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Cheap flights from San Jose (SJC) to Chicago (CHI) from $73

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SJC — CHI
Jun 17 — Jun 241
From?
To?
Mon 6/17
Mon 6/24
1 adult, Economy
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The best prices from San Jose to Chicago are usually found in October or January, booked 86 days in advance, depart on a Wednesday or Monday and return on a Friday

Cheap flight deals from San Jose to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2024.

Popular in

March

Cheapest in

October

Round-trip from

$222

One-way from

$73
High demand for flights, 20% potential price rise
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Best time to find cheap flights, 22% potential price drop
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From San Jose to Chicago (CHI)
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One-way flight from San Jose to Chicago (CHI)
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What is the cheapest day to fly round-trip from San Jose to Chicago?

Travelers have found that booking a Tuesday departure is the best way to save up to 29% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

How far in advance should I book a flight from San Jose to Chicago?

Travelers have found it’s best to book a flight 60 days in advance to save up to 431% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from San Jose to Chicago 1-2 weeks in advance for as low as $201, or $587 for flights within the next 24 hours.

What is the cheapest month to fly from San Jose to Chicago?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from San Jose in October are about $412 on average during October, but can be found for as low as $126.

What is the cheapest time of day to fly from SJC to CHI?

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 20% on your trip compared to booking a flight in the morning.

Cheap San Jose to Chicago flights in June & July 2024

Find cheap flight options from San Jose to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,117,830 searches. Prices were last updated on June 12, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Wed 7/108:15 amSJC - ORD
1 stop7h 14mSpirit Airlines
Mon 7/158:34 pmORD - SJC
1 stop20h 34mSpirit Airlines
Deal found 6/12$200
Mon 7/157:12 pmSJC - ORD
1 stop9h 30mSpirit Airlines
Wed 7/176:19 pmORD - SJC
1 stop7h 27mSpirit Airlines
Deal found 6/10$201
Tue 7/99:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Fri 7/128:34 pmORD - SJC
1 stop20h 34mSpirit Airlines
Deal found 6/12$202
Wed 7/106:10 amSJC - RFD
1 stop6h 40mMultiple Airlines
Wed 7/173:40 pmRFD - SJC
1 stop8h 08mMultiple Airlines
Deal found 6/11$204
Wed 7/2410:45 amSJC - ORD
1 stop17h 21mSpirit Airlines
Wed 8/76:19 pmORD - SJC
1 stop7h 27mSpirit Airlines
Deal found 6/11$204
Wed 6/267:00 amSJC - ORD
1 stop12h 17mSpirit Airlines
Wed 7/171:28 pmORD - SJC
1 stop8h 55mSpirit Airlines
Deal found 6/10$205
Wed 7/2410:45 amSJC - ORD
1 stop17h 21mSpirit Airlines
Mon 8/128:34 pmORD - SJC
2 stops15h 04mSpirit Airlines
Deal found 6/11$206
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Mon 7/228:34 pmORD - SJC
2 stops15h 04mSpirit Airlines
Deal found 6/10$208
Wed 7/178:15 amSJC - ORD
1 stop12h 04mSpirit Airlines
Mon 7/228:34 pmORD - SJC
2 stops23h 48mSpirit Airlines
Deal found 6/12$209

San Jose to Chicago 2024 flight deals

Discover exclusive flight deals for travel between San Jose and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 12, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Sat 8/2410:20 pmSJC - MDW
1 stop6h 13mFrontier
Fri 9/611:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 6/11$176
Thu 9/2610:20 pmSJC - MDW
1 stop6h 13mFrontier
Fri 10/411:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 6/10$177
Tue 9/310:20 pmSJC - MDW
1 stop6h 13mFrontier
Fri 9/611:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 6/10$180
Sat 9/1411:31 amSJC - MDW
1 stop22h 21mFrontier
Wed 9/1810:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 6/11$181
Sat 9/2110:20 pmSJC - MDW
1 stop6h 13mFrontier
Wed 9/2510:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 6/11$182
Mon 8/1211:30 amSJC - MDW
1 stop22h 22mFrontier
Fri 8/1611:32 amMDW - SJC
1 stop8h 34mFrontier
Deal found 6/11$184
Thu 9/2610:20 pmSJC - MDW
1 stop6h 13mFrontier
Sat 10/510:00 pmMDW - SJC
1 stop20h 51mFrontier
Deal found 6/11$188
Fri 8/2310:20 pmSJC - MDW
1 stop6h 13mFrontier
Mon 8/266:00 amMDW - SJC
1 stop12h 57mFrontier
Deal found 6/11$190
Wed 7/108:15 amSJC - ORD
1 stop7h 14mSpirit Airlines
Mon 7/158:34 pmORD - SJC
1 stop20h 34mSpirit Airlines
Deal found 6/12$200

San Jose to Chicago flights leaving soon

Find last-minute flight options from San Jose to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 12, 2024.
Have a look at some of the flights available from San Jose to Chicago departing last-minute. Tip: verify your flight details before completing your reservation.
Wed 6/267:00 amSJC - ORD
1 stop12h 17mSpirit Airlines
Wed 7/171:28 pmORD - SJC
1 stop8h 55mSpirit Airlines
Deal found 6/10$205
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Mon 7/228:34 pmORD - SJC
2 stops15h 04mSpirit Airlines
Deal found 6/10$208
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Sat 7/201:28 pmORD - SJC
1 stop12h 18mSpirit Airlines
Deal found 6/10$228
Mon 6/249:12 pmSJC - ORD
2 stops16h 50mSpirit Airlines
Tue 7/2310:52 pmORD - SJC
1 stop11h 34mSpirit Airlines
Deal found 6/10$229
Tue 6/259:13 pmSJC - ORD
1 stop22h 04mSpirit Airlines
Thu 6/278:26 pmORD - SJC
1 stop20h 16mSpirit Airlines
Deal found 6/11$230
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mMultiple Airlines
Tue 7/236:00 amORD - SJC
1 stop13h 45mMultiple Airlines
Deal found 6/10$235
Mon 6/249:12 pmSJC - ORD
2 stops16h 50mSpirit Airlines
Mon 7/228:34 pmORD - SJC
2 stops15h 04mSpirit Airlines
Deal found 6/10$236
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Mon 7/228:34 pmORD - SJC
3 stops27h 14mSpirit Airlines
Deal found 6/10$237
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Thu 7/186:19 pmORD - SJC
1 stop7h 27mSpirit Airlines
Deal found 6/10$240

One-way flights to Chicago from San Jose

Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 12, 2024.
Users traveling one-way from San Jose to Chicago can select one of these great deals. For those needing a return trip from San Jose, there is a search form available above.
Fri 8/2310:45 pmSJC - ORD
Nonstop4h 15mUnited Airlines
Deal found 6/11$73
Thu 8/157:24 pmSJC - ORD
1 stop8h 27mAmerican Airlines
Deal found 6/11$82
Tue 8/611:30 amSJC - ORD
1 stop11h 05mFrontier
Deal found 6/11$85
Tue 10/810:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/10$88
Sat 9/1410:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/11$90
Fri 8/234:19 pmSJC - ORD
1 stop12h 19mSpirit Airlines
Deal found 6/11$93
Wed 7/178:15 amSJC - ORD
1 stop7h 14mSpirit Airlines
Deal found 6/11$94
Wed 7/108:15 amSJC - ORD
1 stop12h 04mSpirit Airlines
Deal found 6/11$95
Mon 8/2611:30 amSJC - ORD
1 stop11h 33mFrontier
Deal found 6/11$96

Find flights from San Jose to Chicago within your budget

Customize your flight search to find flights from San Jose to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 12, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$164 - $253

Route

Depart

Return

Price

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Thu 8/15

1 stop8h 27m

Chicago O'Hare Intl

Mon 8/19

1 stop6h 15m

$164

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Sat 8/24

1 stop6h 13m

Chicago Midway

Fri 9/6

1 stop8h 34m

$176

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Tue 7/23

1 stop11h 05m

Chicago O'Hare Intl

Tue 8/13

1 stop23h 21m

$176

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Tue 8/27

1 stop10h 11m

Chicago O'Hare Intl

Wed 9/4

1 stop12h 41m

$177

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Tue 7/23

1 stop11h 05m

Chicago O'Hare Intl

Wed 8/7

1 stop7h 27m

$185

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Wed 7/10

1 stop12h 04m

Chicago O'Hare Intl

Wed 7/17

1 stop7h 27m

$189

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Thu 8/15

1 stop32h 15m

Chicago O'Hare Intl

Mon 8/19

Nonstop4h 43m

$202

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Thu 12/5

1 stop7h 24m

Chicago Midway

Wed 12/11

1 stop8h 39m

$236

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Mon 10/21

1 stop9h 45m

Chicago O'Hare Intl

Tue 10/29

1 stop17h 19m

$253

Flights are sorted by cheapest first

Deals found on 6/11

How far ahead should I book a flight from San Jose to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from San Jose to Chicago. Price data was last updated on May 31, 2024.
The best time to book flights from San Jose to Chicago is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Search Deals

What is the cheapest day to fly from San Jose to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Chicago. Price data was last updated on June 9, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their San Jose to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from San Jose to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Jose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Delta and United Airlines from San Jose to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,877 reviews

Entertainment

7.8

Crew

8.7

Boarding

8.3

Food

7.3

Comfort

8.1

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.2
Very good
5,877 reviews
Southwest
8.2
Very good
5,877 reviews

Entertainment

7.8

Crew

8.7

Boarding

8.3

Food

7.3

Comfort

8.1

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.1
Very good
9,269 reviews
Southwest
8.2
Very good
5,877 reviews

Entertainment

7.8

Crew

8.7

Boarding

8.3

Food

7.3

Comfort

8.1

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
10,000 reviews
Southwest
8.2
Very good
5,877 reviews

Entertainment

7.8

Crew

8.7

Boarding

8.3

Food

7.3

Comfort

8.1

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

United Airlines
7.4
Good
10,000 reviews
Southwest
8.2
Very good
5,877 reviews

Entertainment

7.8

Crew

8.7

Boarding

8.3

Food

7.3

Comfort

8.1

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

American Airlines
7.3
Good
10,000 reviews
Southwest
8.2
Very good
5,877 reviews

Entertainment

7.8

Crew

8.7

Boarding

8.3

Food

7.3

Comfort

8.1

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Related info for your journey

Find useful and relevant information for your journey from San Jose to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Jose to Chicago?

    Located just 2.9 mi from the city center, San Jose is the airport most travelers will use when flying to Chicago from San Jose. Booking flights from San Jose (SJC) to Chicago should be relatively easy as there are 6 daily outbound flights to Chicago from 6 different airlines.

  • Can I find flights from San Jose to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from San Jose to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $164, but on average you can expect to pay $181.

  • Are there nonstop flights from San Jose to Chicago for under $300 on Cheapflights?

    Cheapflights has at least 20 direct flights from San Jose to Chicago under $300. A good price for a nonstop flight from San Jose to Chicago is less than $365.

  • Are there last-minute flights available from San Jose to Chicago for under $300?

    There are currently 20+ open flights from San Jose to Chicago within the next 7 days for less than $300.

  • What are the cheapest airlines flying from San Jose to Chicago round-trip?

    Cheapflights users have booked flights from San Jose to Chicago round-trip from $164. Other airlines that can offer you cheap pricing are Frontier, from $176, and Spirit Airlines, from $177. You may be able to fly from San Jose to Chicago for 60% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from San Jose to Chicago one-way?

    One-way options have recently been found by users for as low as $73 on United Airlines. Other airlines that offer cheap prices include American Airlines from $82 and Frontier from $85 one-way.

  • What are the most popular routes from San Jose to Chicago?

    While some choose either San Jose - Chicago Midway or San Jose - Chicago Greater Rockford, San Jose - Chicago O'Hare Intl is the most popular route from San Jose to Chicago.

  • What are the cheapest flights from San Jose to Chicago?

    Looking for the cheapest flight from San Jose to Chicago? While on average our users pay $918, our data indicates the cheapest price to be $144. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $174.

  • What does SJC to ORD mean?

    San Jose Airport is SJC and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from San Jose to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your San Jose to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from San Jose to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter San Jose to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from San Jose to Chicago that include hotel bookings?

    Yes. In addition to deals on San Jose to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Chicago.

  • Can I find deals for business class flights from San Jose to Chicago?

    Yes. Cheapflights offers flight deals from San Jose to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from San Jose to Chicago that allow pets onboard?

    Many airlines flying from San Jose to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from San Jose to Chicago?

    Yes, you can often find last-minute deals on San Jose to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the San Jose to Chicago flight deals updated?

    The San Jose to Chicago flight deals you see on this page were last updated on 6/12.

  • What are the most popular airlines that fly from San Jose to Chicago?

    Before booking your flight from San Jose to Chicago check out the most popular airlines for this route: American Airlines, Alaska Airlines or Delta.

  • What is the cheapest month to book a flight from San Jose to Chicago?

    Currently, February is the cheapest month in which you can book a flight from San Jose to Chicago (average of $244). Flying from San Jose to Chicago in July is currently the most expensive (average of $320). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for San Jose to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

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Top 6 airlines flying from San Jose to Chicago

Discover the top 6 airlines that operate flights from San Jose to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 12, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$208FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$100Average$212FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$149Average$258FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$203Average$465FlexibilityNo cancel feeOn-time69%
DeltaCheapest$251Average$503FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$318Average$519FlexibilityNo cancel feeOn-time71%
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Boise to Las Vegas flights
Seattle to Phoenix flights
San Francisco to Mexico City flights
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Search flights from San Jose to Chicago by cabin class

Find flights from San Jose to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from San Jose to Chicago

Find hourly flight availability from San Jose to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2024.
27%of flight departuresEarly morningMidnight to 6 am
27%of flight departuresMorning6 am to noon
36%of flight departuresAfternoonNoon to 6 pm
10%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from San Jose to Chicago

Explore weekly flight availability from San Jose to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2024.
Sunday2daily flights
Monday8daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday8daily flights
Friday8daily flights
Saturday2daily flights

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