CHI - SJD

$107 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 5/9. 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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KAYAK searches 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.
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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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to San José del Cabo.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
 Logo
6:34 pm - 8:40 amORD-SJD
16h 06m2 stops
 Logo
8:30 am - 11:35 pmSJD-ORD
13h 05m1 stop
Fri, May 2 - Wed, May 7
 Logo
6:34 pm - 8:40 amORD-SJD
16h 06m2 stops
 Logo
9:15 am - 11:35 pmSJD-ORD
12h 20m2 stops
Fri, May 2 - Wed, May 7
 Logo
6:34 pm - 8:00 amORD-SJD
15h 26m1 stop
 Logo
9:15 am - 11:35 pmSJD-ORD
12h 20m2 stops
Fri, May 9 - Sat, May 24
Viva Logo
12:35 pm - 9:00 pmORD-SJD
10h 25m1 stop
Viva Logo
9:15 am - 11:35 pmSJD-ORD
12h 20m2 stops
$347Viva
Find Deal
Sun, May 11 - Tue, May 13
Viva Logo
12:35 pm - 2:25 pmORD-SJD
27h 50m1 stop
Viva Logo
8:30 am - 11:35 pmSJD-ORD
13h 05m1 stop
$351Viva
Find Deal
Sat, May 10 - Sat, May 24
Volaris Logo
6:34 pm - 3:35 pmORD-SJD
23h 01m2 stops
Volaris Logo
4:15 pm - 5:00 pmSJD-ORD
22h 45m3 stops
$362Volaris
Find Deal
Fri, May 9 - Sat, May 24
Volaris Logo
6:34 pm - 3:35 pmORD-SJD
23h 01m2 stops
Volaris Logo
4:15 pm - 5:42 amSJD-ORD
35h 27m3 stops
$365Volaris
Find Deal
Fri, May 2 - Wed, May 7
American Airlines Logo
9:10 am - 11:50 amORD-SJD
4h 40mnonstop
American Airlines Logo
12:50 pm - 7:10 pmSJD-ORD
4h 20mnonstop
$471American Airlines
Find Deal
Sun, May 11 - Thu, May 15
Southwest Logo
5:45 am - 11:20 amMDW-SJD
7h 35m1 stop
Southwest Logo
11:40 am - 10:25 pmSJD-MDW
8h 45m1 stop
$513Southwest
Find Deal
Sun, May 11 - Thu, May 15
Southwest Logo
8:00 am - 1:00 pmMDW-SJD
7h 00m1 stop
Southwest Logo
11:40 am - 11:10 pmSJD-MDW
9h 30m2 stops
$517Southwest
Find Deal
Sat, May 10 - Wed, May 14

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

 
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.
KAYAK teamed up with top travel experts to share the best tips for your 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

KAYAK's insights & trends for Chicago to San José del Cabo flights

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 $481 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 $481.

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 $799 and $698 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 1 stop layover the cheapest option at $1,080 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

$107
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 14% 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 $107 for a one-way ticket and $299 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 $891 and an overall rating of 8.0, 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 $288 or less one-way and $555 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

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, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct 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, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

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.
8.0
SouthwestOverall score based on 4280 reviews
8.2Boarding
7.6Entertainment
8.0Comfort
8.6Crew
7.1Food
Airline reviews

Plz don't take away free bags and free seating

10.0 ExcellentAnonymous, Apr 2025DAL - FLL
Read more Southwest reviews

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

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.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

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..

The boarding process was ridiculous. The boarded groups into a walkway just before the aerobridge (about 20 mins late), whilst we watch the crew stroll casually onto the plane, running late. And then they made us line up on then aerobridge with no aircon for 10 minutes before we boarded. Staff are just as ghetto as the customers. Wouldn’t fly again

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.

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

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

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

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

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

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