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Cheap flights from San José to Chicago from $151

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.
Frontier Logo
12:59 pm - 10:29 pm
SJO
-
MDW
8h 30m
1 stop
Frontier Logo
6:00 am - 12:12 pm
MDW
-
SJO
7h 12m
1 stop
$365Frontier
Sat, Apr 4 - Thu, Apr 9
Frontier Logo
1:27 pm - 8:07 pm
SJO
-
MDW
29h 40m
1 stop
Frontier Logo
6:00 am - 12:12 pm
MDW
-
SJO
7h 12m
1 stop
$418Frontier
Sun, Apr 5 - Thu, Apr 9
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
$462Frontier
Sat, May 30 - Thu, Jun 4
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$463Southwest
Thu, Apr 23 - Thu, Apr 30
Frontier Logo
12:59 pm - 10:29 pm
SJO
-
MDW
8h 30m
1 stop
Frontier Logo
2:56 pm - 9:01 am
MDW
-
SJO
19h 05m
2 stops
$464Frontier
Sat, Apr 4 - Fri, Apr 10
Southwest Logo
9:00 am - 10:45 pm
SJO
-
MDW
12h 45m
2 stops
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$467Southwest
Thu, Apr 23 - Thu, Apr 30
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
$468Southwest
Wed, Sep 9 - Mon, Sep 14
Southwest Logo
9:00 am - 9:50 pm
SJO
-
MDW
11h 50m
2 stops
Southwest Logo
7:40 am - 6:40 pm
MDW
-
SJO
12h 00m
2 stops
$473Southwest
Wed, Sep 9 - Tue, Sep 15
Southwest Logo
9:00 am - 5:30 pm
SJO
-
MDW
7h 30m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$474Southwest
Wed, May 6 - Wed, May 13
Delta Logo
1:21 pm - 12:30 pm
SJO
-
MDW
22h 09m
2 stops
Delta Logo
6:00 am - 11:56 am
MDW
-
SJO
6h 56m
1 stop
$476Delta
Thu, Aug 27 - Sun, Aug 30

Frontier flights from San José to Chicago Midway Airport

Our best Frontier deals on San José to Chicago Midway Airport flight tickets
Frontier
Apr 2
SJO1:27 pmSan José Juan Santamaria Intl
29h 40m
1 stop
MDW8:07 pmChicago Midway
Apr 10
MDW5:30 amChicago Midway
28h 31m
1 stop
SJO9:01 amSan José Juan Santamaria Intl
$350
Frontier
Apr 4
SJO12:59 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW10:29 pmChicago Midway
Apr 9
MDW6:00 amChicago Midway
7h 12m
1 stop
SJO12:12 pmSan José Juan Santamaria Intl
$365
Frontier
Apr 5
SJO1:27 pmSan José Juan Santamaria Intl
29h 40m
1 stop
MDW8:07 pmChicago Midway
Apr 9
MDW6:00 amChicago Midway
7h 12m
1 stop
SJO12:12 pmSan José Juan Santamaria Intl
$418

Delta flights from San José to Chicago Midway Airport

Our best Delta deals on San José to Chicago Midway Airport flight tickets
Delta
Aug 27
SJO1:21 pmSan José Juan Santamaria Intl
22h 09m
2 stops
MDW12:30 pmChicago Midway
Aug 30
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
$476
Delta
Sep 11
SJO1:25 pmSan José Juan Santamaria Intl
7h 21m
1 stop
MDW9:46 pmChicago Midway
Sep 16
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$511
Delta
May 5
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
$521

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 24, 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

Sat 4/4

12:59 pm-10:29 pm

1 stop8h 30m

Chicago Midway

Thu 4/9

6:00 am-12:12 pm

1 stop7h 12m

$365

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 4/5

1:27 pm-8:07 pm

1 stop29h 40m

Chicago Midway

Thu 4/9

6:00 am-12:12 pm

1 stop7h 12m

$418

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/30

9:35 am-10:02 pm

2 stops11h 27m

Chicago Midway

Thu 6/4

3:07 pm-8:19 am

2 stops18h 12m

$462

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/23

1:10 pm-9:55 pm

1 stop7h 45m

Chicago Midway

Thu 4/30

12:10 pm-7:00 pm

1 stop7h 50m

$463

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 4/4

12:59 pm-10:29 pm

1 stop8h 30m

Chicago Midway

Fri 4/10

2:56 pm-9:01 am

2 stops19h 05m

$464

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/23

9:00 am-10:45 pm

2 stops12h 45m

Chicago Midway

Thu 4/30

12:10 pm-7:00 pm

1 stop7h 50m

$467

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/9

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Mon 9/14

10:05 am-6:40 pm

2 stops9h 35m

$468

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/9

9:00 am-9:50 pm

2 stops11h 50m

Chicago Midway

Tue 9/15

7:40 am-6:40 pm

2 stops12h 00m

$473
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/6

9:00 am-5:30 pm

1 stop7h 30m

Chicago Midway

Wed 5/13

12:15 pm-7:00 pm

1 stop7h 45m

$474

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 8/27

1:21 pm-12:30 pm

2 stops22h 09m

Chicago Midway

Sun 8/30

6:00 am-11:56 am

1 stop6h 56m

$476

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 74% 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
4,331 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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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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