SJD - CHI

$166 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 8/30. 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

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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Flights 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

Wed, Jul 9 - Wed, Jul 16
American Airlines Logo
12:45 pm - 7:10 pmSJD-ORD
4h 25mnonstop
American Airlines Logo
9:05 am - 11:45 amORD-SJD
4h 40mnonstop
$350American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
American Airlines Logo
12:45 pm - 7:10 pmSJD-ORD
4h 25mnonstop
American Airlines Logo
9:05 am - 11:45 amORD-SJD
4h 40mnonstop
$351American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
Delta Logo
12:42 pm - 10:08 pmSJD-ORD
7h 26m1 stop
Delta Logo
6:00 am - 7:13 pmORD-SJD
15h 13m2 stops
$355Delta
Find Deal
Thu, Oct 9 - Tue, Oct 14
United Airlines Logo
11:52 am - 6:06 pmSJD-ORD
4h 14mnonstop
United Airlines Logo
5:01 am - 1:43 pmORD-SJD
10h 42m1 stop
$356United Airlines
Find Deal
Thu, Oct 9 - Tue, Oct 14
Delta Logo
12:35 pm - 11:53 pmSJD-ORD
9h 18m1 stop
Delta Logo
6:00 am - 11:30 amORD-SJD
7h 30m1 stop
$359Delta
Find Deal
Sat, Aug 30 - Mon, Sep 1
Volaris Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
Volaris Logo
7:25 am - 8:04 pmORD-SJD
14h 39m1 stop
$369Volaris
Find Deal
Sat, Aug 30 - Sun, Aug 31
 Logo
11:53 am - 12:15 amSJD-ORD
10h 22m1 stop
 Logo
1:55 am - 2:00 pmORD-SJD
14h 05m1 stop
Sat, Aug 30 - Mon, Sep 1
United Airlines Logo
11:52 am - 6:06 pmSJD-ORD
4h 14mnonstop
United Airlines Logo
5:00 am - 12:10 pmORD-SJD
9h 10m1 stop
$391United Airlines
Find Deal
Thu, Jul 31 - Thu, Aug 7
 Logo
11:07 am - 7:50 amSJD-ORD
18h 43m2 stops
 Logo
12:25 pm - 8:35 pmORD-SJD
10h 10m1 stop
Tue, Jul 1 - Sun, Aug 3
Volaris Logo
2:57 pm - 12:15 amSJD-ORD
7h 18m1 stop
Volaris Logo
1:55 am - 11:11 amORD-SJD
11h 16m1 stop
$702Volaris
Find Deal
Expert advice

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

 
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
United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Priority Boarding places you in Zone 2, avoiding overhead bin space issues.

American Airlines

Main Cabin Extra offers early boarding and complimentary alcoholic drinks for a small fee.


American's Wi-Fi offers 20 minutes free by watching an ad, ideal for quick tasks.

Our travel experts
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
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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from San José del Cabo to Chicago.

Our data shows that the cheapest route for a return flight from San José del Cabo to Chicago cost $267 and was between San José del Cabo (SJD) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $267.

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 Tuesday and avoid Sundays if you are looking for the best rates. For your return to San José del Cabo, you’ll find the best rates on Mondays 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 $340 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $1,575 and $958 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.

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 $420 on average.

Good to know

Low seasonJune
High seasonJuly
Cheapest flight$166
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 1% increase 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 $166 for a one-way ticket and $350 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, Delta, Aeromexico, 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 MAX 8 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?

    oneworld, and Star Alliance are the airline alliances operating flights between San José del Cabo and Chicago, with oneworld being the most commonly used for this route.

  • 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 $576 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 $827 and an overall rating of 7.2.

  • 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 $284 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

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 8801 reviews
6.6Food
8.1Crew
7.0Entertainment
7.7Boarding
7.3Comfort
Airline reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

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

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