MDW

$148 Find Cheap Flights from Orange County to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 1/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

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Everything you should know

Cheapest round-trip
$287
Overall average: $333
Multiple Airlines
Thu 2/12Tue 2/17
SNA - MDW • 1 stop
Cheapest non-stop
$414
Southwest
Mon 4/13Fri 4/17
LGB - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Orange County to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Orange County to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Orange County to Midway

Thu, Feb 12 - Tue, Feb 17
Multiple Airlines Logo
12:46 pm - 11:41 pm
SNA
-
MDW
8h 55m1 stop
Multiple Airlines Logo
6:00 am - 8:57 pm
MDW
-
SNA
16h 57m2 stops
$287Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
Southwest Logo
2:15 pm - 9:50 pm
SNA
-
MDW
5h 35m1 stop
Southwest Logo
5:20 am - 12:05 pm
MDW
-
SNA
8h 45m1 stop
$289Southwest
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
7:30 am - 4:40 pm
SNA
-
MDW
7h 10m1 stop
Southwest Logo
8:25 am - 1:40 pm
MDW
-
SNA
7h 15m1 stop
$291Southwest
Fri, Feb 13 - Fri, Mar 13
Frontier Logo
12:36 pm - 11:41 pm
SNA
-
MDW
9h 05m1 stop
Frontier Logo
2:16 pm - 8:55 am
MDW
-
SNA
20h 39m1 stop
$293Frontier
Thu, Jan 22 - Tue, Jan 27
Southwest Logo
11:00 am - 7:55 pm
SNA
-
MDW
6h 55m1 stop
Southwest Logo
1:55 pm - 7:50 pm
MDW
-
SNA
7h 55m2 stops
$294Southwest
Fri, Mar 13 - Wed, Mar 18
Multiple Airlines Logo
3:00 pm - 10:45 pm
SNA
-
MDW
29h 45m1 stop
Multiple Airlines Logo
11:55 am - 8:56 pm
MDW
-
SNA
11h 01m2 stops
$297Multiple Airlines
Sat, Jan 24 - Wed, Jan 28
Southwest Logo
6:45 am - 4:30 pm
SNA
-
MDW
7h 45m2 stops
Southwest Logo
1:55 pm - 7:50 pm
MDW
-
SNA
7h 55m2 stops
$299Southwest
Mon, Feb 16 - Fri, Mar 13
Frontier Logo
12:36 pm - 11:44 pm
SNA
-
MDW
9h 08m1 stop
Frontier Logo
2:16 pm - 8:55 am
MDW
-
SNA
20h 39m1 stop
$310Frontier
Thu, Feb 12 - Mon, Feb 16
Southwest Logo
1:50 pm - 10:15 pm
SNA
-
MDW
6h 25m1 stop
Southwest Logo
8:00 am - 1:55 pm
MDW
-
SNA
7h 55m1 stop
$323Southwest
Wed, Jan 14 - Sat, Jan 17
Southwest Logo
3:05 pm - 10:40 pm
SNA
-
MDW
5h 35m1 stop
Southwest Logo
4:05 pm - 8:15 pm
MDW
-
SNA
6h 10m1 stop
$325Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$148
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from John Wayne (Santa Ana) to Chicago Midway Airport

FAQs for booking Orange County to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Orange County to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Orange County to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Orange County to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Orange County is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Orange County to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Orange County with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Orange County to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Orange County up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Orange County to Midway

 
Need help choosing which airline to fly with from Orange County to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4251 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
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Chesterton
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Munster
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Everything you need to know for your flight to Midway

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