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Cheap flights from San José to Chicago from $169

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 3/9. 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
12:47 pm - 9:15 pm
MDW
-
SJO
9h 28m
1 stop
$334Delta
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
12:35 pm - 1:08 pm
SJO
-
MDW
24h 33m
1 stop
Multiple Airlines Logo
9:51 pm - 10:40 am
MDW
-
SJO
13h 49m
1 stop
$341Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Delta Logo
7:00 am - 10:31 pm
SJO
-
MDW
14h 31m
1 stop
Delta Logo
9:35 am - 9:15 pm
MDW
-
SJO
12h 40m
2 stops
$345Delta
Wed, Mar 11 - Wed, Mar 18
LATAM Airlines Logo
7:00 am - 10:31 pm
SJO
-
MDW
15h 31m
1 stop
LATAM Airlines Logo
12:47 pm - 9:15 pm
MDW
-
SJO
9h 28m
1 stop
$354LATAM Airlines
Fri, Mar 6 - Tue, Mar 17
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
$361Southwest
Fri, May 8 - Tue, May 12
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
Frontier Logo
6:00 am - 12:12 pm
MDW
-
SJO
7h 12m
1 stop
$367Frontier
Sun, Apr 5 - Sun, Apr 12
Multiple Airlines Logo
7:45 am - 1:56 pm
SJO
-
MDW
30h 11m
1 stop
Multiple Airlines Logo
2:56 pm - 10:40 am
MDW
-
SJO
19h 44m
1 stop
$371Multiple Airlines
Wed, Mar 4 - Sat, Mar 7
Multiple Airlines Logo
3:05 pm - 1:56 pm
SJO
-
MDW
22h 51m
2 stops
Multiple Airlines Logo
2:56 pm - 10:40 am
MDW
-
SJO
19h 44m
1 stop
$372Multiple Airlines
Wed, Mar 4 - Sat, Mar 7
Multiple Airlines Logo
12:35 pm - 8:53 pm
SJO
-
MDW
8h 18m
1 stop
Multiple Airlines Logo
6:00 am - 7:45 am
MDW
-
SJO
26h 45m
3 stops
$380Multiple Airlines
Fri, Mar 6 - Tue, Mar 10
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
$387Southwest
Fri, May 8 - Mon, May 11

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 17
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$354
LATAM Airlines
Mar 3
SJO7:00 amSan José Juan Santamaria Intl
15h 33m
1 stop
MDW10:33 pmChicago Midway
Mar 7
MDW6:00 amChicago Midway
16h 02m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$530
LATAM Airlines
Mar 20
SJO7:00 amSan José Juan Santamaria Intl
24h 53m
2 stops
MDW8:53 amChicago Midway
Mar 22
MDW6:00 amChicago Midway
16h 15m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$534

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Mar 6
SJO7:00 amSan José Juan Santamaria Intl
15h 31m
1 stop
MDW10:31 pmChicago Midway
Mar 10
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$334
Delta
Feb 19
SJO2:25 pmSan José Juan Santamaria Intl
8h 06m
1 stop
MDW10:31 pmChicago Midway
Feb 24
MDW9:34 amChicago Midway
12h 28m
2 stops
SJO10:02 pmSan José Juan Santamaria Intl
$408
Delta
Feb 26
SJO2:25 pmSan José Juan Santamaria Intl
8h 06m
1 stop
MDW10:31 pmChicago Midway
Mar 3
MDW12:45 pmChicago Midway
9h 17m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$413

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 February 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 3/6

7:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

Tue 3/10

12:47 pm-9:15 pm

1 stop9h 28m

$334

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 3/5

12:35 pm-1:08 pm

1 stop24h 33m

Chicago Midway

Mon 3/9

9:51 pm-10:40 am

1 stop13h 49m

$341

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 3/11

7:00 am-10:31 pm

1 stop14h 31m

Chicago Midway

Wed 3/18

9:35 am-9:15 pm

2 stops12h 40m

$345

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/6

7:00 am-10:31 pm

1 stop15h 31m

Chicago Midway

Tue 3/17

12:47 pm-9:15 pm

1 stop9h 28m

$354

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/8

9:00 am-10:20 pm

2 stops12h 20m

Chicago Midway

Tue 5/12

6:00 am-12:10 pm

1 stop7h 10m

$361

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 4/5

1:27 pm-8:07 pm

1 stop29h 40m

Chicago Midway

Sun 4/12

6:00 am-12:12 pm

1 stop7h 12m

$367

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 3/4

7:45 am-1:56 pm

1 stop30h 11m

Chicago Midway

Sat 3/7

2:56 pm-10:40 am

1 stop19h 44m

$371

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 3/4

3:05 pm-1:56 pm

2 stops22h 51m

Chicago Midway

Sat 3/7

2:56 pm-10:40 am

1 stop19h 44m

$372

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/6

12:35 pm-8:53 pm

1 stop8h 18m

Chicago Midway

Tue 3/10

6:00 am-7:45 am

3 stops26h 45m

$380

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/8

9:00 am-10:20 pm

2 stops12h 20m

Chicago Midway

Mon 5/11

5:35 am-12:10 pm

1 stop7h 35m

$387

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

8h 06m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 8h 06m
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 8h 06m 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
4,285 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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Hammond
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Saint Joseph
Portage
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Crown Point
Chesterton
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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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