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Cheap flights from San José to Chicago from $173

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 2/16. 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

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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.
Multiple Airlines Logo
12:35 pm - 2:55 pm
SJO
-
MDW
26h 20m
1 stop
Multiple Airlines Logo
9:22 pm - 11:40 am
MDW
-
SJO
14h 18m
1 stop
$328Multiple Airlines
Fri, Feb 13 - Mon, Feb 16
Frontier Logo
2:33 pm - 7:59 pm
SJO
-
MDW
29h 26m
1 stop
Frontier Logo
6:48 pm - 1:15 pm
MDW
-
SJO
18h 27m
1 stop
$331Frontier
Sat, Feb 14 - Fri, Feb 20
Multiple Airlines Logo
1:31 pm - 3:19 pm
SJO
-
MDW
25h 48m
2 stops
Multiple Airlines Logo
9:22 pm - 11:40 am
MDW
-
SJO
14h 18m
1 stop
$347Multiple Airlines
Fri, Feb 13 - Mon, Feb 16
Frontier Logo
2:07 pm - 11:42 pm
SJO
-
MDW
8h 35m
1 stop
Frontier Logo
6:00 am - 12:52 pm
MDW
-
SJO
7h 52m
1 stop
$356Frontier
Mon, Apr 6 - Mon, Apr 13
Multiple Airlines Logo
1:31 pm - 3:19 pm
SJO
-
MDW
25h 48m
2 stops
Multiple Airlines Logo
6:00 am - 3:30 pm
MDW
-
SJO
9h 30m
1 stop
$365Multiple Airlines
Fri, Feb 27 - Fri, Mar 6
Delta Logo
2:31 pm - 10:22 pm
SJO
-
MDW
7h 51m
1 stop
Delta Logo
10:49 am - 10:02 pm
MDW
-
SJO
11h 13m
1 stop
$368Delta
Thu, Feb 5 - Sun, Feb 22
Multiple Airlines Logo
7:45 am - 12:05 pm
SJO
-
MDW
28h 20m
2 stops
Multiple Airlines Logo
7:00 pm - 11:37 am
MDW
-
SJO
16h 37m
1 stop
$370Multiple Airlines
Tue, Feb 3 - Mon, Feb 9
Southwest Logo
9:40 am - 8:25 pm
SJO
-
MDW
10h 45m
1 stop
Southwest Logo
6:15 am - 7:30 pm
MDW
-
SJO
13h 15m
1 stop
$377Southwest
Thu, Feb 12 - Mon, Feb 16
LATAM Airlines Logo
7:00 am - 5:45 pm
SJO
-
MDW
10h 45m
1 stop
LATAM Airlines Logo
6:00 am - 10:02 pm
MDW
-
SJO
16h 02m
1 stop
$387LATAM Airlines
Fri, Feb 13 - Mon, Feb 16
Multiple Airlines Logo
12:35 pm - 2:55 pm
SJO
-
MDW
26h 20m
1 stop
Multiple Airlines Logo
9:51 pm - 11:40 am
MDW
-
SJO
13h 49m
1 stop
$388Multiple Airlines
Fri, Feb 27 - Fri, Mar 6

Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
Feb 12
SJO9:40 amSan José Juan Santamaria Intl
10h 45m
1 stop
MDW8:25 pmChicago Midway
Feb 16
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$377
Southwest
Feb 13
SJO9:40 amSan José Juan Santamaria Intl
11h 15m
2 stops
MDW8:55 pmChicago Midway
Feb 16
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$397
Southwest
Apr 16
SJO9:00 amSan José Juan Santamaria Intl
9h 00m
1 stop
MDW7:00 pmChicago Midway
Apr 19
MDW6:50 amChicago Midway
7h 10m
1 stop
SJO1:00 pmSan José Juan Santamaria Intl
$409

JetBlue flights from San José to Chicago Midway Airport

Our best JetBlue deals on San José to Chicago Midway Airport flight tickets
JetBlue
Feb 11
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Feb 18
MDW6:00 amChicago Midway
7h 00m
1 stop
SJO1:00 pmSan José Juan Santamaria Intl
$468
JetBlue
Jan 19
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Jan 25
MDW6:00 amChicago Midway
7h 00m
1 stop
SJO1:00 pmSan José Juan Santamaria Intl
$592

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 January 15, 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

Fri 2/13

12:35 pm-2:55 pm

1 stop26h 20m

Chicago Midway

Mon 2/16

9:22 pm-11:40 am

1 stop14h 18m

$328

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/14

2:33 pm-7:59 pm

1 stop29h 26m

Chicago Midway

Fri 2/20

6:48 pm-1:15 pm

1 stop18h 27m

$331

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/13

1:31 pm-3:19 pm

2 stops25h 48m

Chicago Midway

Mon 2/16

9:22 pm-11:40 am

1 stop14h 18m

$347

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 4/6

2:07 pm-11:42 pm

1 stop8h 35m

Chicago Midway

Mon 4/13

6:00 am-12:52 pm

1 stop7h 52m

$356

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/27

1:31 pm-3:19 pm

2 stops25h 48m

Chicago Midway

Fri 3/6

6:00 am-3:30 pm

1 stop9h 30m

$365

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/5

2:31 pm-10:22 pm

1 stop7h 51m

Chicago Midway

Sun 2/22

10:49 am-10:02 pm

1 stop11h 13m

$368

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/3

7:45 am-12:05 pm

2 stops28h 20m

Chicago Midway

Mon 2/9

7:00 pm-11:37 am

1 stop16h 37m

$370

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/12

9:40 am-8:25 pm

1 stop10h 45m

Chicago Midway

Mon 2/16

6:15 am-7:30 pm

1 stop13h 15m

$377

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/13

7:00 am-5:45 pm

1 stop10h 45m

Chicago Midway

Mon 2/16

6:00 am-10:02 pm

1 stop16h 02m

$387

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 2/27

12:35 pm-2:55 pm

1 stop26h 20m

Chicago Midway

Fri 3/6

9:51 pm-11:40 am

1 stop13h 49m

$388

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 67% 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 36m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 7h 36m
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.
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  • 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 36m 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
4,258 reviews
Search Southwest flights

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 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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