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$65+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — ORD
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$233
(Kiwi.com)

One-way from

$65
(Priceline)

Popular in

June

Cheapest in

January

Average price

$411

Good round-trip deal

$382 or less

Good one-way deal

$193 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. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:27 pmSJC - STL
1 stop27h 58mFrontier
Wed 12/317:43 pmSTL - SJC
2 stops20h 49mFrontier
Deal found 11/12$233
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:27 pmSJC - STL
1 stop18h 40mFrontier
Thu 11/209:54 pmSTL - SJC
1 stop21h 40mFrontier
Deal found 11/11$252
This Delta deal was found by Cheapflights users on 11/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:15 amSJC - STL
2 stops9h 55mDelta
Tue 1/67:00 amSTL - SJC
2 stops12h 40mDelta
Deal found 11/12$274
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:19 pmSJC - STL
2 stops13h 43mFrontier
Sun 11/239:54 pmSTL - SJC
1 stop20h 01mFrontier
Deal found 11/12$285
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:27 pmSJC - STL
1 stop27h 58mFrontier
Wed 12/317:43 pmSTL - SJC
2 stops20h 49mFrontier
Deal found 11/12$290
This Delta deal was found by Cheapflights users on 11/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:45 amSJC - STL
1 stop5h 45mDelta
Fri 12/52:20 pmSTL - SJC
2 stops9h 53mDelta
Deal found 11/12$296
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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.
Mon 12/87:57 pmSJC - ORD
1 stop16h 12mAlaska Airlines
Sun 12/148:59 pmORD - SJC
1 stop16h 59mAlaska Airlines
Deal found 11/13$302
This Delta deal was found by Cheapflights users on 11/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:15 amSJC - ORD
1 stop8h 00mDelta
Thu 12/187:50 amORD - SJC
1 stop10h 04mDelta
Deal found 11/12$303
This Alaska Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 12/1112:35 pmSJC - ORD
1 stop9h 15mAlaska Airlines
Tue 12/1610:00 amORD - SJC
2 stops14h 59mAlaska Airlines
Deal found 11/11$306
This Alaska Airlines deal was found by Cheapflights users on 11/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:18 amSJC - ORD
1 stop8h 37mAlaska Airlines
Sun 12/148:59 pmORD - SJC
1 stop16h 59mAlaska Airlines
Deal found 11/12$307
This Delta deal was found by Cheapflights users on 11/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/109:04 amSJC - ORD
2 stops12h 55mDelta
Mon 12/157:50 amORD - SJC
1 stop10h 04mDelta
Deal found 11/12$308
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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.
Sat 12/136:40 pmSJC - ORD
1 stop17h 29mAlaska Airlines
Sun 1/48:58 pmORD - SJC
1 stop14h 51mAlaska Airlines
Deal found 11/10$310

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 November 13, 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 JoseSt. Louis

SJC - STL

SJCSTL

San Jose

Mon 2/23

11:42 am-12:24 am

2 stops10h 42m

Lambert-St Louis

Tue 2/24

7:00 am-12:16 pm

1 stop7h 16m

$296

San JoseChicago

SJC - ORD

SJCORD

San Jose

Thu 12/11

11:40 am-11:59 pm

1 stop10h 19m

Chicago O'Hare Intl

Fri 12/12

2:14 pm-10:12 pm

1 stop9h 58m

$303

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 1/5

6:20 pm-9:40 am

2 stops13h 20m

Chicago O'Hare Intl

Wed 1/7

2:20 pm-10:55 pm

2 stops10h 35m

$304

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 2/2

7:15 am-9:42 pm

2 stops12h 27m

Chicago O'Hare Intl

Mon 2/16

7:40 am-4:54 pm

2 stops11h 14m

$304

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 12/16

9:04 am-11:59 pm

2 stops12h 55m

Chicago O'Hare Intl

Thu 12/25

2:15 pm-7:56 pm

1 stop7h 41m

$308

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/8

7:15 am-5:15 pm

1 stop8h 00m

Chicago O'Hare Intl

Thu 12/11

5:30 am-6:56 pm

2 stops15h 26m

$308

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sat 12/6

2:25 pm-11:59 pm

1 stop7h 34m

Chicago O'Hare Intl

Fri 12/12

6:00 am-3:54 pm

2 stops11h 54m

$308

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/8

4:35 pm-8:40 am

2 stops14h 05m

Chicago O'Hare Intl

Fri 12/12

7:50 am-3:54 pm

1 stop10h 04m

$308

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/8

9:04 am-11:59 pm

2 stops12h 55m

Chicago O'Hare Intl

Sun 12/14

7:50 am-3:54 pm

1 stop10h 04m

$308

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 12/8

11:40 am-11:59 pm

1 stop10h 19m

Chicago O'Hare Intl

Wed 12/10

6:00 am-3:54 pm

2 stops11h 54m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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 November 13, 2025.

It’s optimal to fly from San Jose, California to Illinois in the afternoon. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the evening.

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 December 16, 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 November 13, 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
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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
3,109 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

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 8h 15m. 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 Alaska Airlines. According to our data, you can fly for as low as $129. Users have also found prices from $137 and $260 on Delta and American Airlines, 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 $447, our data shows the cheapest flight currently is $171. When looking at the most popular route, (San Jose - Chicago O'Hare Intl), you can expect to pay $138 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$260FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$260FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$170Average$315FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$588FlexibilityNo cancel feeOn-time71%
DeltaCheapest$256Average$385FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$287Average$457FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$331Average$505FlexibilityNo cancel feeOn-time63%

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