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Cheap flights from Santa Ana to Chicago from $127

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 10/8. 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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Cheap round-trip flights

Frontier Logo
4:49 pm - 10:26 amSNA-MDW
15h 37m2 stops
Frontier Logo
12:30 pm - 1:35 pmMDW-SNA
27h 05m1 stop
$271Frontier
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Fri, Oct 31 - Fri, Nov 7
Southwest Logo
8:20 am - 5:15 pmSNA-MDW
6h 55m1 stop
Southwest Logo
8:25 am - 12:35 pmMDW-SNA
6h 10m1 stop
$277Southwest
Find Deal
Wed, Oct 29 - Wed, Nov 12
Southwest Logo
12:45 pm - 10:40 pmSNA-MDW
7h 55m2 stops
Southwest Logo
5:20 pm - 9:15 pmMDW-SNA
5h 55m1 stop
$282Southwest
Find Deal
Wed, Oct 8 - Tue, Oct 14
Southwest Logo
8:50 pm - 5:15 amSNA-MDW
6h 25m1 stop
Southwest Logo
5:20 pm - 9:15 pmMDW-SNA
5h 55m1 stop
$283Southwest
Find Deal
Sat, Oct 11 - Tue, Oct 14
Multiple Airlines Logo
2:15 pm - 9:18 amSNA-MDW
17h 03m2 stops
Multiple Airlines Logo
6:24 pm - 1:35 pmMDW-SNA
21h 11m1 stop
$286Multiple Airlines
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Wed, Oct 1 - Fri, Oct 10
Southwest Logo
6:45 am - 5:00 pmSNA-MDW
8h 15m2 stops
Southwest Logo
2:35 pm - 8:15 pmMDW-SNA
7h 40m2 stops
$287Southwest
Find Deal
Wed, Oct 29 - Wed, Nov 12
Southwest Logo
9:30 am - 7:10 pmSNA-MDW
7h 40m2 stops
Southwest Logo
7:50 am - 1:40 pmMDW-SNA
7h 50m1 stop
$288Southwest
Find Deal
Wed, Nov 5 - Thu, Nov 6
Frontier Logo
9:50 am - 12:36 amSNA-MDW
12h 46m2 stops
Frontier Logo
6:24 pm - 1:35 pmMDW-SNA
21h 11m1 stop
$290Frontier
Find Deal
Thu, Oct 16 - Fri, Oct 17
Delta Logo
8:00 am - 5:35 pmSNA-MDW
7h 35m1 stop
Delta Logo
5:04 pm - 10:28 pmMDW-SNA
7h 24m1 stop
$314Delta
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Sat, Oct 4 - Tue, Oct 7
Delta Logo
8:00 am - 5:43 pmSNA-MDW
7h 43m1 stop
Delta Logo
5:09 pm - 10:28 pmMDW-SNA
7h 19m1 stop
$318Delta
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Tue, Nov 4 - Wed, Nov 5

Southwest flights from Santa Ana to Chicago Midway Airport

Our best Southwest deals on Santa Ana to Chicago Midway Airport flight tickets
Southwest
Oct 29
SNA8:20 amSanta Ana J. Wayne/Orange Cnty
6h 55m
1 stop
MDW5:15 pmChicago Midway
Nov 12
MDW8:25 amChicago Midway
6h 10m
1 stop
SNA12:35 pmSanta Ana J. Wayne/Orange Cnty
$277
Find similar
Southwest
Oct 8
SNA12:45 pmSanta Ana J. Wayne/Orange Cnty
7h 55m
2 stops
MDW10:40 pmChicago Midway
Oct 14
MDW5:20 pmChicago Midway
5h 55m
1 stop
SNA9:15 pmSanta Ana J. Wayne/Orange Cnty
$282
Find similar
Southwest
Oct 11
SNA8:50 pmSanta Ana J. Wayne/Orange Cnty
6h 25m
1 stop
MDW5:15 amChicago Midway
Oct 14
MDW5:20 pmChicago Midway
5h 55m
1 stop
SNA9:15 pmSanta Ana J. Wayne/Orange Cnty
$283
Find similar

Delta flights from Santa Ana to Chicago Midway Airport

Our best Delta deals on Santa Ana to Chicago Midway Airport flight tickets
Delta
Oct 4
SNA8:00 amSanta Ana J. Wayne/Orange Cnty
7h 35m
1 stop
MDW5:35 pmChicago Midway
Oct 7
MDW5:04 pmChicago Midway
7h 24m
1 stop
SNA10:28 pmSanta Ana J. Wayne/Orange Cnty
$314
Find similar
Delta
Nov 4
SNA8:00 amSanta Ana J. Wayne/Orange Cnty
7h 43m
1 stop
MDW5:43 pmChicago Midway
Nov 5
MDW5:09 pmChicago Midway
7h 19m
1 stop
SNA10:28 pmSanta Ana J. Wayne/Orange Cnty
$318
Find similar
Delta
Nov 4
SNA8:00 amSanta Ana J. Wayne/Orange Cnty
7h 43m
1 stop
MDW5:43 pmChicago Midway
Nov 7
MDW5:09 pmChicago Midway
7h 19m
1 stop
SNA10:28 pmSanta Ana J. Wayne/Orange Cnty
$338
Find similar

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 September 16, 2025.
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

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Fri 10/31

4:49 pm-10:26 am

2 stops15h 37m

Chicago Midway

Fri 11/7

12:30 pm-1:35 pm

1 stop27h 05m

$271

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 10/29

8:20 am-5:15 pm

1 stop6h 55m

Chicago Midway

Wed 11/12

8:25 am-12:35 pm

1 stop6h 10m

$277

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 10/8

12:45 pm-10:40 pm

2 stops7h 55m

Chicago Midway

Tue 10/14

5:20 pm-9:15 pm

1 stop5h 55m

$282

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 10/11

8:50 pm-5:15 am

1 stop6h 25m

Chicago Midway

Tue 10/14

5:20 pm-9:15 pm

1 stop5h 55m

$283

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 10/1

2:15 pm-9:18 am

2 stops17h 03m

Chicago Midway

Fri 10/10

6:24 pm-1:35 pm

1 stop21h 11m

$286

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 10/29

6:45 am-5:00 pm

2 stops8h 15m

Chicago Midway

Wed 11/12

2:35 pm-8:15 pm

2 stops7h 40m

$287

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Wed 11/5

9:30 am-7:10 pm

2 stops7h 40m

Chicago Midway

Thu 11/6

7:50 am-1:40 pm

1 stop7h 50m

$288

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Thu 10/16

9:50 am-12:36 am

2 stops12h 46m

Chicago Midway

Fri 10/17

6:24 pm-1:35 pm

1 stop21h 11m

$290

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Sat 10/4

8:00 am-5:35 pm

1 stop7h 35m

Chicago Midway

Tue 10/7

5:04 pm-10:28 pm

1 stop7h 24m

$314

Santa AnaChicago

SNA - MDW

SNAMDW

Santa Ana J. Wayne/Orange Cnty

Tue 11/4

8:00 am-5:43 pm

1 stop7h 43m

Chicago Midway

Wed 11/5

5:09 pm-10:28 pm

1 stop7h 19m

$318

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 May is, on average, the cheapest month to fly to Chicago Midway Airport from Santa Ana, with most prices found around $392. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Santa Ana during the month February is also very affordable. Most momondo users find prices during this month for around $397.

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 $361. 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 $498.

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 $327 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $497. 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.

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

Direct flights

None
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.
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  • 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 30m.

  • 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
FrontierPriceFrom $145Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Santa Ana to Chicago Midway Airport

    Across 2 Southwest flights from Santa Ana to Chicago Midway Airport this week, the average price was $446, with the best Southwest deals starting from $312 round-trip. 4,242 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
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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