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Flights from San Jose to Chicago
Find cheap one-way flights from San Jose to Chicago starting at US$172.
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Fri, May 9 | Volaris Costa RicaORD 17:3119h 24m1 stopsSJO 11:55Chicago - San Jose | Fri, May 16 | Frontier AirlinesUS$316 US$50337% OFF37% OFFUS$503 US$316
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SJO 00:5014h 37m1 stopsORD 16:27San Jose - Chicago | Wed, Apr 2 | Spirit AirlinesORD 21:0814h 16m1 stopsSJO 10:24Chicago - San Jose | Tue, Apr 8 | Spirit AirlinesUS$339 US$50333% OFF33% OFFUS$503 US$339
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SJO 18:0718h 35m1 stopsORD 13:42San Jose - Chicago | Mon, Mar 31 | Copa AirlinesORD 15:0917h 27m1 stopsSJO 07:36Chicago - San Jose | Sun, Apr 6 | Copa AirlinesUS$377 US$50325% OFF25% OFFUS$503 US$377
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SJO 00:5017h1 stopsORD 18:50San Jose - Chicago | Wed, Mar 19 | Spirit AirlinesORD 21:0814h 17m1 stopsSJO 10:25Chicago - San Jose | Wed, Mar 26 | Spirit AirlinesUS$38524% OFFUS$503 US$385
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SJO 11:3510h 57m1 stopsORD 23:32San Jose - Chicago | Sat, May 3 | Spirit AirlinesORD 07:057h1 stopsSJO 13:05Chicago - San Jose | Sat, May 10 | Delta Air LinesUS$40320% OFFUS$503 US$403
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SJO 01:5510h 20m1 stopsORD 13:15San Jose - Chicago | Tue, Apr 1 | aviancaORD 14:359h 55m1 stopsSJO 23:30Chicago - San Jose | Tue, Apr 8 | aviancaUS$40320% OFFUS$503 US$403
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Thu, May 8 | Volaris Costa RicaORD 01:4013h 17m1 stopsSJO 13:57Chicago - San Jose | Sun, May 11 | VolarisUS$40520% OFFUS$503 US$405
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Sun, May 11 | Volaris Costa RicaORD 01:4013h 12m1 stopsSJO 13:52Chicago - San Jose | Sun, May 18 | VolarisUS$41118% OFFUS$503 US$411
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SJO 12:2610h 33m1 stopsORD 23:59San Jose - Chicago | Fri, Apr 4 | Spirit AirlinesORD 13:268h 57m1 stopsSJO 21:23Chicago - San Jose | Mon, Apr 7 | Jetblue AirwaysUS$41218% OFFUS$503 US$412
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Tue, May 6 | Volaris Costa RicaORD 14:3519h 45m1 stopsSJO 09:20Chicago - San Jose | Fri, May 9 | aviancaUS$41318% OFFUS$503 US$413
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SJO 13:0017h 25m1 stopsCHI Invalid DateSan Jose - Chicago | Sat, Mar 15 | Normal AirlineCHI 15:006hNonstopSJO 16:00Chicago - San Jose | Mon, Mar 17 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstopSJO 13:055h 25mNonstopORD 19:30San Jose - Chicago | Sat, Mar 15 | United AirlinesUS$234 US$35834% OFF34% OFFUS$358 US$234
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SJO 13:055h 25mNonstopORD 19:30San Jose - Chicago | Sun, Mar 16 | United AirlinesUS$293 US$35818% OFF18% OFFUS$358 US$293
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SJO 13:0721h 49m1 stopsORD 11:56San Jose - Chicago | Sat, Apr 26 | Frontier AirlinesUS$172 US$35852% OFF52% OFFUS$358 US$172
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Sun, May 11 | Volaris Costa RicaUS$18050% OFFUS$358 US$180
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SJO 15:3118h 34m1 stopsORD 11:05San Jose - Chicago | Sat, May 10 | Volaris Costa RicaUS$18050% OFFUS$358 US$180
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Fri, May 9 | Volaris Costa RicaUS$18349% OFFUS$358 US$183
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Thu, May 8 | Volaris Costa RicaUS$18349% OFFUS$358 US$183
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Mon, May 5 | Volaris Costa RicaUS$19047% OFFUS$358 US$190
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SJO 11:3510h 57m1 stopsORD 23:32San Jose - Chicago | Sat, May 3 | Spirit AirlinesUS$19147% OFFUS$358 US$191
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Thu, Apr 24 | Volaris Costa RicaUS$19944% OFFUS$358 US$199
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SJO 14:4813h 54m1 stopsORD 05:42San Jose - Chicago | Thu, Apr 17 | Volaris Costa RicaUS$20044% OFFUS$358 US$200
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SJO 13:2420h 36m1 stopsORD 11:00San Jose - Chicago | Sat, May 3 | Frontier AirlinesUS$20044% OFFUS$358 US$200
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SJO 13:0017h 25m1 stopsCHI Invalid DateSan Jose - Chicago | Sat, Mar 15 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Cheapest airlines flights from San Jose to Chicago
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Frequently Asked Questions
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When are flight tickets from San Jose (SJO) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from San Jose to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from San Jose (SJO) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $618. -
How long does it take to fly from San Jose (SJO) to Chicago (CHI) and what is the distance?
It takes around 5 hours 34 minutes to fly from San Jose (SJO) to Chicago (CHI). -
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
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What are the most popular airlines that fly from San Jose (SJO) to Chicago (CHI)?
Airlines with flights from San Jose (SJO) to Chicago (CHI): United Airlines.
How to find a cheap flight from San Jose to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from San Jose to Chicago. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest San Jose to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for San Jose to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Mar 15 at US$234 for one-way flights.
Compare cheap San Jose to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from San Jose to Chicago. The cheapest airline operating is United Airlines.
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By setting up a Price Alert for your San Jose to Chicago route, you can easily track the price of your airline tickets from San Jose to Chicago without manually checking every day.
Don't miss cheap San Jose to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights for cheap flights. If registering a free membership, you can receive more deals for your flights.
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com free app and search for cheap flight tickets from San Jose to Chicago to get exclusive deals for you.
San Jose to Chicago Flight Information
Cheapest nonstop flight price | $171 |
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Cheapest round-trip ticket price | $449 |
Off-season for travel | March |
Peak season for travel | December |
Flight distance | 3,568.5 km |
Average flight time | 5 hours 34 minutes |
Popular airline | Aeromexico |
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Popular Flights From San Jose
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Popular Flights to Chicago
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Popular Airlines
- Delta Air Lines
- American Airlines
- United Airlines
- Lufthansa
- KLM
- Turkish Airlines
- China Eastern Airlines
- Air China
- Ryanair
- Aeroflot
- Emirates
- Qatar Airways
- Air France
- British Airways
- Qantas
- Air Canada
- Air India
- All Nippon Airways
- Wizz Air
- TUI Airways
- Aeroméxico
- Singapore Airlines
- Philippine Airlines
- Iberia
- ITA Airways