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Cheap flights from San José to Chicago from $281

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 9/2. 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 - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$404Southwest
Tue, Sep 15 - Fri, Sep 25
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$414Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
7:10 am - 6:40 pm
MDW
-
SJO
12h 30m
2 stops
$415Southwest
Tue, Sep 15 - Sun, Sep 20
Southwest Logo
1:15 pm - 10:00 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$430Southwest
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$439Southwest
Tue, Sep 15 - Mon, Sep 21
Southwest Logo
9:00 am - 9:55 pm
SJO
-
MDW
11h 55m
2 stops
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$456Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
1:15 pm - 10:00 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$462Southwest
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
9:00 am - 6:00 pm
SJO
-
MDW
8h 00m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$469Southwest
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
7:15 am - 12:45 pm
MDW
-
SJO
6h 30m
1 stop
$472Southwest
Tue, Aug 18 - Mon, Aug 31
Southwest Logo
9:00 am - 9:55 pm
SJO
-
MDW
11h 55m
2 stops
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$474Southwest
Thu, Sep 10 - Tue, Sep 15

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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 15
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
Sep 25
MDW10:05 amChicago Midway
9h 35m
1 stop
SJO6:40 pmSan José Juan Santamaria Intl
$404
Southwest
Sep 4
SJO9:00 amSan José Juan Santamaria Intl
11h 30m
1 stop
MDW9:30 pmChicago Midway
Sep 7
MDW5:00 amChicago Midway
8h 45m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
$414
Southwest
Sep 15
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
Sep 20
MDW7:10 amChicago Midway
12h 30m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
$415

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Sep 7
SJO1:14 pmSan José Juan Santamaria Intl
8h 22m
1 stop
MDW10:36 pmChicago Midway
Sep 17
MDW6:05 amChicago Midway
6h 49m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$567
Delta
Sep 3
SJO1:14 pmSan José Juan Santamaria Intl
8h 22m
1 stop
MDW10:36 pmChicago Midway
Sep 13
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$597
Delta
Sep 9
SJO1:19 pmSan José Juan Santamaria Intl
8h 26m
1 stop
MDW10:45 pmChicago Midway
Sep 20
MDW6:05 amChicago Midway
6h 49m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$632

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 June 17, 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

Tue 9/15

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Fri 9/25

10:05 am-6:40 pm

1 stop9h 35m

$404

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/4

9:00 am-9:30 pm

1 stop11h 30m

Chicago Midway

Mon 9/7

5:00 am-12:45 pm

1 stop8h 45m

$414

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 9/15

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Sun 9/20

7:10 am-6:40 pm

2 stops12h 30m

$415

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 9/12

1:15 pm-10:00 pm

1 stop7h 45m

Chicago Midway

Tue 9/15

6:15 am-12:45 pm

1 stop7h 30m

$430

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 9/15

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Mon 9/21

5:00 am-12:45 pm

1 stop8h 45m

$439

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/4

9:00 am-9:55 pm

2 stops11h 55m

Chicago Midway

Mon 9/7

5:00 am-12:45 pm

1 stop8h 45m

$456

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 9/12

1:15 pm-10:00 pm

1 stop7h 45m

Chicago Midway

Tue 9/15

10:10 am-6:40 pm

2 stops9h 30m

$462

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/10

9:00 am-6:00 pm

1 stop8h 00m

Chicago Midway

Tue 9/15

6:15 am-12:45 pm

1 stop7h 30m

$469
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 8/18

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Mon 8/31

7:15 am-12:45 pm

1 stop6h 30m

$472

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/10

9:00 am-9:55 pm

2 stops11h 55m

Chicago Midway

Tue 9/15

6:15 am-12:45 pm

1 stop7h 30m

$474

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 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 $0. If you are unable to visit Chicago Midway Airport during the month of November, then departing from San José during the month June is also very affordable. Most momondo users find prices during this month for around $0.

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

You could potentially save up to 78% 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 40m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 7h 40m
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 40m 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
7.9
4,235 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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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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