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Cheap flights from San José to Chicago from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San José to Chicago departing on 4/22. 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 San José to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$356Southwest
Thu, Apr 16 - Mon, Apr 27
Southwest Logo
9:00 am - 7:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$383Southwest
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$392Southwest
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
7:30 am - 7:00 pm
MDW
-
SJO
12h 30m
2 stops
$397Southwest
Thu, Apr 16 - Mon, Apr 27
Multiple Airlines Logo
11:38 am - 9:21 pm
SJO
-
MDW
8h 43m
1 stop
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
$400Multiple Airlines
Thu, Apr 9 - Tue, Apr 14
Multiple Airlines Logo
7:58 am - 1:41 pm
SJO
-
MDW
29h 43m
1 stop
Multiple Airlines Logo
6:00 am - 3:17 pm
MDW
-
SJO
10h 17m
1 stop
$407Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$411Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
9:00 am - 7:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
9:00 am - 7:00 pm
MDW
-
SJO
11h 00m
2 stops
$416Southwest
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
11:23 am - 1:00 pm
SJO
-
MDW
24h 37m
2 stops
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
$424Multiple Airlines
Wed, Apr 15 - Tue, Apr 28
Southwest Logo
9:00 am - 10:35 pm
SJO
-
MDW
12h 35m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$426Southwest
Sat, May 2 - Wed, May 6

Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
Apr 16
SJO1:10 pmSan José Juan Santamaria Intl
7h 45m
1 stop
MDW9:55 pmChicago Midway
Apr 27
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
$356
Southwest
Apr 16
SJO9:00 amSan José Juan Santamaria Intl
9h 00m
1 stop
MDW7:00 pmChicago Midway
Apr 20
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
$383
Southwest
Apr 22
SJO1:10 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:05 pmChicago Midway
Apr 29
MDW12:15 pmChicago Midway
7h 45m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
$392

LATAM Airlines flights from San José to Chicago Midway Airport

Our best LATAM Airlines deals on San José to Chicago Midway Airport flight tickets
LATAM Airlines
Mar 6
SJO7:00 amSan José Juan Santamaria Intl
15h 31m
1 stop
MDW10:31 pmChicago Midway
Mar 9
MDW1:10 pmChicago Midway
9h 05m
2 stops
SJO9:15 pmSan José Juan Santamaria Intl
$556
LATAM Airlines
Mar 6
SJO2:25 pmSan José Juan Santamaria Intl
8h 06m
1 stop
MDW10:31 pmChicago Midway
Mar 9
MDW1:10 pmChicago Midway
9h 05m
2 stops
SJO9:15 pmSan José Juan Santamaria Intl
$576
LATAM Airlines
Mar 13
SJO7:00 amSan José Juan Santamaria Intl
14h 31m
1 stop
MDW10:31 pmChicago Midway
Mar 16
MDW6:00 amChicago Midway
16h 15m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$667

momondo Fare Finder

 
Customize your flight search to find flights from San José 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 3, 2026.
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

Mon 4/27

12:10 pm-7:00 pm

1 stop7h 50m

$356

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

9:00 am-7:00 pm

1 stop9h 00m

Chicago Midway

Mon 4/20

12:10 pm-7:00 pm

1 stop7h 50m

$383

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/22

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Wed 4/29

12:15 pm-7:00 pm

1 stop7h 45m

$392

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

Mon 4/27

7:30 am-7:00 pm

2 stops12h 30m

$397

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/9

11:38 am-9:21 pm

1 stop8h 43m

Chicago Midway

Tue 4/14

7:30 am-10:38 am

2 stops28h 08m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/6

7:58 am-1:41 pm

1 stop29h 43m

Chicago Midway

Mon 3/9

6:00 am-3:17 pm

1 stop10h 17m

$407

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/14

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Tue 4/21

12:15 pm-7:00 pm

1 stop7h 45m

$411

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

9:00 am-7:00 pm

1 stop9h 00m

Chicago Midway

Mon 4/20

9:00 am-7:00 pm

2 stops11h 00m

$416

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/15

11:23 am-1:00 pm

2 stops24h 37m

Chicago Midway

Tue 4/28

7:30 am-10:38 am

2 stops28h 08m

$424

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/2

9:00 am-10:35 pm

1 stop12h 35m

Chicago Midway

Wed 5/6

12:15 pm-7:00 pm

1 stop7h 45m

$426

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 San José 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

Can stopping save me money on San José to Chicago Midway Airport flights?

You could potentially save up to 60% on your flight if you consider stops on a San José to Chicago Midway Airport flight.

When to book flights from San José to Chicago Midway Airport

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

Cheap San José to Chicago Midway Airport (SJO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José to Chicago Midway Airport

Fastest flight time

7h 45m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 7h 45m
There are no direct flights from San José to Chicago Midway Airport. There are no popular flight routes from San José to Chicago Midway Airport.
Search flight deals

  • How far is San José Juan Santamaria Intl to Chicago Midway by plane?

    San José Juan Santamaria Intl and Chicago Midway are 2210.5 mi apart from one another. Typically, this will take 7h 45m by plane in normal conditions.

  • When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport?

    Prices for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from San José Juan Santamaria Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San José Juan Santamaria Intl Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from San José to Chicago Midway Airport?

Best airlines flying from San José to Chicago Midway Airport

Compare and see reviews for airlines that fly from San José to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $463Free CancellationRating
8.0
4,302 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
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Saint Joseph
Portage
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Schererville
Munster
Crown Point
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Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San José to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San José to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from San José to Chicago with flexible booking policies on momondo?

Flights from San José to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from San José to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San José to Chicago.

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

Price alerts on flights to Chicago from San José 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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