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$88+ Cheap flights from San Jose, CA (SJC) to Illinois

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
nov. 13 — nov. 201
jue. 11/13
jue. 11/20
1 adult, Economy
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Cheap flight deals from San Jose to Illinois

Keep the following information in mind while searching for San Jose to Illinois flight deals. Data was last updated octubre 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$198
(Frontier)

One-way from

$88
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$446

Good round-trip deal

$436 or less

Good one-way deal

$199 or less
Provider with most accurate pricing for San Jose-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Jose-Chicago (CHI) flights.
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From San Jose to Illinois
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One-way flight from San Jose to Illinois
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Highest demand for flights based on searches. 8% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from San Jose to Illinois.
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Price to beat on a one-way flight from San Jose to Illinois.
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Find flight deals from San Jose to Illinois

Cheapest flights from San Jose to Illinois
Explore the most affordable flight options available from San Jose to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 14, 2025.

This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/2012:35 pmSJC - ORD
1 stop10h 24mFrontier
dom. 10/266:50 amORD - SJC
1 stop6h 42mFrontier
Deal found 10/12$197
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2412:27 pmSJC - ORD
1 stop10h 32mFrontier
lun. 10/276:50 amORD - SJC
1 stop6h 42mFrontier
Deal found 10/13$198
This Expedia deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/13:00 pmSJC - ORD
1 stop6h 59mMultiple Airlines
lun. 11/36:00 amORD - SJC
1 stop7h 32mMultiple Airlines
Deal found 10/12$208
This Trip.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3112:27 pmSJC - ORD
1 stop9h 49mFrontier
lun. 11/36:00 amORD - SJC
1 stop7h 32mFrontier
Deal found 10/14$215
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/1412:27 pmSJC - ORD
1 stop9h 48mFrontier
lun. 11/176:00 amORD - SJC
1 stop7h 32mFrontier
Deal found 10/12$216
This SmartFares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/103:00 pmSJC - ORD
1 stop6h 59mAlaska Airlines
mar. 11/182:54 pmORD - SJC
1 stop9h 43mAlaska Airlines
Deal found 10/14$222
This Travelocity deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3112:27 pmSJC - ORD
1 stop9h 49mMultiple Airlines
mar. 11/42:54 pmORD - SJC
1 stop23h 07mMultiple Airlines
Deal found 10/12$226
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/510:25 amSJC - ORD
1 stop7h 30mMultiple Airlines
lun. 11/106:00 amORD - SJC
1 stop7h 32mMultiple Airlines
Deal found 10/13$237
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/1112:38 pmSJC - ORD
1 stop23h 16mAlaska Airlines
mar. 11/188:59 pmORD - SJC
1 stop27h 38mAlaska Airlines
Deal found 10/13$238
This KAYAK deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/133:09 pmSJC - ORD
1 stop6h 41mAlaska Airlines
lun. 12/153:05 pmORD - SJC
1 stop9h 37mAlaska Airlines
Deal found 10/13$239
This KAYAK deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/710:28 amSJC - ORD
1 stop7h 26mAlaska Airlines
jue. 12/118:55 amORD - SJC
1 stop7h 37mAlaska Airlines
Deal found 10/13$240
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/177:46 pmSJC - STL
2 stops12h 00mDelta
jue. 11/206:00 amSTL - SJC
2 stops11h 55mDelta
Deal found 10/14$254

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Illinois 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 2,558,603 searches. Data last updated octubre 14, 2025.
Use the filters below to find and compare flights from San Jose to Illinois that are best for you.

Fly from

San Jose

Fly to

Illinois

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

mar. 11/11

10:25 am-1:54 pm

1 stop25h 29m

Chicago O'Hare Intl

sáb. 11/15

2:54 pm-10:37 pm

1 stop9h 43m

$251

San JoseChicago

SJC - ORD

SJCORD

San Jose

sáb. 11/15

7:05 am-5:18 pm

1 stop8h 13m

Chicago O'Hare Intl

sáb. 12/6

11:20 am-10:13 pm

2 stops12h 53m

$268

San JoseChicago

SJC - ORD

SJCORD

San Jose

sáb. 11/8

2:21 pm-11:50 pm

1 stop7h 29m

Chicago O'Hare Intl

mar. 11/11

7:47 am-6:19 pm

2 stops12h 32m

$268

San JoseChicago

SJC - ORD

SJCORD

San Jose

lun. 11/3

5:58 pm-1:54 pm

1 stop17h 56m

Chicago O'Hare Intl

mar. 11/4

8:59 pm-9:48 am

1 stop14h 49m

$270

San JoseChicago

SJC - MDW

SJCMDW

San Jose

lun. 11/17

4:35 pm-9:52 am

2 stops15h 17m

Chicago Midway

mié. 11/19

9:41 am-10:13 pm

2 stops14h 32m

$274

San JoseChicago

SJC - MDW

SJCMDW

San Jose

mar. 11/11

7:46 pm-9:01 am

2 stops11h 15m

Chicago Midway

sáb. 11/15

1:26 pm-10:13 pm

2 stops10h 47m

$274

San JoseChicago

SJC - ORD

SJCORD

San Jose

vie. 11/14

7:05 am-5:18 pm

1 stop8h 13m

Chicago O'Hare Intl

dom. 11/16

7:47 am-3:55 pm

1 stop10h 08m

$283

San JoseChicago

SJC - ORD

SJCORD

San Jose

jue. 1/1

10:26 am-8:02 pm

1 stop7h 36m

Chicago O'Hare Intl

jue. 1/29

2:06 pm-2:42 pm

2 stops26h 36m

$287

San JoseChicago

SJC - ORD

SJCORD

San Jose

vie. 11/14

2:15 pm-11:59 pm

1 stop7h 44m

Chicago O'Hare Intl

mié. 12/3

6:00 am-3:54 pm

2 stops11h 54m

$288

San JoseChicago

SJC - ORD

SJCORD

San Jose

jue. 11/20

11:40 am-11:59 pm

1 stop10h 19m

Chicago O'Hare Intl

lun. 11/24

2:12 pm-10:13 pm

1 stop10h 01m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 60 results
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Best time to book a flight from San Jose to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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.

Cheapflights Insights

Everything you need to know about your flight from San Jose to Illinois

What is the cheapest month to book a flight from San Jose, California to Illinois?

Currently, December is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $110). Flying from San Jose, California to Illinois in March is currently the most expensive (average of $194). 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.

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

Find hourly flight availability from San Jose to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 14, 2025.

It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 7% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from San Jose, California to Illinois?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Illinois. Price data was last updated on October 20, 2024.

Travelers seeking maximum savings on their San Jose, California to Illinois flight should consider departing on Wednesday afternoons 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.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated octubre 14, 2025.
Read through reviews of airlines operating flights from San Jose to Illinois, such as Southwest, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,096 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,135 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Illinois. 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 Illinois?

    For a flight from San Jose to Illinois, you will be flying from San Jose. San Jose (SJC) is just 2.9 mi from the center of the city.

  • How long is the flight from San Jose, California to Illinois?

    Departing from San Jose, California to Illinois will take you 6h 03m. There are 1734 mi between San Jose, California and Illinois. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from San Jose, California to Illinois one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $96. Users have also found prices from $121 and $127 on Alaska Airlines and Delta, respectively.

  • What are the most popular routes from San Jose, California to Illinois?

    The most popular route from San Jose, California to Illinois is San Jose - Chicago O'Hare Intl. You may also consider San Jose - Chicago Midway or San Jose - Lambert-St Louis.

  • What are the cheapest flights from San Jose, California to Illinois?

    While on average a flight from San Jose, California to Illinois is generally $698, our data shows the cheapest flight currently is $168. When looking at the most popular route, (San Jose - Chicago O'Hare Intl), you can expect to pay $216 for that flight.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from San Jose, California to Illinois?

    Currently, December is the cheapest month in which you can book a flight from San Jose, California to Illinois (average of $110). Flying from San Jose, California to Illinois in March is currently the most expensive (average of $194). 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.

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Alternative routes for San Jose to Illinois

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Top 7 airlines flying from San Jose to Illinois

Discover the top 7 airlines that operate flights from San Jose to Illinois. 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 2,558,603 searches. Data last updated octubre 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$259FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$260FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$331FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$212Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$253Average$560FlexibilityNo cancel feeOn-time71%
DeltaCheapest$256Average$385FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$331Average$505FlexibilityNo cancel feeOn-time63%

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