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.
CHI — SJO
May 30 — Jun 61
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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.

Popular in

December

Cheapest in

September

Round-trip from

$458

One-way from

$174
High demand for flights, 33% potential price rise
Best time to find cheap flights, 22% potential price drop
From Chicago (CHI) to San José Juan Santamaria Intl
One-way flight from Chicago (CHI) to San José Juan Santamaria Intl

CHI - SJO

Price

$458 - $868

SJO

Temperature

64.4 - 69.8 °F

SJO

Rainfall

0 - 11.8 inches

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.

Find flights from Chicago to San José within your budget

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

Fly from

Any airport

Fly to

Any airport

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

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

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

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

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

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

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

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

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

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

Entertainment

7.8

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.1

Crew

8.5

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

Entertainment

7.8

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.1

Crew

8.5

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

Entertainment

7.8

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.1

Crew

8.5

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

Entertainment

7.8

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.1

Crew

8.5

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

Entertainment

7.8

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.1

Crew

8.5

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

Entertainment

7.8

Food

7.2

Overall

8.0

Comfort

7.9

Boarding

8.1

Crew

8.5

Reviews

1 / 10

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

Related info for your journey

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

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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
FrontierCheapest$103Average$307FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
JetBlueCheapest$330Average$573FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
Spirit AirlinesCheapest$351Average$498FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
Copa AirlinesCheapest$466Average$640FlexibilityNo cancel feeOn-time70%COVID-19 safety
Search Copa Airlines flights
AeromexicoCheapest$485Average$669FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Aeromexico flights
American AirlinesCheapest$568Average$882FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Air CanadaCheapest$618Average$748FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
DeltaCheapest$619Average$913FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$664Average$1,121FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

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
Sunday0daily flights
Monday0daily flights
Tuesday0daily flights
Wednesday0daily flights
Thursday0daily flights
Friday0daily flights
Saturday1daily flight