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Midway

$117+ Cheap flights from Santa Ana (SNA) to Midway (MDW)

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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Santa Ana to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Santa Ana (SNA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$272
(Southwest)

One-way from

$117
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$450
From Santa Ana J. Wayne/Orange Cnty to Chicago Midway
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One-way flight from Santa Ana J. Wayne/Orange Cnty to Chicago Midway
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Highest demand for flights based on searches. 18% potential increase in price ($114 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Santa Ana to Midway

Cheapest flights from Santa Ana to Midway
Explore the most affordable flight options available from Santa Ana to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 11/1910:30 amSNA - MDW
1 stop6h 45mSouthwest
Wed 11/264:20 pmMDW - SNA
1 stop8h 00mSouthwest
Deal found 9/10$272
This Trip.com deal was found by Cheapflights users on 9/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:45 amSNA - MDW
2 stops39h 39mMultiple Airlines
Sun 10/1912:09 pmMDW - SNA
2 stops35h 54mMultiple Airlines
Deal found 9/9$273
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:01 pmSNA - MDW
1 stop10h 23mMultiple Airlines
Tue 10/148:05 amMDW - SNA
2 stops37h 09mMultiple Airlines
Deal found 9/9$274
This Southwest deal was found by Cheapflights users on 9/10. 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 9/253:25 pmSNA - MDW
1 stop6h 40mSouthwest
Wed 10/18:25 amMDW - SNA
1 stop7h 25mSouthwest
Deal found 9/10$276
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:52 amSNA - MDW
2 stops17h 19mFrontier
Mon 9/299:47 pmMDW - SNA
2 stops16h 26mFrontier
Deal found 9/10$278
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:58 pmSNA - MDW
2 stops11h 23mFrontier
Mon 10/2712:11 pmMDW - SNA
1 stop27h 24mFrontier
Deal found 9/9$288
This Southwest deal was found by Cheapflights users on 9/9. 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.
Fri 10/316:45 amSNA - MDW
1 stop7h 10mSouthwest
Mon 11/35:30 amMDW - SNA
1 stop6h 15mSouthwest
Deal found 9/9$294
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/252:24 pmSNA - MDW
1 stop5h 34mFrontier
Sun 9/286:21 amMDW - SNA
2 stops30h 46mFrontier
Deal found 9/9$296
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/912:01 pmSNA - MDW
1 stop10h 35mMultiple Airlines
Tue 10/148:05 amMDW - SNA
2 stops37h 09mMultiple Airlines
Deal found 9/9$298
This Southwest deal was found by Cheapflights users on 9/10. 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.
Fri 10/316:45 amSNA - MDW
1 stop7h 10mSouthwest
Sat 11/15:05 pmMDW - SNA
1 stop5h 40mSouthwest
Deal found 9/10$303
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:45 amSNA - MDW
2 stops14h 35mMultiple Airlines
Sun 10/266:24 pmMDW - SNA
1 stop18h 52mMultiple Airlines
Deal found 9/10$304

Cheapflights Fare Finder

 
Customize your flight search to find flights from Santa Ana to Midway 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 September 11, 2025.
Use the filters below to find and compare flights from Santa Ana to Chicago Midway Airport that are best for you.

Fly from

Santa Ana

Fly to

Midway

Route

Depart

Return

Price

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 9/25

3:25 pm-12:05 am

1 stop6h 40m

Chicago Midway

Wed 10/1

8:25 am-1:50 pm

1 stop7h 25m

$276

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 2/20

8:50 pm-5:05 am

1 stop6h 15m

Chicago Midway

Sun 2/22

8:00 am-1:55 pm

1 stop7h 55m

$283

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 11/19

6:45 am-5:10 pm

1 stop8h 25m

Chicago Midway

Sat 11/22

3:45 pm-10:25 pm

2 stops8h 40m

$320

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 10/9

12:01 pm-12:36 am

1 stop10h 35m

Chicago Midway

Sat 10/11

5:20 pm-10:03 pm

2 stops30h 43m

$327

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 11/22

8:25 pm-5:05 am

1 stop6h 40m

Chicago Midway

Tue 11/25

5:40 am-11:00 am

1 stop7h 20m

$327

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 10/17

8:35 pm-5:15 am

1 stop6h 40m

Chicago Midway

Mon 10/20

5:25 pm-10:25 pm

1 stop7h 00m

$327

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 9/26

12:13 pm-9:36 pm

1 stop7h 23m

Chicago Midway

Tue 9/30

6:00 am-11:03 am

1 stop7h 03m

$339

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 10/23

8:35 pm-5:15 am

1 stop6h 40m

Chicago Midway

Sun 10/26

9:05 am-2:15 pm

1 stop7h 10m

$339

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 10/10

4:40 pm-12:10 am

1 stop5h 30m

Chicago Midway

Sat 10/25

9:45 am-6:25 pm

2 stops10h 40m

$354

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 9/26

12:13 pm-9:36 pm

1 stop7h 23m

Chicago Midway

Mon 10/6

5:04 pm-10:28 pm

1 stop7h 24m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Santa Ana to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Santa Ana 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 Santa Ana to Chicago Midway Airport

What is the cheapest month to book a flight from Santa Ana to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Santa Ana to Chicago Midway Airport (average of $160). Flying from Santa Ana to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 SNA to MDW?

Find hourly flight availability from Santa Ana to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 61% on flights from Santa Ana to Chicago Midway Airport by exploring options for tickets in the evening.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 11, 2025.
Read through reviews of airlines operating flights from Santa Ana to Chicago Midway Airport, 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
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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 Santa Ana to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Santa Ana to Chicago Midway?

    For a flight from Santa Ana to Chicago Midway, you will be flying from J. Wayne/Orange Cnty. Santa Ana J. Wayne/Orange Cnty (SNA) is just 4.8 mi from the center of the city. J. Wayne/Orange Cnty is the only Santa Ana airport and it handles 0 outbound flights to Chicago Midway per day. 2 airlines have flights to Chicago Midway from Santa Ana J. Wayne/Orange Cnty on a regular basis.

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

    Southwest can get you from Santa Ana to Chicago Midway Airport in just under 6h 40m. Your travel time can differ by up to . The distance from Santa Ana to Chicago Midway Airport is about 1727 mi.

  • What are the cheapest airlines flying from Santa Ana to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Santa Ana to Chicago Midway Airport round-trip from $145. Another airline that can offer you cheap pricing is Southwest. Users have found that Frontier is 71% cheaper than the other options available to this destination.

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

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

  • How can I find direct flights from Santa Ana to Midway?

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

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

    Yes. Cheapflights offers flight deals from Santa Ana to Midway 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 Santa Ana to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Santa Ana to Chicago Midway Airport (average of $160). Flying from Santa Ana to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Santa Ana to Midway

Discover the top 2 airlines that operate flights from Santa Ana to Midway. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$348FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$446FlexibilityNo cancel feeOn-time63%

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