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Cheap flights from San José to Chicago from $251

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 9/29. 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
2 stops
$405Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
6:45 am - 12:35 pm
MDW
-
SJO
6h 50m
1 stop
$409Southwest
Mon, Sep 28 - Mon, Oct 5
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
9:55 am - 6:00 pm
MDW
-
SJO
9h 05m
2 stops
$410Southwest
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
9:00 am - 9:55 pm
SJO
-
MDW
11h 55m
2 stops
Southwest Logo
6:45 am - 12:35 pm
MDW
-
SJO
6h 50m
1 stop
$414Southwest
Mon, Sep 28 - Mon, Oct 5
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$437Southwest
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$441Southwest
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$443Southwest
Thu, Sep 10 - Thu, Sep 17
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
8:20 am - 6:40 pm
MDW
-
SJO
11h 20m
2 stops
$447Southwest
Wed, Sep 16 - Wed, Sep 23
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$448Southwest
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
10:30 am - 6:40 pm
MDW
-
SJO
9h 10m
1 stop
$453Southwest
Fri, Sep 11 - Tue, Sep 15

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JetBlue flights from San José to Chicago Midway Airport

Our best JetBlue deals on San José to Chicago Midway Airport flight tickets
JetBlue
Aug 28
SJO9:00 amSan José Juan Santamaria Intl
12h 40m
1 stop
MDW10:40 pmChicago Midway
Aug 30
MDW10:40 amChicago Midway
9h 00m
1 stop
SJO6:40 pmSan José Juan Santamaria Intl
$462
JetBlue
Jul 16
SJO1:40 pmSan José Juan Santamaria Intl
8h 25m
1 stop
MDW11:05 pmChicago Midway
Jul 20
MDW6:30 amChicago Midway
7h 15m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
$464
JetBlue
Jul 5
SJO8:45 amSan José Juan Santamaria Intl
11h 05m
1 stop
MDW8:50 pmChicago Midway
Jul 11
MDW5:05 amChicago Midway
9h 30m
1 stop
SJO1:35 pmSan José Juan Santamaria Intl
$466

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 30m
1 stop
MDW11:10 pmChicago Midway
Sep 28
MDW10:05 amChicago Midway
9h 35m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
$405
Southwest
Sep 28
SJO1:40 pmSan José Juan Santamaria Intl
7h 35m
1 stop
MDW10:15 pmChicago Midway
Oct 5
MDW6:45 amChicago Midway
6h 50m
1 stop
SJO12:35 pmSan José Juan Santamaria Intl
$409
Southwest
Sep 2
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
Sep 5
MDW9:55 amChicago Midway
9h 05m
2 stops
SJO6:00 pmSan José Juan Santamaria Intl
$410

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 July 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-11:10 pm

1 stop8h 30m

Chicago Midway

Mon 9/28

10:05 am-6:40 pm

2 stops9h 35m

$405
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/28

1:40 pm-10:15 pm

1 stop7h 35m

Chicago Midway

Mon 10/5

6:45 am-12:35 pm

1 stop6h 50m

$409

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/2

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Sat 9/5

9:55 am-6:00 pm

2 stops9h 05m

$410

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/28

9:00 am-9:55 pm

2 stops11h 55m

Chicago Midway

Mon 10/5

6:45 am-12:35 pm

1 stop6h 50m

$414

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/3

1:40 pm-10:15 pm

1 stop7h 35m

Chicago Midway

Tue 9/8

6:15 am-12:45 pm

1 stop7h 30m

$437

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/3

9:00 am-10:20 pm

2 stops12h 20m

Chicago Midway

Tue 9/8

6:15 am-12:45 pm

1 stop7h 30m

$441

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 9/10

1:40 pm-10:15 pm

1 stop7h 35m

Chicago Midway

Thu 9/17

10:05 am-6:40 pm

1 stop9h 35m

$443

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/16

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Wed 9/23

8:20 am-6:40 pm

2 stops11h 20m

$447

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/2

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Wed 9/9

10:10 am-6:40 pm

2 stops9h 30m

$448

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/11

1:40 pm-10:15 pm

1 stop7h 35m

Chicago Midway

Tue 9/15

10:30 am-6:40 pm

1 stop9h 10m

$453

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?

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 35m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 7h 35m
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 35m 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
7.9
4,250 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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