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$106+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midway to Anaheim

Keep the following information in mind while searching for Midway to Anaheim flight deals. Data was last updated August 18, 2025.

Round-trip from

$249
(CheapOair)

One-way from

$106
(CheapOair)

Popular in

June

Cheapest in

November

Average price

$288
From Chicago Midway to Anaheim
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One-way flight from Chicago Midway to Anaheim
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Highest demand for flights based on searches. 12% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 18, 2025.

This CheapOair deal was found by Cheapflights users on 8/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:00 amMDW - SNA
1 stop7h 57mFrontier
Sun 8/2411:58 amSNA - MDW
1 stop10h 47mFrontier
Deal found 8/16$247
This CheapOair deal was found by Cheapflights users on 8/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/54:48 pmMDW - SNA
1 stop21h 25mFrontier
Sun 9/711:52 amSNA - MDW
1 stop26h 01mFrontier
Deal found 8/16$249
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:00 amMDW - SNA
1 stop7h 57mFrontier
Mon 8/2512:09 pmSNA - MDW
1 stop10h 15mFrontier
Deal found 8/17$251
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 9/193:48 pmMDW - SNA
1 stop22h 25mFrontier
Sun 9/213:07 pmSNA - MDW
2 stops22h 46mFrontier
Deal found 8/18$253
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2410:35 amMDW - SNA
1 stop10h 04mDelta
Thu 11/2712:10 pmSNA - MDW
1 stop7h 34mDelta
Deal found 8/16$257
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/111:53 pmMDW - SNA
1 stop26h 51mFrontier
Sun 9/1411:52 amSNA - MDW
1 stop26h 01mFrontier
Deal found 8/16$258
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 10/34:48 pmMDW - SNA
1 stop21h 25mFrontier
Fri 10/101:06 pmSNA - MDW
2 stops9h 18mFrontier
Deal found 8/18$267
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/51:53 pmMDW - SNA
1 stop22h 03mFrontier
Thu 10/912:01 pmSNA - MDW
1 stop10h 35mFrontier
Deal found 8/17$273
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:24 pmMDW - SNA
1 stop21h 11mFrontier
Sun 10/2612:01 pmSNA - MDW
1 stop10h 35mFrontier
Deal found 8/18$274
This Southwest deal was found by Cheapflights users on 8/15. 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 9/97:25 amMDW - SNA
1 stop6h 50mSouthwest
Tue 9/167:30 amSNA - MDW
1 stop7h 40mSouthwest
Deal found 8/15$277

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 August 18, 2025.
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

Fri 9/5

4:48 pm-12:13 pm

1 stop21h 25m

Santa Ana J. Wayne/Orange Cnty

Sun 9/7

11:52 am-3:53 pm

1 stop26h 01m

$249

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 9/19

3:48 pm-12:13 pm

1 stop22h 25m

Santa Ana J. Wayne/Orange Cnty

Sun 9/21

3:07 pm-3:53 pm

2 stops22h 46m

$253

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Mon 11/24

10:35 am-6:39 pm

1 stop10h 04m

Santa Ana J. Wayne/Orange Cnty

Thu 11/27

12:10 pm-9:44 pm

1 stop7h 34m

$257

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 9/11

1:53 pm-2:44 pm

1 stop26h 51m

Santa Ana J. Wayne/Orange Cnty

Sun 9/14

11:52 am-3:53 pm

1 stop26h 01m

$258

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 10/17

6:24 pm-1:35 pm

1 stop21h 11m

Santa Ana J. Wayne/Orange Cnty

Sun 10/19

7:52 pm-9:46 pm

1 stop23h 54m

$258

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 10/17

9:44 am-8:13 pm

2 stops12h 29m

Santa Ana J. Wayne/Orange Cnty

Sun 10/26

12:01 pm-12:36 am

1 stop10h 35m

$260

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 10/3

4:48 pm-12:13 pm

1 stop21h 25m

Santa Ana J. Wayne/Orange Cnty

Fri 10/10

1:06 pm-12:24 am

2 stops9h 18m

$267

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Wed 11/26

2:00 pm-8:39 pm

1 stop8h 39m

Santa Ana J. Wayne/Orange Cnty

Thu 11/27

12:10 pm-9:44 pm

1 stop7h 34m

$273

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 11/21

2:00 pm-8:39 pm

1 stop8h 39m

Santa Ana J. Wayne/Orange Cnty

Thu 11/27

12:10 pm-9:44 pm

1 stop7h 34m

$273

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sun 10/5

1:53 pm-9:56 am

1 stop22h 03m

Santa Ana J. Wayne/Orange Cnty

Thu 10/9

12:01 pm-12:36 am

1 stop10h 35m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 18 results
1
2

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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Anaheim (average of $298). Flying from Chicago Midway Airport to Anaheim in March is currently the most expensive (average of $377). 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 August 18, 2025.

When flying from Chicago Midway Airport to Anaheim, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 10, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Anaheim flight should consider departing on Thursday mornings when fares are most often at their lowest. Tuesday mornings 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 August 18, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Anaheim, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

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.
Frontier
5.8
Fair
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

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 Frontier and Delta fly from Chicago Midway Airport to Anaheim in about 10h 04m. The time it takes to get you to your destination can typically vary by up to 11h 21m. 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Anaheim (average of $298). Flying from Chicago Midway Airport to Anaheim in March is currently the most expensive (average of $377). 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

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$204FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$229FlexibilityNo cancel feeOn-time62%
DeltaCheapest$192Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$204Average$415FlexibilityNo cancel feeOn-time63%

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