MDW

$127 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 2/23. 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
$275
Overall average: $1,066
Multiple Airlines
Sat 3/14Mon 3/16
SNA - MDW • 1 stop
Cheapest non-stop
$405
Southwest
Tue 7/21Tue 7/28
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

Sat, Mar 14 - Mon, Mar 16
Multiple Airlines Logo
9:50 am - 10:45 pm
SNA
-
MDW
10h 55m
1 stop
Multiple Airlines Logo
9:51 pm - 3:38 pm
MDW
-
SNA
19h 47m
2 stops
$275Multiple Airlines
Sat, Mar 14 - Wed, Mar 18
Multiple Airlines Logo
9:50 am - 10:45 pm
SNA
-
MDW
10h 55m
1 stop
Multiple Airlines Logo
11:25 am - 8:56 pm
MDW
-
SNA
11h 31m
2 stops
$280Multiple Airlines
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
10:35 am - 9:05 pm
SNA
-
MDW
8h 30m
1 stop
Southwest Logo
3:40 pm - 7:50 pm
MDW
-
SNA
6h 10m
1 stop
$289Southwest
Thu, Feb 12 - Mon, Feb 16
Multiple Airlines Logo
12:46 pm - 11:41 pm
SNA
-
MDW
8h 55m
1 stop
Multiple Airlines Logo
8:58 pm - 12:25 pm
MDW
-
SNA
41h 27m
2 stops
$291Multiple Airlines
Wed, Mar 4 - Mon, Mar 9
Southwest Logo
11:05 am - 8:40 pm
SNA
-
MDW
7h 35m
2 stops
Southwest Logo
12:20 pm - 7:10 pm
MDW
-
SNA
8h 50m
1 stop
$294Southwest
Sat, Mar 14 - Mon, Mar 16
Multiple Airlines Logo
9:50 am - 10:45 pm
SNA
-
MDW
10h 55m
1 stop
Multiple Airlines Logo
9:51 pm - 3:38 pm
MDW
-
SNA
19h 47m
2 stops
$303Multiple Airlines
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
1:45 pm - 10:20 pm
SNA
-
MDW
6h 35m
1 stop
Southwest Logo
9:55 am - 6:20 pm
MDW
-
SNA
10h 25m
2 stops
$304Southwest
Fri, Mar 6 - Sun, Mar 8
Frontier Logo
2:34 pm - 10:41 pm
SNA
-
MDW
6h 07m
1 stop
Frontier Logo
2:16 pm - 8:50 am
MDW
-
SNA
20h 34m
1 stop
$307Frontier
Mon, Mar 30 - Sat, Apr 4
Delta Logo
8:00 am - 6:40 pm
SNA
-
MDW
8h 40m
1 stop
Delta Logo
2:05 pm - 8:56 pm
MDW
-
SNA
8h 51m
1 stop
$309Delta
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
12:00 pm - 9:50 pm
SNA
-
MDW
7h 50m
2 stops
Southwest Logo
5:55 am - 1:50 pm
MDW
-
SNA
9h 55m
1 stop
$314Southwest
Useful Info

Good to know

Low seasonDecember
Cheapest flight$132
Best time to beat the crowds but there is an average 11% increase 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 4267 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

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

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on your arrival and departure airports