA
-
MDW
1 stop26h 51m
Multiple Airlines
Deal found 1/22$282
This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
Fri 3/62:16 pm
MDW
-
SNA
1 stop19h 39m
Multiple Airlines
Tue 3/104:37 pm
SNA
-
MDW
2 stops15h 48m
Multiple Airlines
Deal found 1/22$288
This Southwest deal was found by Cheapflights users on 1/22. 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 3/1112:25 pm
MDW
-
SNA
1 stop8h 30m
Southwest
Sat 3/219:10 pm
SNA
-
MDW
1 stop6h 25m
Southwest
Deal found 1/22$289
This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
Tue 3/244:33 pm
MDW
-
SNA
2 stops18h 22m
Frontier
Mon 3/302:23 pm
SNA
-
MDW
1 stop7h 12m
Frontier
Deal found 1/22$291
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
-
SNA
2 stops14h 22m
Frontier
Thu 2/2612:46 pm
SNA
-
MDW
1 stop8h 55m
Frontier
Deal found 1/23$293
This Southwest deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:45 am
MDW
-
SNA
1 stop7h 50m
Southwest
Tue 2/246:45 am
SNA
-
MDW
2 stops10h 00m
Southwest
Deal found 1/23$294
This Southwest deal was found by Cheapflights users on 1/22. 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 4/410:15 am
MDW
-
SNA
2 stops10h 40m
Southwest
Thu 4/99:10 pm
SNA
-
MDW
1 stop5h 50m
Southwest
Deal found 1/22$300

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 January 24, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$273
(Kiwi.com)

One-way from

$173
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$477
Provider with most accurate pricing for Chicago (CHI)-Los Angeles flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Los Angeles flights.
Search Deals
From Chicago Midway to Anaheim
Search Deals
One-way flight from Chicago Midway to Anaheim
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 24, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Anaheim that are best for you.

Fly from

Midway

Fly to

Anaheim

Route

Depart

Return

Price

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Wed 2/25

1:49 pm-8:22 pm

1 stop8h 33m

Santa Ana J. Wayne/Orange Cnty

Wed 3/4

12:04 pm-10:31 pm

1 stop8h 27m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Wed 3/25

4:00 pm-10:15 pm

1 stop8h 15m

Santa Ana J. Wayne/Orange Cnty

Mon 3/30

1:55 pm-11:40 pm

1 stop7h 45m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Wed 3/4

2:10 pm-7:35 pm

1 stop7h 25m

Santa Ana J. Wayne/Orange Cnty

Sat 3/7

3:50 pm-12:10 am

1 stop6h 20m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 4/18

2:12 pm-8:50 pm

1 stop8h 38m

Santa Ana J. Wayne/Orange Cnty

Fri 4/24

9:45 pm-9:56 am

1 stop10h 11m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 3/6

5:40 pm-9:55 pm

1 stop6h 15m

Santa Ana J. Wayne/Orange Cnty

Tue 3/10

7:30 pm-5:00 am

1 stop7h 30m

$323

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 3/6

5:00 am-9:50 am

1 stop6h 50m

Santa Ana J. Wayne/Orange Cnty

Mon 3/9

9:10 pm-5:00 am

1 stop5h 50m

$323

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sun 2/15

4:15 pm-9:05 pm

1 stop6h 50m

Santa Ana J. Wayne/Orange Cnty

Wed 2/18

7:30 am-5:15 pm

1 stop7h 45m

$323

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 3/6

5:00 am-11:05 am

1 stop8h 05m

Santa Ana J. Wayne/Orange Cnty

Sat 3/7

9:10 pm-5:35 am

1 stop6h 25m

$323

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Tue 2/24

12:45 pm-8:10 pm

1 stop9h 25m

Santa Ana J. Wayne/Orange Cnty

Wed 3/4

12:04 pm-10:31 pm

1 stop8h 27m

$324

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 3/20

2:05 pm-8:56 pm

1 stop8h 51m

Santa Ana J. Wayne/Orange Cnty

Wed 3/25

6:45 am-4:55 pm

1 stop8h 10m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 21 results
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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.
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

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 $122). 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 January 24, 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 9% on your trip compared to booking a flight in the afternoon.

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 January 17, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Anaheim flight should consider departing on Tuesday afternoons 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 January 24, 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.
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • How long is the flight from Chicago Midway Airport to Anaheim?

    Airlines like Delta and Southwest fly from Chicago Midway Airport to Anaheim in about 8h 15m. The time it takes to get you to your destination can typically vary by up to 18m. Chicago Midway Airport and Anaheim are separated by a distance of 1727 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Anaheim that include hotel bookings?

    Yes. In addition to deals on Midway to Anaheim flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Anaheim?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Anaheim.

  • Can I find deals for business class flights from Midway to Anaheim?

    Yes. Cheapflights offers flight deals from Midway to Anaheim by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $122). 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.

See more FAQs

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Alternative routes for Midway to Anaheim

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Midway to Anaheim

Discover the top 4 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 January 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$57Average$200FlexibilityNo cancel feeOn-time65%
FrontierCheapest$130Average$272FlexibilityNo cancel feeOn-time62%
DeltaCheapest$183Average$321FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$213Average$411FlexibilityNo cancel feeOn-time63%

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