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Midway

$145+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
SNA — MDW
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$271
(Southwest)

One-way from

$145
(Southwest)

Popular in

December

Cheapest in

September

Average price

$352
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. 12% potential increase in price ($43 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 January 2026
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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 January 8, 2026.

This Southwest deal was found by Cheapflights users on 1/6. 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 1/298:55 amSNA - MDW
2 stops7h 50mSouthwest
Thu 2/55:20 amMDW - SNA
1 stop8h 45mSouthwest
Deal found 1/6$271
This Southwest deal was found by Cheapflights users on 1/8. 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 1/276:45 amSNA - MDW
2 stops10h 00mSouthwest
Wed 1/288:25 amMDW - SNA
1 stop7h 15mSouthwest
Deal found 1/8$272
This Southwest deal was found by Cheapflights users on 1/6. 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.
Mon 1/267:30 amSNA - MDW
1 stop7h 45mSouthwest
Wed 1/288:25 amMDW - SNA
1 stop7h 15mSouthwest
Deal found 1/6$273
This Southwest deal was found by Cheapflights users on 1/6. 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.
Mon 4/208:15 pmSNA - MDW
1 stop7h 30mSouthwest
Thu 4/235:25 amMDW - SNA
1 stop6h 10mSouthwest
Deal found 1/6$277
This Southwest deal was found by Cheapflights users on 1/7. 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 2/67:30 amSNA - MDW
2 stops7h 30mSouthwest
Mon 2/912:50 pmMDW - SNA
1 stop6h 50mSouthwest
Deal found 1/7$278
This Southwest deal was found by Cheapflights users on 1/7. 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 4/16:45 amSNA - MDW
2 stops8h 10mSouthwest
Sat 4/45:55 amMDW - SNA
1 stop6h 05mSouthwest
Deal found 1/7$282
This Southwest deal was found by Cheapflights users on 1/6. 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 1/286:45 amSNA - MDW
1 stop6h 00mSouthwest
Wed 1/284:10 pmMDW - SNA
1 stop6h 50mSouthwest
Deal found 1/6$287
This Southwest deal was found by Cheapflights users on 1/6. 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 1/2411:30 amSNA - MDW
1 stop5h 35mSouthwest
Tue 1/2710:05 amMDW - SNA
1 stop8h 00mSouthwest
Deal found 1/6$288
This Southwest deal was found by Cheapflights users on 1/8. 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 1/307:30 amSNA - MDW
1 stop7h 45mSouthwest
Sun 2/112:55 pmMDW - SNA
1 stop8h 00mSouthwest
Deal found 1/8$289
This Southwest deal was found by Cheapflights users on 1/6. 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 3/48:55 amSNA - MDW
2 stops7h 50mSouthwest
Sun 3/85:55 amMDW - SNA
1 stop6h 10mSouthwest
Deal found 1/6$293
This Southwest deal was found by Cheapflights users on 1/6. 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 2/57:30 pmSNA - MDW
1 stop7h 35mSouthwest
Thu 2/128:00 amMDW - SNA
1 stop7h 55mSouthwest
Deal found 1/6$296
This Southwest deal was found by Cheapflights users on 1/8. 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 4/27:55 pmLGB - MDW
1 stop7h 05mSouthwest
Tue 4/74:30 pmMDW - LGB
Nonstop4h 20mSouthwest
Deal found 1/8$308

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 January 8, 2026.
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

Tue 4/21

7:40 pm-5:25 am

1 stop7h 45m

Chicago Midway

Thu 4/23

4:10 pm-9:35 pm

1 stop7h 25m

$277

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 1/30

7:30 am-5:15 pm

1 stop7h 45m

Chicago Midway

Mon 2/2

1:55 pm-7:50 pm

2 stops7h 55m

$282

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/1

8:10 pm-5:45 am

1 stop7h 35m

Chicago Midway

Sun 4/5

10:00 am-4:10 pm

1 stop8h 10m

$287

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 4/3

8:45 pm-5:45 am

1 stop7h 00m

Chicago Midway

Tue 4/7

12:35 pm-7:05 pm

1 stop8h 30m

$287

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 1/31

7:30 am-6:30 pm

2 stops9h 00m

Chicago Midway

Wed 2/4

8:10 am-4:40 pm

2 stops10h 30m

$288

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 3/28

5:45 pm-5:00 am

1 stop9h 15m

Chicago Midway

Sat 4/4

5:55 am-10:00 am

1 stop6h 05m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 2/6

10:35 am-9:05 pm

1 stop8h 30m

Chicago Midway

Sun 2/8

5:55 am-1:50 pm

1 stop9h 55m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 2/14

7:00 am-5:00 pm

1 stop8h 00m

Chicago Midway

Thu 2/19

4:15 pm-9:05 pm

1 stop6h 50m

$289

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 2/12

6:45 am-4:45 pm

1 stop8h 00m

Chicago Midway

Mon 2/16

8:00 am-1:55 pm

1 stop7h 55m

$296

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Mon 1/26

2:30 pm-10:50 pm

1 stop6h 20m

Chicago Midway

Wed 1/28

9:55 am-6:20 pm

2 stops10h 25m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 40 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.

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 January 8, 2026.
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
4,250 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

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 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?

    Southwest and Delta can get you from Orange County to Chicago Midway Airport in just under 7h 45m. Your travel time can differ by up to 1h 51m. 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
Merrillville
Hammond
Porter
Benton Harbor

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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 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$442FlexibilityNo cancel feeOn-time63%

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