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Cheap flights from San Jose (SJC) to Chicago (CHI) from $60

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 5/14. 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
May 3 — May 101
From?
To?
Fri 5/3
Fri 5/10
1 adult, Economy
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The best prices from San Jose to Chicago are usually found in October or September, booked 86 days in advance, depart on a Saturday or Wednesday 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 April 28, 2024.

Popular in

January

Cheapest in

October

Round-trip from

$222

One-way from

$60
High demand for flights, 23% potential price rise
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Best time to find cheap flights, 31% 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 Friday departure is the best way to save up to 28% 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 17 days in advance to save up to 314% 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 17 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 $373, or $781 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 January. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from San Jose in October are about $458 on average during October, but can be found for as low as $126.

When is the cheapest time to fly from San Jose to Chicago (SJC - 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 11% on your trip compared to booking a flight in the morning.

Cheap Delta flights from San Jose to Chicago

Explore cheap flight options specifically provided by Delta for the route between San Jose and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,991,349 searches. Data last updated April 28, 2024.
Check out some of the cheapest Delta flights we've come across from San Jose to Chicago. Deals update often to give you more flight options matching your criteria
Tue 10/86:00 amSJC - ORD
1 stop9h 43mDelta
Tue 10/156:59 pmORD - SJC
1 stop6h 52mDelta
Deal found 4/26$289
Tue 10/86:00 amSJC - ORD
1 stop9h 43mDelta
Tue 10/151:35 pmORD - SJC
2 stops10h 57mDelta
Deal found 4/26$294
Tue 10/86:30 amSJC - ORD
2 stops9h 27mDelta
Tue 10/151:35 pmORD - SJC
2 stops10h 57mDelta
Deal found 4/26$308
Wed 5/292:29 pmSJC - ORD
1 stop7h 36mDelta
Sat 6/13:50 pmORD - SJC
1 stop6h 43mDelta
Deal found 4/26$309
Sat 6/152:45 pmSJC - ORD
1 stop7h 11mDelta
Tue 6/187:30 amORD - SJC
1 stop8h 05mDelta
Deal found 4/26$321
Wed 9/1111:28 amSJC - ORD
2 stops8h 19mDelta
Mon 9/161:16 pmORD - SJC
1 stop7h 52mDelta
Deal found 4/25$323
Thu 6/62:29 pmSJC - ORD
1 stop7h 34mDelta
Tue 6/117:20 pmORD - SJC
1 stop6h 29mDelta
Deal found 4/26$330
Tue 8/206:50 amSJC - MDW
1 stop9h 09mDelta
Wed 8/289:35 amMDW - SJC
2 stops8h 41mDelta
Deal found 4/28$335
Sat 6/110:20 pmSJC - MDW
1 stop7h 35mDelta
Tue 6/42:15 pmMDW - SJC
1 stop8h 18mDelta
Deal found 4/28$350

Cheap Spirit Airlines flights from San Jose to Chicago

Explore cheap flight options specifically provided by Spirit Airlines for the route between San Jose and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,991,349 searches. Data last updated April 28, 2024.
To aid your search, here are some of the cheapest Spirit Airlines flights we've found from San Jose to Chicago. Deals are refreshing constantly so come back soon for more options.
Sat 5/183:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 4/27$114
Sat 5/113:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 5/184:05 pmORD - SJC
1 stop6h 04mSpirit Airlines
Deal found 4/26$117
Sat 5/187:10 amSJC - ORD
2 stops16h 08mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 4/27$129
Sat 5/113:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 5/181:13 pmORD - SJC
1 stop8h 56mSpirit Airlines
Deal found 4/27$132
Sat 5/183:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Tue 5/217:00 amORD - SJC
3 stops30h 31mSpirit Airlines
Deal found 4/27$142
Wed 5/158:00 amSJC - ORD
1 stop6h 56mSpirit Airlines
Wed 5/221:13 pmORD - SJC
1 stop8h 06mSpirit Airlines
Deal found 4/25$144
Tue 5/74:11 pmSJC - ORD
3 stops29h 18mSpirit Airlines
Tue 5/147:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/25$148
Tue 5/79:15 amSJC - ORD
2 stops26h 51mSpirit Airlines
Tue 5/147:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/25$151
Sat 5/187:10 amSJC - ORD
2 stops16h 08mSpirit Airlines
Tue 5/217:00 amORD - SJC
3 stops30h 31mSpirit Airlines
Deal found 4/27$152

Cheap San Jose to Chicago flights in April & May 2024

Find cheap flight options from San Jose to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,991,349 searches. Prices were last updated on April 28, 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 5/183:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 4/27$114
Sat 5/113:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 5/184:05 pmORD - SJC
1 stop6h 04mSpirit Airlines
Deal found 4/26$117
Sat 5/187:10 amSJC - ORD
2 stops16h 08mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 4/27$129
Sat 5/113:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 5/181:13 pmORD - SJC
1 stop8h 56mSpirit Airlines
Deal found 4/27$132
Sat 5/183:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Tue 5/217:00 amORD - SJC
3 stops30h 31mSpirit Airlines
Deal found 4/27$142
Wed 5/158:00 amSJC - ORD
1 stop6h 56mSpirit Airlines
Wed 5/221:13 pmORD - SJC
1 stop8h 06mSpirit Airlines
Deal found 4/25$144
Mon 5/68:53 pmSJC - ORD
2 stops17h 20mSpirit Airlines
Wed 5/87:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/26$147
Tue 5/74:11 pmSJC - ORD
3 stops29h 18mSpirit Airlines
Tue 5/147:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/25$148
Tue 5/79:15 amSJC - ORD
2 stops26h 51mSpirit Airlines
Tue 5/147:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/25$151

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 2,991,349 searches. Data last updated April 28, 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 5/183:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 4/27$114
Sat 5/113:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 5/184:05 pmORD - SJC
1 stop6h 04mSpirit Airlines
Deal found 4/26$117
Sat 5/187:10 amSJC - ORD
2 stops16h 08mSpirit Airlines
Tue 5/2110:52 pmORD - SJC
1 stop11h 49mSpirit Airlines
Deal found 4/27$129
Sat 5/113:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Sat 5/181:13 pmORD - SJC
1 stop8h 56mSpirit Airlines
Deal found 4/27$132
Sat 5/183:08 pmSJC - ORD
1 stop8h 10mSpirit Airlines
Tue 5/217:00 amORD - SJC
3 stops30h 31mSpirit Airlines
Deal found 4/27$142
Wed 5/158:00 amSJC - ORD
1 stop6h 56mSpirit Airlines
Wed 5/221:13 pmORD - SJC
1 stop8h 06mSpirit Airlines
Deal found 4/25$144
Mon 5/68:53 pmSJC - ORD
2 stops17h 20mSpirit Airlines
Wed 5/87:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/26$147
Tue 5/74:11 pmSJC - ORD
3 stops29h 18mSpirit Airlines
Tue 5/147:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/25$148
Tue 5/79:15 amSJC - ORD
2 stops26h 51mSpirit Airlines
Tue 5/147:00 amORD - SJC
1 stop11h 55mSpirit Airlines
Deal found 4/25$151

Non-stop flights to Chicago from San Jose

Discover non-stop flight options from San Jose to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,991,349 searches. Data last updated April 28, 2024.
For a shorter flight, select one of these non-stop flights from San Jose to Chicago. Users can also choose from other San Jose to Chicago flights by using the search form above.
Wed 5/226:20 amSJC - ORD
Nonstop4h 16mUnited Airlines
Sat 5/259:10 amORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 4/27$299
Tue 10/16:35 amSJC - ORD
Nonstop4h 21mUnited Airlines
Tue 10/159:12 amORD - SJC
Nonstop4h 44mUnited Airlines
Deal found 4/26$321
Fri 8/2311:00 pmSJC - ORD
Nonstop4h 15mUnited Airlines
Mon 8/269:15 amORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 4/26$331
Sun 5/196:20 amSJC - ORD
Nonstop4h 16mUnited Airlines
Wed 5/227:52 pmORD - SJC
Nonstop4h 51mUnited Airlines
Deal found 4/26$354
Mon 6/310:30 pmSJC - ORD
Nonstop4h 09mUnited Airlines
Mon 7/18:02 pmORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 4/25$361
Wed 9/46:40 amSJC - ORD
Nonstop4h 20mUnited Airlines
Tue 9/109:15 amORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 4/27$369
Fri 6/710:30 pmSJC - ORD
Nonstop4h 09mUnited Airlines
Tue 6/119:18 amORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 4/26$373
Fri 5/3110:30 pmSJC - ORD
Nonstop4h 09mUnited Airlines
Wed 6/57:45 pmORD - SJC
Nonstop4h 40mUnited Airlines
Deal found 4/25$389
Wed 5/226:20 amSJC - ORD
Nonstop4h 16mUnited Airlines
Tue 5/289:18 amORD - SJC
Nonstop4h 43mUnited Airlines
Deal found 4/27$393

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 2,991,349 searches. Data last updated April 28, 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.
Sun 5/512:15 pmSJC - ORD
1 stop18h 19mSpirit Airlines
Mon 5/67:52 pmORD - SJC
1 stop14h 28mSpirit Airlines
Deal found 4/27$298
Fri 5/31:26 pmSJC - ORD
1 stop28h 39mSpirit Airlines
Mon 5/67:52 pmORD - SJC
1 stop13h 23mSpirit Airlines
Deal found 4/27$305
Sat 5/47:00 amSJC - ORD
2 stops11h 05mSpirit Airlines
Mon 5/67:52 pmORD - SJC
1 stop13h 23mSpirit Airlines
Deal found 4/27$315
Thu 5/28:05 amSJC - ORD
1 stop20h 24mSpirit Airlines
Mon 5/67:52 pmORD - SJC
1 stop13h 23mSpirit Airlines
Deal found 4/27$342
Sat 5/47:00 amSJC - ORD
2 stops11h 05mSpirit Airlines
Mon 5/67:52 pmORD - SJC
2 stops21h 28mSpirit Airlines
Deal found 4/27$363
Thu 5/28:05 amSJC - ORD
1 stop20h 24mSpirit Airlines
Thu 5/91:13 pmORD - SJC
1 stop26h 03mSpirit Airlines
Deal found 4/27$379
Sat 5/47:00 amSJC - ORD
2 stops11h 05mSpirit Airlines
Mon 5/66:41 pmORD - SJC
3 stops40h 00mSpirit Airlines
Deal found 4/27$389
Sun 5/59:46 pmSJC - ORD
1 stop6h 43mSpirit Airlines
Mon 5/610:00 pmORD - SJC
3 stops36h 41mSpirit Airlines
Deal found 4/27$393
Sun 5/54:11 pmSJC - ORD
3 stops24h 52mMultiple Airlines
Mon 5/610:00 pmORD - SJC
3 stops36h 41mMultiple Airlines
Deal found 4/27$398

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 2,991,349 searches. Data last updated April 28, 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.
Tue 5/145:45 pmSJC - ORD
1 stop13h 39mSpirit Airlines
Deal found 4/26$60
Mon 5/139:28 pmSJC - ORD
2 stops16h 30mSpirit Airlines
Deal found 4/26$72
Tue 5/146:20 amSJC - ORD
3 stops25h 04mSpirit Airlines
Deal found 4/26$75
Mon 5/68:53 pmSJC - ORD
2 stops17h 20mSpirit Airlines
Deal found 4/26$76
Tue 5/144:40 pmSJC - ORD
3 stops28h 49mSpirit Airlines
Deal found 4/27$77
Mon 5/139:28 pmSJC - ORD
1 stop7h 12mSpirit Airlines
Deal found 4/26$79
Tue 5/145:45 pmSJC - ORD
2 stops20h 50mSpirit Airlines
Deal found 4/26$81
Tue 5/74:11 pmSJC - ORD
3 stops29h 18mSpirit Airlines
Deal found 4/26$83
Tue 5/79:15 amSJC - ORD
2 stops26h 51mSpirit Airlines
Deal found 4/26$85

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 2,991,349 searches. Data last updated April 28, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$114 - $331

Route

Depart

Return

Price

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sat 5/18

1 stop8h 10m

Chicago O'Hare Intl

Tue 5/21

1 stop11h 49m

$114

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sat 5/11

1 stop8h 10m

Chicago O'Hare Intl

Sat 5/18

1 stop6h 04m

$117

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sat 5/18

2 stops16h 08m

Chicago O'Hare Intl

Tue 5/21

1 stop11h 49m

$129

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sat 5/11

1 stop8h 10m

Chicago O'Hare Intl

Sat 5/18

1 stop8h 56m

$132

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sat 5/18

1 stop8h 10m

Chicago O'Hare Intl

Tue 5/21

3 stops30h 31m

$142

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sun 5/12

2 stops20h 17m

Chicago O'Hare Intl

Tue 5/14

1 stop11h 55m

$186

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Tue 10/8

1 stop9h 43m

Chicago O'Hare Intl

Tue 10/15

1 stop6h 52m

$289

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sun 5/19

Nonstop4h 16m

Chicago O'Hare Intl

Wed 5/22

1 stop6h 42m

$320

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Thu 5/30

1 stop20h 25m

Chicago O'Hare Intl

Tue 6/4

1 stop10h 46m

$331

Flights are sorted by cheapest first

Deals found on 4/27

When is the best time to 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 January 28, 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

When is the cheapest time 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 April 21, 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. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from San Jose to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from San Jose to Chicago is currently $76 while a round-trip flight costs $196. Price data was last updated on April 21, 2024.

Currently, February 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 June is currently the most expensive (average of $356). 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.

January

$248

February

$245

March

$280

April

$273

May

$282

June

$356

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

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

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 April 28, 2024.
Get a feel of what it's like to fly with Delta, Spirit Airlines and American 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
6,155 reviews
Check prices

Overall

8.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.4

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Southwest
8.2
Very good
6,155 reviews
Southwest
8.2
Very good
6,155 reviews
Check prices

Overall

8.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.4

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Alaska Airlines
8.1
Very good
9,117 reviews
Southwest
8.2
Very good
6,155 reviews
Check prices

Overall

8.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.4

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

Delta
8.1
Very good
10,951 reviews
Southwest
8.2
Very good
6,155 reviews
Check prices

Overall

8.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.4

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

United Airlines
7.4
Good
11,228 reviews
Southwest
8.2
Very good
6,155 reviews
Check prices

Overall

8.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.4

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

American Airlines
7.3
Good
14,875 reviews
Southwest
8.2
Very good
6,155 reviews
Check prices

Overall

8.2

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Food

7.4

Reviews

1 / 10

I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.

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 Spirit Airlines for just $114, but on average you can expect to pay $153.

  • 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 $397.

  • 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 days are nonstop flights available from San Jose to Chicago?

    Nonstop flights are available for this route on the following days: Wednesday.

  • How many flights depart from San Jose to Chicago on average per day?

    On average, you can expect to see 1 flight from San Jose to Chicago a day.
    Early Morning (Midnight to 6am) - 100% of flight departures

  • How long is the flight from San Jose to Chicago?

    Airlines like Spirit Airlines fly from San Jose to Chicago in about 8h 10m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1835 mi.

  • What is the cheapest airline to fly from San Jose to Chicago round-trip?

    Cheapflights users have booked flights from San Jose to Chicago round-trip from $114. You may be able to fly from San Jose to Chicago for 75% less than the average price by searching for this airline.

  • 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 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 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 $839, our data indicates the cheapest price to be $169. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $117.

  • 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 4/27.

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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 2,991,349 searches. Data last updated April 28, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$208FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Alaska AirlinesCheapest$100Average$278FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
Spirit AirlinesCheapest$130Average$277FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
United AirlinesCheapest$203Average$462FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$269Average$436FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$302Average$557FlexibilityNo cancel feeOn-time71%
Search American Airlines 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.
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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 April 28, 2024.
53%of flight departuresEarly morningMidnight to 6 am
47%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%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 April 28, 2024.
Sunday2daily flights
Monday8daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday8daily flights
Friday8daily flights
Saturday2daily flights

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Fly with Cheapflights

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How does Cheapflights help users find flights from San Jose to Chicago?

When you search for this flight from San Jose to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from San Jose to Chicago?

Cheapflights helps you find that perfect flight to Chicago from San Jose by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from San Jose to Chicago with no change fees?

Certainly. Search results for flights to Chicago from San Jose shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from San Jose to Chicago become cheaper?

Yes! Start tracking prices for San Jose to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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