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Cheap flights from Santa Ana, California to Chicago from $174

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Santa Ana, California to Chicago departing on 5/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Santa Ana, California to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:30 pm - 7:13 pm
SNA
-
MDW
22h 43m
1 stop
Multiple Airlines Logo
8:03 pm - 8:05 am
MDW
-
SNA
14h 02m
1 stop
$317Multiple Airlines
Wed, Jun 10 - Sun, Jun 14
Southwest Logo
7:10 pm - 5:00 am
SNA
-
MDW
7h 50m
1 stop
Southwest Logo
6:20 am - 10:30 am
MDW
-
SNA
6h 10m
1 stop
$323Southwest
Sat, Jun 6 - Tue, Jun 9
Allegiant Air Logo
2:30 pm - 6:59 pm
SNA
-
MDW
26h 29m
1 stop
Allegiant Air Logo
7:49 pm - 9:48 am
MDW
-
SNA
15h 59m
1 stop
$325Allegiant Air
Wed, May 27 - Sun, May 31
Southwest Logo
8:15 pm - 5:45 am
SNA
-
MDW
7h 30m
1 stop
Southwest Logo
10:15 am - 6:30 pm
MDW
-
SNA
10h 15m
2 stops
$328Southwest
Wed, Jun 3 - Sat, Jun 6
Delta Logo
8:00 am - 5:56 pm
SNA
-
MDW
7h 56m
1 stop
Delta Logo
6:23 am - 12:40 pm
MDW
-
SNA
8h 17m
1 stop
$329Delta
Fri, May 29 - Wed, Jun 3
Southwest Logo
6:45 pm - 5:00 am
SNA
-
MDW
8h 15m
1 stop
Southwest Logo
5:35 pm - 9:45 pm
MDW
-
SNA
6h 10m
1 stop
$330Southwest
Sun, May 24 - Wed, May 27
Southwest Logo
8:15 pm - 5:45 am
SNA
-
MDW
7h 30m
1 stop
Southwest Logo
6:10 am - 11:05 am
MDW
-
SNA
6h 55m
1 stop
$333Southwest
Thu, May 28 - Wed, Jun 3
Southwest Logo
5:15 pm - 12:35 am
SNA
-
MDW
5h 20m
1 stop
Southwest Logo
11:45 am - 4:45 pm
MDW
-
SNA
7h 00m
2 stops
$334Southwest
Fri, Jun 5 - Tue, Jun 9
Multiple Airlines Logo
2:30 pm - 6:59 pm
SNA
-
MDW
26h 29m
1 stop
Multiple Airlines Logo
7:49 pm - 12:19 pm
MDW
-
SNA
18h 30m
2 stops
$335Multiple Airlines
Wed, May 27 - Sun, May 31
Southwest Logo
7:40 pm - 5:00 am
SNA
-
MDW
7h 20m
1 stop
Southwest Logo
5:20 am - 11:15 am
MDW
-
SNA
7h 55m
1 stop
$337Southwest
Mon, Jun 1 - Thu, Jun 4

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Delta flights from Santa Ana, California to Chicago Midway Airport

Our best Delta deals on Santa Ana, California to Chicago Midway Airport flight tickets
Delta
May 29
SNA8:00 amSanta Ana J. Wayne/Orange Cnty
7h 56m
1 stop
MDW5:56 pmChicago Midway
Jun 3
MDW6:23 amChicago Midway
8h 17m
1 stop
SNA12:40 pmSanta Ana J. Wayne/Orange Cnty
$329
Delta
May 23
SNA6:45 amSanta Ana J. Wayne/Orange Cnty
7h 27m
1 stop
MDW4:12 pmChicago Midway
May 27
MDW12:53 pmChicago Midway
7h 40m
1 stop
SNA6:33 pmSanta Ana J. Wayne/Orange Cnty
$364
Delta
May 27
SNA6:45 amSanta Ana J. Wayne/Orange Cnty
7h 27m
1 stop
MDW4:12 pmChicago Midway
Jun 6
MDW1:59 pmChicago Midway
8h 35m
1 stop
SNA8:34 pmSanta Ana J. Wayne/Orange Cnty
$384

Allegiant Air flights from Santa Ana, California to Chicago Midway Airport

Our best Allegiant Air deals on Santa Ana, California to Chicago Midway Airport flight tickets
Allegiant Air
May 27
SNA2:30 pmSanta Ana J. Wayne/Orange Cnty
26h 29m
1 stop
MDW6:59 pmChicago Midway
May 31
MDW7:49 pmChicago Midway
15h 59m
1 stop
SNA9:48 amSanta Ana J. Wayne/Orange Cnty
$325
Allegiant Air
May 27
SNA2:30 pmSanta Ana J. Wayne/Orange Cnty
26h 29m
1 stop
MDW6:59 pmChicago Midway
Jun 7
MDW8:03 pmChicago Midway
15h 45m
1 stop
SNA9:48 amSanta Ana J. Wayne/Orange Cnty
$352

momondo Fare Finder

 
Customize your flight search to find flights from Santa Ana, California to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Santa Ana, California to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 6/10

6:30 pm-7:13 pm

1 stop22h 43m

Chicago Midway

Sun 6/14

8:03 pm-8:05 am

1 stop14h 02m

$317

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 6/6

7:10 pm-5:00 am

1 stop7h 50m

Chicago Midway

Tue 6/9

6:20 am-10:30 am

1 stop6h 10m

$323

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 5/27

2:30 pm-6:59 pm

1 stop26h 29m

Chicago Midway

Sun 5/31

7:49 pm-9:48 am

1 stop15h 59m

$325

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 6/3

8:15 pm-5:45 am

1 stop7h 30m

Chicago Midway

Sat 6/6

10:15 am-6:30 pm

2 stops10h 15m

$328

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 5/29

8:00 am-5:56 pm

1 stop7h 56m

Chicago Midway

Wed 6/3

6:23 am-12:40 pm

1 stop8h 17m

$329

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sun 5/24

6:45 pm-5:00 am

1 stop8h 15m

Chicago Midway

Wed 5/27

5:35 pm-9:45 pm

1 stop6h 10m

$330

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 5/28

8:15 pm-5:45 am

1 stop7h 30m

Chicago Midway

Wed 6/3

6:10 am-11:05 am

1 stop6h 55m

$333
Quickest round-trip

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 6/5

5:15 pm-12:35 am

1 stop5h 20m

Chicago Midway

Tue 6/9

11:45 am-4:45 pm

2 stops7h 00m

$334

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 5/27

2:30 pm-6:59 pm

1 stop26h 29m

Chicago Midway

Sun 5/31

7:49 pm-12:19 pm

2 stops18h 30m

$335

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Mon 6/1

7:40 pm-5:00 am

1 stop7h 20m

Chicago Midway

Thu 6/4

5:20 am-11:15 am

1 stop7h 55m

$337

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Santa Ana, California to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Santa Ana, California and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Santa Ana, California, with most prices found around $268. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Santa Ana, California during the month November is also very affordable. Most momondo users find prices during this month for around $375.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Santa Ana, California. The lowest ticket price found for a Saturday departure recently was $365. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Santa Ana, California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $449.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Santa Ana, California in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $357 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $440. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Santa Ana J. Wayne/Orange Cnty to Chicago Midway flight route?

Fly from Santa Ana J. Wayne/Orange Cnty to Chicago Midway for the best Santa Ana J. Wayne/Orange Cnty - Chicago Midway flight prices

How have Santa Ana, California to Chicago Midway Airport flight prices changed over time?

As of May 2026, prices for Santa Ana, California to Chicago Midway Airport flights are approximately 9% cheaper when compared to flights at the same time last year.

When to book flights from Santa Ana, California to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Santa Ana, California to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Santa Ana, California to Chicago Midway Airport (SNA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Santa Ana, California to Chicago Midway Airport

Fastest flight time

5h 20m

Direct flights

Mon
The fastest flight from Santa Ana, California to Chicago Midway Airport takes 5h 20m
Direct flights go from Santa Ana, California to Chicago Midway Airport on Monday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Santa Ana, California to Chicago Midway Airport

  • How far is Santa Ana J. Wayne/Orange Cnty to Chicago Midway by plane?

    A flight from Santa Ana J. Wayne/Orange Cnty to Chicago Midway will travel around 1724.9 mi. By plane, this route typically takes 5h 20m.

  • When did momondo last update prices for flights from Santa Ana J. Wayne/Orange Cnty Airport to Chicago Midway Airport?

    Prices for flights from Santa Ana J. Wayne/Orange Cnty Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Santa Ana J. Wayne/Orange Cnty Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Santa Ana J. Wayne/Orange Cnty Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Santa Ana J. Wayne/Orange Cnty Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Santa Ana, California to Chicago Midway Airport?

Best airlines flying from Santa Ana, California to Chicago Midway Airport

Compare and see reviews for airlines that fly from Santa Ana, California to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $288Free CancellationRating
7.9
4,305 reviews
Search Southwest flights

  • Southwest Flights From Santa Ana, California to Chicago Midway Airport

    Across 3 Southwest flights from Santa Ana, California to Chicago Midway Airport this week, the average price was $446, with the best Southwest deals starting from $288 round-trip. 4,305 users have rated Southwest on momondo, with an average score of 7.9/10.

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Why use momondo?

Why should I use momondo to find a flight deal from Santa Ana to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Santa Ana to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Santa Ana to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Santa Ana to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Santa Ana to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Santa Ana.

I’m not ready to book a flight from Santa Ana to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Santa Ana are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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