MDW

$147 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 4/23. 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

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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, Apr 15 - Sat, Apr 18
Southwest Logo
7:30 pm - 6:00 am
SNA
-
MDW
8h 30m
1 stop
Southwest Logo
10:15 am - 6:10 pm
MDW
-
SNA
9h 55m
1 stop
$319Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
7:30 pm - 6:00 am
SNA
-
MDW
8h 30m
1 stop
Southwest Logo
10:15 am - 5:45 pm
MDW
-
SNA
9h 30m
2 stops
$324Southwest
Thu, May 7 - Sun, May 10
Southwest Logo
8:55 pm - 5:25 am
SNA
-
MDW
6h 30m
1 stop
Southwest Logo
5:10 am - 11:35 am
MDW
-
SNA
8h 25m
1 stop
$329Southwest
Sat, Apr 18 - Fri, Apr 24
Multiple Airlines Logo
7:30 am - 10:14 pm
SNA
-
MDW
12h 44m
2 stops
Multiple Airlines Logo
1:30 pm - 1:44 pm
MDW
-
SNA
26h 14m
1 stop
$331Multiple Airlines
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
7:25 am - 3:55 pm
SNA
-
MDW
6h 30m
1 stop
Southwest Logo
10:30 am - 5:05 pm
MDW
-
SNA
8h 35m
2 stops
$334Southwest
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
6:48 pm - 11:39 pm
SNA
-
MDW
26h 51m
1 stop
Multiple Airlines Logo
9:51 pm - 9:13 pm
MDW
-
SNA
25h 22m
2 stops
$336Multiple Airlines
Thu, Apr 16 - Wed, Apr 22
Southwest Logo
12:05 pm - 5:55 pm
LGB
-
MDW
3h 50mnonstop
Southwest Logo
4:30 pm - 6:50 pm
MDW
-
LGB
4h 20mnonstop
$337Southwest
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
8:55 pm - 5:45 am
SNA
-
MDW
6h 50m
1 stop
Southwest Logo
8:00 am - 12:45 pm
MDW
-
SNA
6h 45m
1 stop
$340Southwest
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
11:15 am - 8:40 pm
SNA
-
MDW
7h 25m
1 stop
Southwest Logo
11:45 am - 4:45 pm
MDW
-
SNA
7h 00m
2 stops
$345Southwest
Sat, Apr 25 - Sat, May 2
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
$349Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$147
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 2% 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.
8.0
SouthwestOverall score based on 4320 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

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

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
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)