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Midway

$137+ Cheap flights from Santa Ana, CA (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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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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 November 12, 2025.

This CheapOair deal was found by Cheapflights users on 11/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:01 pmSNA - MDW
1 stop18h 29mFrontier
Mon 11/1712:30 pmMDW - SNA
1 stop27h 00mFrontier
Deal found 11/10$272
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:11 amSNA - MDW
2 stops28h 27mMultiple Airlines
Sun 1/410:50 pmMDW - SNA
1 stop14h 18mMultiple Airlines
Deal found 11/11$277
This CheapOair deal was found by Cheapflights users on 11/11. 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.
Sat 11/152:20 pmSNA - MDW
1 stop19h 10mFrontier
Mon 11/1712:30 pmMDW - SNA
1 stop27h 00mFrontier
Deal found 11/11$282
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/58:00 amSNA - MDW
1 stop8h 18mDelta
Tue 12/96:00 amMDW - SNA
1 stop7h 35mDelta
Deal found 11/11$289
This Delta deal was found by Cheapflights users on 11/11. 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.
Thu 11/2712:45 pmSNA - MDW
1 stop8h 55mDelta
Sat 12/611:05 amMDW - SNA
1 stop9h 30mDelta
Deal found 11/11$290
This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 12/47:30 amSNA - MDW
2 stops7h 45mSouthwest
Sun 12/76:05 pmMDW - SNA
1 stop6h 10mSouthwest
Deal found 11/11$294
This Southwest deal was found by Cheapflights users on 11/11. 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.
Sat 12/67:10 amSNA - MDW
2 stops7h 30mSouthwest
Mon 12/82:35 pmMDW - SNA
2 stops7h 40mSouthwest
Deal found 11/11$299
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Tue 12/161:35 pmSNA - MDW
2 stops17h 11mFrontier
Tue 12/232:01 pmMDW - SNA
1 stop23h 07mFrontier
Deal found 11/9$307
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2810:35 amSNA - MDW
1 stop10h 46mMultiple Airlines
Thu 1/16:33 pmMDW - SNA
2 stops41h 43mMultiple Airlines
Deal found 11/11$311
This Southwest deal was found by Cheapflights users on 11/11. 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.
Sun 12/144:25 pmSNA - MDW
1 stop6h 00mSouthwest
Thu 12/185:15 pmMDW - SNA
1 stop7h 10mSouthwest
Deal found 11/11$313
This Delta deal was found by Cheapflights users on 11/11. 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.
Fri 12/1212:45 pmSNA - MDW
1 stop9h 02mDelta
Sun 12/146:00 amMDW - SNA
1 stop7h 35mDelta
Deal found 11/11$314

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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$277
(Kiwi.com)

One-way from

$137
(CheapOair)

Popular in

March

Cheapest in

November

Average price

$288
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. 21% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($53 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 12, 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 1/8

8:00 am-6:32 pm

1 stop8h 32m

Chicago Midway

Sat 1/10

11:21 am-8:03 pm

1 stop10h 42m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 12/5

8:30 am-5:15 pm

1 stop6h 45m

Chicago Midway

Thu 12/11

9:40 am-3:35 pm

1 stop7h 55m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 12/5

8:00 am-6:18 pm

1 stop8h 18m

Chicago Midway

Tue 12/9

6:00 am-11:35 am

1 stop7h 35m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 1/9

8:00 am-6:32 pm

1 stop8h 32m

Chicago Midway

Sat 1/10

11:21 am-8:03 pm

1 stop10h 42m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sun 12/14

4:25 pm-12:25 am

1 stop6h 00m

Chicago Midway

Thu 12/18

5:15 pm-10:25 pm

1 stop7h 10m

$313

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 2/19

7:30 pm-5:05 am

1 stop7h 35m

Chicago Midway

Sat 2/21

8:05 am-3:00 pm

1 stop8h 55m

$313

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 1/23

11:59 am-10:26 pm

1 stop8h 27m

Chicago Midway

Sun 1/25

1:49 pm-8:32 pm

1 stop8h 43m

$314

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 12/5

9:45 am-5:10 pm

1 stop5h 25m

$145

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 12/3

12:45 pm-11:47 pm

1 stop9h 02m

$145

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 2/19

7:30 pm-5:05 am

1 stop7h 35m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 17 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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, California-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Santa Ana, California-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Santa Ana, California-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Santa Ana, California-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams 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, California-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, California to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Santa Ana, California to Chicago Midway Airport (average of $110). Flying from Santa Ana, California to Chicago Midway Airport in July is currently the most expensive (average of $209). 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 November 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 60% on flights from Santa Ana, California 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 November 12, 2025.
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
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

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 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, California to Chicago Midway Airport?

    Departing from Santa Ana, California to Chicago Midway Airport will take you 6h 45m. The distance between Santa Ana, California and 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, California to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($288), offers the cheapest pricing from Santa Ana, California to Chicago Midway Airport. Users have found that Southwest is 39% 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, California to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Santa Ana, California to Chicago Midway Airport (average of $110). Flying from Santa Ana, California to Chicago Midway Airport in July is currently the most expensive (average of $209). 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$443FlexibilityNo cancel feeOn-time63%

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