Cheap Flights from San Jose to Chicago, IL from $65

Return flight: Chicago – San Jose

On Cheapflightsplus.com you will find 157 connecting flights from San Jose to Chicago. You can compare airfare deals from 11 airlines and multiple travel sites from $211, book and save on cheap plane tickets and last minute offers. Also check out SJO-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip San Jose to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $65 (one-way), $111 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from San Jose to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
07:01 — 23:35
07:01 — 09:18 CM459 Compania Panamena de Aviacion
San Jose — Panama City
8h 38m stop
17:56 — 23:35 CM235 Compania Panamena de Aviacion
Panama City — Chicago
15h 34m
including layover
Find flight
from$247
11:00 — 20:26
11:00 — 16:17 NK674 Spirit Airlines
San Jose — Orlando
2h 2m stop
18:19 — 20:26 NK910 Spirit Airlines
Orlando — Chicago
8h 26m
including layover
Find flight
from$268
13:40 — 21:17
+1 day
13:40 — 18:57 NK924 Spirit Airlines
San Jose — Orlando
24h 11m stop
19:08 — 21:17 NK912 Spirit Airlines
Orlando — Chicago
30h 37m
including layover
Find flight
from$234
14:10 — 00:49
14:10 — 19:20 AA2202 American Airlines
San Jose — Miami
2h 59m stop
22:19 — 00:49 F91422 Frontier Airlines
Miami — Chicago
9h 39m
including layover
Find flight
from$278
17:33 — 14:22
+1 day
17:33 — 20:48 Y45614 Volaris
San Jose — Cancun
13h 39m stop
10:27 — 14:22 NK105 Spirit Airlines
Cancun — Chicago
19h 49m
including layover
Find flight
from$356
00:44 — 18:25
00:44 — 06:06 AA696 American Airlines
San Jose — Dallas
2h 49m stop
08:55 — 10:29 AA2603 American Airlines
Dallas — New Orleans
5h 36m stop
16:05 — 18:25 WN1300 Southwest Airlines
New Orleans — Chicago
16h 41m
including layover
Find flight
from$510
06:20 — 19:49
06:20 — 08:28 CM465 Compania Panamena de Aviacion
San Jose — Panama City
3h 8m stop
11:36 — 15:34 CM265 Compania Panamena de Aviacion
Panama City — Miami
1h 46m stop
17:20 — 19:49 NK6 Spirit Airlines
Miami — Chicago
12h 29m
including layover
Find flight
from$211
08:36 — 00:19
08:36 — 10:44 CM392 Compania Panamena de Aviacion
San Jose — Panama City
52m stop
11:36 — 15:34 CM265 Compania Panamena de Aviacion
Panama City — Miami
6h 34m stop
22:08 — 00:19 NK1 Spirit Airlines
Miami — Chicago
14h 43m
including layover
Find flight
from$231
12:06 — 00:49
12:06 — 14:14 CM796 Compania Panamena de Aviacion
San Jose — Panama City
1h 46m stop
16:00 — 19:53 CM341 Compania Panamena de Aviacion
Panama City — Miami
2h 26m stop
22:19 — 00:49 F91422 Frontier Airlines
Miami — Chicago
11h 43m
including layover
Find flight
from$244
15:14 — 09:39
+1 day
15:14 — 17:22 CM145 Compania Panamena de Aviacion
San Jose — Panama City
42m stop
18:04 — 21:59 CM268 Compania Panamena de Aviacion
Panama City — Miami
9h 16m stop
07:15 — 09:39 NK478 Spirit Airlines
Miami — Chicago
17h 25m
including layover
Find flight
from$231
16:36 — 09:39
+2 days
16:36 — 19:43 P57085 Copa Airlines Colombia
San Jose — Bogota
18h 27m stop
14:10 — 19:15 NK400 Spirit Airlines
Bogota — Miami
12h stop
07:15 — 09:39 NK478 Spirit Airlines
Miami — Chicago
40h 3m
including layover
Find flight
from$437
*Departure and arrival times - local. Updated on February 3, 2023

Flight Information

Below we will explain in detail what the flights cost on the destination from San Jose to Chicago depends on and how to choose the most interesting flight option for you.

Distance between San Jose and Chicago is 3562 miles. Time difference between the cities is 0h. Airplanes depart 00:44 to 23:21 from 2 San Jose airports and arrive 00:44 to 23:21 to 7 Chicago airports. Average flight time is 13h 29m.

  • The fastest flight 7h 45m
  • Average flight time 13h 29m
  • The earliest flight 00:44
  • The latest flight 23:21
  • Distance 2214 ml

What is the lowest airfare San Jose to Chicago?

The cheapest plane ticket found by our users is $211. This airfare is for economy class on one-way CM465 flight by Compania Panamena de Aviacion for July 31, 2021 which leaves Juan Santamaria Intl in San Jose at 06:20 am and arrives at Chicago O'Hare International at 00:19.

Economy class
$211
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Business class
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First class
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Popular Airlines on the Route

The flight San Jose — Chicago is served by 11 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by American Airlines - 27 departures per week at the price of from $ 255 . And the most expensive tickets are offered by Avianca airline - from $ 1732.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 157 flights with layovers on the route. The fastest connecting flight is CM145 by Compania Panamena de Aviacion takes 7h 45m and the cheapest is CM465 by Compania Panamena de Aviacion for $211.

  • AA - American Airlines
    from $255
    Find
  • B6 - JetBlue
    from $291
    Find
  • P5 - Copa Airlines Colombia
    from $437
    Find
  • AV - Avianca
    from $447
    Find
  • WN - Southwest Airlines
    from $608
    Find
  • DL - Delta Air Lines Inc.
    from $434
    Find
  • CM - Compania Panamena de Aviacion
    from $211
    Find
  • Y4 - Volaris
    from $356
    Find
  • UA - United Airlines
    from $507
    Find
  • AM - Aeromexico
    from $582
    Find
  • NK - Spirit Airlines
    from $234
    Find
See more connecting flights

Airports

You can fly from San Jose to Chicago from 2 airports (Juan Santamaria Intl, Tobias Bolanos Intl).

San Jose airports

  • Juan Santamaria Intl-SJO
    from $211
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  • Tobias Bolanos Intl-SYQ
    Find

Chicago airports

  • O'Hare International-ORD
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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