SNA - MDW

$98 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 8/16. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Booking Insights
Flights 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

Sat, Aug 16 - Thu, Aug 21
Frontier Logo
11:56 am - 8:54 pmSNA-MDW
6h 58m1 stop
Frontier Logo
11:00 am - 4:57 pmMDW-SNA
7h 57m1 stop
$238Frontier
Find Deal
Thu, Aug 14 - Sat, Aug 16
Frontier Logo
12:01 pm - 8:54 pmSNA-MDW
6h 53m1 stop
Frontier Logo
2:44 pm - 11:10 amMDW-SNA
22h 26m1 stop
$245Frontier
Find Deal
Thu, Sep 18 - Fri, Oct 3
Frontier Logo
11:52 am - 2:51 pmSNA-MDW
24h 59m1 stop
Frontier Logo
4:48 pm - 12:13 pmMDW-SNA
21h 25m1 stop
$259Frontier
Find Deal
Wed, Sep 24 - Tue, Sep 30
Delta Logo
6:45 am - 5:35 pmSNA-MDW
8h 50m1 stop
Delta Logo
6:00 am - 12:42 pmMDW-SNA
8h 42m1 stop
$279Delta
Find Deal
Wed, Sep 3 - Mon, Sep 8
Delta Logo
8:00 am - 5:37 pmSNA-MDW
7h 37m1 stop
Delta Logo
4:25 pm - 10:12 pmMDW-SNA
7h 47m1 stop
$284Delta
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
12:03 pm - 9:26 pmSNA-MDW
7h 23m1 stop
Delta Logo
6:00 am - 12:42 pmMDW-SNA
8h 42m1 stop
$289Delta
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
11:05 am - 7:35 pmSNA-MDW
6h 30m1 stop
Southwest Logo
6:00 am - 9:45 amMDW-SNA
5h 45m1 stop
$313Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
6:45 am - 3:55 pmSNA-MDW
7h 10m2 stops
Southwest Logo
6:00 am - 9:45 amMDW-SNA
5h 45m1 stop
$318Southwest
Find Deal
Sat, Oct 11 - Mon, Oct 13
Southwest Logo
6:45 am - 4:45 pmSNA-MDW
8h 00m2 stops
Southwest Logo
5:45 am - 10:10 amMDW-SNA
6h 25m1 stop
$319Southwest
Find Deal
Thu, Sep 11 - Sun, Sep 14
Southwest Logo
3:25 pm - 12:05 amSNA-MDW
6h 40m1 stop
Southwest Logo
11:15 am - 5:35 pmMDW-SNA
8h 20m1 stop
$327Southwest
Find Deal
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’s the cheapest day of the week to fly from John Wayne (Santa Ana) to Chicago Midway Airport?

The average price of all round-trip flights from Santa Ana to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from John Wayne (Santa Ana) to Chicago Midway Airport. For your return ticket, we recommend flying on a Thursday and avoiding Wednesdays for the best deals.

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 May, where tickets cost $392 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $1,066 and $615 respectively.

Good to know

Low seasonMay
Cheapest flight$98
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 15% lower on average.
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 $98 for a one-way ticket and $238 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.

  • Which airline alliances offer flights from John Wayne (Santa Ana) to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between John Wayne (Santa Ana) and Chicago Midway Airport.

  • Which is the best airline for flights from Santa Ana to Chicago, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Santa Ana to Chicago are Southwest and Frontier. With an average price for the route of $440 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $348 and an overall rating of 5.9.

  • 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 airlines 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 4241 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

We were delayed three times ,and that destroyed my plans, and reservations

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.

Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.