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Cheap flights from San José to Chicago from $179

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 2/26. 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.
Multiple Airlines Logo
11:35 am - 8:53 pm
SJO
-
MDW
8h 18m
1 stop
Multiple Airlines Logo
6:00 am - 1:40 pm
MDW
-
SJO
32h 40m
2 stops
$358Multiple Airlines
Mon, Mar 9 - Sat, Mar 14
Delta Logo
2:25 pm - 10:31 pm
SJO
-
MDW
8h 06m
1 stop
Delta Logo
6:00 am - 10:02 pm
MDW
-
SJO
16h 02m
1 stop
$359Delta
Sat, Feb 14 - Sat, Feb 21
Delta Logo
7:00 am - 3:21 pm
SJO
-
MDW
8h 21m
1 stop
Delta Logo
6:00 am - 2:21 pm
MDW
-
SJO
8h 21m
1 stop
$367Delta
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
1:15 pm - 9:50 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
11:35 am - 7:30 pm
MDW
-
SJO
7h 55m
1 stop
$368Southwest
Sat, Feb 14 - Sat, Feb 21
Multiple Airlines Logo
11:38 am - 11:51 pm
SJO
-
MDW
11h 13m
1 stop
Multiple Airlines Logo
9:16 pm - 11:14 am
MDW
-
SJO
14h 58m
2 stops
$373Multiple Airlines
Fri, Mar 13 - Sat, Mar 28
Multiple Airlines Logo
11:35 am - 8:53 pm
SJO
-
MDW
8h 18m
1 stop
Multiple Airlines Logo
6:00 am - 11:30 pm
MDW
-
SJO
18h 30m
3 stops
$379Multiple Airlines
Mon, Mar 9 - Sat, Mar 14
Multiple Airlines Logo
11:35 am - 8:53 pm
SJO
-
MDW
8h 18m
1 stop
Multiple Airlines Logo
6:00 am - 11:40 pm
MDW
-
SJO
18h 40m
3 stops
$397Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
$418Southwest
Thu, Apr 16 - Fri, Apr 24
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
9:00 am - 7:00 pm
MDW
-
SJO
11h 00m
2 stops
$447Southwest
Thu, Apr 16 - Fri, Apr 24
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
$450Southwest
Wed, Apr 29 - Wed, May 6

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Feb 14
SJO2:25 pmSan José Juan Santamaria Intl
8h 06m
1 stop
MDW10:31 pmChicago Midway
Feb 21
MDW6:00 amChicago Midway
16h 02m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$359
Delta
Feb 14
SJO7:00 amSan José Juan Santamaria Intl
8h 21m
1 stop
MDW3:21 pmChicago Midway
Feb 21
MDW6:00 amChicago Midway
8h 21m
1 stop
SJO2:21 pmSan José Juan Santamaria Intl
$367
Delta
Feb 6
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Feb 18
MDW10:49 amChicago Midway
11h 13m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$374

Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
Feb 14
SJO1:15 pmSan José Juan Santamaria Intl
8h 35m
1 stop
MDW9:50 pmChicago Midway
Feb 21
MDW11:35 amChicago Midway
7h 55m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$368
Southwest
Feb 7
SJO9:30 amSan José Juan Santamaria Intl
9h 30m
1 stop
MDW7:00 pmChicago Midway
Feb 21
MDW11:35 amChicago Midway
7h 55m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$376
Southwest
Apr 16
SJO1:10 pmSan José Juan Santamaria Intl
7h 45m
1 stop
MDW9:55 pmChicago Midway
Apr 24
MDW5:35 amChicago Midway
7h 35m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
$418

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 4, 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

Mon 3/9

11:35 am-8:53 pm

1 stop8h 18m

Chicago Midway

Sat 3/14

6:00 am-1:40 pm

2 stops32h 40m

$358

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/14

2:25 pm-10:31 pm

1 stop8h 06m

Chicago Midway

Sat 2/21

6:00 am-10:02 pm

1 stop16h 02m

$359

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/14

7:00 am-3:21 pm

1 stop8h 21m

Chicago Midway

Sat 2/21

6:00 am-2:21 pm

1 stop8h 21m

$367

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 2/14

1:15 pm-9:50 pm

1 stop8h 35m

Chicago Midway

Sat 2/21

11:35 am-7:30 pm

1 stop7h 55m

$368

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/13

11:38 am-11:51 pm

1 stop11h 13m

Chicago Midway

Sat 3/28

9:16 pm-11:14 am

2 stops14h 58m

$373

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 3/9

11:35 am-8:53 pm

1 stop8h 18m

Chicago Midway

Sat 3/14

6:00 am-11:30 pm

3 stops18h 30m

$379

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 3/9

11:35 am-8:53 pm

1 stop8h 18m

Chicago Midway

Mon 3/16

6:00 am-11:40 pm

3 stops18h 40m

$397

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

Fri 4/24

5:35 am-12:10 pm

1 stop7h 35m

$418

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

Fri 4/24

9:00 am-7:00 pm

2 stops11h 00m

$447

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 4/29

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Wed 5/6

12:15 pm-7:00 pm

1 stop7h 45m

$450

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

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

  • 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 $463Free CancellationRating
8.0
4,274 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
Benton Harbor
Saint Joseph
Portage
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Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
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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