Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

SJC - CHI

$73 Find cheap flights from San Jose to Chicago

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 9/11. 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
Mon 7/1
Mon 7/8

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 42,787,818 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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

 
These are the cheapest deals for flights from San Jose to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from San Jose to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from San Jose to Chicago.

Recent one-way flight deals from San Jose to Chicago

Only flying one-way? Below are some of the best one-way flight deals from San Jose to Chicago found on KAYAK recently.

Recent last minute flight deals from San Jose to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from San Jose to Chicago.

Recent direct flight deals from San Jose to Chicago

The latest deals for direct flights from San Jose to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from San Jose to Chicago

Find recent round-trip train or bus tickets from San Jose to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:31 am - 6:31 amSJC-ORD
18h 00m2 stops
7:03 am - 3:51 pmORD-SJC
10h 48m1 stop
$157Spirit Airlines
Find Deal
Tue, Aug 27 - Wed, Sep 4
6:00 am - 5:22 pmSJC-ORD
9h 22m1 stop
7:03 am - 3:51 pmORD-SJC
10h 48m1 stop
$159Spirit Airlines
Find Deal
Tue, Aug 27 - Wed, Sep 4
3:32 pm - 1:05 amSJC-ORD
7h 33m1 stop
7:00 am - 5:00 pmORD-SJC
12h 00m1 stop
$164Spirit Airlines
Find Deal
Tue, Jun 11 - Tue, Jun 18
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
10:00 pm - 4:51 pmMDW-SJC
20h 51m1 stop
$178Frontier
Find Deal
Tue, Aug 27 - Wed, Sep 4
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
10:00 pm - 4:51 pmMDW-SJC
20h 51m1 stop
$179Frontier
Find Deal
Sat, Sep 14 - Wed, Sep 18
6:00 am - 2:50 pmSJC-RFD
6h 50m1 stop
3:40 pm - 8:21 pmRFD-SJC
6h 41m1 stop
Wed, Jun 26 - Wed, Jul 3
9:14 am - 6:00 amSJC-ORD
18h 46m2 stops
6:30 pm - 4:55 pmORD-SJC
24h 25m2 stops
Wed, Jun 26 - Thu, Jul 4
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
8:15 pm - 10:58 pmORD-SJC
4h 43mnonstop
$307United Airlines
Find Deal
Wed, Jul 24 - Tue, Jul 30
6:15 am - 4:08 pmSJC-MDW
7h 53m1 stop
6:00 am - 5:12 pmMDW-SJC
13h 12m2 stops
$313Delta
Find Deal
Tue, Aug 27 - Wed, Sep 4
12:05 pm - 9:44 pmSJC-MDW
7h 39m1 stop
2:00 pm - 8:39 pmMDW-SJC
8h 39m1 stop
$328Delta
Find Deal
Sat, Sep 14 - Wed, Sep 18
8:00 am - 5:41 amSJC-ORD
19h 41m2 stops
$73Spirit Airlines
Find Deal
Wed, Sep 11
4:43 pm - 8:26 amSJC-ORD
13h 43m1 stop
$74Spirit Airlines
Find Deal
Wed, Sep 11
10:20 pm - 6:33 amSJC-MDW
6h 13m1 stop
$90Frontier
Find Deal
Sat, Aug 31
11:31 am - 12:11 amSJC-ORD
10h 40m1 stop
$96Frontier
Find Deal
Sat, Aug 31
2:34 pm - 11:58 pmSJC-ORD
7h 24m1 stop
$177Delta
Find Deal
Tue, Nov 26
7:00 pm - 8:38 amSJC-MDW
11h 38m2 stops
$179Delta
Find Deal
Fri, Aug 16
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
$188United Airlines
Find Deal
Fri, Aug 16
6:40 am - 1:00 pmSJC-ORD
4h 20mnonstop
$210United Airlines
Find Deal
Sat, Aug 31
7:14 pm - 5:24 amSJC-ORD
8h 10m1 stop
$276American Airlines
Find Deal
Fri, Jun 21
7:14 pm - 5:24 amSJC-ORD
8h 10m1 stop
$325American Airlines
Find Deal
Mon, Jun 10
7:00 am - 11:50 pmSJC-ORD
14h 50m2 stops
8:00 pm - 9:29 amORD-SJC
15h 29m1 stop
$344Spirit Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 12
6:00 am - 9:14 amSJC-ORD
25h 14m2 stops
10:17 pm - 9:29 amORD-SJC
13h 12m1 stop
$355Spirit Airlines
Find Deal
Thu, Jun 6 - Thu, Jun 13
7:18 pm - 5:16 amSJC-ORD
7h 58m1 stop
6:02 am - 12:22 pmORD-SJC
8h 20m1 stop
$756American Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6
9:54 am - 8:45 pmSJC-ORD
8h 51m2 stops
5:00 am - 10:50 amORD-SJC
7h 50m1 stop
$761American Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6
6:22 am - 12:30 pmSJC-ORD
4h 08mnonstop
7:45 pm - 10:25 pmORD-SJC
4h 40mnonstop
$914United Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6
12:57 pm - 10:55 pmSJC-ORD
7h 58m1 stop
9:18 am - 12:01 pmORD-SJC
4h 43mnonstop
$923United Airlines
Find Deal
Tue, Jun 4 - Thu, Jun 6
6:37 am - 5:58 pmSJC-MDW
9h 21m1 stop
3:45 pm - 10:42 pmMDW-SJC
8h 57m1 stop
$945Delta
Find Deal
Thu, Jun 6 - Mon, Jun 10
6:37 am - 4:47 pmSJC-ORD
8h 10m1 stop
7:45 am - 12:05 pmORD-SJC
6h 20m1 stop
$945Delta
Find Deal
Thu, Jun 6 - Sun, Jun 9
12:35 pm - 11:49 pmSJC-ORD
9h 14m1 stop
8:00 am - 8:02 pmORD-SJC
14h 02m2 stops
$1,003Alaska Airlines
Find Deal
Sun, Jun 2 - Tue, Jun 4
8:50 am - 4:40 amSJC-ORD
17h 50m1 stop
5:50 pm - 11:56 pmORD-SJC
8h 06m1 stop
$1,465Alaska Airlines
Find Deal
Mon, Jun 3 - Fri, Jun 14
6:40 am - 1:00 pmSJC-ORD
4h 20mnonstop
9:15 am - 11:58 amORD-SJC
4h 43mnonstop
$289United Airlines
Find Deal
Tue, Aug 27 - Wed, Sep 4
6:35 am - 12:56 pmSJC-ORD
4h 21mnonstop
9:12 am - 11:56 amORD-SJC
4h 44mnonstop
$300United Airlines
Find Deal
Tue, Oct 1 - Tue, Oct 22
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
8:15 pm - 10:58 pmORD-SJC
4h 43mnonstop
$307United Airlines
Find Deal
Wed, Jul 24 - Tue, Jul 30
10:50 am - 5:03 pmSJC-ORD
4h 13mnonstop
9:15 am - 11:58 amORD-SJC
4h 43mnonstop
$309United Airlines
Find Deal
Tue, Aug 20 - Sat, Aug 24
6:40 am - 1:00 pmSJC-ORD
4h 20mnonstop
9:11 am - 11:59 amORD-SJC
4h 48mnonstop
$329United Airlines
Find Deal
Sat, Nov 2 - Thu, Nov 7
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
8:02 pm - 10:45 pmORD-SJC
4h 43mnonstop
$347United Airlines
Find Deal
Wed, Jul 10 - Mon, Jul 15
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
8:15 pm - 10:58 pmORD-SJC
4h 43mnonstop
$348United Airlines
Find Deal
Tue, Jul 30 - Tue, Aug 6
6:39 am - 12:48 pmSJC-ORD
4h 09mnonstop
8:10 pm - 10:53 pmORD-SJC
4h 43mnonstop
$359United Airlines
Find Deal
Mon, Jul 15 - Wed, Jul 17
6:50 pm - 12:55 amSJC-MDW
4h 05mnonstop
8:15 pm - 10:45 pmMDW-SJC
4h 30mnonstop
$440Southwest
Find Deal
Mon, Jun 24 - Thu, Jun 27
6:50 pm - 12:55 amSJC-MDW
4h 05mnonstop
8:15 pm - 10:45 pmMDW-SJC
4h 30mnonstop
$460Southwest
Find Deal
Mon, Jun 24 - Fri, Jun 28
8:25 am - 2:39 pmEmeryville-
Chicago Union
52h 14mnonstop
2:00 pm - 4:57 pmChicago Union-
Emeryville
52h 57mnonstop
$625Amtrak
Find Deal
Thu, Jun 20 - Mon, Jun 24

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 $144 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 $338.

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, Friday 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 $322 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $517 and $485 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 $73. KAYAK users also found San Jose to Chicago round-trip flights on Spirit Airlines from $157 and on Frontier from $178.

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 3 and 5 nonstop flights that take off from San Jose and land in Chicago, with an average flight time of 4h 08m. 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 30 flights. The most frequent day of departure is Wednesday, when 17% of all weekly flights depart. The fewest flights depart on a Sunday.

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 05m, 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 6:21 am and will be landing in Chicago at 12:30 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

January

High season

May

Cheapest flight

$73
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 4% increase in price.
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 $73 for a one-way ticket and $157 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, SWISS, Iberia, British Airways, Finnair, and Air Canada.

  • 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, Delta or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Delta and Alaska Airlines. With an average price for the route of $421 and an overall rating of 8.0, Delta is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $288 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 $206 or less one-way and $440 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.
8.0
DeltaOverall score based on 10419 reviews
8.2Boarding
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

There was a loud squeaky sound the whole time we were flying.

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).

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

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.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

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.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

It wasn’t as horrible as I would have expected, however, to not provide water and change so much for bags is a ripoff to say the least.

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

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

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.
9/11Wed
2 stopsSpirit Airlines
19h 41mSJC-ORD
$73
9/11Wed
1 stopSpirit Airlines
13h 43mSJC-ORD
$74
8/31Sat
1 stopFrontier
6h 13mSJC-MDW
$90
8/31Sat
1 stopFrontier
10h 40mSJC-ORD
$96
11/26Tue
1 stopDelta
7h 24mSJC-ORD
$177
8/16Fri
2 stopsDelta
11h 38mSJC-MDW
$179
8/16Fri
nonstopUnited Airlines
4h 09mSJC-ORD
$188
8/31Sat
nonstopUnited Airlines
4h 20mSJC-ORD
$210
6/21Fri
1 stopAmerican Airlines
8h 10mSJC-ORD
$276
6/10Mon
1 stopAmerican Airlines
8h 10mSJC-ORD
$325

Search by stops

Search by airline

Search by price

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.
6/5Wed
multi-stopSpirit Airlines
14h 50mSJC-ORD
6/12Wed
multi-stopSpirit Airlines
15h 29mORD-SJC
$344
6/6Thu
multi-stopSpirit Airlines
25h 14mSJC-ORD
6/13Thu
multi-stopSpirit Airlines
13h 12mORD-SJC
$355
6/4Tue
multi-stopAmerican Airlines
7h 58mSJC-ORD
6/6Thu
multi-stopAmerican Airlines
8h 20mORD-SJC
$756
6/4Tue
multi-stopAmerican Airlines
8h 51mSJC-ORD
6/6Thu
multi-stopAmerican Airlines
7h 50mORD-SJC
$761
6/4Tue
nonstopUnited Airlines
4h 08mSJC-ORD
6/6Thu
nonstopUnited Airlines
4h 40mORD-SJC
$914
6/4Tue
multi-stopUnited Airlines
7h 58mSJC-ORD
6/6Thu
nonstopUnited Airlines
4h 43mORD-SJC
$923
6/6Thu
multi-stopDelta
9h 21mSJC-MDW
6/10Mon
multi-stopDelta
8h 57mMDW-SJC
$945
6/6Thu
multi-stopDelta
8h 10mSJC-ORD
6/9Sun
multi-stopDelta
6h 20mORD-SJC
$945
6/2Sun
multi-stopAlaska Airlines
9h 14mSJC-ORD
6/4Tue
multi-stopAlaska Airlines
14h 02mORD-SJC
$1,003
6/3Mon
multi-stopAlaska Airlines
17h 50mSJC-ORD
6/14Fri
multi-stopAlaska Airlines
8h 06mORD-SJC
$1,465

Search by stops

Search by airline

Search by price

San Jose - Chicago Flights

Departure:

San Jose (SJC)United States

Return flight deals:

Chicago - San Jose

Cabin classes:

$1,259
$1,229
$1,002
$338

Compare transportation modes for San Jose to Chicago

Average priceAverage duration
Flights$9474h 05m
Trains$6250h 00m