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Cheap flights from San José to Chicago from $238

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 5/4. 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

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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.
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
$452Frontier
Thu, May 28 - Wed, Jun 3
Delta Logo
1:20 pm - 8:43 am
SJO
-
MDW
18h 23m
2 stops
Delta Logo
6:05 am - 11:49 am
MDW
-
SJO
6h 44m
1 stop
$476Delta
Fri, Jun 5 - Mon, Jun 8
Southwest Logo
9:00 am - 10:35 pm
SJO
-
MDW
12h 35m
2 stops
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
$481Southwest
Sat, Apr 25 - Tue, Apr 28
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
$492Frontier
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
10:06 am - 11:05 pm
SJO
-
MDW
11h 59m
1 stop
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$493Multiple Airlines
Sat, Apr 11 - Mon, Apr 13
Frontier Logo
9:35 am - 11:04 am
SJO
-
MDW
48h 29m
2 stops
Frontier Logo
6:00 am - 8:20 am
MDW
-
SJO
27h 20m
2 stops
$496Frontier
Thu, Jun 4 - Wed, Jun 10
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$502Southwest
Tue, May 5 - Tue, May 12
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
$507Frontier
Sun, May 24 - Wed, Jun 3
Delta Logo
1:20 pm - 8:43 am
SJO
-
MDW
18h 23m
2 stops
Delta Logo
6:05 am - 11:49 am
MDW
-
SJO
6h 44m
1 stop
$511Delta
Wed, Jun 3 - Tue, Jun 9
Southwest Logo
9:00 am - 10:35 pm
SJO
-
MDW
12h 35m
2 stops
Southwest Logo
10:05 am - 7:00 pm
MDW
-
SJO
9h 55m
2 stops
$515Southwest
Sat, Apr 25 - Tue, Apr 28

Frontier flights from San José to Chicago Midway Airport

Our best Frontier deals on San José to Chicago Midway Airport flight tickets
Frontier
Apr 9
SJO1:27 pmSan José Juan Santamaria Intl
29h 40m
1 stop
MDW8:07 pmChicago Midway
Apr 12
MDW6:00 amChicago Midway
7h 12m
1 stop
SJO12:12 pmSan José Juan Santamaria Intl
$340
Frontier
May 28
SJO9:35 amSan José Juan Santamaria Intl
11h 27m
2 stops
MDW10:02 pmChicago Midway
Jun 3
MDW3:07 pmChicago Midway
18h 12m
2 stops
SJO8:19 amSan José Juan Santamaria Intl
$452
Frontier
May 28
SJO9:35 amSan José Juan Santamaria Intl
11h 27m
2 stops
MDW10:02 pmChicago Midway
Jun 4
MDW3:07 pmChicago Midway
18h 12m
2 stops
SJO8:19 amSan José Juan Santamaria Intl
$492

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Jun 5
SJO1:20 pmSan José Juan Santamaria Intl
18h 23m
2 stops
MDW8:43 amChicago Midway
Jun 8
MDW6:05 amChicago Midway
6h 44m
1 stop
SJO11:49 amSan José Juan Santamaria Intl
$476
Delta
Jun 3
SJO1:20 pmSan José Juan Santamaria Intl
18h 23m
2 stops
MDW8:43 amChicago Midway
Jun 9
MDW6:05 amChicago Midway
6h 44m
1 stop
SJO11:49 amSan José Juan Santamaria Intl
$511
Delta
May 30
SJO2:40 pmSan José Juan Santamaria Intl
21h 02m
2 stops
MDW12:42 pmChicago Midway
Jun 7
MDW6:58 pmChicago Midway
17h 51m
2 stops
SJO11:49 amSan José Juan Santamaria Intl
$581

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 April 7, 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

Thu 5/28

9:35 am-10:02 pm

2 stops11h 27m

Chicago Midway

Wed 6/3

3:07 pm-8:19 am

2 stops18h 12m

$452

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 6/5

1:20 pm-8:43 am

2 stops18h 23m

Chicago Midway

Mon 6/8

6:05 am-11:49 am

1 stop6h 44m

$476

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 4/25

9:00 am-10:35 pm

2 stops12h 35m

Chicago Midway

Tue 4/28

6:00 am-12:10 pm

1 stop7h 10m

$481

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/28

9:35 am-10:02 pm

2 stops11h 27m

Chicago Midway

Thu 6/4

3:07 pm-8:19 am

2 stops18h 12m

$492

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 4/11

10:06 am-11:05 pm

1 stop11h 59m

Chicago Midway

Mon 4/13

6:30 am-3:05 pm

1 stop9h 35m

$493

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 6/4

9:35 am-11:04 am

2 stops48h 29m

Chicago Midway

Wed 6/10

6:00 am-8:20 am

2 stops27h 20m

$496
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 5/5

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Tue 5/12

12:15 pm-7:00 pm

1 stop7h 45m

$502

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 5/24

9:35 am-10:02 pm

2 stops11h 27m

Chicago Midway

Wed 6/3

3:07 pm-8:19 am

2 stops18h 12m

$507

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 6/3

1:20 pm-8:43 am

2 stops18h 23m

Chicago Midway

Tue 6/9

6:05 am-11:49 am

1 stop6h 44m

$511

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 4/25

9:00 am-10:35 pm

2 stops12h 35m

Chicago Midway

Tue 4/28

10:05 am-7:00 pm

2 stops9h 55m

$515

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?

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

You could potentially save up to 83% 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 21m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 7h 21m
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 21m 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
4,338 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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