What are the cheapest airlines to fly from Chicago to San José, San José Province one-way?

The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from Undisclosed Carrier and Spirit Airlines, as they are both options that can get you from Chicago to San José, San José Province for a low price.

What are the most popular airlines that fly from Chicago to San José, San José Province?

Consider American Airlines, Air Canada or Aeromexico when booking your flight. These represent the most popular airlines when flying from Chicago to San José, San José Province.

What are the cheapest flights from Chicago to San José, San José Province?

The cheapest flight price from Chicago to San José, San José Province is $382. On average you can expect to pay $669. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $316.

Can I find flights from Chicago to San José, San José Province for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to San José, San José Province for under $300. The cheapest flight booked recently is on Frontier for just $279, but on average you can expect to pay $336.

Are there nonstop flights from Chicago to San José, San José Province for under $900 on Cheapflights?

Cheapflights has at least 9 direct flights from Chicago to San José, San José Province under $900. A good price for a nonstop flight from Chicago to San José, San José Province is less than $1,034.

Are there last-minute flights available from Chicago to San José, San José Province for under $400?

There are currently 20+ open flights from Chicago to San José, San José Province within the next 7 days for less than $400.

Which airlines flying from Chicago to San José Juan Santamaria Intl have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to San José Juan Santamaria Intl have new flexible policies in place due to COVID-19. Spirit Airlines, American Airlines, and Copa Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Spirit Airlines with this kind of flexibility.

What is the cheapest day to fly round-trip from Chicago to San José, San José Province?

Users have found that leaving on a Tuesday can be a cost-effective option. It’s possible to save up to 15% on your flight compared to booking on days when demand is much higher.

How far in advance should I book a flight from Chicago to San José, San José Province?

To save up to 18% on this flight, we recommend booking at least 61 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to San José, San José Province from $648 1-2 weeks out and tickets from $709 for flights departing within the next 72 hours.

When is the cheapest time to fly from Chicago to San José, San José Province (CHI - SJO)?

One of the essential ways to save on airfare from Chicago to San José, San José Province is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 31% on airfare.

What airport do you fly into for flights to San José from Chicago?

Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago. Booking flights from Chicago to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago from 9 different airlines.

What does ORD to SJO mean?

This is defined as Chicago O'Hare Intl Airport (ORD) and San José Juan Santamaria Intl Airport (SJO). Codes like San José Juan Santamaria Intl Airport are often used to just call airports uniquely. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

Flights from Chicago, IL to San José, Costa Rica from $98

How to find the cheapest flight from Chicago (CHI) to San José (SJO)

Popular in	December
Cheapest in	September
Round-trip from	$458
One-way from	$174

High demand for flights, 33% potential price rise

Search Deals

Best time to find cheap flights, 22% potential price drop

Search Deals

From Chicago (CHI) to San José Juan Santamaria Intl

Search Deals

One-way flight from Chicago (CHI) to San José Juan Santamaria Intl

Search Deals

CHI - SJO Price	$458 - $868
SJO Temperature	64.4 - 69.8 °F
SJO Rainfall	0 - 11.8 inches

CHI - SJO

Price

$458 - $868

SJO

Temperature

64.4 - 69.8 °F

SJO

Rainfall

0 - 11.8 inches

The best pricing can be found in the month of September. Prices to San José, San José Province from Chicago average $585. You can even find prices in September for less than $585, as users have found deals to San José, San José Province from as low as $349. The month of December appears to be one of the more expensive times to travel to San José, San José Province from Chicago. Flying in the targeted month can save you up to 48%.

Cheap flights from Chicago to San José in May, June 2023

The lowest fares we've come across on flights traveling from Chicago to San José in May and June 2023. Check back in a little while for more flight options.

Jun 8 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

11h 11m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$345

Spirit Airlines

Deal found 5/24

Jun 1 - Aug 7

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

14h 24m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 31m

$363

Frontier

Deal found 5/24

Jun 6 - Jun 9

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 54m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

9h 15m

$363

Multiple Airlines

Deal found 5/24

Jun 8 - Jun 12

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 36m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

12h 49m

$367

Spirit Airlines

Deal found 5/24

Jun 7 - Jun 13

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

18h 08m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

17h 20m

$368

Spirit Airlines

Deal found 5/25

Jun 9 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

18h 08m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$375

Spirit Airlines

Deal found 5/24

Jun 17 - Jun 21

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 48m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

17h 20m

$376

Multiple Airlines

Deal found 5/24

Jun 9 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

29h 39m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$378

Spirit Airlines

Deal found 5/24

Jun 17 - Jun 21

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 48m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

16h 05m

$379

Multiple Airlines

Deal found 5/24

Chicago to San José 2023 flight deals

The lowest fares we've come across on flights traveling from Chicago to San José in May and June 2023. Check back in a little while for more flight options.

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$279

Frontier

Deal found 5/24

Aug 16 - Aug 21

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

11h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

31h 55m

$281

Undisclosed Carrier

Deal found 5/25

Aug 16 - Aug 21

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

15h 43m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

18h 04m

$304

Frontier

Deal found 5/24

Aug 17 - Aug 25

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 41m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

22h 36m

$307

Frontier

Deal found 5/23

Aug 17 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 41m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$308

Frontier

Deal found 5/24

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$312

Frontier

Deal found 5/24

Aug 19 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

25h 03m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$314

Frontier

Deal found 5/24

Aug 19 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

21h 07m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$339

Frontier

Deal found 5/24

Jun 8 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

11h 11m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$345

Spirit Airlines

Deal found 5/24

Cheap Spirit Airlines flights from Chicago to San José

Peruse some of the lowest-priced Spirit Airlines flights we've found from Chicago to San José. Be sure to come back soon if the deals available don't appeal to you at this time.

Jun 8 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

11h 11m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$345

Spirit Airlines

Deal found 5/24

Jun 7 - Jun 13

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

18h 08m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

17h 20m

$368

Spirit Airlines

Deal found 5/25

Jun 9 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

18h 08m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$375

Spirit Airlines

Deal found 5/24

Jun 9 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

29h 39m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$378

Spirit Airlines

Deal found 5/24

Jun 10 - Jun 20

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

11h 11m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

17h 20m

$381

Spirit Airlines

Deal found 5/24

Jun 13 - Aug 21

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

11h 11m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

10h 59m

$383

Spirit Airlines

Deal found 5/25

Jul 11 - Jul 18

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

19h 38m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

28h 21m

$384

Spirit Airlines

Deal found 5/24

Jun 7 - Jun 16

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 46m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

17h 20m

$386

Spirit Airlines

Deal found 5/23

Jun 26 - Jul 6

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

20h 31m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

7h 46m

$387

Spirit Airlines

Deal found 5/23

Cheap Frontier flights from Chicago to San José

Browse through some of the cheapest Frontier flights traveling from Chicago to San José. Deals frequently update to provide users with more options.

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$279

Frontier

Deal found 5/24

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 58m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$282

Frontier

Deal found 5/25

Aug 16 - Aug 21

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

15h 43m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

2 stops

18h 04m

$304

Frontier

Deal found 5/24

Aug 17 - Aug 25

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 41m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

22h 36m

$307

Frontier

Deal found 5/23

Aug 17 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 41m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$308

Frontier

Deal found 5/24

Aug 16 - Aug 21

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

20h 12m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$312

Frontier

Deal found 5/24

Aug 19 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

25h 03m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$314

Frontier

Deal found 5/24

Aug 19 - Aug 28

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

21h 07m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 21m

$339

Frontier

Deal found 5/24

Aug 17 - Aug 25

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

2 stops

29h 30m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

2 stops

33h 07m

$356

Frontier

Deal found 5/23

Non-stop flights to San José from Chicago

Consider booking one of these non-stop flights heading from Chicago to San José. Search for alternative flights from Chicago to San José by utilizing the search form above.

Jun 24 - Jul 8

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$875

United Airlines

Deal found 5/24

Jul 22 - Jul 29

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$916

United Airlines

Deal found 5/24

Jun 10 - Jun 17

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$971

United Airlines

Deal found 5/24

Jul 1 - Jul 8

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$1,029

United Airlines

Deal found 5/25

Aug 5 - Aug 12

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$1,034

United Airlines

Deal found 5/24

Jul 22 - Jul 29

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$1,035

United Airlines

Deal found 5/25

Jun 17 - Jun 24

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$1,103

United Airlines

Deal found 5/24

Jul 29 - Aug 12

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$1,105

United Airlines

Deal found 5/23

Jun 17 - Jun 24

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 10m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 23m

$1,245

United Airlines

Deal found 5/25

Last minute flights from Chicago to San José

Have a look at some of the last-minute flights available departing from Chicago to San José. It's wise to confirm all flight details are correct before booking.

Jun 1 - Aug 7

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

14h 24m

SJO

San José Juan Santamaria Intl

MDW

Chicago Midway

1 stop

21h 31m

$363

Frontier

Deal found 5/24

Jun 3 - Jun 10

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

19h 49m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$388

Multiple Airlines

Deal found 5/24

Jun 3 - Jun 9

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

19h 49m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

16h 05m

$395

Multiple Airlines

Deal found 5/24

Jun 4 - Jun 9

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 36m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

20h 53m

$403

Undisclosed Carrier

Deal found 5/24

Jun 2 - Jun 13

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 28m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

8h 50m

$406

Spirit Airlines

Deal found 5/25

Jun 3 - Jun 9

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

11h 22m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

7h 46m

$413

Spirit Airlines

Deal found 5/24

May 30 - Jun 5

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

10h 05m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

27h 47m

$418

Multiple Airlines

Deal found 5/24

May 30 - Jun 4

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

19h 58m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

16h 41m

$420

Multiple Airlines

Deal found 5/24

May 30 - Jun 4

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

2 stops

14h 54m

SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

16h 41m

$423

Multiple Airlines

Deal found 5/24

One-way flights to San José from Chicago

If you're seeking multiple options on one-way flights from Chicago to San José, be sure to check out these deals, which are updated often. Users needing a return flight from Chicago to San José should utilize the search form above.

Jun 17

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 48m

$98

Frontier

Deal found 5/24

Jun 18

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

8h 51m

$101

Frontier

Deal found 5/23

Jun 17

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 48m

$101

Frontier

Deal found 5/23

Jun 17

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

24h 22m

$113

Frontier

Deal found 5/23

Aug 19

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

25h 03m

$125

Frontier

Deal found 5/23

Jul 2

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

14h 58m

$133

Frontier

Deal found 5/23

Jul 2

MDW

Chicago Midway

SJO

San José Juan Santamaria Intl

1 stop

14h 58m

$138

Frontier

Deal found 5/25

Jul 2

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

20h 31m

$138

Undisclosed Carrier

Deal found 5/23

Jun 24

ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

17h 46m

$147

Spirit Airlines

Deal found 5/23

Find flights from Chicago to San José within your budget

Fly from

Fly to

Budget

$279 - $368

Route

Depart

Return

Price

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/16

1 stop24h 58m

San José Juan Santamaria Intl

Mon 8/21

1 stop21h 21m

$279

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 8/16

1 stop11h 10m

San José Juan Santamaria Intl

Mon 8/21

1 stop31h 55m

$281

Pick Dates

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/16

1 stop24h 58m

San José Juan Santamaria Intl

Mon 8/21

1 stop21h 21m

$282

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 8/16

1 stop15h 43m

San José Juan Santamaria Intl

Mon 8/21

2 stops18h 04m

$304

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Thu 6/8

2 stops11h 11m

San José Juan Santamaria Intl

Tue 6/20

1 stop8h 50m

$345

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 10/24

1 stop14h 00m

San José Juan Santamaria Intl

Mon 10/30

1 stop11h 46m

$355

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 8/16

1 stop15h 43m

San José Juan Santamaria Intl

Sun 8/20

1 stop16h 09m

$359

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Tue 6/6

1 stop7h 54m

San José Juan Santamaria Intl

Fri 6/9

1 stop9h 15m

$363

Pick Dates

Chicago O'Hare IntlSan José Juan Santamaria Intl

ORD - SJO

ORDSJO

Chicago O'Hare Intl

Wed 6/7

2 stops18h 08m

San José Juan Santamaria Intl

Tue 6/13

2 stops17h 20m

$368

Pick Dates

Flights are sorted by cheapest first

Deals found on 5/24

Reviews of Airlines Servicing San José

See what other customers who have flown with Spirit Airlines, Frontier and Undisclosed Carrier from Chicago to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

2,341 reviews

Check prices

Reviews

1 / 10

Few on the plane on Saturday night. Lots of space. Crew was great.

Delta

8.0

Very good

2,341 reviews

Delta

8.0

Very good

2,341 reviews

Check prices

Reviews

1 / 10

Few on the plane on Saturday night. Lots of space. Crew was great.

JetBlue

7.5

Good

593 reviews

Delta

8.0

Very good

2,341 reviews

Check prices

Reviews

1 / 10

Few on the plane on Saturday night. Lots of space. Crew was great.

Avianca

7.1

Good

710 reviews

Delta

8.0

Very good

2,341 reviews

Check prices

Reviews

1 / 10

Few on the plane on Saturday night. Lots of space. Crew was great.

Spirit Airlines

6.6

Okay

1,007 reviews

Delta

8.0

Very good

2,341 reviews

Check prices

Reviews

1 / 10

Few on the plane on Saturday night. Lots of space. Crew was great.

Frontier

5.9

Fair

643 reviews

Delta

8.0

Very good

2,341 reviews

Check prices

Reviews

1 / 10

Few on the plane on Saturday night. Lots of space. Crew was great.

Related info for your journey

Currently priced at $279, Frontier will fly you from Chicago to San José, San José Province and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Undisclosed Carrier and Spirit Airlines - these airlines can fly you to your destination from $281 and $345, respectively. Frontier is currently priced 52% below the average price you’ll pay for this route.

Top 9 airlines flying from Chicago to San José

Airline	Cheapest	Average	Flexibility	On-time	COVID-19 safety
Frontier	Cheapest$103	Average$307	FlexibilityNo cancel fee	On-time62%	COVID-19 safety	Search Frontier flights
JetBlue	Cheapest$330	Average$573	FlexibilityNo cancel fee	On-time62%	COVID-19 safety	Search JetBlue flights
Spirit Airlines	Cheapest$351	Average$498	FlexibilityNo cancel fee	On-time65%	COVID-19 safety	Search Spirit Airlines flights
Copa Airlines	Cheapest$466	Average$640	FlexibilityNo cancel fee	On-time70%	COVID-19 safety	Search Copa Airlines flights
Aeromexico	Cheapest$485	Average$669	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Aeromexico flights
American Airlines	Cheapest$568	Average$882	FlexibilityNo cancel fee	On-time71%	COVID-19 safety	Search American Airlines flights
Air Canada	Cheapest$618	Average$748	FlexibilityNo cancel fee	On-time67%	COVID-19 safety	Search Air Canada flights
Delta	Cheapest$619	Average$913	FlexibilityNo cancel fee	On-timeN/A	COVID-19 safety	Search Delta flights
United Airlines	Cheapest$664	Average$1,121	FlexibilityNo cancel fee	On-time69%	COVID-19 safety	Search United Airlines flights

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Weekly flight availability from Chicago to San José

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Cheap flights from Chicago (CHI) to San José (SJO) from $98

This is the cheapest one-way flight price, found on 5/24. Prices may vary by date and flight preferences.

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The best prices from Chicago to San José Juan Santamaria Intl are usually found in September or October, booked 60 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

How to find the cheapest flight from Chicago (CHI) to San José (SJO)

All the information you need to plan the best CHI to SJO flight in 2023: compare Chicago to San José flight prices with the expected peak season, weather and rainfall in San José.

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Cheap flights from Chicago to San José in May, June 2023

The best prices found for CHI to SJO flights for May, June

The lowest fares we've come across on flights traveling from Chicago to San José in May and June 2023. Check back in a little while for more flight options.

Chicago to San José 2023 flight deals

Cheap flights to San José from Chicago found for this year

The lowest fares we've come across on flights traveling from Chicago to San José in May and June 2023. Check back in a little while for more flight options.

Cheap Spirit Airlines flights from Chicago to San José

Peruse some of the lowest-priced Spirit Airlines flights we've found from Chicago to San José. Be sure to come back soon if the deals available don't appeal to you at this time.

Cheap Frontier flights from Chicago to San José

Browse through some of the cheapest Frontier flights traveling from Chicago to San José. Deals frequently update to provide users with more options.

Non-stop flights to San José from Chicago

Save time with Chicago to San José direct flight deals

Consider booking one of these non-stop flights heading from Chicago to San José. Search for alternative flights from Chicago to San José by utilizing the search form above.

Last minute flights from Chicago to San José

Late deals on return flights to San José from Chicago, departing today and this week

Have a look at some of the last-minute flights available departing from Chicago to San José. It's wise to confirm all flight details are correct before booking.

One-way flights to San José from Chicago

The cheapest one-way flights from Chicago to San José

If you're seeking multiple options on one-way flights from Chicago to San José, be sure to check out these deals, which are updated often. Users needing a return flight from Chicago to San José should utilize the search form above.

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Use the slider to find flights from Chicago to San José that fit your budget.

Reviews of Airlines Servicing San José

See what other customers who have flown with Spirit Airlines, Frontier and Undisclosed Carrier from Chicago to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Useful info, stats and facts about Chicago to San José flights.

What airport do you fly into for flights to San José from Chicago?

Which airlines flying from Chicago to San José Juan Santamaria Intl have flexible cancellations due to COVID-19?

Can I find flights from Chicago to San José, San José Province for under $300 on Cheapflights?

Are there nonstop flights from Chicago to San José, San José Province for under $900 on Cheapflights?

Are there last-minute flights available from Chicago to San José, San José Province for under $400?

What are the cheapest airlines flying from Chicago to San José, San José Province round-trip?

What are the cheapest airlines to fly from Chicago to San José, San José Province one-way?

What are the most popular airlines that fly from Chicago to San José, San José Province?

What are the cheapest flights from Chicago to San José, San José Province?

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Top 9 airlines flying from Chicago to San José

The chart below displays the airlines Cheapflights users traveling from Chicago to San José choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Popular flight searches

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Weekly flight availability from Chicago to San José

See how many times per day planes take to the skies headed from Chicago to San José