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Cheap flights San Jose — Chicago

San Jose (SJO, CR) Chicago (CHI, US)
from $305 3 569 km ~4h 42m 11 flights found 5 airlines cheapest on Friday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $305 on 25.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
Mo
Tu
We
Th
Fr
Sa
Su
December 2026
Mo
Tu
We
Th
Fr
Sa
Su
January 2027
Mo
Tu
We
Th
Fr
Sa
Su
Prices found for 15 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
25 Dec 2026, Fri
jetBlue B6 38
00:06
SJO Juan Santamaria International Airport
06:42
ORD O'Hare International Airport
6h 36m 1 stop
Kupi.com
$305
View this ticket
19 Dec 2026, Sat
Southwest Airlines WN 707
23:45
SJO Juan Santamaria International Airport
07:40
MDW Chicago Midway International Airport
7h 55m 1 stop
City.Travel
$345
View this ticket
04 Jan 2027, Mon
Frontier Airlines F9 214
22:31
SJO Juan Santamaria International Airport
04:56
MDW Chicago Midway International Airport
6h 25m 1 stop
Kiwi.com
$439
View this ticket
09 Jan 2027, Sat
avianca airlines AV 610
00:10
SJO Juan Santamaria International Airport
10:11
MDW Chicago Midway International Airport
10h 1m 3 stops
Kiwi.com
$494
View this ticket
19 Dec 2026, Sat
United Airlines UA 1952
22:25
SJO Juan Santamaria International Airport
03:57
ORD O'Hare International Airport
5h 32m Direct
City.Travel
$536
View this ticket
24 Dec 2026, Thu
United Airlines UA 1952
22:25
SJO Juan Santamaria International Airport
03:57
ORD O'Hare International Airport
5h 32m Direct
City.Travel
$536
View this ticket
Route characteristics
Distance
3 569 km
Flight time
4h 42m
Time difference
+0h
Minimum price
from $305 (25.12.2026)
Average price
$452
Maximum price
$690
Departures per week
1
Cheapest day
Friday
Departure airports (1)
SJO Juan Santamaria International Airport
Arrival airports (2)
MDW Chicago Midway International Airport ORD O'Hare International Airport
Airlines (5)
B6 jetBlue WN Southwest Airlines F9 Frontier Airlines AV avianca airlines UA United Airlines
Agencies (4)
Kupi.com City.Travel Kiwi.com Farera
Prices by day of week
Monday
$439
avg $439
Thursday
$536
avg $536
Friday
$305
avg $305
Cheapest
Saturday
$345
avg $458
Price trend by month
December 2026
from $305
avg $431
4 flights
January 2027
from $439
avg $467
2 flights
Airlines — cheapest prices 5
jetBlue
jetBlue
Low-cost 1 flights · 1 days
$305
Southwest Airlines
Southwest Airlines
Low-cost 1 flights · 1 days
$345
Frontier Airlines
Frontier Airlines
Low-cost 1 flights · 1 days
$439
avianca airlines
avianca airlines
2 flights · 2 days
$494
United Airlines
United Airlines
6 flights · 6 days
$536
Where to buy tickets 4
Kupi.com
1 tickets · 1 days
from $305
City.Travel
3 tickets · 2 days
from $345
Kiwi.com
3 tickets · 2 days
from $439
Farera
4 tickets · 4 days
from $577
Airports

From — San Jose (1)

  • SJO Juan Santamaria International Airport

To — Chicago (2)

  • MDW Chicago Midway International Airport
  • ORD O'Hare International Airport
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Frequently asked questions about the route San Jose — Chicago
How long is the flight from San Jose to Chicago?
Approximate flight time — 4h 42m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from San Jose to Chicago?
The straight-line distance — 3 569 km.
How much do flights from San Jose to Chicago cost?
The minimum price over 3 months — from $305 on 25.12.2026.
What is the average ticket price?
The average price — $452. Range: $305 — $690.
What is the time difference between San Jose and Chicago?
The difference — +0h.
From which airports does San Jose operate flights?
From San Jose: SJO (Juan Santamaria International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport), ORD (O'Hare International Airport).
Which airlines fly this route?
This route is served by 5 airlines: jetBlue, Southwest Airlines, Frontier Airlines, avianca airlines, United Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $536. Total direct flights found: 2.
Which day of the week is cheapest?
The cheapest day of the week — Friday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route San Jose — Chicago

Flights San Jose — Chicago is a popular route. The straight-line distance is 3 569 km. Flight time 4h 42m. Time difference +0h.

From San Jose (SJO) flights depart from 1 airport: SJO. To Chicago (CHI) — 2 arrival airports: MDW, ORD.

5 airlines operate on this route: jetBlue, Southwest Airlines, Frontier Airlines, avianca airlines, United Airlines.

The minimum price for the next 3 months — from $305 (25.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $452, ranging from $305 to $690. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Friday.

Other destinations in United States from San Jose
Orlando
US
Los Angeles
US
Miami
US
New York
US
Oakland
US
Ontario
US
San Francisco
US
Newburgh
US

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