MDW

$144 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 2/5. 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
$271
Overall average: $333
Multiple Airlines
Sun 2/15Mon 2/16
SNA - MDW • 1 stop
Cheapest non-stop
$431
Southwest
Wed 3/11Mon 3/16
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

Sun, Feb 15 - Mon, Feb 16
Multiple Airlines Logo
12:36 pm - 11:41 pm
SNA
-
MDW
9h 05m
1 stop
Multiple Airlines Logo
3:24 pm - 12:25 pm
MDW
-
SNA
23h 01m
2 stops
$271Multiple Airlines
Thu, Feb 5 - Thu, Feb 19
Frontier Logo
10:25 am - 3:58 pm
SNA
-
MDW
27h 33m
1 stop
Frontier Logo
3:00 pm - 4:25 pm
MDW
-
SNA
27h 25m
2 stops
$272Frontier
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
10:25 am - 3:58 pm
SNA
-
MDW
27h 33m
1 stop
Multiple Airlines Logo
9:45 am - 8:57 pm
MDW
-
SNA
13h 12m
2 stops
$273Multiple Airlines
Fri, Feb 13 - Sat, Feb 14
Frontier Logo
12:36 pm - 11:41 pm
SNA
-
MDW
9h 05m
1 stop
Frontier Logo
9:15 am - 6:40 pm
MDW
-
SNA
11h 25m
2 stops
$277Frontier
Thu, Feb 5 - Sun, Feb 8
Frontier Logo
2:39 pm - 3:58 pm
SNA
-
MDW
23h 19m
2 stops
Frontier Logo
7:30 am - 4:26 pm
MDW
-
SNA
10h 56m
1 stop
$278Frontier
Fri, Feb 20 - Mon, Feb 23
Southwest Logo
7:30 am - 3:00 pm
SNA
-
MDW
5h 30m
1 stop
Southwest Logo
12:50 pm - 5:40 pm
MDW
-
SNA
6h 50m
1 stop
$285Southwest
Wed, Apr 1 - Sun, Apr 5
Southwest Logo
8:10 pm - 5:45 am
SNA
-
MDW
7h 35m
1 stop
Southwest Logo
5:00 am - 9:50 am
MDW
-
SNA
6h 50m
1 stop
$289Southwest
Thu, Feb 5 - Fri, Feb 13
Multiple Airlines Logo
1:20 pm - 3:58 pm
SNA
-
MDW
24h 38m
2 stops
Multiple Airlines Logo
8:58 pm - 6:40 pm
MDW
-
SNA
23h 42m
1 stop
$292Multiple Airlines
Wed, Feb 18 - Mon, Feb 23
Southwest Logo
6:40 pm - 5:05 am
SNA
-
MDW
8h 25m
1 stop
Southwest Logo
8:05 am - 3:20 pm
MDW
-
SNA
9h 15m
2 stops
$294Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
5:35 pm - 6:00 am
SNA
-
MDW
10h 25m
1 stop
Southwest Logo
5:10 am - 9:40 am
MDW
-
SNA
6h 30m
1 stop
$295Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$144
Most popular time to fly with an average 2% 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 4261 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

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

10.0 ExcellentJohn, Jan 2026
BWI - MDW
Read more Southwest reviews

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

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

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
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Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

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