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Cheap flights from San José to Chicago from $161

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 3/14. 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.
Delta Logo
7:00 am - 10:31 pm
SJO
-
MDW
15h 31m
1 stop
Delta Logo
12:45 pm - 10:02 pm
MDW
-
SJO
9h 17m
1 stop
$325Delta
vie., feb. 13 - lun., mar. 2
Multiple Airlines Logo
3:05 pm - 1:41 pm
SJO
-
MDW
21h 36m
2 stops
Multiple Airlines Logo
11:19 am - 10:42 am
MDW
-
SJO
24h 23m
1 stop
$332Multiple Airlines
mié., mar. 11 - mié., mar. 18
Multiple Airlines Logo
11:38 am - 11:51 pm
SJO
-
MDW
11h 13m
1 stop
Multiple Airlines Logo
9:51 pm - 11:19 am
MDW
-
SJO
14h 28m
2 stops
$361Multiple Airlines
vie., mar. 13 - lun., mar. 16
Southwest Logo
9:40 am - 8:55 pm
SJO
-
MDW
11h 15m
2 stops
Southwest Logo
7:45 am - 7:30 pm
MDW
-
SJO
11h 45m
2 stops
$416Southwest
vie., feb. 13 - lun., mar. 2
Southwest Logo
9:00 am - 7:45 pm
SJO
-
MDW
9h 45m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$418Southwest
mar., abr. 14 - mar., abr. 21
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
6:50 am - 1:00 pm
MDW
-
SJO
7h 10m
1 stop
$419Southwest
vie., may. 1 - dom., may. 3
Southwest Logo
9:00 am - 7:45 pm
SJO
-
MDW
9h 45m
2 stops
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$422Southwest
mar., abr. 14 - mar., abr. 21
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
$436Southwest
vie., may. 1 - jue., may. 7
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
10:50 am - 7:00 pm
MDW
-
SJO
9h 10m
2 stops
$447Southwest
vie., may. 1 - dom., may. 3
Southwest Logo
9:40 am - 8:55 pm
SJO
-
MDW
11h 15m
2 stops
Southwest Logo
9:55 am - 7:30 pm
MDW
-
SJO
9h 35m
2 stops
$449Southwest
jue., feb. 12 - mar., feb. 24

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Feb 13
SJO2:25 pmSan José Juan Santamaria Intl
8h 06m
1 stop
MDW10:31 pmChicago Midway
Mar 2
MDW1:29 pmChicago Midway
8h 33m
2 stops
SJO10:02 pmSan José Juan Santamaria Intl
$325
Delta
Feb 5
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Feb 22
MDW12:45 pmChicago Midway
9h 17m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$359
Delta
Feb 5
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Feb 22
MDW12:45 pmChicago Midway
9h 17m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$385

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
16h 02m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$468
JetBlue
Feb 11
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Feb 18
MDW6:00 amChicago Midway
16h 02m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$522
JetBlue
Feb 18
SJO7:00 amSan José Juan Santamaria Intl
15h 31m
1 stop
MDW10:31 pmChicago Midway
Feb 21
MDW11:06 amChicago Midway
10h 56m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$553

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 enero 29, 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

vie. 2/13

7:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

lun. 3/2

12:45 pm-10:02 pm

1 stop9h 17m

$325

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mié. 3/11

3:05 pm-1:41 pm

2 stops21h 36m

Chicago Midway

mié. 3/18

11:19 am-10:42 am

1 stop24h 23m

$332

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 3/13

11:38 am-11:51 pm

1 stop11h 13m

Chicago Midway

lun. 3/16

9:51 pm-11:19 am

2 stops14h 28m

$361

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 2/13

9:40 am-8:55 pm

2 stops11h 15m

Chicago Midway

lun. 3/2

7:45 am-7:30 pm

2 stops11h 45m

$416

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mar. 4/14

9:00 am-7:45 pm

1 stop9h 45m

Chicago Midway

mar. 4/21

12:15 pm-7:00 pm

1 stop7h 45m

$418

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 5/1

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

dom. 5/3

6:50 am-1:00 pm

1 stop7h 10m

$419

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

mar. 4/14

9:00 am-7:45 pm

2 stops9h 45m

Chicago Midway

mar. 4/21

12:15 pm-7:00 pm

1 stop7h 45m

$422

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 5/1

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

jue. 5/7

12:10 pm-7:00 pm

1 stop7h 50m

$436

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

vie. 5/1

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

dom. 5/3

10:50 am-7:00 pm

2 stops9h 10m

$447

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

jue. 2/12

9:40 am-8:55 pm

2 stops11h 15m

Chicago Midway

mar. 2/24

9:55 am-7:30 pm

2 stops9h 35m

$449

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 71% 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
4,267 reviews
Search Southwest flights

Traveling to a place near Chicago?

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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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