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$132+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$277
(Delta)

One-way from

$132
(Booking.com)

Popular in

December

Cheapest in

August

Average price

$381
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. 5% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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 8/126:04 amMDW - SNA
1 stop8h 38mDelta
Wed 8/138:00 amSNA - MDW
1 stop7h 37mDelta
Deal found 7/1$277
This Southwest deal was found by Cheapflights users on 7/1. 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 8/142:15 pmMDW - SNA
1 stop5h 30mSouthwest
Tue 8/199:05 amSNA - MDW
1 stop5h 55mSouthwest
Deal found 7/1$280
This FlightHub deal was found by Cheapflights users on 6/30. 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 7/242:44 pmMDW - SNA
1 stop22h 26mFrontier
Sat 7/2611:56 amSNA - MDW
1 stop6h 58mFrontier
Deal found 6/30$282

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 July 1, 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

Tue 8/12

6:04 am-12:42 pm

1 stop8h 38m

Santa Ana J. Wayne/Orange Cnty

Wed 8/13

8:00 am-5:37 pm

1 stop7h 37m

$277

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 8/14

2:15 pm-5:45 pm

1 stop5h 30m

Santa Ana J. Wayne/Orange Cnty

Tue 8/19

9:05 am-5:00 pm

1 stop5h 55m

$280

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 7/24

2:44 pm-11:10 am

1 stop22h 26m

Santa Ana J. Wayne/Orange Cnty

Sat 7/26

11:56 am-8:54 pm

1 stop6h 58m

$282

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Tue 8/12

6:02 pm-11:11 am

2 stops19h 09m

$132

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Tue 8/12

6:04 am-12:42 pm

1 stop8h 38m

$139

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Mon 7/28

5:00 pm-10:15 pm

1 stop7h 15m

$145

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Mon 7/28

9:12 am-11:26 am

2 stops28h 14m

$153

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sun 7/13

8:14 pm-8:46 am

1 stop14h 32m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 July 1, 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 June 29, 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 July 1, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Anaheim, such as Southwest, Delta, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Allegiant Air
7.2
Good
710 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
5.9
Fair
3,291 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.6

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Anaheim one-way?

    One-way options have recently been found by users for as low as $132 on Frontier. Other airlines that offer cheap prices include Delta from $139 and Southwest from $145 one-way.

  • 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.

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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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$261FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$227FlexibilityNo cancel feeOn-time62%
DeltaCheapest$192Average$368FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$209Average$425FlexibilityNo cancel feeOn-time63%

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