SJD - CHI

$196 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 1/24. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$347
Typical prices: $360-$362
Volaris
Sun 9/13Mon 9/28
SJD - ORD • 1 stop
Cheapest non-stop
$437
Typical prices: $368-$444
United Airlines
Thu 11/12Tue 11/17
SJD - ORD • Non-stop
Top airlines
Cheapest • from $347 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with United Airlines and American Airlines. Average duration is 4h 32m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $363 (round-trip)
Shortest trip • 7h 07m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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Flight Deals
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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

Sun, Sep 13 - Mon, Sep 28
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$347Volaris
Sun, Sep 13 - Mon, Sep 28
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$348Volaris
Tue, Sep 15 - Sat, Sep 19
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
1:40 am - 10:09 am
ORD
-
SJD
10h 29m
1 stop
$353Volaris
Sun, Sep 13 - Mon, Sep 28
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$355Volaris
Tue, Sep 15 - Mon, Sep 21
Volaris Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$356Volaris
Thu, Sep 24 - Mon, Sep 28
Volaris Logo
12:06 pm - 12:55 am
SJD
-
ORD
10h 49m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$358Volaris
Sat, Nov 14 - Tue, Nov 24
Volaris Logo
3:36 pm - 11:39 pm
SJD
-
ORD
7h 03m
1 stop
Volaris Logo
6:23 am - 3:35 pm
ORD
-
SJD
10h 12m
1 stop
$363Volaris
Fri, Nov 13 - Tue, Nov 24
Volaris Logo
11:16 am - 11:39 pm
SJD
-
ORD
11h 23m
1 stop
Volaris Logo
6:23 am - 3:35 pm
ORD
-
SJD
10h 12m
1 stop
$363Volaris
Fri, Oct 9 - Mon, Oct 12
United Airlines Logo
11:52 am - 6:07 pm
SJD
-
ORD
4h 15mnonstop
United Airlines Logo
9:38 pm - 10:30 am
ORD
-
SJD
14h 52m
1 stop
$437United Airlines
Thu, Nov 12 - Tue, Nov 17
United Airlines Logo
12:55 pm - 6:11 pm
SJD
-
ORD
4h 16mnonstop
United Airlines Logo
7:00 am - 1:18 pm
ORD
-
SJD
7h 18m
1 stop
$437United Airlines
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.

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 $583 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 October, where tickets cost $356 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $642 and $634 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.

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.

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

May

Cheapest flight

$196
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

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

    Each day, there are between 1 and 2 nonstop flights that take off from San José del Cabo and land in Chicago, with an average flight time of 4h 32m. The most common departure time is 11:00 am and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. 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 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 $196 for a one-way ticket and $347 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 Airbus A321-100/200 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?

    You can catch a nonstop flight from San José del Cabo to Chicago on on Saturday.

  • 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 $368 or less one-way and $583 or less round-trip.

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,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United 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

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

United Airlines

United Airlines

Thursday

United 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 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 10061 reviews
7.1Entertainment
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

4.0 OkayN, Jul 2026
PHL - ORD
Read more United Airlines reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I just think it’s unfortunate that Airlines have completely abandoned the idea of serving any kind of decent or even real food on flights, not even on a four hour flight!? Those days are gone, I guess.

Excellent all round, first time flying United. App is very helpful.

The ground crew in Houston were not friendly. The security staff were very rude and reflected an attitude of superiority with rude remarks.

It started with multiple delays, cancellations, re booking, 5 hour lay over and finally on a plane from Chicago to Pittsburgh. Gates, times, etc were changed multiply times. Once on the plane, staff was fine, but built in tv did not work and could not even turn it off. Light at eye level the entire trip, so sleeping was near impossible. No snacks or drinks given.

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

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

Information on your arrival and departure airports