MDW

$164 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 8/20. 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

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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

Wed, Aug 19 - Fri, Aug 21
Southwest Logo
11:10 am - 5:00 pm
LGB
-
MDW
3h 50mnonstop
Southwest Logo
5:00 pm - 7:15 pm
MDW
-
LGB
4h 15mnonstop
$347Southwest
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
11:05 am - 8:05 pm
SNA
-
MDW
7h 00m
1 stop
Southwest Logo
7:10 am - 11:35 am
MDW
-
SNA
6h 25m
1 stop
$348Southwest
Fri, Aug 14 - Sun, Aug 16
Southwest Logo
11:05 am - 8:05 pm
SNA
-
MDW
7h 00m
1 stop
Southwest Logo
7:10 am - 11:35 am
MDW
-
SNA
6h 25m
1 stop
$349Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
6:45 am - 4:00 pm
SNA
-
MDW
7h 15m
2 stops
Southwest Logo
8:00 am - 3:45 pm
MDW
-
SNA
9h 45m
2 stops
$350Southwest
Mon, Aug 17 - Mon, Aug 24
Southwest Logo
8:30 pm - 5:45 am
SNA
-
MDW
7h 15m
1 stop
Southwest Logo
5:00 pm - 9:55 pm
MDW
-
SNA
6h 55m
2 stops
$352Southwest
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
8:00 am - 5:00 pm
SNA
-
MDW
7h 00m
2 stops
Southwest Logo
5:40 am - 11:35 am
MDW
-
SNA
7h 55m
1 stop
$353Southwest
Fri, Aug 28 - Sun, Aug 30
Southwest Logo
6:45 am - 4:50 pm
SNA
-
MDW
8h 05m
2 stops
Southwest Logo
6:30 am - 10:05 am
MDW
-
SNA
5h 35m
1 stop
$354Southwest
Wed, Aug 19 - Fri, Aug 21
Southwest Logo
1:45 pm - 11:20 pm
LGB
-
MDW
7h 35m
1 stop
Southwest Logo
5:00 pm - 7:15 pm
MDW
-
LGB
4h 15mnonstop
$357Southwest
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
7:20 pm - 5:55 am
SNA
-
MDW
8h 35m
1 stop
Southwest Logo
2:15 pm - 8:55 pm
MDW
-
SNA
8h 40m
1 stop
$358Southwest
Thu, Sep 24 - Mon, Sep 28
Delta Logo
6:10 pm - 8:48 am
SNA
-
MDW
12h 38m
2 stops
Delta Logo
2:00 pm - 10:04 pm
MDW
-
SNA
10h 04m
2 stops
$359Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$164
Most popular time to fly and prices are also 11% lower on average.
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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Wifi didn’t work, no service, seats are hard as rocks

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
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)