SJD - CHI

$212 Find Cheap Flights from San José del Cabo to Chicago - 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 San José del Cabo to Chicago departing on 9/15. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José del Cabo to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José del Cabo to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$354
Typical prices: $400-$360
Volaris
Tue 9/1Sat 9/5
SJD - ORD • 1 stop
Cheapest non-stop
$590
American Airlines
Fri 7/10Sun 7/19
SJD - ORD • Non-stop
Top airlines
Volaris
Cheapest • from $354 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 4h 31m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
SJD
-
ORD
Cheapest
SJD
-
ORD
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Houston (IAH)
Cheapest • Avg $377 (round-trip)
Houston (IAH)
Shortest trip • 6h 55m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 25% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from San José del Cabo to Chicago (SJD-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San José del Cabo to Chicago 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 San José del Cabo to Chicago

Tue, Sep 1 - Sat, Sep 5
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$354Volaris
Thu, Jul 2 - Mon, Jul 6
Volaris Logo
3:36 pm - 4:41 am
SJD
-
ORD
11h 05m
1 stop
Volaris Logo
2:53 am - 11:29 am
ORD
-
SJD
10h 36m
1 stop
$359Volaris
Wed, Jul 8 - Wed, Jul 22
Volaris Logo
2:02 pm - 4:41 am
SJD
-
ORD
36h 39m
2 stops
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$369Volaris
Thu, Sep 3 - Sat, Sep 5
Volaris Logo
12:06 pm - 12:55 am
SJD
-
ORD
10h 49m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$372Volaris
Tue, Sep 1 - Sat, Sep 5
Volaris Logo
3:36 pm - 12:55 am
SJD
-
ORD
7h 19m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$373Volaris
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$535Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$539Delta
Tue, Sep 1 - Sun, Sep 6
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$570Delta
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
11:40 am - 11:45 pm
SJD
-
MDW
10h 05m
2 stops
Southwest Logo
5:55 am - 12:50 pm
MDW
-
SJD
8h 55m
1 stop
$600Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
11:40 am - 11:20 pm
SJD
-
MDW
9h 40m
2 stops
Southwest Logo
5:30 am - 12:50 pm
MDW
-
SJD
9h 20m
2 stops
$604Southwest
Booking Insights

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

Get data-powered insights and trends into flights from San José del Cabo to Chicago to help you find the cheapest flights, the best time to fly and much more.

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

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

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

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

The cheapest return flight from San José del Cabo to Chicago costs $763 on the route between San José del Cabo (SJD) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

The average price of all round-trip flights from San José del Cabo to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from San José del Cabo to Chicago, you should consider leaving on a Thursday and avoid Saturdays if you are looking for the best rates. For your return to San José del Cabo, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

What is the cheapest month to fly from San José del Cabo to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San José del Cabo to Chicago, 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 San José del Cabo to Chicago is September, where tickets cost $262 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $425 and $397 respectively.

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

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.

No, with an average price for the route of $569, prices are generally cheapest when you fly direct.

Find deals
Expert advice

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

 
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.

Read more
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.

Read more

Good to know

Low seasonMay
Cheapest flight$212
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San José del Cabo to Chicago O'Hare Airport

When to book flights from San José del Cabo to Chicago

Are your dates flexible? Find out the best times to travel from San José del Cabo to Chicago 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 San José del Cabo to Chicago

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

    In the last 5 days, the lowest price for a flight from San José del Cabo to Chicago was $212 for a one-way ticket and $354 for a round-trip.

  • Do I need a passport to fly between San José del Cabo and Chicago?

    A passport is required to fly from San José del Cabo to Chicago.

  • Which airports will I be using when flying from San José del Cabo to Chicago?

    On your way to Chicago, you’ll fly out from San José del Cabo Los Cabos. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from San José del Cabo to Chicago?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the San José del Cabo to Chicago flight route.

  • Which aircraft models fly most regularly from San José del Cabo to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the San José del Cabo to Chicago flight route.

  • Which airline alliances offer flights from San José del Cabo to Chicago?

    Star Alliance is the only airline alliance operating flights between San José del Cabo and Chicago.

  • On which days can I fly direct from San José del Cabo to Chicago?

    There are nonstop flights from San José del Cabo to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from San José del Cabo to Chicago?

    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 San José del Cabo to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San José del Cabo to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San José del Cabo 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 San José del Cabo to Chicago?

    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 Chicago with an airline and back to San José del Cabo with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San José del Cabo to Chicago?

    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 Chicago from San José del Cabo 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 San José del Cabo to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $342 or less one-way.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San José del Cabo Los Cabos to Chicago.
Find which airlines fly direct from San José del Cabo Los Cabos Airport to Chicago, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top airline flying from San José del Cabo to Chicago

 
See real verified KAYAK customer reviews for airlines flying from San José del Cabo to Chicago. 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 San José del Cabo to Chicago? 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.
7.4
United AirlinesOverall score based on 9845 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

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

Information on your arrival and departure airports

San José del Cabo (SJD)