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Midway

$118+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap 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 February 21, 2026.

This Frontier deal was found by Cheapflights users on 2/20. 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.
Sat 3/219:50 am
SNA
-
MDW
1 stop10h 55m
Frontier
Fri 3/2710:36 pm
MDW
-
SNA
1 stop12h 19m
Frontier
Deal found 2/20$270
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 3/232:23 pm
SNA
-
MDW
1 stop6h 22m
Multiple Airlines
Mon 3/3010:36 pm
MDW
-
SNA
2 stops24h 37m
Multiple Airlines
Deal found 2/20$284
This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:15 pm
SNA
-
MDW
1 stop7h 30m
Southwest
Tue 4/2110:20 am
MDW
-
SNA
1 stop7h 20m
Southwest
Deal found 2/18$289
This Expedia deal was found by Cheapflights users on 2/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/203:00 pm
SNA
-
MDW
1 stop5h 45m
Frontier
Fri 3/2710:36 pm
MDW
-
SNA
1 stop12h 19m
Frontier
Deal found 2/20$290
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/149:50 am
SNA
-
MDW
1 stop10h 55m
Frontier
Sun 3/294:02 pm
MDW
-
SNA
1 stop18h 48m
Frontier
Deal found 2/17$291
This Southwest deal was found by Cheapflights users on 2/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:10 pm
SNA
-
MDW
1 stop9h 30m
Southwest
Wed 5/65:30 pm
MDW
-
SNA
1 stop6h 20m
Southwest
Deal found 2/17$294
This Southwest deal was found by Cheapflights users on 2/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/138:45 pm
SNA
-
MDW
1 stop7h 00m
Southwest
Tue 3/175:55 am
MDW
-
SNA
2 stops8h 15m
Southwest
Deal found 2/17$299
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/512:46 pm
SNA
-
MDW
1 stop9h 05m
Frontier
Sun 3/82:16 pm
MDW
-
SNA
1 stop20h 34m
Frontier
Deal found 2/19$302
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sat 3/219:50 am
SNA
-
MDW
1 stop10h 55m
Frontier
Tue 3/244:33 pm
MDW
-
SNA
2 stops18h 22m
Frontier
Deal found 2/20$303
This Southwest deal was found by Cheapflights users on 2/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:30 pm
SNA
-
MDW
1 stop7h 30m
Southwest
Tue 3/245:55 am
MDW
-
SNA
2 stops8h 15m
Southwest
Deal found 2/17$304
This Delta deal was found by Cheapflights users on 2/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:54 am
SNA
-
MDW
1 stop8h 34m
Delta
Sun 4/196:00 am
MDW
-
SNA
1 stop8h 01m
Delta
Deal found 2/17$309
This Southwest deal was found by Cheapflights users on 2/19. 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.
Sat 5/306:10 pm
SNA
-
MDW
1 stop9h 30m
Southwest
Wed 6/36:10 am
MDW
-
SNA
1 stop6h 25m
Southwest
Deal found 2/19$311

Find 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 February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$270
(Frontier)

One-way from

$118
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$424
Provider with most accurate pricing for Santa Ana J. Wayne/Orange Cnty-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Santa Ana J. Wayne/Orange Cnty-Chicago Midway flights.
Search Deals
From Santa Ana J. Wayne/Orange Cnty to Chicago Midway
Search Deals
One-way flight from Santa Ana J. Wayne/Orange Cnty to Chicago Midway
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 21, 2026.
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

Fri 3/13

8:10 pm-5:00 am

1 stop6h 50m

Chicago Midway

Tue 3/17

1:55 pm-7:40 pm

1 stop7h 45m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

8:00 am-6:36 pm

1 stop8h 36m

Chicago Midway

Sat 4/18

6:00 am-12:01 pm

1 stop8h 01m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 5/2

6:10 pm-5:40 am

1 stop9h 30m

Chicago Midway

Wed 5/6

5:30 pm-9:50 pm

1 stop6h 20m

$294

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Mon 5/4

3:50 pm-11:40 pm

1 stop5h 50m

Chicago Midway

Wed 5/6

5:30 pm-9:50 pm

1 stop6h 20m

$294

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 4/30

7:40 pm-5:00 am

1 stop7h 20m

Chicago Midway

Fri 5/1

4:10 pm-8:20 pm

1 stop6h 10m

$294

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/8

6:45 am-4:35 pm

2 stops7h 50m

Chicago Midway

Tue 4/14

5:30 pm-9:50 pm

1 stop6h 20m

$299

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 3/25

7:30 pm-5:00 am

1 stop7h 30m

Chicago Midway

Tue 3/31

5:55 am-12:10 pm

2 stops8h 15m

$304

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Mon 4/13

7:40 pm-5:00 am

1 stop7h 20m

Chicago Midway

Thu 4/16

5:15 pm-9:55 pm

1 stop6h 40m

$323

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 3/4

10:25 am-9:05 pm

1 stop8h 40m

Chicago Midway

Tue 3/10

4:00 pm-10:15 pm

1 stop8h 15m

$324

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

12:55 pm-9:00 pm

1 stop6h 05m

Chicago Midway

Sat 4/18

10:15 am-5:45 pm

2 stops9h 30m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 20 results
1
2

Compare providers for flights from Santa Ana to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Santa Ana to Midway in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Santa Ana-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Santa Ana-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Santa Ana-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Santa Ana-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Santa Ana-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $110). Flying from Santa Ana to Chicago Midway Airport in December is currently the most expensive (average of $229). 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.

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 February 21, 2026.
Read through reviews of airlines operating flights from Santa Ana to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,298 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,298 reviews
Southwest
8.0
Very good
4,298 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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. 1 airline has 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 and Delta can get you from Santa Ana to Chicago Midway Airport in just under 6h 50m. Your travel time can differ by up to 1h 46m. The distance from Santa Ana to Chicago Midway Airport is about 1727 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Santa Ana to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Santa Ana to Chicago Midway Airport round-trip from $288. Users have found that Southwest is 43% 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 $110). Flying from Santa Ana to Chicago Midway Airport in December is currently the most expensive (average of $229). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Santa Ana to Midway

Discover the top airline 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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$446FlexibilityNo cancel feeOn-time63%

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