C Cityvator Cheap flights worldwide Part of Putivator
Flights Destinations Beaches Map Services Booking Collections Ratings
Home / San Jose — Chicago

Cheap flights San Jose — Chicago

San Jose (SJC, US) Chicago (CHI, US)
from $182 2 958 km ~3h 59m 7 flights found 2 airlines cheapest on Thursday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $182 on 26.11.2026
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 2 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
26 Nov 2026, Thu
Southwest Airlines WN 3895
10:00
SJC Norman Y. Mineta San Jose International Airport
14:00
MDW Chicago Midway International Airport
4h Direct
Tickets
$182
View this ticket
15 Nov 2026, Sun
Frontier Airlines F9 2930
10:47
SFO San Francisco International Airport
16:54
ORD O'Hare International Airport
6h 7m 1 stop
Kupi.com
$194
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 3220
10:50
OAK Metropolitan Oakland International Airport
14:55
MDW Chicago Midway International Airport
4h 5m Direct
Tickets
$282
View this ticket
Route characteristics
Distance
2 958 km
Flight time
3h 59m
Time difference
+2h
Minimum price
from $182 (26.11.2026)
Average price
$188
Maximum price
$194
Departures per week
1
Cheapest day
Thursday
Departure airports (3)
OAK Metropolitan Oakland International Airport SFO San Francisco International Airport SJC Norman Y. Mineta San Jose International Airport
Arrival airports (2)
MDW Chicago Midway International Airport ORD O'Hare International Airport
Airlines (2)
WN Southwest Airlines F9 Frontier Airlines
Agencies (2)
Tickets Kupi.com
Prices by day of week
Thursday
$182
avg $182
Cheapest
Sunday
$194
avg $238
Airlines — cheapest prices 2
Southwest Airlines
Southwest Airlines
Low-cost 4 flights · 4 days
$182
Frontier Airlines
Frontier Airlines
Low-cost 3 flights · 3 days
$194
Where to buy tickets 2
Tickets
4 tickets · 4 days
from $182
Kupi.com
3 tickets · 3 days
from $194
Airports

From — San Jose (3)

  • OAK Metropolitan Oakland International Airport
  • SFO San Francisco International Airport
  • SJC Norman Y. Mineta San Jose International Airport

To — Chicago (2)

  • MDW Chicago Midway International Airport
  • ORD O'Hare International Airport
Other destinations from San Jose
Accra
GH
Arcata
US
Adler/Sochi
RU
Auckland
NZ
Almaty
KZ
Ahmedabad
IN
Amsterdam
NL · Hub
Anchorage
US
Ankara
TR
Aspen
US
Athens
GR
Atlanta
US · Hub
Frequently asked questions about the route San Jose — Chicago
How long is the flight from San Jose to Chicago?
Approximate flight time — 3h 59m. 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 — 2 958 km.
How much do flights from San Jose to Chicago cost?
The minimum price over 3 months — from $182 on 26.11.2026.
What is the average ticket price?
The average price — $188. Range: $182 — $194.
What is the time difference between San Jose and Chicago?
The difference — +2h.
From which airports does San Jose operate flights?
From San Jose: OAK (Metropolitan Oakland International Airport), SFO (San Francisco International Airport), SJC (Norman Y. Mineta San Jose 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 2 airlines: Southwest Airlines, Frontier Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $182. Total direct flights found: 2.
Which day of the week is cheapest?
The cheapest day of the week — Thursday.
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 2 958 km. Flight time 3h 59m. Time difference +2h.

From San Jose (SJC) flights depart from 3 airports: OAK, SFO, SJC. To Chicago (CHI) — 2 arrival airports: MDW, ORD.

2 airlines operate on this route: Southwest Airlines, Frontier Airlines.

The minimum price for the next 3 months — from $182 (26.11.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $188, ranging from $182 to $194. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Thursday.

Other destinations in United States from San Jose
Everett
US
Ontario
US
Orlando
US
Owensboro
US
Page
US
Philadelphia
US
Kahului
US
Portland
US

Cheap flights worldwide. Search and compare prices from 1 159 airlines across 9 546 cities.

Flights

Flight search Destinations Beaches Map Services Booking Collections Ratings

Data

Open API for AI llms.txt ai.txt

Documents

Privacy Policy Terms of Use

Contacts

info@cityvator.com Part of Putivator
© 2026 Cityvator — flight search engine Data from open sources · Open API for AI