HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$187+ Cheap flights from San José del Cabo (SJD) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San José del Cabo to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from San José del Cabo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San José del Cabo (SJD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 29, 2025.

Round-trip from

$300
(Mytrip)

One-way from

$187
(Booking.com)

Popular in

May

Cheapest in

September

Average price

$734

Good one-way deal

$281 or less
From San José del Cabo Los Cabos to Chicago (CHI)
Search Deals
One-way flight from San José del Cabo Los Cabos to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 39% potential increase in price ($435 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($92 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a one-way flight from San José del Cabo Los Cabos to Chicago (CHI).
Search Deals

Find flight deals from San José del Cabo to Chicago

Cheapest flights from San José del Cabo to Chicago
Explore the most affordable flight options available from San José del Cabo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Mytrip deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2711:07 amSJD - ORD
1 stop10h 25mVolaris
Wed 9/37:25 amORD - SJD
1 stop14h 29mVolaris
Deal found 7/28$300
This Booking.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/278:30 amSJD - ORD
1 stop13h 20mViva
Tue 9/22:00 amORD - SJD
1 stop14h 55mViva
Deal found 7/28$321
This Mytrip deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/278:30 amSJD - ORD
1 stop13h 20mMultiple Airlines
Wed 9/36:21 pmORD - SJD
2 stops23h 14mMultiple Airlines
Deal found 7/28$342
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:01 amSJD - ORD
2 stops14h 36mDelta
Wed 9/37:05 amORD - SJD
2 stops14h 18mDelta
Deal found 7/28$355
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:52 amSJD - ORD
Nonstop4h 14mUnited Airlines
Mon 10/279:30 pmORD - SJD
1 stop16h 40mUnited Airlines
Deal found 7/28$356
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:01 amSJD - MDW
2 stops13h 35mDelta
Thu 9/186:00 amMDW - SJD
2 stops15h 23mDelta
Deal found 7/28$406
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:40 amSJD - MDW
1 stop11h 25mSouthwest
Sun 8/176:00 amMDW - SJD
1 stop9h 10mSouthwest
Deal found 7/27$409
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/281:16 pmSJD - ORD
1 stop9h 19mAmerican Airlines
Sat 8/307:30 amORD - SJD
Nonstop4h 25mAmerican Airlines
Deal found 7/27$451
This Mytrip deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/118:37 pmSJD - MDW
2 stops20h 39mVolaris
Thu 9/188:39 pmMDW - SJD
1 stop16h 32mVolaris
Deal found 7/28$520
This Aeromexico deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/231:35 pmSJD - MDW
1 stop7h 30mAeromexico
Mon 12/2912:10 pmMDW - SJD
1 stop26h 42mAeromexico
Deal found 7/27$724

Cheapflights Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
Use the filters below to find and compare flights from San José del Cabo to Chicago that are best for you.

Fly from

San José del Cabo

Fly to

Chicago

Route

Depart

Return

Price

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 8/27

11:07 am-11:32 pm

1 stop10h 25m

Chicago O'Hare Intl

Wed 9/3

7:25 am-7:54 pm

1 stop14h 29m

$300

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 8/27

8:30 am-11:50 pm

1 stop13h 20m

Chicago O'Hare Intl

Tue 9/2

2:00 am-2:55 pm

1 stop14h 55m

$321

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 8/27

8:30 am-11:50 pm

1 stop13h 20m

Chicago O'Hare Intl

Wed 9/3

6:21 pm-3:35 pm

2 stops23h 14m

$342

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 8/27

6:01 am-10:37 pm

2 stops14h 36m

Chicago O'Hare Intl

Wed 9/3

7:05 am-7:23 pm

2 stops14h 18m

$355

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 10/24

11:52 am-6:06 pm

Nonstop4h 14m

Chicago O'Hare Intl

Mon 10/27

9:30 pm-12:10 pm

1 stop16h 40m

$356

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/11

6:01 am-9:36 pm

2 stops13h 35m

Chicago Midway

Thu 9/18

6:00 am-7:23 pm

2 stops15h 23m

$406

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/14

10:40 am-12:05 am

1 stop11h 25m

Chicago Midway

Sun 8/17

6:00 am-1:10 pm

1 stop9h 10m

$409

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 8/28

1:16 pm-12:35 am

1 stop9h 19m

Chicago O'Hare Intl

Sat 8/30

7:30 am-9:55 am

Nonstop4h 25m

$451

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/11

8:37 pm-7:16 pm

2 stops20h 39m

Chicago Midway

Thu 9/18

8:39 pm-11:11 am

1 stop16h 32m

$520

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/11

12:30 pm-5:35 pm

1 stop27h 05m

Chicago Midway

Thu 9/18

6:00 am-11:25 am

1 stop7h 25m

$896

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from San José del Cabo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San José del Cabo with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest time of day to fly from SJD to CHI?

Find hourly flight availability from San José del Cabo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

It’s typically best to fly out from San José del Cabo to Chicago in the morning. Doing so could potentially save you 6% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from San José del Cabo to Chicago

Explore weekly flight availability from San José del Cabo to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 29, 2025.

The most flights from SJD to CHI are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico from San José del Cabo to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Aeromexico
7.5
Good
1,720 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from San José del Cabo to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San José del Cabo to Chicago?

    Most people fly from San José del Cabo Los Cabos (SJD) if they book a flight from San José del Cabo to Chicago. On average, Los Cabos has 1 outbound flight to Chicago per day from 1 airline. San José del Cabo Los Cabos is conveniently located just 6.6 mi from San José del Cabo’s city center.

  • What are the cheapest airlines flying from San José del Cabo to Chicago round-trip?

    Our cheapest airline available from San José del Cabo to Chicago is Volaris. Our recent data shows that you can find tickets from as low as $300 on this airline. Additional options worth looking into are Viva and Delta, starting at $321 and $355 round-trip. Volaris is priced at 54% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from San José del Cabo to Chicago one-way?

    $187 is the cheapest one-way deal found within the past few days, from Viva. You may also be able to find cheap deals on Volaris and United Airlines, with prices starting from $190 and $221, respectively.

  • What are the most reliable airlines from San José del Cabo to Chicago?

    No one likes to see their flight delayed. When booking a flight from San José del Cabo to Chicago consider choosing Emirates (89%), United Airlines (89%) or American Airlines (86%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from San José del Cabo to Chicago?

    The cheapest flight price from San José del Cabo to Chicago is $258. On average you can expect to pay $397. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $300.

  • Can I find deals for flights from San José del Cabo to Chicago that include hotel bookings?

    Yes. In addition to deals on San José del Cabo to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José del Cabo to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José del Cabo to Chicago.

  • Can I find deals for business class flights from San José del Cabo to Chicago?

    Yes. Cheapflights offers flight deals from San José del Cabo to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San José del Cabo to Chicago?

    Currently, August is the cheapest month in which you can book a flight from San José del Cabo to Chicago (average of $245). Flying from San José del Cabo to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San José del Cabo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
San José del Cabo to O'Hare Intl flights
San José del Cabo to Midway flights

Top airline flying from San José del Cabo to Chicago

Discover the top airline that operate flights from San José del Cabo to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$420Average$612FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.