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Cheap flights from San José to Chicago from $210

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 4/9. 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.
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
6:00 am - 12:10 pm
MDW
-
SJO
7h 10m
1 stop
$356Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
9:00 am - 8:15 pm
SJO
-
MDW
10h 15m
2 stops
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$410Southwest
Thu, May 14 - Mon, May 18
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
10:05 am - 7:00 pm
MDW
-
SJO
9h 55m
2 stops
$415Southwest
Tue, May 5 - Tue, May 12
Frontier Logo
10:00 am - 7:00 am
SJO
-
MDW
20h 00m
2 stops
Frontier Logo
7:41 pm - 8:45 am
MDW
-
SJO
14h 04m
1 stop
$423Frontier
Thu, May 28 - Sun, May 31
Multiple Airlines Logo
7:45 am - 10:19 pm
SJO
-
MDW
13h 34m
2 stops
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$424Multiple Airlines
Tue, Apr 7 - Fri, Apr 10
Multiple Airlines Logo
7:45 am - 10:19 pm
SJO
-
MDW
37h 34m
2 stops
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$431Multiple Airlines
Mon, Apr 6 - Mon, Apr 13
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
5:00 am - 12:15 pm
MDW
-
SJO
8h 15m
1 stop
$451Southwest
Fri, Apr 17 - Sat, Apr 25
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$453Southwest
Fri, May 8 - Tue, May 12
Delta Logo
1:21 pm - 10:28 pm
SJO
-
MDW
8h 07m
1 stop
Delta Logo
6:23 am - 1:15 pm
MDW
-
SJO
7h 52m
1 stop
$455Delta
Sat, May 2 - Sat, May 9
Southwest Logo
9:00 am - 8:15 pm
SJO
-
MDW
10h 15m
2 stops
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$459Southwest
Thu, May 14 - Mon, May 18

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
May 2
SJO1:21 pmSan José Juan Santamaria Intl
8h 07m
1 stop
MDW10:28 pmChicago Midway
May 9
MDW6:23 amChicago Midway
7h 52m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
$455
Delta
May 8
SJO1:20 pmSan José Juan Santamaria Intl
22h 22m
2 stops
MDW12:42 pmChicago Midway
May 27
MDW1:22 pmChicago Midway
23h 33m
2 stops
SJO11:55 amSan José Juan Santamaria Intl
$476
Delta
Mar 18
SJO7:00 amSan José Juan Santamaria Intl
9h 54m
2 stops
MDW5:54 pmChicago Midway
Mar 22
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$525

Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
May 5
SJO1:10 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:05 pmChicago Midway
May 12
MDW6:00 amChicago Midway
7h 10m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
$356
Southwest
May 14
SJO9:00 amSan José Juan Santamaria Intl
10h 15m
2 stops
MDW8:15 pmChicago Midway
May 18
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
$410
Southwest
May 5
SJO1:10 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:05 pmChicago Midway
May 12
MDW10:05 amChicago Midway
9h 55m
2 stops
SJO7:00 pmSan José Juan Santamaria Intl
$415

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 March 10, 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 5/5

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Tue 5/12

6:00 am-12:10 pm

1 stop7h 10m

$356

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/14

9:00 am-8:15 pm

2 stops10h 15m

Chicago Midway

Mon 5/18

12:10 pm-7:00 pm

1 stop7h 50m

$410

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

10:05 am-7:00 pm

2 stops9h 55m

$415

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/28

10:00 am-7:00 am

2 stops20h 00m

Chicago Midway

Sun 5/31

7:41 pm-8:45 am

1 stop14h 04m

$423

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/7

7:45 am-10:19 pm

2 stops13h 34m

Chicago Midway

Fri 4/10

6:30 am-3:05 pm

1 stop9h 35m

$424

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 4/6

7:45 am-10:19 pm

2 stops37h 34m

Chicago Midway

Mon 4/13

6:30 am-3:05 pm

1 stop9h 35m

$431

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 4/17

9:00 am-9:00 pm

2 stops11h 00m

Chicago Midway

Sat 4/25

5:00 am-12:15 pm

1 stop8h 15m

$451
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/8

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

Tue 5/12

12:15 pm-7:00 pm

1 stop7h 45m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/2

1:21 pm-10:28 pm

1 stop8h 07m

Chicago Midway

Sat 5/9

6:23 am-1:15 pm

1 stop7h 52m

$455

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/14

9:00 am-8:15 pm

2 stops10h 15m

Chicago Midway

Mon 5/18

12:10 pm-7:00 pm

1 stop7h 50m

$459

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

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

You could potentially save up to 72% 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

  • 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
4,317 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
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Valparaiso
Schererville
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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