SJC - CHI

$86 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 4/21. 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
1 adult, Economy, 0 bags

KAYAK searches 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.
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Everything you should know

Cheapest round-trip
$277
Overall average: $437
Southwest
Tue 4/14Sat 4/25
SJC - MDW • Non-stop
Cheapest non-stop
$282
Typical prices: $307-$470
United Airlines
Fri 4/17Wed 4/22
SJC - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags offer great value.
Expect a smooth security process at San Jose Airport.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $277 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest and United Airlines. Average duration is 4h 10m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 13% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 5h 47m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 12% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Jose to Chicago

Tue, Apr 14 - Sat, Apr 25
Southwest Logo
10:55 pm - 5:00 am
SJC
-
MDW
4h 05mnonstop
Southwest Logo
10:10 am - 4:40 pm
MDW
-
SJC
8h 30m
2 stops
$277Southwest
Tue, Mar 31 - Mon, Apr 6
Alaska Airlines Logo
6:15 am - 11:59 pm
SJC
-
ORD
15h 44m
1 stop
Alaska Airlines Logo
4:10 pm - 10:10 pm
ORD
-
SJC
8h 00m
1 stop
$277Alaska Airlines
Tue, Apr 7 - Thu, Apr 16
Alaska Airlines Logo
8:39 pm - 7:02 pm
SJC
-
ORD
20h 23m
1 stop
Alaska Airlines Logo
4:10 pm - 10:10 pm
ORD
-
SJC
8h 00m
1 stop
$278Alaska Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
12:57 pm - 11:27 pm
SJC
-
ORD
8h 30m
1 stop
Multiple Airlines Logo
5:15 am - 11:59 am
ORD
-
SJC
8h 44m
1 stop
$279Multiple Airlines
Thu, Apr 16 - Sat, Apr 18
Frontier Logo
8:11 pm - 6:08 am
SJC
-
ORD
7h 57m
1 stop
Frontier Logo
7:21 pm - 7:27 pm
ORD
-
SJC
26h 06m
1 stop
$280Frontier
Thu, May 7 - Mon, May 11
Southwest Logo
8:40 pm - 5:50 am
SJC
-
MDW
7h 10m
1 stop
Southwest Logo
6:15 am - 10:30 am
MDW
-
SJC
6h 15m
1 stop
$280Southwest
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
8:11 pm - 11:27 pm
SJC
-
ORD
25h 16m
2 stops
Multiple Airlines Logo
5:15 am - 7:27 pm
ORD
-
SJC
16h 12m
1 stop
$281Multiple Airlines
Wed, Apr 1 - Mon, Apr 6
Southwest Logo
7:50 pm - 5:40 am
SJC
-
MDW
7h 50m
1 stop
Southwest Logo
11:50 am - 4:25 pm
MDW
-
SJC
6h 35m
1 stop
$282Southwest
Thu, Apr 16 - Sat, Apr 18
Alaska Airlines Logo
2:35 pm - 11:59 pm
SJC
-
ORD
7h 24m
1 stop
Alaska Airlines Logo
6:00 am - 1:35 pm
ORD
-
SJC
9h 35m
1 stop
$282Alaska Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
11:00 am - 10:20 pm
SJC
-
ORD
9h 20m
1 stop
American Airlines Logo
5:00 am - 10:07 am
ORD
-
SJC
7h 07m
1 stop
$285American Airlines
Booking Insights

KAYAK's insights & trends for San Jose to Chicago flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from San Jose to Chicago costs $267 on the route between San Jose (SJC) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between San Jose (SJC) and Chicago Midway Airport (MDW) were, on average, 13% cheaper than other San Jose-Chicago routes. The most popular route is between San Jose (SJC) and Chicago O'Hare Intl Airport (ORD).

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

The average price of all round-trip flights from San Jose to Chicago clicked on KAYAK for each day over the last 12 months.

For San Jose to Chicago, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to San Jose, the best deals are generally found on Wednesday, with Sunday being the most expensive.

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 round-trip 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 February, where tickets cost $390 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $543 and $472 respectively.

Can I save money by flying with a layover from San Jose to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $449, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from San Jose to Chicago, you should book around 4 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from San Jose to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Bill Fink

Bill Fink

Expert on SJC

Bill is an award-winning travel writer with extensive credits covering airlines and the aviation industry for publications including AARP, AFAR, The Points Guy and Yahoo. Based in Portland, Oregon, Bill has traveled to more than 75 countries - and been late for his flight in most of them. He once achieved top-level frequent flier status for all of American, Delta and United Airlines during a single year.

Good to know

Low seasonFebruary
Cheapest flight$86
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 6% 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 $86 for a one-way ticket and $277 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?

    Alaska Airlines, American Airlines, Hawaiian Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the San Jose to Chicago flight route.

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

    The Boeing 737 MAX 8 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between San Jose and Chicago, with SkyTeam being the most commonly used for this route.

  • 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, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from San Jose to Chicago are Southwest and Alaska Airlines. With an average price for the route of $473 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $258 and an overall rating of 7.9.

  • 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.

KAYAK’s 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 $204 or less one-way and $387 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.

Prefer to fly direct from San Jose to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San Jose to Chicago.
Find which airlines fly direct from San Jose Airport to Chicago, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the 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
SouthwestOverall score based on 4318 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

in-flight wifi was not working well. also the cabin temperature was a bit hot.

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

I wasn’t able to check in prior to arriving at the airport, I was told by the agent I may not get a seat on the plane as others were waiting for seats, I sat there for 2 hours before being assigned a seat, very stressful. The plane was delayed. Overall not a great travel experience for a 44 minute flight.

Larger seats and more room would elevate the experience. Otherwise, it was good!

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Got on the plane and sat there for an hour before departure.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Remind customers of the need to have passport or new ID for boarding.

The flight never took off and we spent 7 hours at the airport

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

Information on your arrival and departure airports