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Cheap flights from San José to Chicago from $153

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 1/17. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$302Frontier
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$333Frontier
Sat, Jan 10 - Sat, Jan 17
Delta Logo
7:00 am - 10:22 pm
SJO
-
MDW
15h 22m1 stop
Delta Logo
12:46 pm - 10:02 pm
MDW
-
SJO
9h 16m1 stop
$345Delta
Tue, Feb 3 - Tue, Feb 17
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
Southwest Logo
6:15 am - 7:30 pm
MDW
-
SJO
13h 15m1 stop
$354Southwest
Thu, Jan 29 - Wed, Feb 4
Frontier Logo
3:10 pm - 11:31 am
SJO
-
MDW
20h 21m1 stop
Frontier Logo
6:10 am - 1:36 pm
MDW
-
SJO
7h 26m1 stop
$361Frontier
Wed, Jan 7 - Mon, Jan 12
Delta Logo
7:00 am - 10:07 pm
SJO
-
MDW
15h 07m1 stop
Delta Logo
9:33 am - 10:15 pm
MDW
-
SJO
12h 42m2 stops
$373Delta
Wed, Jan 14 - Wed, Jan 28
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
Southwest Logo
8:55 am - 7:30 pm
MDW
-
SJO
10h 35m1 stop
$376Southwest
Thu, Jan 22 - Tue, Jan 27
Multiple Airlines Logo
1:35 pm - 10:59 pm
SJO
-
MDW
33h 24m2 stops
Multiple Airlines Logo
8:19 pm - 3:17 pm
MDW
-
SJO
18h 58m1 stop
$383Multiple Airlines
Sat, Jan 10 - Sun, Jan 18
Multiple Airlines Logo
1:30 pm - 7:07 pm
SJO
-
MDW
29h 37m2 stops
Multiple Airlines Logo
9:22 pm - 11:40 am
MDW
-
SJO
14h 18m1 stop
$385Multiple Airlines
Mon, Feb 9 - Mon, Feb 16
Multiple Airlines Logo
1:35 pm - 11:31 am
SJO
-
MDW
21h 56m1 stop
Multiple Airlines Logo
8:19 pm - 3:17 pm
MDW
-
SJO
18h 58m1 stop
$388Multiple Airlines
Sat, Jan 10 - Sun, Jan 18

Frontier flights from San José to Chicago Midway Airport

Our best Frontier deals on San José to Chicago Midway Airport flight tickets
Frontier
Jan 10
SJO1:35 pmSan José Juan Santamaria Intl
8h 52m
1 stop
MDW10:27 pmChicago Midway
Jan 17
MDW6:10 amChicago Midway
7h 32m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
$302
Find similar
Frontier
Jan 10
SJO1:35 pmSan José Juan Santamaria Intl
8h 52m
1 stop
MDW10:27 pmChicago Midway
Jan 17
MDW6:10 amChicago Midway
7h 32m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
$333
Find similar
Frontier
Jan 7
SJO3:10 pmSan José Juan Santamaria Intl
20h 21m
1 stop
MDW11:31 amChicago Midway
Jan 12
MDW6:10 amChicago Midway
7h 26m
1 stop
SJO1:36 pmSan José Juan Santamaria Intl
$361
Find similar

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Feb 6
SJO7:00 amSan José Juan Santamaria Intl
10h 29m
1 stop
MDW5:29 pmChicago Midway
Feb 15
MDW11:01 amChicago Midway
11h 01m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$345
Find similar
Delta
Jan 14
SJO7:00 amSan José Juan Santamaria Intl
15h 07m
1 stop
MDW10:07 pmChicago Midway
Jan 28
MDW10:46 amChicago Midway
11h 29m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
$373
Find similar
Delta
Mar 24
SJO1:20 pmSan José Juan Santamaria Intl
8h 09m
1 stop
MDW10:29 pmChicago Midway
Apr 6
MDW6:35 pmChicago Midway
27h 40m
2 stops
SJO9:15 pmSan José Juan Santamaria Intl
$400
Find similar

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 December 18, 2025.
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

Sat 1/10

1:35 pm-10:27 pm

1 stop8h 52m

Chicago Midway

Sat 1/17

6:10 am-1:42 pm

1 stop7h 32m

$302

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/10

1:35 pm-10:27 pm

1 stop8h 52m

Chicago Midway

Sat 1/17

6:10 am-1:42 pm

1 stop7h 32m

$333

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 2/3

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Tue 2/17

12:46 pm-10:02 pm

1 stop9h 16m

$345

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 1/29

9:40 am-10:55 pm

1 stop13h 15m

Chicago Midway

Wed 2/4

6:15 am-7:30 pm

1 stop13h 15m

$354

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 1/7

3:10 pm-11:31 am

1 stop20h 21m

Chicago Midway

Mon 1/12

6:10 am-1:36 pm

1 stop7h 26m

$361

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 1/14

7:00 am-10:07 pm

1 stop15h 07m

Chicago Midway

Wed 1/28

9:33 am-10:15 pm

2 stops12h 42m

$373

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 1/22

9:40 am-10:55 pm

1 stop13h 15m

Chicago Midway

Tue 1/27

8:55 am-7:30 pm

1 stop10h 35m

$376

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/10

1:35 pm-10:59 pm

2 stops33h 24m

Chicago Midway

Sun 1/18

8:19 pm-3:17 pm

1 stop18h 58m

$383

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 2/9

1:30 pm-7:07 pm

2 stops29h 37m

Chicago Midway

Mon 2/16

9:22 pm-11:40 am

1 stop14h 18m

$385

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/10

1:35 pm-11:31 am

1 stop21h 56m

Chicago Midway

Sun 1/18

8:19 pm-3:17 pm

1 stop18h 58m

$388

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from San José. The lowest ticket price found for a Thursday departure recently was $599. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from San José because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $976.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San José in the morning is the least expensive time of day to depart. momondo users have found prices as low as $610 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $896. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You could potentially save up to 76% 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 45m

Direct flights

None
The fastest flight from San José to Chicago Midway Airport takes 7h 45m
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 45m 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
4,250 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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Porter
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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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