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$116+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SNA
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Kiwi.com)

One-way from

$116
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$344
Provider with most accurate pricing for Chicago (CHI)-Los Angeles flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Los Angeles flights.
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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. 14% potential increase in price ($67 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 October 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/99:00 amMDW - SNA
1 stop9h 27mFrontier
Sun 11/167:11 pmSNA - MDW
1 stop19h 41mFrontier
Deal found 10/12$276
This CheapOair deal was found by Cheapflights users on 10/13. 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 11/139:00 amMDW - SNA
1 stop6h 04mFrontier
Sun 11/1612:01 pmSNA - MDW
1 stop21h 29mFrontier
Deal found 10/13$278
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/243:27 pmMDW - SNA
2 stops22h 13mFrontier
Thu 1/111:20 amSNA - MDW
1 stop6h 05mFrontier
Deal found 10/12$279
This CheapOair deal was found by Cheapflights users on 10/12. 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.
Mon 11/1012:30 pmMDW - SNA
1 stop27h 00mFrontier
Sun 11/1612:01 pmSNA - MDW
1 stop21h 29mFrontier
Deal found 10/12$285
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 10/308:30 amMDW - SNA
1 stop7h 34mMultiple Airlines
Thu 11/66:45 amSNA - MDW
2 stops13h 18mMultiple Airlines
Deal found 10/13$288
This Delta deal was found by Cheapflights users on 10/13. 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 12/61:50 pmMDW - SNA
1 stop8h 28mDelta
Mon 12/86:45 amSNA - MDW
1 stop7h 58mDelta
Deal found 10/13$289
This Delta deal was found by Cheapflights users on 10/13. 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 10/313:00 pmMDW - SNA
1 stop7h 08mDelta
Tue 11/46:45 amSNA - MDW
1 stop7h 29mDelta
Deal found 10/13$290
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 10/308:30 amMDW - SNA
1 stop7h 34mFrontier
Sun 11/28:16 pmSNA - MDW
2 stops13h 14mFrontier
Deal found 10/12$294
This CheapOair deal was found by Cheapflights users on 10/12. 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 10/176:24 pmMDW - SNA
1 stop21h 11mFrontier
Thu 10/2312:01 pmSNA - MDW
1 stop10h 35mFrontier
Deal found 10/12$295
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 10/205:28 pmMDW - SNA
2 stops27h 46mMultiple Airlines
Thu 10/2312:01 pmSNA - MDW
1 stop10h 35mMultiple Airlines
Deal found 10/13$300
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/38:30 amMDW - SNA
1 stop6h 34mMultiple Airlines
Thu 11/66:45 amSNA - MDW
2 stops13h 18mMultiple Airlines
Deal found 10/13$301
This Southwest deal was found by Cheapflights users on 10/13. 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 11/76:05 pmMDW - SNA
1 stop6h 10mSouthwest
Thu 11/136:45 amSNA - MDW
2 stops8h 40mSouthwest
Deal found 10/13$308

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 October 14, 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 12/16

9:40 am-1:25 pm

1 stop5h 45m

Santa Ana J. Wayne/Orange Cnty

Sun 1/11

10:35 am-9:05 pm

1 stop8h 30m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 11/7

5:09 pm-10:28 pm

1 stop7h 19m

Santa Ana J. Wayne/Orange Cnty

Sat 11/8

8:00 am-5:43 pm

1 stop7h 43m

$289

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Wed 12/24

2:35 pm-8:15 pm

2 stops7h 40m

Santa Ana J. Wayne/Orange Cnty

Tue 1/6

2:30 pm-10:50 pm

1 stop6h 20m

$294

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 11/13

5:30 am-12:05 pm

1 stop8h 35m

Santa Ana J. Wayne/Orange Cnty

Sat 11/15

7:10 am-4:40 pm

2 stops7h 30m

$308

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Sun 10/26

6:24 pm-11:16 am

1 stop18h 52m

Santa Ana J. Wayne/Orange Cnty

Thu 10/30

12:01 pm-11:30 am

1 stop21h 29m

$312

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Wed 11/5

9:40 am-3:35 pm

1 stop7h 55m

Santa Ana J. Wayne/Orange Cnty

Fri 11/7

6:45 am-3:30 pm

1 stop6h 45m

$313

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Thu 11/13

9:00 am-1:04 pm

1 stop6h 04m

Santa Ana J. Wayne/Orange Cnty

Thu 11/20

12:04 pm-6:12 pm

1 stop28h 08m

$314

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 10/31

3:00 pm-8:08 pm

1 stop7h 08m

Santa Ana J. Wayne/Orange Cnty

Mon 11/3

12:26 pm-10:14 pm

1 stop7h 48m

$315

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 12/12

6:00 am-1:36 pm

1 stop9h 36m

Santa Ana J. Wayne/Orange Cnty

Sun 12/14

10:42 am-8:36 pm

1 stop7h 54m

$316

ChicagoSanta Ana

MDW - SNA

MDWSNA

Chicago Midway

Fri 12/12

2:45 pm-1:36 pm

2 stops24h 51m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 19 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Anaheim (average of $121). Flying from Chicago Midway Airport to Anaheim in July is currently the most expensive (average of $216). 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 October 14, 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 October 12, 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 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 October 14, 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
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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 5h 45m. The time it takes to get you to your destination can typically vary by up to 1h 34m. 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Anaheim (average of $121). Flying from Chicago Midway Airport to Anaheim in July is currently the most expensive (average of $216). 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 5 airlines flying from Midway to Anaheim

Discover the top 5 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$224FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$235FlexibilityNo cancel feeOn-time62%
DeltaCheapest$183Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$204Average$414FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$309FlexibilityNo cancel feeOn-time71%

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