CHI - SJD

$114 Find Cheap Flights from Chicago to San José del Cabo - Compare and Save

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 11/4. 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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Everything you should know

Cheapest round-trip
$348
Typical prices: $450-$627
Volaris
Mon 8/24Mon 8/31
ORD - SJD • 1 stop
Cheapest non-stop
$483
Typical prices: $502-$663
United Airlines
Mon 9/28Fri 10/2
ORD - SJD • Non-stop
Top airlines
Cheapest • from $349 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 4h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 16% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $347 (round-trip)
Shortest trip • 6h 49m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 21% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 20% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to San José del Cabo!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

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

Mon, Aug 24 - Mon, Aug 31
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
$348Volaris
Wed, Oct 7 - Sun, Oct 11
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
$348Volaris
Tue, Oct 20 - Sat, Oct 24
Multiple Airlines Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$348Multiple Airlines
Wed, Oct 21 - Wed, Oct 28
Multiple Airlines Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
Multiple Airlines Logo
12:36 pm - 11:59 pm
SJD
-
ORD
33h 23m
2 stops
$348Multiple Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
10:35 pm - 12:23 pm
ORD
-
SJD
15h 48m
1 stop
American Airlines Logo
12:41 pm - 7:15 pm
SJD
-
ORD
4h 34mnonstop
$476American Airlines
Mon, Oct 5 - Fri, Oct 9
American Airlines Logo
9:00 am - 11:41 am
ORD
-
SJD
4h 41mnonstop
American Airlines Logo
12:41 pm - 7:15 pm
SJD
-
ORD
4h 34mnonstop
$483American Airlines
Mon, Oct 5 - Fri, Oct 9
United Airlines Logo
8:52 am - 11:25 am
ORD
-
SJD
4h 33mnonstop
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
$483United Airlines
Mon, Sep 28 - Fri, Oct 2
United Airlines Logo
8:52 am - 11:25 am
ORD
-
SJD
4h 33mnonstop
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
$483United Airlines
Tue, Aug 18 - Fri, Aug 21
Southwest Logo
6:00 am - 12:50 pm
MDW
-
SJD
8h 50m
2 stops
Southwest Logo
10:40 am - 10:15 pm
SJD
-
MDW
9h 35m
1 stop
$502Southwest
Tue, Aug 18 - Fri, Aug 21
Southwest Logo
6:40 am - 12:50 pm
MDW
-
SJD
8h 10m
2 stops
Southwest Logo
10:40 am - 10:40 pm
SJD
-
MDW
10h 00m
2 stops
$502Southwest
Booking Insights

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.

How much is a round-trip flight from Chicago to San José del Cabo?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to San José del Cabo departing in October.

Flight prices are below average for this route right now.

Flights to San José del Cabo from Chicago usually cost between $476 and $693 in October.
The lowest price found in the past 5 days was $348 on Multiple Airlines (Oct 21-Oct 28).

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to San José del Cabo costs $539 on the route between Chicago O'Hare Intl Airport (ORD) and San José del Cabo (SJD). Over the past month, this route was, on average, 16% cheaper than other Chicago-San José del Cabo routes. It is also the most popular route.

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, Thursday is the cheapest day to fly and Saturday 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 September, where tickets cost $486 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $691 and $671 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 $637 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 2 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

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

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Good to know

Low season

August

Cheapest flight

$114
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 20% 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

  • 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 36m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 4 flights. The most frequent day of departure is Saturday, when 50% of all weekly flights depart. The fewest flights depart on a Monday.

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

    In the last 5 days, the lowest price for a flight from Chicago to San José del Cabo was $114 for a one-way ticket and $348 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, Iberia, Delta, and JetBlue 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 Airbus A321-100/200 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San José del Cabo, with Star Alliance 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to San José del Cabo are Southwest and United Airlines. With an average price for the route of $636 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $636 and an overall rating of 7.4.

  • 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.

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 $295 or less one-way and $659 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to San José del Cabo Los Cabos.
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,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

San José del Cabo Los Cabos to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the 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 4228 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

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

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

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

Great flight. WiFi worked great and the crew was awesome.

All planes flying to Mexico City are very old. Seats don’t even have power outlets.

Great crew, smooth flight. 30 minute delay on the tarmac with no status updates or information from captain. However, that was the only negative on the trip.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

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.

With a business flight, having a designated seat in the aircraft, I was denied boarding at the gate at last minute without any genuine explanation. The staff used profane language when asked for reasons. Viva overbooked and passenger had to pay for it. The food voucher that was provided did not even cover the the full meal and water for a single person. It should not be running in service.

Super BAD Everyone Behind the counters in Cancun Not Helpful At All And then on the second flight I Had to purchase Cancun - Guadalajara one of the flight Attendants Kick Out a Couple Out of the Plane and that Flight Attendant Had a Mask So People wouldn’t take pics of her and she was kind of Mean ! I Would NEVER Flight VIVA EVER THEY ARE NOT FRIENDLY AT ALL ! People think They Are Cheap but They Arent!!!

It was cancelled at the last moment and the customer services seemed unnoticed to this change and hanged me off the phone the first time I called.

Staff especially Alan Hernandez was a great help with arrangements for my partner and me sit together. This made the trip do much more enjoyable. Thanks so much.

One of the flight was delayed an hour. We then boarded a new flight. We were told to unboard after some other time. To wait for the next flight for another hour. I paid for a short flight that turned in to half a day of travel.

No entertainment, charging, nor wifi on board but I napped for basically the entire time so it was alright. Was allowed to switch seats because the flight was not full but everyone was assigned to the back. Comfortable seats and we got moved to the emergency exit so the extra room was nice.

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

They cancel the fly and don’t give a money refund.

The air conditioner was poor and we were delayed 1 hour for no apparent reasons and no information provided

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

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.

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;(

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

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

The whole experience was good. We left a little late but that seems pretty normal we it’s anybairline these days. No free snacks or drinks provided.

We paid for Premium seats and no one, EVER asked us for a drink or snack! No one

The flight was 3 hrs delayed and no remorse from airline

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

Information on your arrival and departure airports