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$156+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This CheapOair deal was found by Cheapflights users on 12/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:15 amMDW - SNA
1 stop11h 40mFrontier
Sat 12/131:35 pmSNA - MDW
1 stop19h 33mFrontier
Deal found 12/9$319
This CheapOair deal was found by Cheapflights users on 12/11. 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 12/126:15 amMDW - SNA
1 stop11h 40mFrontier
Sun 12/1411:15 amSNA - MDW
1 stop21h 53mFrontier
Deal found 12/11$383
This Delta deal was found by Cheapflights users on 12/11. 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 12/131:50 pmMDW - SNA
1 stop8h 28mDelta
Tue 12/168:00 amSNA - MDW
1 stop8h 18mDelta
Deal found 12/11$405
This Southwest deal was found by Cheapflights users on 12/9. 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 12/162:35 pmMDW - SNA
2 stops7h 40mSouthwest
Wed 12/171:10 pmSNA - MDW
1 stop7h 00mSouthwest
Deal found 12/9$410
This Southwest deal was found by Cheapflights users on 12/10. 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 12/185:30 amMDW - SNA
1 stop8h 35mSouthwest
Sun 1/188:25 amSNA - MDW
1 stop6h 50mSouthwest
Deal found 12/10$417
This Delta deal was found by Cheapflights users on 12/11. 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 12/136:00 amMDW - SNA
1 stop7h 35mDelta
Thu 12/1812:45 pmSNA - MDW
1 stop9h 02mDelta
Deal found 12/11$441
This Southwest deal was found by Cheapflights users on 12/11. 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 12/155:25 amMDW - SNA
1 stop7h 35mSouthwest
Wed 12/179:30 amSNA - MDW
2 stops7h 40mSouthwest
Deal found 12/11$446
This Southwest deal was found by Cheapflights users on 12/11. 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 12/233:35 pmMDW - SNA
1 stop8h 20mSouthwest
Fri 12/265:40 pmSNA - MDW
1 stop5h 30mSouthwest
Deal found 12/11$448
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:15 amMDW - SNA
1 stop11h 40mFrontier
Sun 12/2111:52 amSNA - MDW
1 stop7h 58mFrontier
Deal found 12/11$462

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 December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$282
(Kiwi.com)

One-way from

$156
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$485
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.
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From Chicago Midway to Anaheim
Search Deals
One-way flight from Chicago Midway to Anaheim
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 12, 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 1/16

9:09 pm-3:00 pm

1 stop19h 51m

Santa Ana J. Wayne/Orange Cnty

Wed 1/21

4:37 pm-11:45 am

2 stops17h 08m

$282

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 2/26

7:45 am-2:15 pm

1 stop8h 30m

Santa Ana J. Wayne/Orange Cnty

Sun 3/1

7:45 am-6:30 pm

1 stop8h 45m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 1/16

1:49 pm-8:32 pm

1 stop8h 43m

Santa Ana J. Wayne/Orange Cnty

Wed 1/21

8:00 am-6:36 pm

1 stop8h 36m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 3/5

5:05 am-9:35 am

1 stop6h 30m

Santa Ana J. Wayne/Orange Cnty

Sat 3/7

7:00 pm-5:55 am

1 stop8h 55m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 1/17

11:21 am-8:14 pm

1 stop10h 53m

Santa Ana J. Wayne/Orange Cnty

Wed 1/21

8:00 am-6:36 pm

1 stop8h 36m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 4/16

4:10 pm-9:35 pm

1 stop7h 25m

Santa Ana J. Wayne/Orange Cnty

Sun 4/19

8:40 pm-5:45 am

1 stop7h 05m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Tue 1/6

11:21 am-8:04 pm

1 stop10h 43m

Santa Ana J. Wayne/Orange Cnty

Sat 1/10

8:00 am-4:16 pm

1 stop6h 16m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 1/17

8:20 am-3:35 pm

1 stop9h 15m

Santa Ana J. Wayne/Orange Cnty

Wed 1/21

9:00 am-6:50 pm

1 stop7h 50m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sat 2/28

8:00 am-2:15 pm

1 stop8h 15m

Santa Ana J. Wayne/Orange Cnty

Sat 3/14

5:40 pm-5:00 am

1 stop9h 20m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 3/6

3:00 pm-7:35 pm

1 stop6h 35m

Santa Ana J. Wayne/Orange Cnty

Mon 3/9

7:55 pm-5:00 am

1 stop7h 05m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 22 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 $124). 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 December 12, 2025.

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 29% on your trip compared to booking a flight at noon.

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 December 6, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Anaheim flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons 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 December 12, 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
7.9
Good
4,252 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

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
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

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.
Frontier
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,252 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

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 Southwest and Delta fly from Chicago Midway Airport to Anaheim in about 8h 30m. The time it takes to get you to your destination can typically vary by up to 13m. 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 $124). 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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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$204FlexibilityNo cancel feeOn-time65%
FrontierCheapest$130Average$235FlexibilityNo cancel feeOn-time62%
DeltaCheapest$192Average$323FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$413FlexibilityNo cancel feeOn-time63%

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