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Midway

$112+ Cheap flights from Orange County 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Orange County to Midway

Keep the following information in mind while searching for Orange County to Midway flight deals. Data was last updated August 18, 2025.

Round-trip from

$276
(Frontier)

One-way from

$112
(Priceline)

Popular in

December

Cheapest in

February

Average price

$283
From Orange County to Chicago Midway
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One-way flight from Orange County to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Orange County to Midway

Cheapest flights from Orange County to Midway
Explore the most affordable flight options available from Orange County to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Frontier deal was found by Cheapflights users on 8/16. 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 10/912:01 pmSNA - MDW
1 stop10h 35mFrontier
Mon 10/135:10 amMDW - SNA
2 stops15h 58mFrontier
Deal found 8/16$276
This Delta deal was found by Cheapflights users on 8/16. 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.
Tue 9/912:03 pmSNA - MDW
1 stop7h 23mDelta
Wed 9/106:00 amMDW - SNA
1 stop8h 42mDelta
Deal found 8/16$277
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:52 amSNA - MDW
1 stop26h 01mFrontier
Sun 9/141:53 pmMDW - SNA
1 stop22h 03mFrontier
Deal found 8/16$280
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:01 pmSNA - MDW
1 stop10h 23mFrontier
Mon 10/135:10 amMDW - SNA
2 stops15h 58mFrontier
Deal found 8/17$282
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1612:13 pmSNA - MDW
1 stop7h 23mDelta
Sat 9/201:43 pmMDW - SNA
1 stop8h 44mDelta
Deal found 8/18$283
This Southwest deal was found by Cheapflights users on 8/16. 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 9/276:45 amSNA - MDW
2 stops7h 50mSouthwest
Wed 10/16:10 amMDW - SNA
1 stop5h 40mSouthwest
Deal found 8/16$288
This Southwest deal was found by Cheapflights users on 8/15. 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 9/512:15 pmSNA - MDW
1 stop6h 20mSouthwest
Sun 9/78:20 amMDW - SNA
1 stop6h 10mSouthwest
Deal found 8/15$289
This Southwest deal was found by Cheapflights users on 8/16. 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 11/74:20 pmSNA - MDW
1 stop6h 30mSouthwest
Mon 11/104:40 pmMDW - SNA
2 stops7h 35mSouthwest
Deal found 8/16$294
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/1611:20 amLGB - MDW
Nonstop3h 55mSouthwest
Tue 9/239:20 amMDW - LGB
Nonstop4h 15mSouthwest
Deal found 8/18$297
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:58 pmSNA - MDW
2 stops11h 23mFrontier
Mon 10/206:20 amMDW - SNA
2 stops15h 53mFrontier
Deal found 8/17$301
This Frontier deal was found by Cheapflights users on 8/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:01 pmSNA - MDW
1 stop10h 35mFrontier
Sun 10/199:26 pmMDW - SNA
2 stops15h 50mFrontier
Deal found 8/18$305
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/911:20 amLGB - MDW
Nonstop3h 55mSouthwest
Fri 9/1211:20 amMDW - LGB
Nonstop4h 15mSouthwest
Deal found 8/18$307

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orange County 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 August 18, 2025.
Use the filters below to find and compare flights from Orange County to Chicago Midway Airport that are best for you.

Fly from

Orange County

Fly to

Midway

Route

Depart

Return

Price

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

Mon 10/13

5:10 am-7:08 pm

2 stops15h 58m

$276

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 9/9

12:03 pm-9:26 pm

1 stop7h 23m

Chicago Midway

Wed 9/10

6:00 am-12:42 pm

1 stop8h 42m

$277

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 10/22

9:20 am-5:00 pm

1 stop5h 40m

Chicago Midway

Tue 10/28

6:25 am-12:05 pm

1 stop7h 40m

$277

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 9/24

8:00 am-5:35 pm

1 stop7h 35m

Chicago Midway

Tue 9/30

6:00 am-11:03 am

1 stop7h 03m

$277

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 9/16

12:13 pm-9:36 pm

1 stop7h 23m

Chicago Midway

Tue 9/23

6:00 am-11:03 am

1 stop7h 03m

$277

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 9/11

11:52 am-3:53 pm

1 stop26h 01m

Chicago Midway

Sun 9/14

1:53 pm-9:56 am

1 stop22h 03m

$280

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 9/16

6:45 am-3:55 pm

2 stops7h 10m

Chicago Midway

Tue 9/23

2:15 pm-7:20 pm

1 stop7h 05m

$282

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 10/10

12:01 pm-12:24 am

1 stop10h 23m

Chicago Midway

Mon 10/13

5:10 am-7:08 pm

2 stops15h 58m

$282

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Tue 9/16

11:20 am-5:15 pm

Nonstop3h 55m

Chicago Midway

Tue 9/23

9:20 am-11:35 am

Nonstop4h 15m

$297

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Wed 10/1

1:00 pm-9:30 pm

1 stop6h 30m

Chicago Midway

Wed 10/15

1:50 pm-4:10 pm

Nonstop4h 20m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 31 results
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Best time to book a flight from Orange County to Midway

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

What is the cheapest month to book a flight from Orange County to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Orange County to Chicago Midway Airport (average of $160). Flying from Orange County 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 KFI to MDW?

Find hourly flight availability from Orange County 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 August 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Orange County to Chicago Midway Airport as you normally would.

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 August 18, 2025.
Peruse reviews from past customers who have flown with Southwest and Frontier from Orange County to Chicago Midway Airport to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

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 Orange County to Midway. 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 Orange County to Chicago Midway Airport?

    Frontier, Delta, and Southwest can get you from Orange County to Chicago Midway Airport in just under 5h 40m. Your travel time can differ by up to 4h 55m. Orange County and Chicago Midway Airport are separated by a distance of 1727 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Orange County to Midway that include hotel bookings?

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

  • How can I find direct flights from Orange County to Midway?

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

  • Can I find deals for business class flights from Orange County to Midway?

    Yes. Cheapflights offers flight deals from Orange County 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 Orange County to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Orange County to Chicago Midway Airport (average of $160). Flying from Orange County 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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Alternative routes for Orange County to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Orange County to Midway

Discover the top 2 airlines that operate flights from Orange County 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$348FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$446FlexibilityNo cancel feeOn-time63%

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