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Midway

$140+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$271
(Trip.com)

One-way from

$140
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$343
Provider with most accurate pricing for Los Angeles-Chicago (CHI) flight deals.
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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. 9% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 20, 2025.

This Trip.com deal was found by Cheapflights users on 11/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:11 amSNA - MDW
2 stops24h 10mMultiple Airlines
Sun 12/2110:50 pmMDW - SNA
1 stop14h 18mMultiple Airlines
Deal found 11/18$271
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/116:45 amSNA - MDW
2 stops13h 27mMultiple Airlines
Fri 12/126:15 amMDW - SNA
1 stop11h 40mMultiple Airlines
Deal found 11/19$274
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/171:35 pmSNA - MDW
2 stops30h 37mFrontier
Sun 12/2110:50 pmMDW - SNA
1 stop14h 18mFrontier
Deal found 11/18$281
This Southwest deal was found by Cheapflights users on 11/18. 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 12/106:45 amSNA - MDW
1 stop7h 10mSouthwest
Thu 12/115:15 amMDW - SNA
1 stop8h 15mSouthwest
Deal found 11/18$289
This Frontier deal was found by Cheapflights users on 11/20. 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.
Sun 12/710:10 amSNA - MDW
1 stop6h 13mFrontier
Fri 12/126:15 amMDW - SNA
1 stop11h 40mFrontier
Deal found 11/20$292
This Southwest deal was found by Cheapflights users on 11/18. 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.
Fri 12/128:20 pmSNA - MDW
1 stop6h 45mSouthwest
Mon 12/152:35 pmMDW - SNA
2 stops7h 40mSouthwest
Deal found 11/18$294
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:35 pmSNA - MDW
1 stop19h 33mFrontier
Sun 1/410:50 pmMDW - SNA
1 stop14h 18mFrontier
Deal found 11/20$303
This CheapOair deal was found by Cheapflights users on 11/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:15 amSNA - MDW
1 stop21h 53mFrontier
Sun 12/712:18 pmMDW - SNA
1 stop26h 24mFrontier
Deal found 11/18$312
This Southwest deal was found by Cheapflights users on 11/18. 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.
Thu 12/111:10 pmSNA - MDW
1 stop5h 50mSouthwest
Sat 12/132:45 pmMDW - SNA
1 stop7h 20mSouthwest
Deal found 11/18$313
This Delta deal was found by Cheapflights users on 11/19. 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 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 11/19$314
This Southwest deal was found by Cheapflights users on 11/19. 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.
Thu 12/1110:20 amLGB - MDW
Nonstop3h 50mSouthwest
Fri 12/127:50 amMDW - LGB
Nonstop4h 30mSouthwest
Deal found 11/19$317
This Southwest deal was found by Cheapflights users on 11/18. 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.
Sat 12/137:10 amSNA - MDW
2 stops7h 30mSouthwest
Tue 12/162:35 pmMDW - SNA
2 stops7h 40mSouthwest
Deal found 11/18$323

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 November 20, 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 1/8

11:45 am-10:07 pm

1 stop8h 22m

Chicago Midway

Sat 1/10

11:21 am-8:04 pm

1 stop10h 43m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 12/12

9:10 pm-5:05 am

1 stop5h 55m

Chicago Midway

Mon 12/15

2:35 pm-8:05 pm

1 stop7h 30m

$289

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

Sun 1/11

1:49 pm-8:32 pm

1 stop8h 43m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 1/16

2:25 pm-10:25 pm

1 stop6h 00m

Chicago Midway

Tue 1/20

3:40 pm-7:50 pm

1 stop6h 10m

$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-8:04 pm

1 stop10h 43m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sun 12/7

10:10 am-6:23 pm

1 stop6h 13m

Chicago Midway

Fri 12/12

6:15 am-3:55 pm

1 stop11h 40m

$292

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 12/13

7:05 pm-5:05 am

1 stop8h 00m

Chicago Midway

Tue 12/16

2:35 pm-8:15 pm

2 stops7h 40m

$294

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Fri 12/12

12:25 pm-6:15 pm

Nonstop3h 50m

Chicago Midway

Sun 12/14

7:50 am-10:20 am

Nonstop4h 30m

$317

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Sun 1/18

10:10 am-6:50 pm

1 stop6h 40m

Chicago Midway

Thu 1/22

5:05 am-9:25 am

1 stop6h 20m

$362

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Wed 12/10

7:00 am-6:18 pm

2 stops9h 18m

Chicago Midway

Mon 12/15

9:34 am-4:09 pm

2 stops8h 35m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 35 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, February is the cheapest month in which you can book a flight from Orange County to Chicago Midway Airport (average of $147). Flying from Orange County to Chicago Midway Airport in March is currently the most expensive (average of $597). 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 November 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 60% on flights from Orange County 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 20, 2025.
Peruse reviews from past customers who have flown with Southwest 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
4,249 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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?

    Delta and Southwest can get you from Orange County to Chicago Midway Airport in just under 5h 55m. Your travel time can differ by up to 2h 27m. 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, February is the cheapest month in which you can book a flight from Orange County to Chicago Midway Airport (average of $147). Flying from Orange County to Chicago Midway Airport in March is currently the most expensive (average of $597). 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 Orange County to Midway

Discover the top airline 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$443FlexibilityNo cancel feeOn-time63%

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