Flights from Chicago to San Jose
CHI
Chicago
17h 39m avg
SJO
San Jose
Flights from
$408
Compare 1 options across 1 airline
Updated 3 months ago
$408
Cheapest Flight
$408
Average Price
0
Direct Flights
1
Airlines
Compare All CHI to SJO Flights
Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.
1 of 1 flight
| Airline | Schedule | Stops | Duration | Price | |
|---|---|---|---|---|---|
NK
NK · 2
|
05:05
CHI
22:44
SJO
|
0 stop(s) | 17h 39m | $408 Best | Book → |
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Airport Information
Key details about departure and arrival airports for this route
SJO
Juan Santamaría International Airport
City: San José (Alajuela)
Country: CR
Type: Large Airport
Elevation: 3,021 ft
SJO Airport Guide →
Country: CR
Type: Large Airport
Elevation: 3,021 ft
Tips for Chicago to San Jose Flights
Save money and travel smarter with these route-specific tips
When to Book
Book CHI–SJO flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.
Price Trends
The average fare is $408, but prices as low as $408 are available.
Direct vs Connecting
No direct flights currently listed. Consider flexible dates or nearby airports for better connections.
Flexible Dates
Flying midweek (Tuesday–Thursday) on CHI–SJO is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.
Top Hotels in San Jose
Book accommodation at your destination — top-rated stays near SJO airport
Vista Canyon Inn
San Jose, 3.5★
10.0
$87/night
AC Hotel San Jose Escazu
San Jose, 3.5★
9.8
$169/night
Hotel Casa Roland San Jose
San Jose, 4★
9.4
$60/night
Apartamentos Julio Visconti
San José, 4.5★
9.3
$87/night
Alta Las Palomas Hotel
San Jose, 5★
9.2
$175/night
Holiday Inn San Jose La Sabana
San Jose, 3.5★
9.2
$98/night
Frequently Asked Questions
Everything you need to know about flying CHI to SJO
What is the cheapest flight from Chicago to San Jose?
The cheapest flight from Chicago (CHI) to San Jose (SJO) currently starts at $408 with NK. Prices are updated regularly and may vary by date and availability.
How many airlines fly from CHI to SJO?
We found 1 airline(s) operating on the CHI–SJO route, including NK.
Are there direct flights from Chicago to San Jose?
No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.
What is the average flight price on this route?
The average flight price from Chicago to San Jose is approximately $408. Prices range from $408 to $408 depending on airline, time, and class.
How long is the flight from CHI to SJO?
The average flight duration from Chicago to San Jose is approximately 17 hours 39 minutes. Direct flights are typically shorter than connecting options.
What is the baggage allowance on CHI–SJO flights?
Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.
From
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