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SJC - CHI

Find cheap flights from San Jose to Chicago from $82

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Chicago departing on 5/15. 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.
1 adult
0 bags
Sun 5/19
Sun 5/26

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Chicago.
In the last 7 days travelers have searched 44,553,814 times on KAYAK, and here is why:

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Cheap flight deals from San Jose to Chicago (SJC-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:40 pm - 6:40 amSJC-ORD
12h 00m1 stop
10:52 pm - 8:41 amORD-SJC
11h 49m1 stop
$153Spirit Airlines
Find Deal
Thu, May 9 - Tue, May 21
9:28 pm - 6:40 amSJC-ORD
7h 12m1 stop
1:13 pm - 7:19 pmORD-SJC
8h 06m1 stop
$155Spirit Airlines
Find Deal
Mon, May 13 - Tue, May 21
6:00 am - 5:43 pmSJC-ORD
9h 43m1 stop
6:59 pm - 11:51 pmORD-SJC
6h 52m1 stop
$289Delta
Find Deal
Tue, Oct 8 - Tue, Oct 15
10:25 am - 11:49 pmSJC-ORD
11h 24m1 stop
6:00 am - 5:55 pmORD-SJC
13h 55m1 stop
$294Alaska Airlines
Find Deal
Tue, Jun 4 - Wed, Jun 5
3:47 pm - 6:20 amSJC-ORD
12h 33m2 stops
1:18 pm - 11:46 pmORD-SJC
12h 28m1 stop
Wed, Jul 17 - Wed, Jul 24
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
5:16 am - 9:41 amORD-SJC
6h 25m1 stop
$306United Airlines
Find Deal
Wed, Jul 17 - Wed, Jul 24
4:11 pm - 6:07 amSJC-ORD
11h 56m2 stops
7:45 pm - 10:48 pmORD-SJC
29h 03m3 stops
Tue, Apr 30 - Fri, May 3
6:22 am - 12:30 pmSJC-ORD
4h 08mnonstop
5:04 am - 9:39 amORD-SJC
6h 35m1 stop
$320United Airlines
Find Deal
Sun, Jun 2 - Wed, Jun 5
12:05 pm - 9:47 pmSJC-MDW
7h 42m1 stop
2:00 pm - 8:39 pmMDW-SJC
8h 39m1 stop
$330Delta
Find Deal
Wed, Aug 14 - Tue, Aug 20
6:55 pm - 5:45 amSJC-ORD
8h 50m1 stop
6:00 am - 11:40 amORD-SJC
7h 40m1 stop
$331Alaska Airlines
Find Deal
Sat, May 11 - Tue, May 21

Flights from San Jose to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from San Jose to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest San Jose to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from San Jose to Chicago.
Our data shows that the cheapest route for a one-way flight from San Jose to Chicago cost $156 and was between San Jose and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $289.

What’s the cheapest day of the week to fly from San Jose to Chicago?

The average price of all flights from San Jose to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from San Jose to Chicago. For your return ticket, we recommend flying on a Friday and avoiding Mondays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San Jose to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from San Jose to Chicago is October, where tickets cost $318 on average. On the other hand, the most expensive months are January and June, where the average cost of tickets is $599 and $521 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San Jose to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from San Jose to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 86 days before departure.

Which airlines provide the cheapest flights from San Jose to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Spirit Airlines offered the best one-way deal for that route, at $82. KAYAK users also found San Jose to Chicago round-trip flights on Spirit Airlines from $153 and on Delta from $289.

Which airlines fly non-stop between San Jose and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from San Jose to Chicago.
There are 2 airlines that fly nonstop from San Jose to Chicago. They are Southwest and United Airlines. The cheapest airline for this route is United Airlines, with the best one-way deal found costing $203. On average, the best prices for this route can be found at United Airlines.

How many flights are there between San Jose and Chicago per day?

Each day, there are between 2 and 3 nonstop flights that take off from San Jose and land in Chicago, with an average flight time of 4h 09m. The most common departure time is 6:00 am and most flights take off in the morning, while the most flights land at Chicago Midway Airport. Each week, there are 19 flights. The most frequent day of departure is Tuesday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between San Jose and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from San Jose to Chicago take?

The average nonstop flight takes 4h 08m, covering a distance of 1,838 miles.

What’s the earliest departure time from San Jose to Chicago?

Early birds can take the earliest flight from San Jose at 6:20 am and will be landing in Chicago at 12:36 pm.

What’s the latest departure time from San Jose to Chicago?

If you prefer to fly at night, the latest flight from San Jose to Chicago jets off at 10:30 pm and lands at 4:39 am.

Good to know

Low season

February

High season

October

Cheapest flight

$82
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 31% lower on average.
Flight from San Jose to Chicago O'Hare Airport

When to book flights from San Jose to Chicago

Are your dates flexible? Find out the best times to travel from San Jose to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from San Jose to Chicago

  • Are there exchange rate centers at O'Hare International airport?

    Yes, there is an exchange rate center. Each terminal at O'Hare International Airport has a foreign currency exchange counter operated by Seaway Bank. Seaway is a service that assists passengers in getting ready for their trips to international locations by facilitating the acquisition of foreign currency before departure and currency exchange upon return. There are automated teller machines (ATMs) positioned throughout the airport, both before and after security checkpoints, as well as in each terminal. These ATMs are offered by both local and national financial organizations.

  • Can I have access to a nursing room at San Jose International Airport?

    Yes, you can access a nursing room. The Nursing Rooms may be found just inside the door of the women's toilet (with the exception of the Gate 8 site), and they are furnished with a comfy chair, sink, changing station, and outlets.

  • At O'Hare International Airport, do they provide car rental services?

    Yes, there is car rental services. You don’t have to worry when traveling to Chicago O’Hare International Airport (ORD) because there are a variety of car rental services. Car rentals provide flexible rentals with no hidden fees. Rental companies include Alamo, Goldcar, Megadrive, Europcar, Centaura. They are located inside the terminal building, usually in arrivals.

  • What services are available for passengers with reduced mobility?

    When departing from San Jose International Airport, it is feasible to request special assistance to go through security and to your gate in advance. The airport has accessible facilities as well as additional assistance for those with concealed disabilities. O'Hare International Airport, the airport of arrival, also provides accessible services like wheelchairs and adapted facilities.

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

    In the last 3 days, the lowest price for a flight from San Jose to Chicago was $82 for a one-way ticket and $153 for a round-trip.

  • Do I need a passport to fly between San Jose and Chicago?

    No

  • Which airlines offer Wi-Fi service onboard planes from San Jose to Chicago?

    All the following airlines offer inflight Wi-Fi service on the San Jose to Chicago flight route: Alaska Airlines, American Airlines, JetBlue, Delta, Iberia, Air Canada, British Airways, SWISS, Finnair, and United Airlines.

  • Which aircraft models fly most regularly from San Jose to Chicago?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the San Jose to Chicago flight route.

  • Which airline alliances offer flights from San Jose to Chicago?

    Star Alliance is the only airline alliance operating flights between San Jose and Chicago.

  • On which days can I fly direct from San Jose to Chicago?

    There are nonstop flights from San Jose to Chicago on a daily basis.

  • Which is the best airline for flights from San Jose to Chicago, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Alaska Airlines and Delta. With an average price for the route of $318 and an overall rating of 8.1, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $448 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from San Jose to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Jose to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Jose is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Jose to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to San Jose with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from San Jose up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from San Jose to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $238 or less one-way and $454 or less round-trip.
  • You can use Terminal 2 United Club at San Jose International Airport (SJC) if you want to refresh or even take a shower before starting your flight to Chicago. You may purchase a day ticket for around $50 or be invited by a member to have access to free Wi-Fi and an open bar.
  • There is Public Transit and Scheduled/Charter Buses websites for the most up-to-date schedule information on ground transportation (including Valley Transportation Authority [VTA] bus and light rail services) at San Jose International Airport.
  • Free Wi-Fi is accessible for a short period in all O'Hare International Airport (ORD) and Chicago Midway Airport (MDW) terminals. Terminal 3 of the O’Hare Airport has a Yoga Room for passengers who need to relieve tension after a flight delay.
  • At San Jose International Airport (SJC) there is discounted airport parking which one can book online before you even leave your home and there is ample space.
  • Arrive up to 2h before your domestic flight's departure time and 3h before your international flight's departure time at San Jose International Airport. Prepare in advance, a valid ID and boarding pass are required. Avoid carrying too much in your carry-on and consider checking luggage wherever possible.
  • At San Jose International Airport (SJC), there is a pet relief stations available both outside and within the airport. Constant changes are made to airline legislation regulating animals in cabins.
See more tips

Prefer to fly non-stop from San Jose to Chicago?

Find which airlines fly direct from San Jose to Chicago, which days they fly and book direct flights.

Nonstop departures

San Jose to Chicago

Monday

Southwest, United Airlines

Southwest, United Airlines

Tuesday

Southwest, United Airlines

Southwest, United Airlines

Wednesday

Southwest, United Airlines

Southwest, United Airlines

Thursday

Southwest, United Airlines

Southwest, United Airlines

Friday

Southwest, United Airlines

Southwest, United Airlines

Saturday

Southwest, United Airlines

Southwest, United Airlines

Sunday

Southwest, United Airlines

Southwest, United Airlines

See more direct flights

Nonstop returns

Chicago to San Jose

Monday

Southwest, United Airlines

Southwest, United Airlines

Tuesday

Southwest, United Airlines

Southwest, United Airlines

Wednesday

Southwest, United Airlines

Southwest, United Airlines

Thursday

Southwest, United Airlines

Southwest, United Airlines

Friday

Southwest, United Airlines

Southwest, United Airlines

Saturday

Southwest, United Airlines

Southwest, United Airlines

Sunday

Southwest, United Airlines

Southwest, United Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from San Jose to Chicago

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Jose to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
Alaska AirlinesOverall score based on 9108 reviews
8.6crew
8.2boarding
7.3food
7.9comfort
7.3entertainment
Airline reviews

I like that we took off on time and arrived a bit early. I like that I could gate check my bag and board early. I don't like how crowded the flight was. I had ok leg room, but could feel every move of the person next to me. And the aisles are very narrow. The gate and flight crews were terrific.

8.0 ExcellentKaren, Apr 2024SFO - JFK
Read more about Alaska Airlines reviews

I like that we took off on time and arrived a bit early. I like that I could gate check my bag and board early. I don't like how crowded the flight was. I had ok leg room, but could feel every move of the person next to me. And the aisles are very narrow. The gate and flight crews were terrific.

I appreciated the ability to choose between multiple flights both into and out of Portland from Burbank on the same day, so we were able to attend an event and return without spending the night. I am unable to appreciate what Alaska Air calls "streamlining" the checkin/boarding process at Burbank Airport. If you have a smartphone and the Alaska Air app, it is probably fine, but removing the option of using onsite kiosks to print boarding passes does not meet my definition of "streamlined". I also found it challenging that both Portland and Burbank airports required the plane to sit on the runway for some time due to lack of an open gate at which to disembark. It would not be so bad if we could at least remove our seat belts and move a little bit while we waited, but that is not an option. I honestly don't know whether this is because of how Alaska Air operates, or just the circumstances of the particular day and airports we were using, but I normally do not experience these kinds of delays to reach a gate using Southwest Air.

This flight was significantly affected by poor wifi connections. I couldn’t get my work done because the wifi kept dropping. Even texts were not going through. There is no seat power in premium class either. I fly a lot. Today was my 10th flight in 4 weeks. This was by far the only flight that was sub par.

the departure got delayed due to SJC situation, but it was a quite good waiting thanks to Alaska airline teams.

I was not given a seat when I bought the ticket. I know airlines are trying to squeeze every penny out ot the customer, but we are buying a seat on the airplane, right? I find this irritating with all airlines, but especially Alaska because I fly it so often. No sense of customer use and loyalty.

WiFi connection bad. Food is really awful. Crew very nice and efficient

It was the worst experience because they delayed the flight by 2 and half hours. We were supposed to depart by 3:41 but they did the depart by 6 pm. It was so boring!!

Due to delayed flight, we missed our connecting flight as well as had to wait for 11 hours for next availaible flight. Not good experience

The flight was diverted and departed from San Jose instead of San Francisco. This could’ve been executed more smoothly because after arriving in San Jose it seemed like nothing was being processed correctly as needed for the gate agents to do their jobs well and the flight to leave on time

I’m a first time mom and traveled with my 18mo old boy and it was not a great experience with the flight attendants. They were not friendly or helpful at all. It’s hard enough traveling with a toddler and have people be rude and unkind does not help.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

I guess they don’t serve drinks on planes anymore

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Perfect flight. On time departure and early arrival. Smooth flight.

Overall pleasant was delayed and caused transportation issue when landing

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

My first time to fly Frontier and loved it! Boarding was super easy as we only had personal items. Crew was helpful and funny and the plane was clean. Pilot was also great at landing the plane smoothly.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

late late late late no accountability no refund no adjustment no reasonable solution

This isna terribly run airlines. If you're one minute late, they will deny your ticket. Don't waste your time or money

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

Book cheap flights from San Jose to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Jose to Chicago found on KAYAK in the last 72 hours.
5/15Wed
1 stopSpirit Airlines
10h 20mSJC-ORD
$82
5/7Tue
1 stopSpirit Airlines
6h 02mSJC-ORD
$92
5/11Sat
1 stopDelta
7h 36mSJC-ORD
$142
8/17Sat
nonstopUnited Airlines
4h 09mSJC-ORD
$160
5/13Mon
1 stopDelta
7h 35mSJC-MDW
$169
5/17Fri
1 stopAmerican Airlines
7h 58mSJC-ORD
$169
7/5Fri
1 stopAmerican Airlines
13h 05mSJC-ORD
$179
5/22Wed
nonstopUnited Airlines
4h 16mSJC-ORD
$185
5/20Mon
1 stopAlaska Airlines
21h 25mSJC-ORD
$191
5/17Fri
1 stopAlaska Airlines
21h 25mSJC-ORD
$218

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Last minute flights from San Jose to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from San Jose to Chicago that are departing in the next 10 days.
4/24Wed
multi-stopSpirit Airlines
20h 24mSJC-ORD
4/25Thu
multi-stopSpirit Airlines
14h 24mORD-SJC
$265
4/24Wed
multi-stopSpirit Airlines
22h 29mSJC-ORD
4/25Thu
multi-stopSpirit Airlines
9h 17mORD-SJC
$300
4/24Wed
multi-stopAlaska Airlines
13h 48mSJC-ORD
5/9Thu
multi-stopAlaska Airlines
19h 05mORD-SJC
$548
4/23Tue
multi-stopAlaska Airlines
15h 50mSJC-ORD
5/1Wed
multi-stopAlaska Airlines
9h 57mORD-SJC
$676
4/24Wed
multi-stopDelta
8h 50mSJC-MDW
4/25Thu
multi-stopDelta
8h 57mMDW-SJC
$680
4/24Wed
multi-stopDelta
8h 50mSJC-MDW
4/25Thu
multi-stopDelta
9h 19mMDW-SJC
$685
4/24Wed
nonstopUnited Airlines
4h 16mSJC-ORD
5/2Thu
nonstopUnited Airlines
4h 51mORD-SJC
$794
4/22Mon
multi-stopAmerican Airlines
9h 52mSJC-ORD
4/25Thu
multi-stopAmerican Airlines
8h 23mORD-SJC
$832
4/22Mon
multi-stopAmerican Airlines
8h 53mSJC-ORD
4/28Sun
multi-stopAmerican Airlines
7h 27mORD-SJC
$837
4/23Tue
nonstopUnited Airlines
4h 16mSJC-ORD
4/26Fri
nonstopUnited Airlines
4h 51mORD-SJC
$905

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San Jose - Chicago Flights

Departure:

San Jose (SJC)United States

Return flight deals:

Chicago - San Jose

Cabin classes:

$1,010
$1,337
$783
$289