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Cheap flights from San José to Chicago from $155

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 12/20. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:58 pm - 10:34 amSJO-MDW
19h 36m1 stop
Multiple Airlines Logo
7:20 pm - 11:25 amMDW-SJO
16h 05m2 stops
$281Multiple Airlines
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Mon, Jan 12 - Mon, Jan 19
Multiple Airlines Logo
2:58 pm - 10:34 amSJO-MDW
19h 36m1 stop
Multiple Airlines Logo
7:20 pm - 3:30 pmMDW-SJO
20h 10m1 stop
$284Multiple Airlines
Find Deal
Mon, Jan 12 - Mon, Jan 19
Frontier Logo
2:52 pm - 5:38 pmSJO-MDW
26h 46m1 stop
Frontier Logo
6:12 am - 9:21 amMDW-SJO
51h 09m2 stops
$313Frontier
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Wed, Dec 24 - Thu, Jan 1
Frontier Logo
2:52 pm - 5:38 pmSJO-MDW
26h 46m1 stop
Frontier Logo
6:33 pm - 1:42 pmMDW-SJO
19h 09m1 stop
$318Frontier
Find Deal
Wed, Dec 24 - Thu, Jan 1
Delta Logo
2:31 pm - 8:52 amSJO-MDW
18h 21m2 stops
Delta Logo
12:48 pm - 10:15 pmMDW-SJO
9h 27m1 stop
$344Delta
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Wed, Jan 21 - Mon, Jan 26
Frontier Logo
2:52 pm - 5:38 pmSJO-MDW
26h 46m1 stop
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
7h 30m1 stop
$349Frontier
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Wed, Dec 24 - Wed, Dec 31
Southwest Logo
1:50 pm - 10:15 pmSJO-MDW
8h 25m1 stop
Southwest Logo
6:15 am - 7:30 pmMDW-SJO
13h 15m1 stop
$352Southwest
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Thu, Feb 12 - Mon, Feb 16
Delta Logo
7:00 am - 5:45 pmSJO-MDW
10h 45m1 stop
Delta Logo
12:47 pm - 9:15 pmMDW-SJO
9h 28m1 stop
$353Delta
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Fri, Mar 6 - Mon, Mar 23
Frontier Logo
1:35 pm - 10:27 pmSJO-MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pmMDW-SJO
7h 32m1 stop
$357Frontier
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Sat, Jan 10 - Sat, Jan 17
Delta Logo
2:31 pm - 8:52 amSJO-MDW
18h 21m2 stops
Delta Logo
12:48 pm - 10:15 pmMDW-SJO
9h 27m1 stop
$358Delta
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Thu, Jan 22 - Mon, Jan 26

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Jan 21
SJO2:31 pmSan José Juan Santamaria Intl
18h 21m
2 stops
MDW8:52 amChicago Midway
Jan 26
MDW12:48 pmChicago Midway
9h 27m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
$344
Find similar
Delta
Mar 6
SJO7:00 amSan José Juan Santamaria Intl
10h 45m
1 stop
MDW5:45 pmChicago Midway
Mar 23
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$353
Find similar
Delta
Jan 22
SJO2:31 pmSan José Juan Santamaria Intl
18h 21m
2 stops
MDW8:52 amChicago Midway
Jan 26
MDW12:48 pmChicago Midway
9h 27m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
$358
Find similar

Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
Feb 12
SJO1:50 pmSan José Juan Santamaria Intl
8h 25m
1 stop
MDW10:15 pmChicago Midway
Feb 16
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$352
Find similar
Southwest
Jan 22
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
Jan 28
MDW8:55 amChicago Midway
10h 35m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$375
Find similar
Southwest
Jan 22
SJO9:40 amSan José Juan Santamaria Intl
11h 00m
2 stops
MDW8:40 pmChicago Midway
Jan 26
MDW8:55 amChicago Midway
10h 35m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$379
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 3, 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

Mon 1/12

2:58 pm-10:34 am

1 stop19h 36m

Chicago Midway

Mon 1/19

7:20 pm-11:25 am

2 stops16h 05m

$281

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 1/12

2:58 pm-10:34 am

1 stop19h 36m

Chicago Midway

Mon 1/19

7:20 pm-3:30 pm

1 stop20h 10m

$284

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 12/24

2:52 pm-5:38 pm

1 stop26h 46m

Chicago Midway

Thu 1/1

6:12 am-9:21 am

2 stops51h 09m

$313

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 12/24

2:52 pm-5:38 pm

1 stop26h 46m

Chicago Midway

Thu 1/1

6:33 pm-1:42 pm

1 stop19h 09m

$318

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 1/21

2:31 pm-8:52 am

2 stops18h 21m

Chicago Midway

Mon 1/26

12:48 pm-10:15 pm

1 stop9h 27m

$344

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 12/24

2:52 pm-5:38 pm

1 stop26h 46m

Chicago Midway

Wed 12/31

6:12 am-1:42 pm

1 stop7h 30m

$349

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/12

1:50 pm-10:15 pm

1 stop8h 25m

Chicago Midway

Mon 2/16

6:15 am-7:30 pm

1 stop13h 15m

$352

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 3/6

7:00 am-5:45 pm

1 stop10h 45m

Chicago Midway

Mon 3/23

12:47 pm-9:15 pm

1 stop9h 28m

$353

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

$357

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 1/22

2:31 pm-8:52 am

2 stops18h 21m

Chicago Midway

Mon 1/26

12:48 pm-10:15 pm

1 stop9h 27m

$358

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 cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from San José, with most prices found around $486. If you are unable to visit Chicago Midway Airport during the month of August, then departing from San José during the month October is also very affordable. Most momondo users find prices during this month for around $505.

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 73% 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.
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  • 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 40m 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
4,253 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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