Cheap Flights from Santa Ana John Wayne to Chicago Midway

Compare Santa Ana John Wayne to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Santa Ana John Wayne to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Santa Ana John Wayne Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $559. Find the lowest prices on one-way and return tickets right here.

Chicago.$544 per passenger.Departing Tue, 7 Jul, returning Tue, 14 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Tue, 7 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 14 Jul, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $544, select.

Chicago.$550 per passenger.Departing Tue, 18 Aug, returning Mon, 24 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Santa Ana John Wayne on Tue, 18 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 24 Aug, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $550, select.

Chicago.$560 per passenger.Departing Wed, 11 Nov, returning Wed, 18 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Santa Ana John Wayne on Wed, 11 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 18 Nov, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $560, select.

Chicago.$560 per passenger.Departing Sat, 27 Jun, returning Tue, 30 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Sat, 27 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 30 Jun, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $560, select.

Chicago.$560 per passenger.Departing Wed, 12 Aug, returning Tue, 1 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Wed, 12 Aug, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 1 Sep, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $560, select.

Chicago.$562 per passenger.Departing Wed, 2 Sep, returning Wed, 9 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Wed, 2 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 9 Sep, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $562, select.

Chicago.$577 per passenger.Departing Fri, 31 Jul, returning Wed, 5 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Santa Ana John Wayne on Fri, 31 Jul, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 5 Aug, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $577, select.

Chicago.$596 per passenger.Departing Thu, 22 Oct, returning Tue, 27 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Thu, 22 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 27 Oct, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $596, select.

Chicago.$599 per passenger.Departing Wed, 27 May, returning Fri, 29 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Santa Ana John Wayne on Wed, 27 May, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 29 May, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $599, select.

Chicago.$604 per passenger.Departing Mon, 28 Sep, returning Sat, 3 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Mon, 28 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 3 Oct, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $604, select.

Chicago.$635 per passenger.Departing Thu, 25 Jun, returning Tue, 14 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Santa Ana John Wayne on Thu, 25 Jun, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 14 Jul, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $635, select.

Chicago.$673 per passenger.Departing Thu, 29 Oct, returning Sun, 1 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Santa Ana John Wayne on Thu, 29 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 1 Nov, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $673, select.

Chicago.$723 per passenger.Departing Fri, 29 May, returning Sat, 6 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Fri, 29 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 6 Jun, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $723, select.

Chicago.$1,518 per passenger.Departing Sun, 7 Feb, returning Sun, 14 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Santa Ana John Wayne on Sun, 7 Feb, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 14 Feb, arriving in Santa Ana John Wayne.Price includes taxes and charges.From $1,518, select.

Find the cheapest month to fly from Santa Ana John Wayne to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Santa Ana John Wayne to Chicago Midway flights are currently cheapest in July.

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Santa Ana John Wayne to Chicago Midway: Alternative routes

Compare routes from Santa Ana John Wayne to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Santa Ana to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$543
Cheapest month to fly	July

Finding cheap flights from Santa Ana John Wayne to Chicago Midway: Frequently asked questions

How much are return flights from Santa Ana John Wayne to Chicago Midway?

The best price we found for a return flight from Santa Ana John Wayne to Chicago Midway is $543. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Santa Ana John Wayne to Chicago Midway?

Currently, there are no airlines that fly direct from Santa Ana John Wayne to Chicago Midway. But we found flights with one or more stops from $543.

How many flights are there a week from Santa Ana John Wayne to Chicago Midway?

As of May 2026, there are no flights flying from Santa Ana John Wayne to Chicago Midway.

When is the cheapest time to fly from Santa Ana John Wayne to Chicago Midway?

The cheapest month to fly from Santa Ana John Wayne to Chicago Midway is usually July.

Which upcoming date is cheapest to fly from Santa Ana John Wayne Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Santa Ana John Wayne Airport to Chicago Midway Airport on Tuesday, 7 July 2026.

Can I get a direct flight from Santa Ana John Wayne Airport to Chicago Midway Airport?

No airlines currently offer direct flights between Santa Ana John Wayne Airport and Chicago Midway Airport. Most routes have one or more stops.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Santa Ana John Wayne Airport to Chicago Midway with?

Currently, Delta offers the cheapest flight tickets to Chicago Midway.

Flying from John Wayne Airport (SNA) to Chicago Midway International Airport (MDW): what you need to know

Chicago's timezone is UTC-5, which makes Chicago two hours ahead of Santa Ana.
For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This will give you enough time to catch your SNA to MDW flight.
Travelling during a peak month such as July? Public holidays and other popular periods can mean longer queues and delays at airport checkpoints. Be extra cautious and get there up to four hours ahead of an international flight and two hours before domestic departures.
We make it a breeze to book a flight with a stopover. To see all your options for tickets from John Wayne Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight with a stop long enough to visit your chosen city. Stopovers between SNA and MDW include:
- Denver International Airport
- Harry Reid Airport (formerly McCarran Airport)
- Phoenix Sky Harbour International Airport

How to find the cheapest flights from John Wayne Airport (SNA) to Chicago Midway International Airport (MDW)

At the moment, $262 is the cheapest price we've seen for a one-way John Wayne Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is $544. Bear in mind that fares could change due to availability at the time of booking.
It's usually smart to book in advance if you're looking for cheap tickets from SNA to MDW. That's because flight prices are based on demand, which tends to rise closer to departure.
The 'Whole month' tool shows you the cheapest flights from John Wayne Airport to Chicago Midway International Airport throughout the entire month. It's an easy way to find a bargain if your travel plans are flexible.
Save time searching for cheap flights from SNA to MDW by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.
Discover the perfect flight for you by using the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from John Wayne Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter by airline, departure and arrival times, and journey duration.

Handy information about John Wayne Airport (SNA)

SNA is located at 18601 Airport Way.
John Wayne Airport has a strong on-time performance, reducing your chances of a delayed flight. Departures from SNA land at their destination as scheduled 81.53% of the time.
John Wayne Airport is about 8 kilometres from central Santa Ana. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 15 minutes or so to get there, depending on the traffic.
Planning to take public transport? Expect a journey time of around 1 hour 5 minutes.
Looking for a convenient hotel near SNA? If you're boarding an early flight from John Wayne Airport to Chicago Midway International Airport, these stays will have you moments from your check-in counter:

Arriving at Chicago Midway International Airport (MDW)

If you're coming in on a late John Wayne Airport to Chicago Midway International Airport flight, nothing beats the convenience of being close to the terminal. Grab your suitcases from the carousel and then be resting not long after at one of these hotels near MDW:
Fast-track your adventure by picking up a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and explore beyond Chicago's main sights.
Reserving your ride from Chicago Midway International Airport around four weeks in advance can help you secure the lowest rate.

Getting from Chicago Midway International Airport (MDW) to central Chicago

You'll find MDW at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre driving.
Getting there by public transport typically takes 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

July is the most popular month for flights from John Wayne Airport to Chicago Midway International Airport. To skip the crowds, head to Chicago in May.
Book your flight from John Wayne Airport to Chicago Midway International Airport for July if you'd like to go to Chicago during its warmest month. You can expect temperatures of between 15ºC and 29ºC.
January sees average temperatures of between -12ºC and 3ºC. Look for cheap tickets from SNA to MDW sometime around then if you'd rather travel in cooler conditions.

Explore more of United States

Columbus is just one of the many places in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience the best of this destination with a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.