SJD - CHI

$148 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 6/15. 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
$248
Typical prices: $532-$703
Volaris
Wed 4/15Sun 4/19
SJD - ORD • 1 stop
Cheapest non-stop
$407
Typical prices: $447-$789
United Airlines
Thu 4/23Mon 4/27
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 $289 (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, United Airlines and Southwest. Average duration is 4h 11m
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
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

Wed, Apr 15 - Sun, Apr 19
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
$248Volaris
Sun, Apr 26 - Sun, May 3
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
$273Volaris
Fri, May 1 - Tue, May 5
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
$289Volaris
Fri, May 1 - Tue, May 5
Multiple Airlines Logo
12:02 pm - 12:45 am
SJD
-
ORD
10h 43m
2 stops
Multiple Airlines Logo
7:35 am - 7:25 am
ORD
-
SJD
25h 50m
1 stop
$319Multiple Airlines
Wed, Apr 29 - Wed, May 6
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
$326Volaris
Wed, Apr 15 - Sat, Apr 18
Multiple Airlines Logo
7:47 pm - 5:52 am
SJD
-
ORD
8h 05m
1 stop
Multiple Airlines Logo
2:35 am - 7:35 pm
ORD
-
SJD
19h 00m
2 stops
$333Multiple Airlines
Fri, May 1 - Tue, May 5
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
Delta Logo
6:00 am - 1:04 pm
MDW
-
SJD
9h 04m
1 stop
$390Delta
Fri, May 1 - Tue, May 5
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
Delta Logo
6:00 am - 5:48 pm
MDW
-
SJD
13h 48m
2 stops
$406Delta
Mon, Apr 27 - Mon, May 4
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
5:25 am - 10:45 am
MDW
-
SJD
7h 20m
1 stop
$538Southwest
Mon, Apr 27 - Mon, May 4
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
5:30 am - 12:10 pm
MDW
-
SJD
8h 40m
2 stops
$597Southwest
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 $470 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.

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 $592, 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

Cheapest flight$148
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 $148 for a one-way ticket and $289 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, Aeromexico, Delta, 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 $301 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,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to San José del Cabo Los Cabos

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

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 9431 reviews
8.1Crew
7.7Boarding
7.3Comfort
7.1Entertainment
6.6Food
Airline reviews

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

6.0 GoodAnonymous, Mar 2026
FRA - ORD
Read more United Airlines reviews

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

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

Information on your arrival and departure airports