SNA - MDW

$127 Find Cheap Flights from John Wayne (Santa Ana) 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 from Santa Ana to Midway departing on 2/27. 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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Santa Ana to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Santa Ana to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$278
Overall average: $333
Frontier
Thu 2/19Sun 2/22
SNA - MDW • 1 stop
Cheapest one-way
$131
Overall average: $63
Frontier
Fri 2/27
SNA - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $278 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 32% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Santa Ana to Midway (SNA-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Santa Ana 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 Santa Ana to Midway

Thu, Feb 19 - Sun, Feb 22
Frontier Logo
12:46 pm - 11:41 pm
SNA
-
MDW
8h 55m
1 stop
Frontier Logo
3:21 pm - 8:13 am
MDW
-
SNA
18h 52m
2 stops
$278Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
5:27 pm - 2:49 pm
SNA
-
MDW
19h 22m
1 stop
Frontier Logo
6:15 am - 1:44 pm
MDW
-
SNA
9h 29m
1 stop
$281Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
12:46 pm - 11:41 pm
SNA
-
MDW
8h 55m
1 stop
Frontier Logo
6:25 am - 6:40 pm
MDW
-
SNA
14h 15m
2 stops
$285Frontier
Thu, Feb 19 - Sat, Feb 28
Frontier Logo
12:46 pm - 11:41 pm
SNA
-
MDW
8h 55m
1 stop
Frontier Logo
9:15 am - 6:40 pm
MDW
-
SNA
11h 25m
2 stops
$287Frontier
Thu, Feb 19 - Mon, Feb 23
Southwest Logo
7:30 pm - 5:05 am
SNA
-
MDW
7h 35m
1 stop
Southwest Logo
2:05 pm - 9:05 pm
MDW
-
SNA
9h 00m
1 stop
$289Southwest
Fri, Feb 13 - Mon, Feb 16
Multiple Airlines Logo
12:36 pm - 11:41 pm
SNA
-
MDW
9h 05m
1 stop
Multiple Airlines Logo
3:24 pm - 3:42 pm
MDW
-
SNA
26h 18m
2 stops
$297Multiple Airlines
Fri, Feb 13 - Sun, Feb 15
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
$300Frontier
Mon, Feb 23 - Mon, Mar 2
Multiple Airlines Logo
12:36 pm - 11:44 pm
SNA
-
MDW
9h 08m
1 stop
Multiple Airlines Logo
7:25 pm - 8:57 pm
MDW
-
SNA
27h 32m
2 stops
$303Multiple Airlines
Sat, Mar 14 - Tue, Mar 17
Southwest Logo
5:45 pm - 5:00 am
SNA
-
MDW
9h 15m
1 stop
Southwest Logo
1:05 pm - 7:40 pm
MDW
-
SNA
8h 35m
2 stops
$304Southwest
Fri, Mar 6 - Sun, Mar 8
Frontier Logo
2:34 pm - 10:41 pm
SNA
-
MDW
6h 07m
1 stop
Frontier Logo
2:16 pm - 8:50 am
MDW
-
SNA
20h 34m
1 stop
$307Frontier
Booking Insights

KAYAK's insights & trends for Santa Ana to Midway flights

Get data-powered insights and trends into flights from Santa Ana to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Santa Ana to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Santa Ana to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Santa Ana to Chicago Midway Airport is February, where tickets cost $333 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $1,066 and $635 respectively.

Find deals

Good to know

Low seasonMay
Cheapest flight$131
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from John Wayne (Santa Ana) to Chicago Midway Airport

When to book flights from Santa Ana to Midway

Are your dates flexible? Find out the best times to travel from Santa Ana to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking John Wayne (Santa Ana) to Chicago Midway Airport flights

  • What is the cheapest flight from Santa Ana to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Santa Ana to Chicago Midway Airport was $127 for a one-way ticket and $278 for a round-trip.

  • Do I need a passport to fly between John Wayne (Santa Ana) and Chicago Midway Airport?

    No, a passport isn't needed to fly from John Wayne (Santa Ana) to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from John Wayne (Santa Ana) to Chicago Midway Airport?

    When flying out of John Wayne (Santa Ana) you will be using Santa Ana J. Wayne/Orange Cnty. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which aircraft models fly most regularly from John Wayne (Santa Ana) to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from John Wayne (Santa Ana) 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 John Wayne (Santa Ana) to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from John Wayne (Santa Ana) 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 John Wayne (Santa Ana) 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 John Wayne (Santa Ana) 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 John Wayne (Santa Ana) with another airline. Booking your flights between John Wayne (Santa Ana) and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from John Wayne (Santa Ana) 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 John Wayne (Santa Ana) 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 Santa Ana to Midway

 
See real verified KAYAK customer reviews for airlines flying from Santa Ana to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Santa Ana 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 4268 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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.

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

Everything you need to know for your flight from Santa Ana to Midway

Information on your arrival and departure airports

John Wayne (Santa Ana) (SNA)
Midway (MDW)