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

SJD - CHI

$185 Find cheap flights from San José del Cabo 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 José del Cabo to Chicago departing on 10/4. 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 6/30
Sun 7/7

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 José del Cabo to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José del Cabo to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,361,115 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 José del Cabo to Chicago (SJD-CHI)

 
These are the cheapest deals for flights from San José del Cabo 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 José del Cabo to Chicago

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

Recent one-way flight deals from San José del Cabo to Chicago

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

Recent last minute flight deals from San José del Cabo to Chicago

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

Recent direct flight deals from San José del Cabo to Chicago

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

Cheap bus & train deals from San José del Cabo to Chicago

Find recent round-trip train or bus tickets from San José del Cabo 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
7:25 am - 12:20 amSJD-ORD
14h 55m1 stop
4:40 pm - 9:20 amORD-SJD
18h 40m1 stop
$375VivaAerobus
Find Deal
Fri, Oct 25 - Fri, Nov 1
1:10 pm - 12:19 amSJD-ORD
9h 09m1 stop
5:00 am - 11:20 amORD-SJD
8h 20m1 stop
$382American Airlines
Find Deal
Thu, Aug 8 - Tue, Aug 13
11:27 am - 7:47 amSJD-ORD
18h 20m1 stop
9:10 pm - 12:43 pmORD-SJD
17h 33m1 stop
$401United Airlines
Find Deal
Thu, Sep 12 - Fri, Sep 20
6:01 am - 11:27 amSJD-ORD
27h 26m2 stops
1:55 am - 9:47 pmORD-SJD
21h 52m1 stop
$413Aeromexico
Find Deal
Fri, Oct 25 - Thu, Oct 31
8:04 pm - 5:58 amSJD-ORD
7h 54m1 stop
1:55 am - 9:53 pmORD-SJD
21h 58m1 stop
$414Aeromexico
Find Deal
Thu, Aug 8 - Mon, Aug 12
12:12 pm - 11:59 pmSJD-ORD
9h 47m1 stop
9:30 am - 10:03 pmORD-SJD
14h 33m2 stops
$420Delta
Find Deal
Thu, Sep 12 - Fri, Sep 20
10:00 am - 12:13 amSJD-ORD
12h 13m1 stop
8:45 am - 11:23 amORD-SJD
4h 38mnonstop
$421United Airlines
Find Deal
Wed, Jul 3 - Sun, Jul 7
12:05 pm - 9:46 pmSJD-MDW
7h 41m1 stop
6:00 am - 11:00 amMDW-SJD
7h 00m1 stop
$461Delta
Find Deal
Fri, Aug 9 - Tue, Aug 13
7:20 am - 12:34 amSJD-ORD
15h 14m1 stop
2:52 pm - 6:55 amORD-SJD
18h 03m2 stops
Fri, Jun 28 - Thu, Jul 4
2:30 pm - 2:47 pmSJD-ORD
22h 17m2 stops
2:52 pm - 9:53 pmORD-SJD
9h 01m1 stop
Wed, Jul 3 - Sun, Jul 7
7:25 am - 12:20 amSJD-ORD
14h 55m1 stop
$185VivaAerobus
Find Deal
Fri, Oct 4
7:25 am - 12:30 amSJD-ORD
15h 05m1 stop
$187VivaAerobus
Find Deal
Wed, Aug 28
8:21 pm - 5:44 amSJD-ORD
7h 23m1 stop
$193Volaris
Find Deal
Mon, Jun 10
8:21 pm - 5:44 amSJD-ORD
7h 23m1 stop
$195Volaris
Find Deal
Mon, Jun 24
2:38 pm - 12:20 amSJD-ORD
7h 42m1 stop
$220Aeromexico
Find Deal
Tue, Oct 15
11:59 am - 6:24 pmSJD-ORD
4h 25mnonstop
$221American Airlines
Find Deal
Fri, Aug 2
12:05 pm - 9:46 pmSJD-MDW
7h 41m1 stop
$226Aeromexico
Find Deal
Tue, Aug 27
4:14 pm - 7:28 amSJD-ORD
13h 14m1 stop
$273American Airlines
Find Deal
Mon, Aug 5
11:53 am - 6:12 pmSJD-ORD
4h 19mnonstop
$310United Airlines
Find Deal
Sun, Jun 9
11:53 am - 6:05 pmSJD-ORD
4h 12mnonstop
$318United Airlines
Find Deal
Fri, Oct 4
1:49 pm - 11:59 pmSJD-ORD
8h 10m1 stop
2:01 am - 9:43 pmORD-SJD
21h 42m1 stop
$813Aeromexico
Find Deal
Fri, May 31 - Sun, Jun 2
10:49 am - 11:59 pmSJD-ORD
11h 10m1 stop
9:32 am - 9:43 pmORD-SJD
14h 11m2 stops
$815Delta
Find Deal
Fri, May 31 - Mon, Jun 3
6:53 am - 11:55 pmSJD-ORD
15h 02m2 stops
2:01 am - 9:43 pmORD-SJD
21h 42m1 stop
$819Aeromexico
Find Deal
Fri, May 31 - Sun, Jun 2
6:53 am - 11:55 pmSJD-ORD
15h 02m2 stops
9:32 am - 9:43 pmORD-SJD
14h 11m2 stops
$821Delta
Find Deal
Fri, May 31 - Mon, Jun 3
12:20 pm - 6:35 pmSJD-ORD
4h 15mnonstop
8:50 am - 11:20 amORD-SJD
4h 30mnonstop
$858American Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
12:20 pm - 6:35 pmSJD-ORD
4h 15mnonstop
5:00 am - 11:24 amORD-SJD
8h 24m1 stop
$862American Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
12:15 pm - 6:35 pmSJD-ORD
4h 20mnonstop
8:44 am - 10:59 amORD-SJD
4h 15mnonstop
$442American Airlines
Find Deal
Wed, Jul 3 - Sun, Jul 7
12:29 pm - 6:55 pmSJD-ORD
4h 26mnonstop
8:20 am - 10:34 amORD-SJD
4h 14mnonstop
$461American Airlines
Find Deal
Thu, Oct 10 - Wed, Oct 16
12:29 pm - 6:55 pmSJD-ORD
4h 26mnonstop
8:20 am - 11:06 amORD-SJD
4h 46mnonstop
$500American Airlines
Find Deal
Fri, Oct 25 - Fri, Nov 1
12:15 pm - 6:35 pmSJD-ORD
4h 20mnonstop
8:50 am - 11:15 amORD-SJD
4h 25mnonstop
$619American Airlines
Find Deal
Tue, Jun 11 - Tue, Jun 18
12:15 pm - 6:35 pmSJD-ORD
4h 20mnonstop
8:50 am - 11:15 amORD-SJD
4h 25mnonstop
$758American Airlines
Find Deal
Fri, Jun 28 - Thu, Jul 4
12:15 pm - 6:35 pmSJD-ORD
4h 20mnonstop
8:50 am - 11:15 amORD-SJD
4h 25mnonstop
$824American Airlines
Find Deal
Fri, Jun 28 - Thu, Jul 4
12:15 pm - 6:35 pmSJD-ORD
4h 20mnonstop
8:50 am - 11:15 amORD-SJD
4h 25mnonstop
$986American Airlines
Find Deal
Fri, Jun 28 - Wed, Jul 3
12:15 pm - 6:35 pmSJD-ORD
4h 20mnonstop
8:50 am - 11:15 amORD-SJD
4h 25mnonstop
$1,047American Airlines
Find Deal
Fri, Jun 28 - Wed, Jul 3

Flights from San José del Cabo to Chicago - Travel Insights & Trends

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

What is the cheapest San José del Cabo 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 José del Cabo to Chicago.
Our data shows that the cheapest route for a one-way flight from San José del Cabo to Chicago cost $221 and was between San José del Cabo 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 $262.

What’s the cheapest day of the week to fly from San José del Cabo to Chicago?

The average price of all flights from San José del Cabo to Chicago clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Monday and more expensive on a Thursday. On your return trip to San José del Cabo, you should consider flying back on a Tuesday, and avoid Thursdays for better deals.

What is the cheapest month to fly from San José del Cabo to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San José del Cabo 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 José del Cabo to Chicago is September, where tickets cost $388 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $682 and $628 respectively.

Which airlines provide the cheapest flights from San José del Cabo 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, VivaAerobus offered the best one-way deal for that route, at $185. KAYAK users also found San José del Cabo to Chicago round-trip flights on VivaAerobus from $375 and on American Airlines from $382.

Which airlines fly non-stop between San José del Cabo and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from San José del Cabo to Chicago.
There are 2 airlines that fly nonstop from San José del Cabo to Chicago. They are American Airlines and United Airlines. The cheapest airline for this route is American Airlines, with the best one-way deal found costing $438. On average, the best prices for this route can be found at American Airlines.

How many flights are there between San José del Cabo and Chicago per day?

Each day, there are between 1 and 3 nonstop flights that take off from San José del Cabo and land in Chicago, with an average flight time of 4h 19m. The most common departure time is 11:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 11 flights. The most frequent day of departure is Saturday, when 27% of all weekly flights depart. The fewest flights depart on a Monday.

Which cabin class options are there for flights between San José del Cabo 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 3 cabin class options for the route. These are 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 José del Cabo to Chicago take?

The duration of a nonstop flight to Chicago from San José del Cabo is typically 4h 20m. The journey crosses a distance of 1,813 miles.

What’s the earliest departure time from San José del Cabo to Chicago?

Early birds can take the earliest flight from San José del Cabo at 11:53 am and will be landing in Chicago at 6:12 pm.

What’s the latest departure time from San José del Cabo to Chicago?

If you prefer to fly at night, the latest flight from San José del Cabo to Chicago jets off at 12:15 pm and lands at 6:35 pm.

Good to know

Low season

January

High season

May

Cheapest flight

$185
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from San José del Cabo to Chicago O'Hare Airport

When to book flights from San José del Cabo to Chicago

Are your dates flexible? Find out the best times to travel from San José del Cabo 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 José del Cabo to Chicago

  • What is the cheapest flight from San José del Cabo to Chicago?

    In the last 3 days, the lowest price for a flight from San José del Cabo to Chicago was $185 for a one-way ticket and $375 for a round-trip.

  • Do I need a passport to fly between San José del Cabo and Chicago?

    A passport is required to fly from San José del Cabo to Chicago.

  • Which airports will I be using when flying from San José del Cabo to Chicago?

    On your way to Chicago, you’ll fly out from San José del Cabo Los Cabos. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from San José del Cabo to Chicago?

    Only American Airlines offers inflight Wi-Fi service on the San José del Cabo to Chicago flight route.

  • Which aircraft models fly most regularly from San José del Cabo to Chicago?

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

  • Which airline alliances offer flights from San José del Cabo to Chicago?

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

  • On which days can I fly direct from San José del Cabo to Chicago?

    There are nonstop flights from San José del Cabo to Chicago on a daily basis.

  • Which is the best airline for flights from San José del Cabo to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from San José del Cabo to Chicago are United Airlines and American Airlines. With an average price for the route of $632 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $576 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from San José del Cabo 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 José del Cabo to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San José del Cabo 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 José del Cabo 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 José del Cabo with another airline.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $278 or less one-way and $271 or less round-trip.

Prefer to fly non-stop from San José del Cabo to Chicago?

Find which airlines fly direct from Los Cabos to Chicago, which days they fly and book direct flights.

Nonstop departures

San José del Cabo Los Cabos to Chicago

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Sunday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

See more direct flights

Nonstop returns

Chicago to San José del Cabo Los Cabos

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Sunday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

See more direct flights
See more direct flights

Top airlines flying from San José del Cabo to Chicago

 
See real verified KAYAK customer reviews for airlines flying from San José del Cabo 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 José del Cabo 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.
7.4
United AirlinesOverall score based on 10778 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.2Comfort
6.7Food
Airline reviews

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.

10.0 ExcellentEllen, May 2024GSP - ORD
Read more about United Airlines reviews

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.

It started with multiple delays, cancellations, re booking, 5 hour lay over and finally on a plane from Chicago to Pittsburgh. Gates, times, etc were changed multiply times. Once on the plane, staff was fine, but built in tv did not work and could not even turn it off. Light at eye level the entire trip, so sleeping was near impossible. No snacks or drinks given.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

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.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

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

Wifi wasn't working on one of the UA flights after boarding.

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.

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

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

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

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.

Book cheap flights from San José del Cabo to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San José del Cabo to Chicago found on KAYAK in the last 72 hours.
10/4Fri
1 stopVivaAerobus
14h 55mSJD-ORD
$185
8/28Wed
1 stopVivaAerobus
15h 05mSJD-ORD
$187
6/10Mon
1 stopVolaris
7h 23mSJD-ORD
$193
6/24Mon
1 stopVolaris
7h 23mSJD-ORD
$195
10/15Tue
1 stopAeromexico
7h 42mSJD-ORD
$220
8/2Fri
nonstopAmerican Airlines
4h 25mSJD-ORD
$221
8/27Tue
1 stopAeromexico
7h 41mSJD-MDW
$226
8/5Mon
1 stopAmerican Airlines
13h 14mSJD-ORD
$273
6/9Sun
nonstopUnited Airlines
4h 19mSJD-ORD
$310
10/4Fri
nonstopUnited Airlines
4h 12mSJD-ORD
$318

Search by stops

Search by airline

Search by price

Last minute flights from San José del Cabo 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 José del Cabo to Chicago that are departing in the next 10 days.
5/31Fri
multi-stopAeromexico
8h 10mSJD-ORD
6/2Sun
multi-stopAeromexico
21h 42mORD-SJD
$813
5/31Fri
multi-stopDelta
11h 10mSJD-ORD
6/3Mon
multi-stopDelta
14h 11mORD-SJD
$815
5/31Fri
multi-stopAeromexico
15h 02mSJD-ORD
6/2Sun
multi-stopAeromexico
21h 42mORD-SJD
$819
5/31Fri
multi-stopDelta
15h 02mSJD-ORD
6/3Mon
multi-stopDelta
14h 11mORD-SJD
$821
5/31Fri
nonstopAmerican Airlines
4h 15mSJD-ORD
6/3Mon
nonstopAmerican Airlines
4h 30mORD-SJD
$858
5/31Fri
nonstopAmerican Airlines
4h 15mSJD-ORD
6/3Mon
multi-stopAmerican Airlines
8h 24mORD-SJD
$862

Search by stops

Search by airline

Search by price

San José del Cabo - Chicago Flights

Departure:

San José del Cabo (SJD)Mexico

Return flight deals:

Chicago - San José del Cabo

Cabin classes:

$581
$761
$262