CHI - SJD

$88 Find Cheap Flights from Chicago to San José del Cabo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San José del Cabo departing on 1/19. 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.
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Search hundreds of travel sites at once for deals on flights to San José del Cabo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José del Cabo.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José del Cabo.
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago to San José del Cabo (CHI-SJD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San José del Cabo 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.

Recent round-trip flight deals from Chicago to San José del Cabo

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to San José del Cabo.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$257Viva
Find Deal
Sun, Jan 26 - Wed, Jan 29
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$258Viva
Find Deal
Thu, Jan 16 - Tue, Jan 21
1:55 am - 7:33 amORD-SJD
7h 38m1 stop
12:20 pm - 12:15 amSJD-ORD
9h 55m1 stop
$333Volaris
Find Deal
Wed, Jun 11 - Sun, Jun 15
7:25 am - 8:08 pmORD-SJD
14h 43m1 stop
11:01 am - 11:34 pmSJD-ORD
10h 33m1 stop
$360Volaris
Find Deal
Sat, May 10 - Sat, May 17
6:00 am - 9:47 pmMDW-SJD
16h 47m2 stops
6:02 am - 10:20 pmSJD-MDW
15h 18m2 stops
$505Aeromexico
Find Deal
Sun, Mar 2 - Thu, Mar 6
6:00 am - 2:11 pmMDW-SJD
9h 11m1 stop
1:41 pm - 10:20 pmSJD-MDW
7h 39m1 stop
$517Delta
Find Deal
Sun, Feb 23 - Thu, Feb 27
6:00 am - 6:32 pmMDW-SJD
13h 32m2 stops
5:35 pm - 8:51 amSJD-MDW
14h 16m2 stops
$522Delta
Find Deal
Mon, Feb 17 - Fri, Feb 21
10:35 pm - 11:40 amMDW-SJD
14h 05m1 stop
1:35 pm - 12:25 amSJD-MDW
9h 50m2 stops
$537Southwest
Find Deal
Sun, Mar 2 - Thu, Mar 6
9:15 pm - 11:40 amMDW-SJD
15h 25m2 stops
11:40 am - 12:05 amSJD-MDW
11h 25m2 stops
$552Southwest
Find Deal
Mon, Mar 3 - Fri, Mar 7
6:00 am - 2:02 pmMDW-SJD
9h 02m1 stop
1:41 pm - 10:20 pmSJD-MDW
7h 39m1 stop
$652Aeromexico
Find Deal
Sat, Jan 4 - Fri, Jan 10

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

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to San José del Cabo.
Our data shows that the cheapest route for a return flight from Chicago to San José del Cabo cost $482 and was between Chicago O'Hare Intl Airport (ORD) and San José del Cabo (SJD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $482.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San José del Cabo, 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 Chicago to San José del Cabo is July, where tickets cost $524 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $802 and $636 respectively.

Can I save money by flying with a layover from Chicago to San José del Cabo?

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.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $341 on average.

How far in advance should I book a flight from Chicago to San José del Cabo?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San José del Cabo, 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 Chicago to San José del Cabo, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$88
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to San José del Cabo

When to book flights from Chicago to San José del Cabo

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

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

    In the last 3 days, the lowest price for a flight from Chicago to San José del Cabo was $88 for a one-way ticket and $257 for a round-trip.

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

    Yes, you’ll need a passport to travel to San José del Cabo from Chicago.

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

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

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

    American Airlines, Aeromexico, Delta, and British Airways offer inflight Wi-Fi service on the Chicago to San José del Cabo flight route.

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to San José del Cabo flight route.

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

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

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

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

  • Which is the best airline for flights from Chicago to San José del Cabo, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San José del Cabo are Southwest and Delta. With an average price for the route of $1,005 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $640 and an overall rating of 8.0.

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

    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 Chicago to San José del Cabo.

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

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

    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 San José del Cabo with an airline and back to Chicago with another airline.

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

    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 San José del Cabo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago to San José del Cabo

  • Looking for a cheap flight? 25% of our users found flights on this route for $276 or less one-way and $889 or less round-trip.

Prefer to fly direct from Chicago to San José del Cabo?

Find which airlines fly direct from Chicago to San José del Cabo Los Cabos Airport, which days they fly and book direct flights.

Direct departures

Chicago to San José del Cabo Los Cabos

Monday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Tuesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Wednesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Thursday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Friday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Saturday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Sunday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

See more direct flights

Direct returns

San José del Cabo Los Cabos to Chicago

Monday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Tuesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Wednesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Thursday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Friday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Saturday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Sunday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to San José del Cabo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San José del Cabo. 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 Chicago to San José del Cabo? 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.
7.5
AeromexicoOverall score based on 1909 reviews
8.0Crew
7.6Comfort
7.1Entertainment
6.7Food
7.5Boarding
Airline reviews

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

4.0 OkayAndrea, Dec 2024MID - MEX
Read more Aeromexico reviews

The airplane was an old airplane, seats were very uncomfortable and very little space, they changed my seat and that was no option to get back into my seat even when I was traveling a senior who required assistance.

This is not a low cost airline. Stop acting like o e.

Aeromexico crew made me check my hand luggage in the door of the plane. As soon as I reach Mexico City, I notice that my luggage was opened and 8 games of Nintendo Switch were stolen (700 dllrs value aprox) (the console was there) but the games were stolen. I am very dissapointed of Aeromexico and all the crew. Instead of being a good trip, It was a sad trip

Ok. But we arrived to a remote terminal which meant that a bus had to take us to the terminal building

Old aircraft the audio of the entertainment dosent work Dirty seats

The plane was so outdated, that it made it uncomfortable. The temperature was hot during the whole flight

Happy attentive flight crew. All in all good flight the night flight works well. Getting into Mexico City early so you don't get caught up it all the immigration and custom ques, additionally, this helps when exiting the airport and crossing the city to your final destination. All works very well and would do it again

Some entertainment and food/snack service would have been nice

All the pessengers should be wait in a line útil the creo and piloto are arrived.

Planes seat could be bigger very uncomfortable for tall humans.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Checkin was painful and slow! Lady didn’t seem to know what was going on and couldn’t explain the delay. Seemed ahe couldnt see the computer scree and we couldn’t hear her talk through her mask.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

They no longer offer anything free to eat or drink, everything is sold, not even a bottle of water is offered for free.

I paid for Viva play and most of the time didn’t work and also I order some drinks and the price was to expensive.

The terminal and gate was never the right one announced in the Viva App, neither in screens, moved from one terminal to another

The smart/express line to check in was a mess, employees not doing the process smooth and quick, using their mobile phones, talking to their coworkers

My flight was changed 4 tienes , delaying my arrival lore than 5 hours

Everything was okay, but boarding begins late and when I was returning there was a gate change. The app never showed the change.

Flights were delayed both ways, with no communication provided by the boarding desk. Delay time kept changing and the boarding process is a pain, as it is so disorganized. Would not recommend.

NOTHING.. THEY CANCEL MY FLIGHT WITHOUT NOTICE AND ENDED UP BUYING A NEW ONE..

They changed the booking I had twice. I got an email last night at 10pm (which I missed of course). Went to the airport this morning and found out it got cancelled due to plane maintenance issues. They offered a flight for tomorrow morning and I just got an email with cancellation notice. Again!! I would not recommend booking with this airline.

THE AIRLINE FUCKEN SUCKS... NO DAMN PROFESIONALS.. NO CURTESY THEY CANCEL THE DAMN FLIGHT AS ITS ABOUT TO TAKE OFF

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

Stood inside the plane for more than an hour before take off

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

When booking I was not made aware that my flight would be standby. I was told when checking my bags that I purchased standby tickets. Luckily there was enough room but an unpleasant experience to say the least.

Overall good flight. The flight attendants were annoying and unfriendly. They would ask me to grab someone else’s trash can just waiting until the person woke up or after the flight is done. It’s not my job to pick up someone else’s trash. Especially when it’s not easily reachable.

The WiFi tv wasn’t working. The flight was over sold and moved several times. The gate assignment appeared on the screens right as we were supposed to board. Because of the flight being over sold we were almost stuck in Cancun for a couple of a days. The flight attendants were unfriendly and would wake you up to pick up other people’s trash.

The reason we chose Volaris to fly from LAX to Mazatlan, Mexico was because of the DATES and TIMES for the NON-STOP flights. When those flights got Totally Changed that was UNACCEPTABLE ! ! ! Also, when my husband Died unexpectedly, the Only statement that Customer Service kept repeating was "they would only offer Credit on a future flight". REALLY?! Volaris was only going to offer CREDIT on another flight to a DEAD PERSON ! ! !

Service of the person who gave us the boarding pass

Book cheap flights from Chicago to San José del Cabo

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San José del Cabo found on KAYAK in the last 72 hours.
1/19Sun
1 stopViva
18h 35mORD-SJD
$88
2/5Wed
1 stopViva
18h 35mORD-SJD
$92
1/24Fri
2 stopsVolaris
19h 54mORD-SJD
$112
1/27Mon
2 stopsVolaris
27h 47mORD-SJD
$117
2/24Mon
nonstopUnited Airlines
4h 53mORD-SJD
$233
3/26Wed
nonstopAmerican Airlines
4h 45mORD-SJD
$253
1/25Sat
nonstopAmerican Airlines
5h 00mORD-SJD
$263
3/25Tue
nonstopUnited Airlines
4h 53mORD-SJD
$266
12/31Tue
1 stopAeromexico
7h 26mMDW-SJD
$283
1/4Sat
1 stopAeromexico
7h 26mMDW-SJD
$323

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to San José del Cabo

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 Chicago to San José del Cabo that are departing in the next 10 days.
12/30Mon
multi-stopViva
9h 10mORD-SJD
12/31Tue
multi-stopViva
7h 00mSJD-ORD
$571
12/27Fri
multi-stop
23h 05mORD-SJD
12/29Sun
multi-stop
18h 35mSJD-ORD
$588
12/30Mon
multi-stopAmerican Airlines
7h 15mORD-SJD
1/1Wed
nonstopAmerican Airlines
4h 16mSJD-ORD
$712
12/30Mon
multi-stopAeromexico
7h 57mORD-SJD
1/1Wed
multi-stopAeromexico
7h 42mSJD-ORD
$722
12/27Fri
multi-stopAmerican Airlines
13h 43mORD-SJD
1/1Wed
nonstopAmerican Airlines
4h 20mSJD-ORD
$776
12/29Sun
multi-stopUnited Airlines
15h 12mORD-SJD
12/31Tue
nonstopUnited Airlines
4h 09mSJD-ORD
$849
12/27Fri
multi-stopUnited Airlines
18h 03mORD-SJD
1/1Wed
multi-stopUnited Airlines
7h 58mSJD-ORD
$851
12/26Thu
multi-stopAeromexico
7h 41mORD-SJD
1/5Sun
multi-stopAeromexico
7h 20mSJD-ORD
$1,171
12/27Fri
multi-stopVolaris
12h 36mMDW-SJD
1/1Wed
multi-stopVolaris
14h 37mSJD-MDW
$1,314
12/30Mon
multi-stopVolaris
15h 47mMDW-SJD
1/2Thu
multi-stopVolaris
14h 37mSJD-MDW
$1,430

Search by stops

Search by airline

Search by price

Everything you need to know for your flight from Chicago to San José del Cabo

Information on your arrival and departure airports

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