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 $230. Other airlines that can offer you cheap pricing are Frontier, from $278, and Alaska Airlines, from $294. You may be able to fly from San Jose to Chicago for 43% 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 $123 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $126 and Alaska Airlines from $147 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 $908, our data indicates the cheapest price to be $176. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $149.

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 day to fly round-trip from San Jose to Chicago?

Travelers have found that booking a Monday departure is the best way to save up to 25% 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 43% 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 $215, or $522 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, January can be a great choice for travel to Chicago. Flights to Chicago from San Jose in January are about $409 on average during January, but can be found for as low as $148.

Most accurate provider : When it comes to deals on San Jose-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on San Jose-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Jose-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 2 daily outbound flights to Chicago from 7 different 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.

$123+ Flights from San Jose to Chicago

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Cheapflights Tip: The best prices from San Jose to Chicago are usually found in January or September, booked 80 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from San Jose to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$230 (Mytrip)
One-way from	$123 (Mytrip)
Popular in	March
Cheapest in	January
Average price	$482
Good round-trip deal	$402 or less
Good one-way deal	$173 or less

Provider with most accurate pricing for San Jose-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for San Jose-Chicago (CHI) flights.

Search Deals

From San Jose to Chicago (CHI)

Search Deals

One-way flight from San Jose to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 2025

Search Deals

Price to beat on a round-trip flight from San Jose to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from San Jose to Chicago (CHI).

Search Deals

Find flight deals from San Jose to Chicago

Cheapest flights from San Jose to Chicago
Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Sun 4/202:50 pmSJC - ORD

2 stops31h 41mSpirit Airlines

Wed 4/233:32 pmORD - SJC

2 stops17h 57mSpirit Airlines

Deal found 3/25

$230

Wed 4/97:54 pmSJC - ORD

1 stop8h 39mMultiple Airlines

Wed 4/166:40 amORD - SJC

1 stop10h 19mMultiple Airlines

Deal found 3/25

$247

Tue 4/152:04 pmSJC - MDW

1 stop13h 19mMultiple Airlines

Fri 4/188:50 pmMDW - SJC

1 stop16h 23mMultiple Airlines

Deal found 3/25

$271

Mon 4/78:12 pmSJC - MDW

1 stop7h 11mFrontier

Fri 4/186:45 amMDW - SJC

1 stop10h 14mFrontier

Deal found 3/24

$278

Wed 4/164:03 pmSJC - ORD

1 stop6h 34mFrontier

Sat 4/196:45 amORD - SJC

1 stop9h 05mFrontier

Deal found 3/25

$278

Tue 4/298:24 amSJC - ORD

1 stop19h 41mAlaska Airlines

Wed 5/79:00 amORD - SJC

1 stop9h 58mAlaska Airlines

Deal found 3/24

$294

Tue 4/1511:45 amSJC - ORD

1 stop10h 14mDelta

Tue 4/227:50 amORD - SJC

1 stop8h 10mDelta

Deal found 3/24

$295

Wed 4/161:05 pmSJC - MDW

1 stop7h 17mDelta

Tue 4/221:16 pmMDW - SJC

1 stop9h 22mDelta

Deal found 3/25

$319

Wed 5/144:28 pmSJC - RFD

1 stop17h 10mMultiple Airlines

Sun 5/1812:28 pmRFD - SJC

2 stops28h 03mMultiple Airlines

Deal found 3/25

$329

Tue 4/156:35 amSJC - ORD

Nonstop4h 26mUnited Airlines

Thu 4/177:45 pmORD - SJC

Nonstop5h 01mUnited Airlines

Deal found 3/25

$351

Mon 4/145:10 pmSJC - MDW

1 stop6h 10mSouthwest

Wed 4/168:40 amMDW - SJC

Nonstop4h 35mSouthwest

Deal found 3/24

$361

Wed 6/49:30 amSJC - ORD

2 stops10h 00mSouthwest

Tue 6/107:30 amORD - SJC

2 stops9h 10mSouthwest

Deal found 3/25

$381

Best flights from San Jose to Chicago
Discover carefully curated flight deals from San Jose to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 26, 2025.

Sun 4/202:50 pmSJC - ORD

2 stops31h 41mSpirit Airlines

Wed 4/233:32 pmORD - SJC

2 stops17h 57mSpirit Airlines

Deal found 3/25

$230

Wed 4/97:54 pmSJC - ORD

1 stop8h 39mMultiple Airlines

Wed 4/166:40 amORD - SJC

1 stop10h 19mMultiple Airlines

Deal found 3/25

$247

Mon 4/78:12 pmSJC - MDW

1 stop7h 11mFrontier

Fri 4/186:45 amMDW - SJC

1 stop10h 14mFrontier

Deal found 3/24

$278

Tue 4/298:24 amSJC - ORD

1 stop7h 37mAlaska Airlines

Tue 5/66:00 amORD - SJC

1 stop8h 01mAlaska Airlines

Deal found 3/24

$294

Tue 4/1511:45 amSJC - ORD

1 stop10h 14mDelta

Tue 4/227:50 amORD - SJC

1 stop8h 10mDelta

Deal found 3/24

$295

Tue 4/156:35 amSJC - ORD

Nonstop4h 26mUnited Airlines

Thu 4/177:45 pmORD - SJC

Nonstop5h 01mUnited Airlines

Deal found 3/25

$351

Mon 4/145:10 pmSJC - MDW

1 stop6h 10mSouthwest

Wed 4/168:40 amMDW - SJC

Nonstop4h 35mSouthwest

Deal found 3/24

$361

Tue 4/152:04 pmSJC - MDW

1 stop13h 19mMultiple Airlines

Fri 4/188:50 pmMDW - SJC

1 stop16h 23mMultiple Airlines

Deal found 3/25

$271

Wed 4/164:03 pmSJC - ORD

1 stop6h 34mFrontier

Sat 4/196:45 amORD - SJC

1 stop9h 05mFrontier

Deal found 3/25

$278

Wed 4/307:54 pmSJC - RFD

1 stop22h 52mMultiple Airlines

Sun 5/49:36 pmRFD - SJC

1 stop11h 53mMultiple Airlines

Deal found 3/24

$282

Wed 4/161:05 pmSJC - MDW

1 stop7h 17mDelta

Tue 4/221:16 pmMDW - SJC

1 stop9h 22mDelta

Deal found 3/25

$319

Wed 6/49:30 amSJC - ORD

2 stops10h 00mSouthwest

Tue 6/107:30 amORD - SJC

2 stops9h 10mSouthwest

Deal found 3/25

$381

Last-minute flights from San Jose to Chicago
Discover last-minute flight deals from San Jose to Chicago. Data last updated March 26, 2025 and is based on user searches.

Tue 4/18:50 pmSJC - ORD

1 stop7h 52mSpirit Airlines

Tue 4/89:57 pmORD - SJC

1 stop14h 15mSpirit Airlines

Deal found 3/25

$257

Tue 4/110:48 amSJC - ORD

2 stops18h 16mMultiple Airlines

Sat 4/57:46 pmORD - SJC

1 stop26h 23mMultiple Airlines

Deal found 3/25

$507

Tue 4/18:35 amSJC - MDW

Nonstop4h 10mSouthwest

Sat 4/57:20 pmMDW - SJC

Nonstop4h 40mSouthwest

Deal found 3/25

$823

Tue 4/16:15 amSJC - ORD

1 stop8h 05mDelta

Thu 4/31:45 pmORD - SJC

2 stops10h 24mDelta

Deal found 3/25

$1,383

Tue 4/19:53 amSJC - ORD

2 stops12h 25mAmerican Airlines

Thu 4/35:00 amORD - SJC

2 stops9h 14mAmerican Airlines

Deal found 3/25

$1,448

Fri 4/43:49 pmSJC - ORD

1 stop6h 48mFrontier

Wed 4/96:40 amORD - SJC

1 stop10h 19mFrontier

Deal found 3/24

$288

Fri 4/46:15 amSJC - ORD

2 stops15h 44mAlaska Airlines

Tue 4/810:00 amORD - SJC

1 stop11h 55mAlaska Airlines

Deal found 3/24

$597

Fri 4/48:30 amSJC - ORD

1 stop12h 32mUnited Airlines

Tue 4/87:50 pmORD - SJC

Nonstop5h 01mUnited Airlines

Deal found 3/24

$703

Fri 4/47:39 pmSJC - MDW

2 stops11h 04mDelta

Tue 4/81:15 pmMDW - SJC

1 stop9h 08mDelta

Deal found 3/24

$756

Sat 4/52:40 pmSJC - MDW

1 stop7h 41mFrontier

Wed 4/96:45 amMDW - SJC

1 stop10h 14mFrontier

Deal found 3/25

$278

Mon 4/78:12 pmSJC - MDW

1 stop7h 11mFrontier

Fri 4/186:45 amMDW - SJC

1 stop10h 14mFrontier

Deal found 3/24

$278

Mon 4/78:12 pmSJC - ORD

1 stop6h 56mFrontier

Mon 4/148:01 pmORD - SJC

1 stop24h 37mFrontier

Deal found 3/25

$280

One-way flights from San Jose to Chicago
Search for one-way flight options from San Jose to Chicago. Find affordable one-way fares based on user searches. Data last updated March 26, 2025.

Sun 5/46:35 pmSJC - ORD

3 stops33h 10mSpirit Airlines

Deal found 3/25

$123

Mon 5/1912:20 pmSJC - ORD

1 stop9h 21mFrontier

Deal found 3/25

$126

Sat 4/122:40 pmSJC - MDW

1 stop7h 41mFrontier

Deal found 3/26

$139

Tue 4/2910:14 amSJC - ORD

1 stop9h 45mAlaska Airlines

Deal found 3/25

$147

Wed 5/147:20 amSJC - ORD

1 stop8h 05mDelta

Deal found 3/24

$148

Sun 5/181:38 pmSJC - ORD

2 stops22h 37mMultiple Airlines

Deal found 3/25

$167

Wed 4/306:40 amSJC - MDW

Nonstop4h 10mSouthwest

Deal found 3/25

$176

Wed 5/286:35 amSJC - ORD

Nonstop4h 22mUnited Airlines

Deal found 3/25

$176

Thu 5/16:15 amSJC - MDW

1 stop9h 04mDelta

Deal found 3/25

$186

Sat 5/176:00 amSJC - MDW

3 stops30h 13mMultiple Airlines

Deal found 3/25

$198

Thu 4/103:00 pmSJC - ORD

1 stop6h 59mHawaiian Airlines

Deal found 3/25

$291

Cheapflights Fare Finder

Use the filters below to find and compare flights from San Jose to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseChicago

SJC - ORD

SJCORD

San Jose

Sun 4/20

2:50 pm-12:31 am

2 stops31h 41m

Chicago O'Hare Intl

Wed 4/23

3:32 pm-7:29 am

2 stops17h 57m

$230

San JoseChicago

SJC - ORD

SJCORD

San Jose

Wed 4/9

7:54 pm-6:33 am

1 stop8h 39m

Chicago O'Hare Intl

Wed 4/16

6:40 am-2:59 pm

1 stop10h 19m

$247

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Tue 4/15

2:04 pm-5:23 am

1 stop13h 19m

Chicago Midway

Fri 4/18

8:50 pm-11:13 am

1 stop16h 23m

$271

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Mon 4/7

3:58 pm-12:21 am

1 stop6h 23m

Chicago Midway

Wed 4/16

6:45 am-2:59 pm

1 stop10h 14m

$278

San JoseChicago

SJC - ORD

SJCORD

San Jose

Mon 4/7

8:12 pm-5:08 am

1 stop6h 56m

Chicago O'Hare Intl

Mon 4/14

8:01 pm-6:38 pm

1 stop24h 37m

$280

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 4/29

8:24 am-6:01 pm

1 stop7h 37m

Chicago O'Hare Intl

Tue 5/6

6:00 am-12:01 pm

1 stop8h 01m

$294

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 4/15

11:45 am-11:59 pm

1 stop10h 14m

Chicago O'Hare Intl

Tue 4/22

7:50 am-2:00 pm

1 stop8h 10m

$295

San JoseChicago

SJC - MDW

SJCMDW

San Jose

Wed 4/16

1:05 pm-10:22 pm

1 stop7h 17m

Chicago Midway

Tue 4/22

1:16 pm-8:38 pm

1 stop9h 22m

$319

San JoseChicago

SJC - RFD

SJCRFD

San Jose

Wed 5/14

4:28 pm-11:38 am

1 stop17h 10m

Chicago Greater Rockford

Sun 5/18

12:28 pm-2:31 pm

2 stops28h 03m

$329

San JoseChicago

SJC - ORD

SJCORD

San Jose

Tue 4/15

6:35 am-1:01 pm

Nonstop4h 26m

Chicago O'Hare Intl

Thu 4/17

7:45 pm-10:46 pm

Nonstop5h 01m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 23 results

Compare providers for flights from San Jose to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Jose to Chicago in March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Gotogate	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on San Jose-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on San Jose-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Jose-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Cheapflights Insights

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

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

The best time to book flights from San Jose to Chicago is 80 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.

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

Currently, August is the cheapest month in which you can book a flight from San Jose to Chicago (average of $245). Flying from San Jose to Chicago in March is currently the most expensive (average of $323). 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 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 23% on your trip compared to booking a flight in the evening.

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

Travelers seeking maximum savings on their San Jose to Chicago flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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 a feel of what it's like to fly with Southwest, Alaska Airlines and Delta 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

8.1

Very good

4,273 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest

8.1

Very good

4,273 reviews

Southwest

8.1

Very good

4,273 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Alaska Airlines

8.0

Very good

9,789 reviews

Southwest

8.1

Very good

4,273 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta

8.0

Very good

7,891 reviews

Southwest

8.1

Very good

4,273 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Hawaiian Airlines

7.9

Good

2,331 reviews

Southwest

8.1

Very good

4,273 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

United Airlines

7.4

Good

8,608 reviews

Southwest

8.1

Very good

4,273 reviews

Reviews

1 / 20

10.0

Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

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 2 daily outbound flights to Chicago from 7 different airlines.
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 $230. Other airlines that can offer you cheap pricing are Frontier, from $278, and Alaska Airlines, from $294. You may be able to fly from San Jose to Chicago for 43% 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 $123 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $126 and Alaska Airlines from $147 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 $908, our data indicates the cheapest price to be $176. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $149.
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.
What is the cheapest month to book a flight from San Jose to Chicago?
Currently, August is the cheapest month in which you can book a flight from San Jose to Chicago (average of $245). Flying from San Jose to Chicago in March is currently the most expensive (average of $323). 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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Top 7 airlines flying from San Jose to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$98	Average$245	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$134	Average$256	FlexibilityNo cancel fee	On-time65%
Alaska Airlines	Cheapest$197	Average$297	FlexibilityNo cancel fee	On-time75%
United Airlines	Cheapest$203	Average$509	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$236	Average$496	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$279	Average$537	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$370	Average$506	FlexibilityNo cancel fee	On-time63%

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$123+ Cheap flights from San Jose (SJC) to Chicago (CHI)

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from San Jose to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from San Jose to Chicago are usually found in January or September, booked 80 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap flight deals from San Jose to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from San Jose to Chicago

Cheapest flights from San Jose to ChicagoExplore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from San Jose to Chicago that are best for you.

Compare providers for flights from San Jose to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Jose to Chicago in March.

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.

Cheapflights Insights

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

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 March 21, 2025.

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

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

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 March 26, 2025.

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 March 23, 2025.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta 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.

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?

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

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

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

What are the cheapest flights from San Jose to Chicago?

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

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

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

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

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Alternative routes for San Jose to Chicago

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Top 7 airlines flying from San Jose to Chicago

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Cheapest flights from San Jose to Chicago
Explore the most affordable flight options available from San Jose to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.