Cheap Flights from San José to Chicago
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With a stop
10 Nov
05:07
SJC → LAX → CHI
Frontier Airlines + Southwest Airlines · 1d 1h stopover in Los Angeles
€113
2 flights
☕ 25h in Los Angeles — enough time to explore
3 Nov
15:37
SJC → SAN → CHI
Alaska Airlines + Frontier Airlines · 0d 21h stopover in San Diego
€115
2 flights
☕ 21h in San Diego — enough time to explore
15 Nov
01:15
SJC → LAX → CHI
Alaska Airlines + Frontier Airlines · 1d 5h stopover in Los Angeles
€118
2 flights
☕ 29h in Los Angeles — enough time to explore
8 Dec
01:15
SJC → LAX → CHI
Alaska Airlines + Southwest Airlines · 5h layover in Los Angeles
€126
2 flights
2 Nov
15:37
SJC → SAN → CHI
Alaska Airlines + Frontier Airlines · 1d 2h stopover in San Diego
€134
2 flights
☕ 26h in San Diego — enough time to explore
2 Dec
03:59
SJC → LAX → CHI
Alaska Airlines + WN · 2h layover in Los Angeles
€144
2 flights
29 Oct
19:25
SJC → LAX → CHI
Southwest Airlines + Southwest Airlines · 2h layover in Los Angeles
€145
2 flights
13 Nov
22:41
SJC → LAS → CHI
Frontier Airlines + Frontier Airlines · 7h layover in Las Vegas
€145
2 flights
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SJC → ONT·Thu 22 Oct·1h 20m
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Las Vegas
SJC → LAS·Fri 13 Nov·1h 33m
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Las Vegas
SJC → LAS·Mon 9 Nov·1h 33m
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Seattle
SJC → SEA·Sun 15 Nov·2h 15m
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San Diego
SJC → SAN·Sun 22 Nov·1h 30m
Southwest Airlines
€118€63
Get offerBook this route
SJC → CHI from €118
Cheapest departure we are tracking San José–Chicago · 22 Oct 2026. Live availability and prices are checked on the booking site.
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San José to Chicago flights: what the prices say
PirateFly is currently tracking 20 fares from San José to Chicago, from €118 to €234 (median €159).
| Cheapest fare tracked | €118 · 22 Oct 2026 · Southwest Airlines |
|---|---|
| Departure airport | Norman Y. Mineta San Jose International Airport (SJC) |
| Median fare | €159 |
| Arrival airport | Chicago All Airports (CHI) |
| Airlines seen | Alaska Airlines, Southwest Airlines and jetBlue |
| Cheapest month tracked | October 2026 · from €118 |
Cheapest San José–Chicago fare by departure month
| Month | From |
|---|---|
| October 2026 | €118 |
| November 2026 | €135 |
| December 2026 | €147 |
San José to Chicago: frequently asked questions
How much is the cheapest flight from San José to Chicago?
The cheapest San José–Chicago fare currently listed on PirateFly is €118 on 22 October 2026 with Southwest Airlines. Across all 20 fares we are currently tracking on this route the median is €159 and the highest is €234.
When is the cheapest time to fly from San José to Chicago?
Of the departure months we currently have fares for, October 2026 is the cheapest, starting at €118.
Which airlines fly from San José to Chicago?
The fares we are tracking on this route are operated by Alaska Airlines, Southwest Airlines and jetBlue.
Figures are computed from the fares PirateFly is tracking right now for future departures and change as prices move. Prices are indicative.