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CHI - SJD

$152 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 6/3. 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
Wed 6/5
Wed 6/12

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 42,573,820 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:40 am - 3:08 pmORD-SJD
9h 28m1 stop
8:21 pm - 5:44 amSJD-ORD
7h 23m1 stop
$401Volaris
Find Deal
Tue, Jun 25 - Tue, Jul 2
2:56 pm - 6:50 amORD-SJD
17h 54m2 stops
3:51 pm - 5:44 amSJD-ORD
11h 53m1 stop
Tue, Jun 4 - Tue, Jun 11
8:40 pm - 8:00 amORD-SJD
13h 20m1 stop
11:59 am - 6:24 pmSJD-ORD
4h 25mnonstop
$406American Airlines
Find Deal
Sat, Jul 13 - Tue, Jul 16
8:34 am - 1:14 pmORD-SJD
6h 40m1 stop
11:59 am - 6:24 pmSJD-ORD
4h 25mnonstop
$409American Airlines
Find Deal
Mon, Jul 1 - Wed, Jul 10
2:25 am - 3:20 pmORD-SJD
14h 55m1 stop
7:20 am - 1:10 amSJD-ORD
15h 50m1 stop
$410VivaAerobus
Find Deal
Sat, Jun 1 - Thu, Jun 6
2:25 am - 3:20 pmORD-SJD
14h 55m1 stop
7:20 am - 12:30 amSJD-ORD
15h 10m1 stop
$412VivaAerobus
Find Deal
Tue, Jun 4 - Wed, Jun 12
8:15 pm - 8:48 amORD-SJD
14h 33m1 stop
10:00 am - 12:08 amSJD-ORD
12h 08m1 stop
$424United Airlines
Find Deal
Mon, Jul 15 - Fri, Jul 19
1:55 am - 7:09 pmORD-SJD
19h 14m1 stop
12:12 pm - 11:59 pmSJD-ORD
9h 47m1 stop
$440Aeromexico
Find Deal
Tue, Jul 2 - Wed, Jul 10
5:59 pm - 4:20 pmORD-SJD
24h 21m2 stops
7:59 pm - 12:37 pmSJD-ORD
14h 38m1 stop
$449Aeromexico
Find Deal
Sat, Jul 20 - Tue, Jul 23
8:45 am - 11:23 amORD-SJD
4h 38mnonstop
11:53 am - 6:12 pmSJD-ORD
4h 19mnonstop
$508United Airlines
Find Deal
Sat, Jul 20 - Sat, Jul 27

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 $200 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 $433.

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 Fridays.

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 January, where tickets cost $504 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $734 and $615 respectively.

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 22 days before departure.

Which airlines provide the cheapest flights from Chicago to San José del Cabo?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to San José del Cabo found by KAYAK users in the last 72 hours was for $401 on Volaris, followed by American Airlines ($406). One-way flight deals have also been found from as low as $152 on Volaris and from $182 on VivaAerobus.

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

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to San José del Cabo.
There are 2 airlines that fly nonstop from Chicago to San José del Cabo. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best one-way deal found costing $310. On average, the best prices for this route can be found at American Airlines.

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

Each day, there are between 1 and 2 nonstop flights that take off from Chicago and land in San José del Cabo, with an average flight time of 4h 31m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 9 flights. The most frequent day of departure is Sunday, when 22% of all weekly flights depart. The fewest flights depart on a Tuesday.

Which cabin class options are there for flights between Chicago and San José del Cabo?

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 2 cabin class options for the route. These are Business and 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 Chicago to San José del Cabo take?

Direct flights cover the 1,813 miles separating Chicago to San José del Cabo in about 4h 14m.

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

Early birds can take the earliest flight from Chicago at 8:45 am and will be landing in San José del Cabo at 11:23 am.

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

If you prefer to fly at night, the latest flight from Chicago to San José del Cabo jets off at 8:50 am and lands at 11:20 am.

Good to know

Low season

September

High season

March

Cheapest flight

$152
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 $152 for a one-way ticket and $401 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, British Airways, and Aeromexico 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, Delta or Aeromexico?

    The two airlines most popular with KAYAK users for flights from Chicago to San José del Cabo are Delta and Aeromexico. With an average price for the route of $610 and an overall rating of 8.0, Delta is the most popular choice. Aeromexico is also a great choice for the route, with an average price of $565 and an overall rating of 7.6.

  • 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

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 $225 or less one-way and $506 or less round-trip.

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

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

Nonstop departures

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

Nonstop returns

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
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.
7.6
AeromexicoOverall score based on 2585 reviews
8.1Crew
7.3Entertainment
6.9Food
7.6Boarding
7.6Comfort
Airline reviews

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

6.0 GoodAnonymous, May 2024SFO - MEX
Read more about Aeromexico reviews

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

Great airplane The confort was within the high standards. My only little problem was That all the movies ( only 3) was on Spanish, even though I was selecting the audio on English it didn't happen. After that I highly recommend aeromexico

1 hour waiting for suitcases to come out traveling in business class and food in business class is a sandwich? Avoid Aeromexico .

No space reserved for anyone who didn’t have underseat in front of them. Made it inconvenient to get the backs secured. No inflight entertainment in the 190. Bring your own! Food was excellent and we were surprised to get a full breakfast.

Cons: "left Houston more than 2 hours later, arrive in Mexico over 2 am"

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

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

Delayed 6 hours! finally able to board, then had to wait 45 minutes for the plane to fill up. Mid flight when food service started, they had nothing to offer with the exception of chips and cookies. Worst flight ever!

The priority seat are great especially the first row! Crew was very cordial and helpful, airplane efficient, the departure and arrival was on time.

I had a flight before this one and I was able to get to the plane, the doors were open and they didn’t let me in. It was still 15 min before departure and the plane was there with the doors open and the hall as well and I went all the way there and they didn’t let me in. Then they tried selling me another flight 4 times more expensive than what the original cost and with a 7 hour layover in a different state when my flight was direct and cheaper. Very disappointed, specially with their 0 flexibility when it comes to travelers with multiple connections.

They not allowed to bord flight, arguing that was cancelled the flight reservation. No chance to find and explain answers, very bad treated by Airline staff… At the end we buying a flight ticket with Aeromexico. Is a low Price Flight Company (cheap), as it is cheap treatment for customers… seme with Kiwi .com app. With we did our reservation. with KAYAK.com never get this kind of treatment.

Buen servicio y muy puntual El problema ENORME es pagar por la página de Viva Aerobús lo cual es imposible aún con fondos suficientes en la tarjeta. Eso te obliga a acudir al callcenter de la aerolínea, en donde para que te atiendan transcurren 45 minutos, y ya que se tiene la suerte de comenzar la llamada, te toma otros 60 minutos terminar el proceso de pago de los tickets o de la maleta extra que deseas comprar.

It is ridiculous that electronic checkin for under age kids can be done and need to be done over the counter. Having said so, we were requested to do the single line for this as if we never did any checkin or made services for this to happen fast. Just ridiculous. Flight delayed as it is the regular business for this airline.

an absolute joke. couldn’t even board because they sold our tickets out from underneath us. we had tickets in hand with assigned seats and they still denied boarding at the gate. i’m sure you guys won’t follow up or do anything so merry christmas.

Flight was on time Flight attendants should be kind and empathetic

Viva continues to strive for the worst airline experience ever.

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

It was unfortunate that I paid more than $120 one way to carry on my luggage to only have to have them checked baggage. We board the flight and there’s a lot of overhead space. They checked our bags in Group 2 but Group 3 was able to board with their luggage. I would not fly Volaris again. The flight attendance on the plane was very nice but the employees at the gate prior to boarding was very rude.

For the price, you pretty much can't beat this airlines. As far as comfort, you could do a lot better, but it'll cost you. Over all cheapest way to get from point A to point B.

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

I am disabled and was unable to get any assistance from Volaris. I had to wait in line at front desk for 45 minutes, I am by myself, and unable to stand. When I got to front desk check in, they had no assistance for me. I did however, have wheelchair assistance when I arrived in Mexico City. Thank God for that!

It was horrible, our flight back was overbooked and had to take a flight 12hours later in the day but to LAX. Volaris is horrible.

necesitan mejorar el entretenimiento, en vuelos de mas de 3 horas

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.
6/3Mon
1 stopVolaris
9h 43mORD-SJD
$152
10/6Sun
1 stopVolaris
14h 03mORD-SJD
$159
6/1Sat
1 stopVivaAerobus
23h 25mORD-SJD
$182
5/31Fri
1 stopVivaAerobus
18h 30mORD-SJD
$190
7/14Sun
1 stopAeromexico
21h 58mORD-SJD
$214
6/19Wed
1 stopAeromexico
21h 52mORD-SJD
$226
5/25Sat
1 stopAmerican Airlines
17h 25mORD-SJD
$270
6/22Sat
nonstopUnited Airlines
4h 38mORD-SJD
$301
7/11Thu
nonstopAmerican Airlines
4h 15mORD-SJD
$316
10/6Sun
nonstopUnited Airlines
4h 37mORD-SJD
$356

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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.
5/10Fri
multi-stopVivaAerobus
18h 40mORD-SJD
5/14Tue
multi-stopVivaAerobus
21h 05mSJD-ORD
$434
5/10Fri
multi-stopVivaAerobus
15h 20mORD-SJD
5/15Wed
multi-stopVivaAerobus
14h 55mSJD-ORD
$442
5/10Fri
multi-stopVolaris
24h 41mORD-SJD
5/15Wed
multi-stopVolaris
7h 23mSJD-ORD
$472
5/10Fri
multi-stopVivaAerobus
18h 40mORD-SJD
5/15Wed
multi-stopVivaAerobus
14h 55mSJD-ORD
$473
5/8Wed
multi-stopVolaris
9h 43mORD-SJD
5/18Sat
multi-stopVolaris
7h 34mSJD-ORD
$555
5/10Fri
nonstopAmerican Airlines
4h 30mORD-SJD
5/15Wed
nonstopAmerican Airlines
4h 15mSJD-ORD
$657
5/10Fri
multi-stopAmerican Airlines
10h 12mORD-SJD
5/15Wed
nonstopAmerican Airlines
4h 15mSJD-ORD
$661
5/11Sat
multi-stopAeromexico
22h 49mORD-SJD
5/18Sat
multi-stopAeromexico
15h 06mSJD-ORD
$716
5/9Thu
multi-stopAeromexico
11h 07mORD-SJD
5/13Mon
multi-stopAeromexico
25h 26mSJD-ORD
$722
5/7Tue
multi-stopUnited Airlines
6h 31mORD-SJD
5/7Tue
multi-stopUnited Airlines
16h 06mSJD-ORD
$3,994

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Flights to San José del Cabo

Destination:

San José del Cabo (SJD)Mexico

Return flight deals:

San José del Cabo - Chicago

Cabin classes:

$3,041
$514
$1,186
$424