CHI - SJD

$90 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 3/24. 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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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)

 
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
1:00 am - 3:10 pmORD-SJD
15h 10m1 stop
5:05 pm - 5:40 pmSJD-ORD
23h 35m1 stop
$243Viva
Find Deal
Tue, Mar 4 - Thu, Nov 6
1:00 am - 3:10 pmORD-SJD
15h 10m1 stop
3:40 pm - 12:30 amSJD-ORD
6h 50m1 stop
$247Viva
Find Deal
Tue, Mar 4 - Mon, Mar 10
1:40 am - 10:09 amORD-SJD
10h 29m1 stop
12:01 pm - 12:15 amSJD-ORD
10h 14m1 stop
$306Volaris
Find Deal
Fri, May 2 - Wed, May 7
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
12:01 pm - 12:15 amSJD-ORD
10h 14m1 stop
$308Volaris
Find Deal
Wed, May 14 - Sat, May 17
6:00 am - 11:32 amMDW-SJD
7h 32m1 stop
12:37 pm - 10:23 pmSJD-MDW
7h 46m1 stop
$511Delta
Find Deal
Wed, Mar 12 - Tue, Mar 18
12:51 pm - 9:47 pmMDW-SJD
10h 56m2 stops
4:25 pm - 8:45 amSJD-MDW
14h 20m2 stops
$516Delta
Find Deal
Tue, Mar 11 - Fri, Mar 14
6:04 am - 1:05 pmMDW-SJD
9h 01m1 stop
12:15 pm - 10:26 pmSJD-MDW
8h 11m1 stop
$521Aeromexico
Find Deal
Sun, Apr 27 - Thu, May 1
9:10 am - 12:10 pmMDW-SJD
5h 00mnonstop
11:40 am - 10:50 pmSJD-MDW
9h 10m1 stop
$541Southwest
Find Deal
Sun, Apr 6 - Wed, Apr 9
9:00 am - 12:00 pmMDW-SJD
5h 00mnonstop
1:00 pm - 11:30 pmSJD-MDW
8h 30m1 stop
$549Southwest
Find Deal
Wed, Mar 12 - Sat, Mar 15
6:00 am - 12:36 pmMDW-SJD
7h 36m1 stop
6:00 am - 9:47 pmSJD-MDW
14h 47m2 stops
$620Aeromexico
Find Deal
Wed, Mar 5 - Thu, Nov 6

Expert advice for your flight from Chicago to San José del Cabo

Our travel pros reveal their best tips for your Chicago to San José del Cabo journey.
Airlines
American Airlines

Main Cabin Extra offers early boarding and complimentary alcoholic drinks for a small fee.


American's Flagship Lounges provide upgraded seating, meals, and cocktail service.

United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


United's Priority Boarding puts you in Zone 2, avoiding overhead bin space issues.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

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

Read more

Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.

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 $535 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 $535.

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

The average price of all round-trip flights from Chicago to San José del Cabo clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago to San José del Cabo, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from San José del Cabo, Saturday is the cheapest day to fly and Sunday is the most expensive.

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 $532 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $808 and $676 respectively.

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 4 weeks before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$90
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 11% 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 $90 for a one-way ticket and $243 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, Alaska Airlines, 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 $938 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 $653 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 $245 or less one-way and $703 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, Southwest, +1 more

American Airlines, Emirates, +2 more

Tuesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Wednesday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Thursday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Friday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Saturday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Sunday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

See more direct flights

Direct returns

San José del Cabo Los Cabos to Chicago

Monday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Tuesday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Wednesday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Thursday

American Airlines, Emirates, United Airlines

American Airlines, Emirates, +1 more

Friday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Saturday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 more

Sunday

American Airlines, Emirates, Southwest, +1 more

American Airlines, Emirates, +2 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.
8.1
SouthwestOverall score based on 4411 reviews
7.1Food
8.2Boarding
7.6Entertainment
8.1Comfort
8.7Crew
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Old and out of date plane, it seem like every time I fly with united there’s and issue. We were delayed,

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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.

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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.

They closed the gate over 25 minutes before departure and I didn’t get to board.

No empathy for my situation, arriving at the check-in counter 5 minutes after the deadline to deposit baggage due to a very delayed incoming intercontinental flight. The attendant simply stared past my shoulder and picked up the microphone to announce a "reminder that all passengers must arrive at least one hour before the flight" before speaking to the passenger behind me. I understand that there are rules above deadlines but at least show some damn empathy. It was Christmas morning and I'd been travelling for 20 hours for goodness sake!

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..

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

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.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

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

I never got an email for checking in for my flight back to Los Angeles so I got to airport extra early to sort it. they changed the gate, and so I had to run to the other end of the airport. Their app is wonky. They are not on WhatsApp and I didn’t have cell service to call for help. I think they need to up their game with communicating.

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.

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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