MDW

$163 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 5/19. 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

seg, mai 4 - qua, mai 6
Southwest Logo
8:55 pm - 5:25 am
SNA
-
MDW
6h 30m
1 stop
Southwest Logo
10:20 am - 3:40 pm
MDW
-
SNA
7h 20m
1 stop
$323Southwest
seg, mai 4 - qua, mai 6
Southwest Logo
2:20 pm - 11:55 pm
SNA
-
MDW
7h 35m
2 stops
Southwest Logo
3:40 pm - 9:25 pm
MDW
-
SNA
7h 45m
1 stop
$328Southwest
ter, abr 21 - sex, abr 24
Southwest Logo
7:40 pm - 5:25 am
SNA
-
MDW
7h 45m
1 stop
Southwest Logo
6:55 am - 11:55 am
MDW
-
SNA
7h 00m
1 stop
$329Southwest
dom, mai 3 - ter, mai 5
Southwest Logo
8:10 am - 5:40 pm
SNA
-
MDW
7h 30m
2 stops
Southwest Logo
10:00 am - 2:50 pm
MDW
-
SNA
6h 50m
1 stop
$334Southwest
qui, abr 16 - seg, abr 20
Multiple Airlines Logo
3:23 pm - 7:31 pm
SNA
-
MDW
26h 08m
2 stops
Multiple Airlines Logo
6:20 am - 1:44 pm
MDW
-
SNA
9h 24m
1 stop
$335Multiple Airlines
seg, mai 11 - sáb, mai 16
Southwest Logo
2:10 pm - 11:40 pm
SNA
-
MDW
7h 30m
1 stop
Southwest Logo
1:00 pm - 5:05 pm
MDW
-
SNA
6h 05m
1 stop
$337Southwest
ter, mai 5 - qua, mai 6
Southwest Logo
11:10 am - 5:00 pm
LGB
-
MDW
3h 50mnonstop
Southwest Logo
4:30 pm - 6:50 pm
MDW
-
LGB
4h 20mnonstop
$337Southwest
seg, mai 4 - sex, mai 8
Southwest Logo
3:50 pm - 11:40 pm
SNA
-
MDW
5h 50m
1 stop
Southwest Logo
10:10 am - 2:40 pm
MDW
-
SNA
6h 30m
1 stop
$338Southwest
dom, mai 3 - ter, mai 5
Southwest Logo
8:10 am - 5:40 pm
SNA
-
MDW
7h 30m
2 stops
Southwest Logo
1:05 pm - 7:05 pm
MDW
-
SNA
8h 00m
2 stops
$339Southwest
seg, mai 11 - ter, mai 12
Southwest Logo
2:20 pm - 11:55 pm
SNA
-
MDW
7h 35m
2 stops
Southwest Logo
7:55 am - 1:10 pm
MDW
-
SNA
7h 15m
1 stop
$342Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$163
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 1% 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 4344 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

10.0 ExcellentAnthony & Kathy, Mar 2026
LAX - PHX
Read more Southwest reviews

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

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.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

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.

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

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