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Cheap flights from Santa Ana to Chicago from $152

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 to Chicago departing on 4/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Santa Ana to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:15 pm - 5:45 am
SNA
-
MDW
7h 30m
1 stop
Southwest Logo
3:40 pm - 9:25 pm
MDW
-
SNA
7h 45m
1 stop
$309Southwest
Tue, Apr 14 - Wed, Apr 15
Frontier Logo
5:28 pm - 10:14 pm
SNA
-
MDW
26h 46m
2 stops
Frontier Logo
6:20 am - 1:44 pm
MDW
-
SNA
9h 24m
1 stop
$312Frontier
Fri, Apr 17 - Mon, Apr 20
Southwest Logo
9:00 am - 7:30 pm
SNA
-
MDW
8h 30m
2 stops
Southwest Logo
3:40 pm - 9:25 pm
MDW
-
SNA
7h 45m
1 stop
$314Southwest
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
7:30 am - 10:14 pm
SNA
-
MDW
12h 44m
2 stops
Multiple Airlines Logo
6:20 am - 1:44 pm
MDW
-
SNA
9h 24m
1 stop
$320Multiple Airlines
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
7:05 am - 4:15 pm
SNA
-
MDW
7h 10m
1 stop
Southwest Logo
2:10 pm - 8:55 pm
MDW
-
SNA
8h 45m
1 stop
$323Southwest
Thu, Apr 9 - Wed, Apr 15
Southwest Logo
7:40 pm - 5:25 am
SNA
-
MDW
7h 45m
1 stop
Southwest Logo
10:30 am - 5:05 pm
MDW
-
SNA
8h 35m
2 stops
$328Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
8:15 pm - 5:45 am
SNA
-
MDW
7h 30m
1 stop
Southwest Logo
4:10 pm - 9:35 pm
MDW
-
SNA
7h 25m
1 stop
$329Southwest
Wed, Apr 29 - Fri, May 1
Multiple Airlines Logo
6:30 pm - 7:30 pm
SNA
-
MDW
23h 00m
1 stop
Multiple Airlines Logo
8:20 pm - 8:05 am
MDW
-
SNA
13h 45m
1 stop
$332Multiple Airlines
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
9:45 am - 8:10 pm
SNA
-
MDW
8h 25m
2 stops
Southwest Logo
10:10 am - 5:00 pm
MDW
-
SNA
8h 50m
2 stops
$334Southwest
Tue, Apr 28 - Tue, May 5
Southwest Logo
7:25 pm - 5:25 am
SNA
-
MDW
8h 00m
1 stop
Southwest Logo
3:05 pm - 8:20 pm
MDW
-
SNA
7h 15m
1 stop
$337Southwest
Sat, Apr 18 - Mon, Apr 20

Frontier flights from Santa Ana to Chicago Midway Airport

Our best Frontier deals on Santa Ana to Chicago Midway Airport flight tickets
Frontier
Apr 17
SNA5:28 pmSanta Ana J. Wayne/Orange Cnty
26h 46m
2 stops
MDW10:14 pmChicago Midway
Apr 20
MDW6:20 amChicago Midway
9h 24m
1 stop
SNA1:44 pmSanta Ana J. Wayne/Orange Cnty
$312
Frontier
Mar 27
SNA3:21 pmSanta Ana J. Wayne/Orange Cnty
6h 18m
1 stop
MDW11:39 pmChicago Midway
Mar 28
MDW2:16 pmChicago Midway
20h 34m
1 stop
SNA8:50 amSanta Ana J. Wayne/Orange Cnty
$420
Frontier
Mar 27
SNA3:21 pmSanta Ana J. Wayne/Orange Cnty
6h 18m
1 stop
MDW11:39 pmChicago Midway
Mar 29
MDW4:02 pmChicago Midway
18h 48m
1 stop
SNA8:50 amSanta Ana J. Wayne/Orange Cnty
$479

Southwest flights from Santa Ana to Chicago Midway Airport

Our best Southwest deals on Santa Ana to Chicago Midway Airport flight tickets
Southwest
Apr 14
SNA8:15 pmSanta Ana J. Wayne/Orange Cnty
7h 30m
1 stop
MDW5:45 amChicago Midway
Apr 15
MDW3:40 pmChicago Midway
7h 45m
1 stop
SNA9:25 pmSanta Ana J. Wayne/Orange Cnty
$309
Southwest
Apr 15
SNA9:00 amSanta Ana J. Wayne/Orange Cnty
8h 30m
2 stops
MDW7:30 pmChicago Midway
Apr 22
MDW3:40 pmChicago Midway
7h 45m
1 stop
SNA9:25 pmSanta Ana J. Wayne/Orange Cnty
$314
Southwest
Apr 9
SNA7:05 amSanta Ana J. Wayne/Orange Cnty
7h 10m
1 stop
MDW4:15 pmChicago Midway
Apr 15
MDW2:10 pmChicago Midway
8h 45m
1 stop
SNA8:55 pmSanta Ana J. Wayne/Orange Cnty
$323

momondo Fare Finder

 
Customize your flight search to find flights from Santa Ana 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 March 23, 2026.
Use the filters below to find and compare flights from Santa Ana 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

Tue 4/14

8:15 pm-5:45 am

1 stop7h 30m

Chicago Midway

Wed 4/15

3:40 pm-9:25 pm

1 stop7h 45m

$309

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 4/17

5:28 pm-10:14 pm

2 stops26h 46m

Chicago Midway

Mon 4/20

6:20 am-1:44 pm

1 stop9h 24m

$312

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

9:00 am-7:30 pm

2 stops8h 30m

Chicago Midway

Wed 4/22

3:40 pm-9:25 pm

1 stop7h 45m

$314

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

7:30 am-10:14 pm

2 stops12h 44m

Chicago Midway

Mon 4/20

6:20 am-1:44 pm

1 stop9h 24m

$320

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 4/9

7:05 am-4:15 pm

1 stop7h 10m

Chicago Midway

Wed 4/15

2:10 pm-8:55 pm

1 stop8h 45m

$323

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/15

7:40 pm-5:25 am

1 stop7h 45m

Chicago Midway

Sat 4/18

10:30 am-5:05 pm

2 stops8h 35m

$328
Quickest round-trip

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 4/29

8:15 pm-5:45 am

1 stop7h 30m

Chicago Midway

Fri 5/1

4:10 pm-9:35 pm

1 stop7h 25m

$329

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 8/12

6:30 pm-7:30 pm

1 stop23h 00m

Chicago Midway

Sun 8/16

8:20 pm-8:05 am

1 stop13h 45m

$332

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 4/28

9:45 am-8:10 pm

2 stops8h 25m

Chicago Midway

Tue 5/5

10:10 am-5:00 pm

2 stops8h 50m

$334

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 4/18

7:25 pm-5:25 am

1 stop8h 00m

Chicago Midway

Mon 4/20

3:05 pm-8:20 pm

1 stop7h 15m

$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 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 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, with most prices found around $323. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Santa Ana 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. The lowest ticket price found for a Saturday departure recently was $360. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $457.

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

Flying to Chicago Midway Airport from Santa Ana in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $346 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $446. 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

What cabin class options are available on Santa Ana J. Wayne/Orange Cnty to Chicago Midway flights?

There is only 1 cabin class available to choose from on Santa Ana J. Wayne/Orange Cnty to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of March 2026, prices for Santa Ana to Chicago Midway Airport flights are approximately 34% more expensive when compared to flights at the same time last year.

When to book flights from Santa Ana to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Santa Ana 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 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 to Chicago Midway Airport

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Santa Ana to Chicago Midway Airport takes 5h 25m
There are no direct flights from Santa Ana to Chicago Midway Airport. There are no popular flight routes from Santa Ana to Chicago Midway Airport.
Search flight deals

  • 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 25m.

  • 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 to Chicago Midway Airport?

Best airlines flying from Santa Ana to Chicago Midway Airport

Compare and see reviews for airlines that fly from Santa Ana to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $288Free CancellationRating
8.0
4,324 reviews
Search Southwest flights

  • Southwest Flights From Santa Ana to Chicago Midway Airport

    Across 1 Southwest flight from Santa Ana to Chicago Midway Airport this week, the average price was $446, with the best Southwest deals starting from $288 round-trip. 4,324 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
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Saint John

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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