SJD - CHI

$176 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 3/3. 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
$314
Volaris
Tue 3/24Sat 3/28
SJD - ORD • 1 stop
Cheapest non-stop
$446
Typical prices: $774-$815
United Airlines
Fri 2/13Tue 2/17
SJD - ORD • Non-stop
Our travelers' advice
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
Volaris
Cheapest • from $370 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
SJD-ORD
Cheapest
SJD-ORD
Most popular
Insights
Insights
Insights
Insights
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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, Mar 24 - Sat, Mar 28
Volaris Logo
12:11 pm - 10:29 pm
SJD
-
ORD
8h 18m1 stop
Volaris Logo
2:19 am - 11:29 am
ORD
-
SJD
11h 10m1 stop
$314Volaris
Fri, Apr 24 - Tue, Apr 28
Volaris Logo
11:07 am - 11:47 pm
SJD
-
ORD
10h 40m1 stop
Volaris Logo
7:40 am - 7:04 pm
ORD
-
SJD
13h 24m1 stop
$364Volaris
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
2:15 pm - 11:50 pm
SJD
-
ORD
32h 35m2 stops
Multiple Airlines Logo
11:59 pm - 4:30 pm
ORD
-
SJD
17h 31m1 stop
$369Multiple Airlines
Thu, Jan 29 - Thu, Feb 5
Volaris Logo
12:11 pm - 10:29 pm
SJD
-
ORD
9h 18m1 stop
Volaris Logo
11:59 pm - 11:30 am
ORD
-
SJD
12h 31m1 stop
$370Volaris
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
6:30 pm - 11:50 pm
SJD
-
ORD
52h 20m2 stops
Multiple Airlines Logo
12:59 pm - 10:45 am
ORD
-
SJD
22h 46m1 stop
$390Multiple Airlines
Fri, Feb 13 - Tue, Feb 17
Alaska Airlines Logo
12:21 pm - 11:59 pm
SJD
-
ORD
10h 38m1 stop
Alaska Airlines Logo
8:20 am - 12:41 pm
ORD
-
SJD
29h 21m1 stop
$404Alaska Airlines
Fri, Feb 13 - Tue, Feb 17
Alaska Airlines Logo
3:16 pm - 4:33 pm
SJD
-
ORD
24h 17m2 stops
Alaska Airlines Logo
3:07 pm - 12:41 pm
ORD
-
SJD
22h 34m1 stop
$425Alaska Airlines
Fri, Feb 13 - Tue, Feb 17
Aeromexico Logo
1:45 pm - 10:42 pm
SJD
-
MDW
7h 57m1 stop
Aeromexico Logo
6:00 am - 2:09 pm
MDW
-
SJD
9h 09m1 stop
$452Aeromexico
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
3:05 pm - 5:00 am
SJD
-
MDW
11h 55m1 stop
Southwest Logo
6:30 am - 11:30 am
MDW
-
SJD
7h 00m1 stop
$490Southwest
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
12:25 pm - 11:40 pm
SJD
-
MDW
9h 15m2 stops
Southwest Logo
7:30 am - 1:25 pm
MDW
-
SJD
7h 55m1 stop
$495Southwest
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 $411 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 Mondays 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 $446, prices are generally cheapest when you fly direct.

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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.
Airlines
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.

Read more about American AirlinesBy Harriet Baskas
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.

Read more about United AirlinesBy Stefanie Waldek
Our travel experts
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
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

Good to know

Low seasonSeptember
Cheapest flight$176
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 27% 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 3 days, the lowest price for a flight from San José del Cabo to Chicago was $176 for a one-way ticket and $314 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 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?

    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 $254 or less one-way and $428 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

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

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

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

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 9095 reviews
6.6Food
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

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

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)