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 1/13. 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
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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.
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Cheap Flight Deals from Chicago to San José del Cabo (CHI-SJD)

 
These are the cheapest deals for flights from Chicago to San José del Cabo 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 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
3:45 pm - 11:30 pmSJD-ORD
6h 45m1 stop
$262Viva
Find Deal
Sat, Jan 18 - Fri, Jan 24
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
8:00 am - 11:30 pmSJD-ORD
14h 30m1 stop
$264Viva
Find Deal
Sat, Feb 15 - Fri, Feb 21
7:25 am - 3:08 pmORD-SJD
9h 43m1 stop
3:51 pm - 5:44 amSJD-ORD
11h 53m1 stop
$327Volaris
Find Deal
Thu, May 15 - Sun, May 18
5:40 pm - 10:42 amORD-SJD
18h 02m2 stops
3:39 pm - 4:37 amSJD-ORD
11h 58m1 stop
$328Volaris
Find Deal
Mon, Jan 13 - Mon, Jan 20
6:00 am - 2:11 pmMDW-SJD
9h 11m1 stop
1:38 pm - 10:20 pmSJD-MDW
7h 42m1 stop
$491Delta
Find Deal
Sun, Jan 12 - Wed, Jan 15
8:35 pm - 11:40 amMDW-SJD
16h 05m2 stops
12:15 pm - 11:20 pmSJD-MDW
10h 05m2 stops
$504Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:00 am - 12:33 pmMDW-SJD
7h 33m1 stop
1:38 pm - 10:20 pmSJD-MDW
7h 42m1 stop
$505Aeromexico
Find Deal
Tue, Jan 14 - Thu, Jan 16
10:10 am - 9:40 pmMDW-SJD
13h 30m2 stops
5:05 pm - 9:23 amSJD-MDW
14h 18m2 stops
$509Delta
Find Deal
Wed, Mar 12 - Tue, Mar 18
9:10 am - 3:35 pmMDW-SJD
7h 25m1 stop
2:45 pm - 9:20 amSJD-MDW
17h 35m2 stops
$539Southwest
Find Deal
Sat, Mar 1 - Tue, Mar 4
6:00 am - 12:26 pmMDW-SJD
7h 26m1 stop
1:38 pm - 10:20 pmSJD-MDW
7h 42m1 stop
$550Aeromexico
Find Deal
Sun, Jan 5 - Thu, Jan 9

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 one-way flights from Chicago to San José del Cabo.
Our data shows that the cheapest route for a one-way flight from Chicago to San José del Cabo cost $205 and was between Chicago O'Hare Intl Airport and San José del Cabo. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $448.

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

The average price of all flights from Chicago to San José del Cabo clicked on KAYAK for each day over the last 12 months.
When flying from Chicago to San José del Cabo, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Thursdays.

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 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 $520 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $747 and $617 respectively.

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

The average 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 1 stop layover the cheapest option at $938 on average

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago to San José del Cabo, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 161 days before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$88
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 6% 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 $262 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, Delta, Aeromexico, 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 $912 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 $645 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 $230 or less one-way and $756 or less round-trip.

Prefer to fly non-stop 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.

Nonstop 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

Nonstop 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 2004 reviews
7.6Comfort
6.7Food
8.0Crew
7.2Entertainment
7.5Boarding
Airline reviews

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

4.0 OkayIgnacio, Nov 2024MEX - MTY
Read more Aeromexico reviews

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.

Atraso de dos horas y media con vuelos sobre vendidos

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

United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.

Didn't make it dir to delays - no support from United staff

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.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

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 need to have enough immigration forms for every one. They should offer free water to everyone, unless some one needs bottled water

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

Overall good but we had a minor scare when a wind shear caused the plane to re take off on the first landing attempt. The crew handled it well and we landed safely on the second attempt

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.
1/13Mon
1 stopViva
18h 35mORD-SJD
$88
1/16Thu
1 stopViva
18h 35mORD-SJD
$91
1/9Thu
1 stopViva
18h 35mORD-SJD
$96
3/3Mon
2 stopsVolaris
18h 02mORD-SJD
$118
1/24Fri
2 stopsVolaris
19h 54mORD-SJD
$119
1/13Mon
nonstopAmerican Airlines
4h 50mORD-SJD
$215
12/31Tue
nonstopAmerican Airlines
4h 55mORD-SJD
$220
3/2Sun
nonstopUnited Airlines
4h 53mORD-SJD
$243
12/17Tue
nonstopUnited Airlines
4h 53mORD-SJD
$246
12/19Thu
1 stopAeromexico
7h 21mMDW-SJD
$274

Search by stops

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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.
11/25Mon
multi-stop
16h 40mORD-SJD
11/28Thu
multi-stop
18h 35mSJD-ORD
$334
11/24Sun
multi-stopViva
9h 05mORD-SJD
11/29Fri
multi-stopViva
8h 55mSJD-ORD
$336
11/25Mon
multi-stopVolaris
9h 00mORD-SJD
11/30Sat
multi-stopVolaris
7h 18mSJD-ORD
$454
11/23Sat
multi-stopVolaris
14h 41mORD-SJD
11/26Tue
multi-stopVolaris
15h 47mSJD-ORD
$456
11/26Tue
nonstopAmerican Airlines
4h 45mORD-SJD
12/3Tue
nonstopAmerican Airlines
4h 10mSJD-ORD
$664
11/25Mon
nonstopUnited Airlines
4h 53mORD-SJD
11/28Thu
nonstopUnited Airlines
4h 09mSJD-ORD
$809
11/24Sun
multi-stopUnited Airlines
16h 41mORD-SJD
11/28Thu
nonstopUnited Airlines
4h 09mSJD-ORD
$814
11/23Sat
multi-stopAmerican Airlines
13h 55mORD-SJD
11/27Wed
nonstopAmerican Airlines
4h 10mSJD-ORD
$824
11/23Sat
multi-stopAeromexico
11h 54mORD-SJD
11/28Thu
multi-stopAeromexico
26h 23mSJD-ORD
$987
11/24Sun
multi-stopAeromexico
10h 40mORD-SJD
11/28Thu
multi-stopAeromexico
26h 23mSJD-ORD
$991

Search by stops

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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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