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Midway

$131+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
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 October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$273
(Delta)

One-way from

$131
(Frontier)

Popular in

December

Cheapest in

February

Average price

$278
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. 8% potential increase in price ($27 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 October 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 October 2, 2025.

This Delta deal was found by Cheapflights users on 9/30. 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.
Sat 10/258:00 amSNA - MDW
1 stop7h 43mDelta
Wed 10/296:00 amMDW - SNA
1 stop7h 16mDelta
Deal found 9/30$273
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/2012:01 pmSNA - MDW
1 stop10h 23mFrontier
Thu 10/235:20 pmMDW - SNA
2 stops27h 48mFrontier
Deal found 10/1$274
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 11/18:09 pmSNA - MDW
2 stops12h 03mMultiple Airlines
Thu 11/612:30 pmMDW - SNA
1 stop24h 46mMultiple Airlines
Deal found 10/2$276
This CheapOair deal was found by Cheapflights users on 9/30. 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 10/912:01 pmSNA - MDW
1 stop10h 35mFrontier
Sun 10/126:24 pmMDW - SNA
1 stop18h 52mFrontier
Deal found 9/30$278
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/312:49 pmSNA - MDW
1 stop22h 08mFrontier
Thu 11/612:30 pmMDW - SNA
1 stop24h 46mFrontier
Deal found 10/2$281
This Frontier deal was found by Cheapflights users on 9/30. 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.
Mon 10/2012:01 pmSNA - MDW
1 stop10h 23mFrontier
Thu 10/309:43 pmMDW - SNA
2 stops15h 33mFrontier
Deal found 9/30$283
This Southwest deal was found by Cheapflights users on 10/1. 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 10/296:45 amSNA - MDW
1 stop6h 00mSouthwest
Wed 11/55:35 amMDW - SNA
1 stop7h 45mSouthwest
Deal found 10/1$284
This Southwest deal was found by Cheapflights users on 10/2. 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 10/313:30 pmSNA - MDW
1 stop5h 55mSouthwest
Mon 11/312:55 pmMDW - SNA
1 stop7h 55mSouthwest
Deal found 10/2$289
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 11/43:01 pmSNA - MDW
2 stops19h 40mFrontier
Thu 11/612:30 pmMDW - SNA
1 stop24h 46mFrontier
Deal found 10/2$291
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 11/27:11 pmSNA - MDW
2 stops14h 19mFrontier
Thu 11/612:30 pmMDW - SNA
1 stop24h 46mFrontier
Deal found 10/2$293
This Southwest deal was found by Cheapflights users on 10/1. 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 12/46:45 amSNA - MDW
1 stop7h 35mSouthwest
Mon 12/82:35 pmMDW - SNA
2 stops7h 40mSouthwest
Deal found 10/1$294
This Southwest deal was found by Cheapflights users on 9/30. 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 10/3012:00 pmLGB - MDW
Nonstop3h 55mSouthwest
Wed 11/59:35 amMDW - LGB
Nonstop4h 30mSouthwest
Deal found 9/30$314

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 October 2, 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

Wed 10/29

8:00 am-5:43 pm

1 stop7h 43m

Chicago Midway

Sat 11/1

3:00 pm-8:08 pm

1 stop7h 08m

$273

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 10/28

8:00 am-5:43 pm

1 stop7h 43m

Chicago Midway

Sat 11/1

3:00 pm-8:08 pm

1 stop7h 08m

$273

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 10/29

6:45 am-2:45 pm

1 stop6h 00m

Chicago Midway

Wed 11/5

5:35 am-11:20 am

1 stop7h 45m

$284

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 11/14

2:45 pm-10:05 pm

1 stop5h 20m

Chicago Midway

Sun 11/16

6:05 pm-10:15 pm

1 stop6h 10m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 10/31

3:30 pm-11:25 pm

1 stop5h 55m

Chicago Midway

Mon 11/3

12:55 pm-6:50 pm

1 stop7h 55m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 12/4

6:45 am-4:20 pm

1 stop7h 35m

Chicago Midway

Mon 12/8

2:35 pm-8:15 pm

2 stops7h 40m

$294

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 10/28

8:00 am-5:43 pm

1 stop7h 43m

Chicago Midway

Thu 11/6

6:00 am-11:16 am

1 stop7h 16m

$298

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Thu 10/30

12:00 pm-5:55 pm

Nonstop3h 55m

Chicago Midway

Wed 11/5

9:35 am-12:05 pm

Nonstop4h 30m

$314

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Tue 11/4

10:20 am-4:10 pm

Nonstop3h 50m

Chicago Midway

Thu 11/6

7:50 am-10:20 am

Nonstop4h 30m

$314

Long BeachChicago

LGB - MDW

LGBMDW

Long Beach Municipal

Thu 12/4

10:20 am-4:10 pm

Nonstop3h 50m

Chicago Midway

Mon 12/8

9:35 am-12:05 pm

Nonstop4h 30m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 33 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 October 2, 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 October 2, 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
4,248 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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 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 6h. Your travel time can differ by up to 1h 43m. 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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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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$446FlexibilityNo cancel feeOn-time63%

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