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Cheap flights from San José to Chicago from $241

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 9/24. 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
1 adult, Economy, 0 bags

Find the cheapest flights from San José to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:40 pm - 11:15 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$422Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 11:15 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
9:20 am - 6:45 pm
MDW
-
SJO
10h 25m
2 stops
$438Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm
SJO
-
MDW
7h 40m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$453Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm
SJO
-
MDW
7h 40m
1 stop
Southwest Logo
7:55 am - 6:45 pm
MDW
-
SJO
11h 50m
2 stops
$458Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
9:00 am - 9:35 pm
SJO
-
MDW
11h 35m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$468Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm
SJO
-
MDW
7h 40m
1 stop
Southwest Logo
9:55 am - 7:40 pm
MDW
-
SJO
10h 45m
2 stops
$468Southwest
Thu, Sep 24 - Sun, Oct 4
Southwest Logo
9:00 am - 10:25 pm
SJO
-
MDW
12h 25m
2 stops
Southwest Logo
7:55 am - 6:45 pm
MDW
-
SJO
11h 50m
2 stops
$470Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
7:55 am - 6:45 pm
MDW
-
SJO
11h 50m
2 stops
$473Southwest
Fri, Sep 25 - Mon, Sep 28
JetBlue Logo
9:00 am - 7:15 pm
SJO
-
MDW
9h 15m
1 stop
JetBlue Logo
8:05 am - 6:40 pm
MDW
-
SJO
11h 35m
1 stop
$488JetBlue
Wed, Sep 9 - Sun, Sep 20
JetBlue Logo
9:00 am - 10:40 pm
SJO
-
MDW
12h 40m
1 stop
JetBlue Logo
8:05 pm - 12:45 pm
MDW
-
SJO
17h 40m
1 stop
$488JetBlue
Thu, Sep 17 - Sun, Sep 20

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Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
Sep 23
SJO1:40 pmSan José Juan Santamaria Intl
8h 35m
1 stop
MDW11:15 pmChicago Midway
Sep 28
MDW5:00 amChicago Midway
8h 45m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
$422
Southwest
Sep 23
SJO1:40 pmSan José Juan Santamaria Intl
8h 35m
1 stop
MDW11:15 pmChicago Midway
Sep 28
MDW9:20 amChicago Midway
10h 25m
2 stops
SJO6:45 pmSan José Juan Santamaria Intl
$438
Southwest
Sep 21
SJO1:40 pmSan José Juan Santamaria Intl
7h 40m
1 stop
MDW10:20 pmChicago Midway
Sep 28
MDW5:00 amChicago Midway
8h 45m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
$453

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Oct 24
SJO1:25 pmSan José Juan Santamaria Intl
8h 08m
1 stop
MDW10:33 pmChicago Midway
Nov 15
MDW6:44 pmChicago Midway
27h 31m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
$529
Delta
Oct 30
SJO1:25 pmSan José Juan Santamaria Intl
18h 52m
2 stops
MDW9:17 amChicago Midway
Nov 10
MDW9:30 amChicago Midway
12h 45m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
$585
Delta
Aug 12
SJO1:14 pmSan José Juan Santamaria Intl
8h 22m
1 stop
MDW10:36 pmChicago Midway
Aug 24
MDW6:05 amChicago Midway
6h 44m
1 stop
SJO11:49 amSan José Juan Santamaria Intl
$887

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 August 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

Cheapest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/23

1:40 pm-11:15 pm

1 stop8h 35m

Chicago Midway

Mon 9/28

5:00 am-12:45 pm

1 stop8h 45m

$422

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/23

1:40 pm-11:15 pm

1 stop8h 35m

Chicago Midway

Mon 9/28

9:20 am-6:45 pm

2 stops10h 25m

$438
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/21

1:40 pm-10:20 pm

1 stop7h 40m

Chicago Midway

Mon 9/28

5:00 am-12:45 pm

1 stop8h 45m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/21

1:40 pm-10:20 pm

1 stop7h 40m

Chicago Midway

Mon 9/28

7:55 am-6:45 pm

2 stops11h 50m

$458

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/25

9:00 am-9:35 pm

1 stop11h 35m

Chicago Midway

Mon 9/28

5:00 am-12:45 pm

1 stop8h 45m

$468

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/24

1:40 pm-10:20 pm

1 stop7h 40m

Chicago Midway

Sun 10/4

9:55 am-7:40 pm

2 stops10h 45m

$468

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/23

9:00 am-10:25 pm

2 stops12h 25m

Chicago Midway

Mon 9/28

7:55 am-6:45 pm

2 stops11h 50m

$470

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/25

9:00 am-9:00 pm

2 stops11h 00m

Chicago Midway

Mon 9/28

7:55 am-6:45 pm

2 stops11h 50m

$473

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/9

9:00 am-7:15 pm

1 stop9h 15m

Chicago Midway

Sun 9/20

8:05 am-6:40 pm

1 stop11h 35m

$488

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/17

9:00 am-10:40 pm

1 stop12h 40m

Chicago Midway

Sun 9/20

8:05 pm-12:45 pm

1 stop17h 40m

$488

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

What is the typical price of a round-trip flight between San José and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $515 to $767.
The lowest price recently found on this route was $422.

What is the cheapest month to fly to Chicago Midway Airport?

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from San José, with most prices found around $358. If you are unable to visit Chicago Midway Airport during the month of November, then departing from San José during the month January is also very affordable. Most momondo users find prices during this month for around $385.

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

Frequently asked questions about flying from San José to Chicago Midway Airport

  • 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 $390Free CancellationRating
8.0
4,224 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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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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