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Cheap flights from San José to Chicago from $240

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San José to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:00 am - 10:22 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:58 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 48m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sun, Dec 20 - Thu, Dec 31
Delta Logo
7:00 am - 5:44 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
10h 44m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 46m1 stop Atlanta Hartsfield-Jackson
$409Delta
Fri, Dec 25 - Thu, Dec 31
Delta Logo
2:24 pm - 10:22 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
7h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 46m1 stop Atlanta Hartsfield-Jackson
$409Delta
Thu, Dec 24 - Thu, Dec 31
Delta Logo
2:24 pm - 10:22 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
7h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:58 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 48m1 stop Atlanta Hartsfield-Jackson
$409Delta
Thu, Dec 24 - Thu, Dec 31
Delta Logo
7:00 am - 8:50 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
25h 50m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 46m1 stop Atlanta Hartsfield-Jackson
$409Delta
Mon, Dec 21 - Thu, Dec 31
Delta Logo
7:00 am - 8:50 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
25h 50m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 46m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sun, Dec 20 - Thu, Dec 31
Delta Logo
7:00 am - 10:22 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
15h 46m1 stop Atlanta Hartsfield-Jackson
$409Delta
Mon, Dec 21 - Thu, Dec 31
Delta Logo
3:55 pm - 9:13 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
17h 18m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:58 am - 9:46 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 48m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sat, Dec 19 - Thu, Dec 31
Southwest Logo
2:15 pm - 11:10 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 55m1 stop Houston Hobby
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
$460Southwest
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
$460Southwest
Thu, Jan 28 - Tue, Feb 2

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Frontier flights from San José to Chicago Midway Airport

Our best Frontier deals on San José to Chicago Midway Airport flight tickets
Frontier
Dec 23
SJO1:31 pmSan José Juan Santamaria Intl
17h 30m
1 stop
MDW7:01 amChicago Midway
Dec 31
MDW9:23 pmChicago Midway
14h 53m
1 stop
SJO12:16 pmSan José Juan Santamaria Intl
$535
Frontier
Dec 26
SJO3:31 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW12:01 amChicago Midway
Dec 31
MDW1:11 pmChicago Midway
25h 05m
1 stop
SJO2:16 pmSan José Juan Santamaria Intl
$551
Frontier
Dec 23
SJO3:31 pmSan José Juan Santamaria Intl
20h 39m
1 stop
MDW12:10 pmChicago Midway
Dec 31
MDW1:11 pmChicago Midway
25h 05m
1 stop
SJO2:16 pmSan José Juan Santamaria Intl
$553

Southwest flights from San José to Chicago Midway Airport

Our best Southwest deals on San José to Chicago Midway Airport flight tickets
Southwest
Nov 11
SJO2:15 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:10 pmChicago Midway
Nov 15
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
$460
Southwest
Oct 28
SJO1:00 pmSan José Juan Santamaria Intl
9h 15m
1 stop
MDW11:15 pmChicago Midway
Nov 1
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
$507
Southwest
Apr 14
SJO1:10 pmSan José Juan Santamaria Intl
8h 35m
1 stop
MDW10:45 pmChicago Midway
Apr 21
MDW5:50 amChicago Midway
7h 20m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
$510

momondo Fare Finder

 
Use the filters below to find and compare flights from San José to Chicago Midway Airport that are best for you.

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Route

Depart

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Price

Cheapest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sun 12/20

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Thu 12/31

9:58 am-9:46 pm

1 stop11h 48m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Fri 12/25

7:00 am-5:44 pm

2 stops10h 44m

Chicago Midway

Thu 12/31

6:00 am-9:46 pm

1 stop15h 46m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 12/24

2:24 pm-10:22 pm

1 stop7h 58m

Chicago Midway

Thu 12/31

6:00 am-9:46 pm

1 stop15h 46m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 12/24

2:24 pm-10:22 pm

1 stop7h 58m

Chicago Midway

Thu 12/31

9:58 am-9:46 pm

1 stop11h 48m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Mon 12/21

7:00 am-8:50 am

2 stops25h 50m

Chicago Midway

Thu 12/31

6:00 am-9:46 pm

1 stop15h 46m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sun 12/20

7:00 am-8:50 am

2 stops25h 50m

Chicago Midway

Thu 12/31

6:00 am-9:46 pm

1 stop15h 46m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Mon 12/21

7:00 am-10:22 pm

1 stop15h 22m

Chicago Midway

Thu 12/31

6:00 am-9:46 pm

1 stop15h 46m

$409

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Sat 12/19

3:55 pm-9:13 am

1 stop17h 18m

Chicago Midway

Thu 12/31

9:58 am-9:46 pm

1 stop11h 48m

$409
Quickest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Wed 11/11

2:15 pm-11:10 pm

1 stop8h 55m

Chicago Midway

Sun 11/15

5:15 am-12:20 pm

1 stop7h 05m

$460

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 1/28

1:50 pm-10:50 pm

1 stop9h 00m

Chicago Midway

Tue 2/2

5:25 am-1:45 pm

1 stop8h 20m

$460

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 typical price of a round-trip flight between San José and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $436 to $563.
The lowest price recently found on this route was $409.

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from San José, with most prices found around $437. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San José during the month October is also very affordable. Most momondo users find prices during this month for around $462.

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

Best Price Found

$240

Fastest flight time

7h 55m

Direct flights

None
The best one-way flight to Chicago Midway Airport from San José in the past 72 hours is $240. The best round-trip flight deal from San José to Chicago Midway Airport found on momondo in the last 72 hours is $409.
The fastest flight from San José to Chicago Midway Airport takes 7h 55m
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

Frequently asked questions about flying from San José to Chicago Midway Airport

  • 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 55m 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 $390Free CancellationRating
7.9
4,209 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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