MDW

$111 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 3/4. 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
$273
Overall average: $1,066
Multiple Airlines
Mon 3/30Thu 4/2
SNA - MDW • 1 stop
Cheapest non-stop
$328
Southwest
Tue 3/10Tue 3/17
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

Mon, Mar 30 - Thu, Apr 2
Multiple Airlines Logo
2:23 pm - 11:39 pm
SNA
-
MDW
7h 16m
1 stop
Multiple Airlines Logo
5:11 pm - 9:53 am
MDW
-
SNA
18h 42m
2 stops
$273Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
8:10 am - 4:55 pm
SNA
-
MDW
6h 45m
2 stops
Southwest Logo
1:20 pm - 8:20 pm
MDW
-
SNA
9h 00m
1 stop
$274Southwest
Thu, May 14 - Mon, May 18
Multiple Airlines Logo
7:45 am - 10:21 pm
SNA
-
MDW
12h 36m
2 stops
Multiple Airlines Logo
6:15 am - 1:44 pm
MDW
-
SNA
9h 29m
1 stop
$277Multiple Airlines
Wed, Mar 11 - Wed, Mar 18
Southwest Logo
7:30 am - 4:40 pm
SNA
-
MDW
7h 10m
2 stops
Southwest Logo
5:55 am - 12:10 pm
MDW
-
SNA
8h 15m
2 stops
$279Southwest
Fri, Feb 27 - Sun, Mar 1
Frontier Logo
12:36 pm - 11:41 pm
SNA
-
MDW
9h 05m
1 stop
Frontier Logo
3:21 pm - 8:13 am
MDW
-
SNA
18h 52m
2 stops
$288Frontier
Fri, Apr 17 - Mon, Apr 20
Delta Logo
8:00 am - 6:36 pm
SNA
-
MDW
8h 36m
1 stop
Delta Logo
2:12 pm - 8:57 pm
MDW
-
SNA
8h 45m
1 stop
$289Delta
Mon, Mar 30 - Fri, Apr 3
Multiple Airlines Logo
2:23 pm - 11:39 pm
SNA
-
MDW
7h 16m
1 stop
Multiple Airlines Logo
5:11 pm - 9:53 am
MDW
-
SNA
18h 42m
2 stops
$292Multiple Airlines
Mon, Mar 9 - Tue, Mar 17
Southwest Logo
9:10 pm - 5:00 am
SNA
-
MDW
5h 50m
1 stop
Southwest Logo
1:55 pm - 7:40 pm
MDW
-
SNA
7h 45m
1 stop
$293Southwest
Sun, Mar 8 - Wed, Mar 11
Southwest Logo
9:05 pm - 5:45 am
SNA
-
MDW
6h 40m
1 stop
Southwest Logo
5:55 am - 12:10 pm
MDW
-
SNA
8h 15m
2 stops
$294Southwest
Mon, Mar 9 - Wed, Mar 11
Southwest Logo
7:55 pm - 5:00 am
SNA
-
MDW
7h 05m
1 stop
Southwest Logo
5:55 am - 12:10 pm
MDW
-
SNA
8h 15m
2 stops
$298Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$111
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 1% 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 4280 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

2.0 MediocreDavid, Feb 2026
SAN - LAS
Read more Southwest reviews

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

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.

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

Chicago Midway Airport (MDW)