SJD - CHI

$204 Find Cheap Flights from San José del Cabo to Chicago

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 6/25. 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
$348
Volaris
Thu 6/18Sun 6/21
SJD - ORD • 1 stop
Cheapest non-stop
$547
American Airlines
Thu 6/11Mon 6/15
SJD - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus gives 6 inches more legroom.
American's Wi-Fi offers 20 minutes free with an ad.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $348 (round-trip)
Best reviews • 7.4 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 21m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $377 (round-trip)
Shortest trip • 6h 55m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
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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

Thu, Jun 18 - Sun, Jun 21
Volaris Logo
12:06 pm - 12:55 am
SJD
-
ORD
10h 49m
1 stop
Volaris Logo
2:53 am - 8:16 am
ORD
-
SJD
7h 23m
1 stop
$348Volaris
Wed, Sep 9 - Wed, Sep 16
Volaris Logo
12:02 pm - 11:47 pm
SJD
-
ORD
9h 45m
1 stop
Volaris Logo
7:35 am - 7:04 pm
ORD
-
SJD
13h 29m
1 stop
$359Volaris
Wed, Jun 3 - Sun, Jun 7
Viva Logo
8:20 am - 11:55 pm
SJD
-
ORD
13h 35m
1 stop
Viva Logo
1:30 am - 7:30 am
ORD
-
SJD
8h 00m
1 stop
$381Viva
Fri, May 22 - Sat, Jun 6
Viva Logo
8:40 am - 12:45 am
SJD
-
ORD
14h 05m
1 stop
Viva Logo
8:40 pm - 12:30 pm
ORD
-
SJD
17h 50m
1 stop
$386Viva
Thu, Jun 18 - Fri, Jun 19
Multiple Airlines Logo
8:20 am - 11:55 pm
SJD
-
ORD
13h 35m
1 stop
Multiple Airlines Logo
2:53 am - 11:29 am
ORD
-
SJD
10h 36m
1 stop
$393Multiple Airlines
Fri, May 22 - Sat, Jun 6
Multiple Airlines Logo
8:40 am - 12:45 am
SJD
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
2:53 am - 8:16 am
ORD
-
SJD
7h 23m
1 stop
$394Multiple Airlines
Tue, Jun 16 - Sat, Jun 20
Delta Logo
6:07 am - 10:17 pm
SJD
-
MDW
14h 10m
2 stops
Delta Logo
6:00 am - 12:30 pm
MDW
-
SJD
8h 30m
1 stop
$601Delta
Tue, Jun 16 - Fri, Jun 19
Delta Logo
12:30 pm - 10:17 pm
SJD
-
MDW
7h 47m
1 stop
Delta Logo
6:00 am - 11:25 am
MDW
-
SJD
7h 25m
1 stop
$622Delta
Fri, May 22 - Mon, May 25
Southwest Logo
12:25 pm - 10:20 pm
SJD
-
MDW
7h 55m
1 stop
Southwest Logo
6:55 am - 1:25 pm
MDW
-
SJD
8h 30m
1 stop
$623Southwest
Thu, Jun 18 - Mon, Jun 22
Southwest Logo
11:15 am - 12:35 am
SJD
-
MDW
11h 20m
1 stop
Southwest Logo
5:45 am - 11:00 am
MDW
-
SJD
7h 15m
1 stop
$633Southwest
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 June.

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 $569 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 Tuesdays 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 June, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $598 and $448 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
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.

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.

Good to know

Low seasonMarch
Cheapest flight$204
Best time to beat the crowds with an average 22% drop in price.
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 3 days, the lowest price for a flight from San José del Cabo to Chicago was $204 for a one-way ticket and $348 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?

    Delta, Aeromexico, 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.

  • Which is the best airline for flights from San José del Cabo to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from San José del Cabo to Chicago are United Airlines and American Airlines. With an average price for the route of $446 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $525 and an overall rating of 7.1.

  • 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 $265 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,United Airlines

American Airlines,United 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,United Airlines

American Airlines,United 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 airlines 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 9678 reviews
7.3Comfort
6.6Food
7.1Entertainment
7.7Boarding
8.1Crew
Airline reviews

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.

8.0 ExcellentAnonymous, Apr 2026
ZRH - ORD
Read more United Airlines reviews

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

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

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

Information on your arrival and departure airports