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$172+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/132:22 pmSJD - ORD
1 stop27h 31mUnited Airlines
Thu 11/279:05 amORD - SJD
Nonstop4h 58mUnited Airlines
Deal found 10/28$330
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Thu 11/612:50 pmSJD - ORD
Nonstop4h 13mUnited Airlines
Thu 11/139:08 pmORD - SJD
1 stop15h 35mUnited Airlines
Deal found 10/30$357
This Aeromexico deal was found by Cheapflights users on 10/29. 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.
Sat 11/226:00 amSJD - ORD
2 stops15h 30mAeromexico
Sat 11/295:23 amORD - SJD
1 stop9h 12mAeromexico
Deal found 10/29$385
This Delta deal was found by Cheapflights users on 10/30. 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 11/69:32 amSJD - ORD
1 stop12h 09mDelta
Thu 11/135:23 amORD - SJD
2 stops13h 42mDelta
Deal found 10/30$388
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:15 pmSJD - ORD
1 stop7h 47mMultiple Airlines
Fri 1/28:39 amORD - SJD
1 stop8h 21mMultiple Airlines
Deal found 10/29$404
This OneTravel deal was found by Cheapflights users on 10/29. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:11 pmSJD - ORD
1 stop9h 18mMultiple Airlines
Sat 11/295:23 amORD - SJD
1 stop7h 47mMultiple Airlines
Deal found 10/29$410
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 11/112:47 pmSJD - MDW
1 stop7h 27mDelta
Sat 11/156:00 amMDW - SJD
1 stop7h 10mDelta
Deal found 10/30$414
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 11/12:04 pmSJD - ORD
1 stop7h 54mDelta
Sat 11/156:00 amORD - SJD
2 stops10h 30mDelta
Deal found 10/30$414
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/291:52 pmSJD - MDW
1 stop7h 30mDelta
Fri 1/26:00 amMDW - SJD
1 stop9h 10mDelta
Deal found 10/29$448
This Southwest deal was found by Cheapflights users on 10/30. 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.
Mon 11/101:25 pmSJD - MDW
1 stop11h 05mSouthwest
Sun 11/235:10 amMDW - SJD
1 stop9h 35mSouthwest
Deal found 10/30$844
This Delta deal was found by Cheapflights users on 10/30. 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.
Mon 11/109:32 amSJD - MDW
2 stops13h 08mDelta
Sun 11/236:00 amMDW - SJD
2 stops13h 07mDelta
Deal found 10/30$856

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$330
(United Airlines)

One-way from

$172
(Trip.com)

Popular in

May

Cheapest in

September

Average price

$661

Good round-trip deal

$441 or less

Good one-way deal

$256 or less
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago (CHI) flights.
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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. 40% potential increase in price ($443 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($93 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from San José del Cabo Los Cabos to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San José del Cabo Los Cabos to Chicago (CHI).
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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 October 30, 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

Thu 11/13

2:22 pm-6:53 pm

1 stop27h 31m

Chicago O'Hare Intl

Thu 11/27

9:05 am-1:03 pm

Nonstop4h 58m

$330

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 3/3

12:11 pm-10:29 pm

1 stop9h 18m

Chicago O'Hare Intl

Tue 3/17

7:23 am-3:25 pm

1 stop10h 02m

$337

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sat 11/22

12:11 pm-10:29 pm

1 stop9h 18m

Chicago O'Hare Intl

Sat 11/29

5:23 am-12:10 pm

1 stop7h 47m

$410

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 11/13

12:11 pm-10:29 pm

1 stop9h 18m

Chicago O'Hare Intl

Thu 11/27

6:45 pm-4:12 pm

2 stops46h 27m

$426

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 12/29

11:44 am-11:59 pm

1 stop11h 15m

Chicago O'Hare Intl

Fri 1/2

8:58 pm-12:35 pm

1 stop16h 37m

$440

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 12/29

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Fri 1/2

9:23 pm-11:43 am

1 stop15h 20m

$444

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 12/29

1:52 pm-10:22 pm

1 stop7h 30m

Chicago Midway

Fri 1/2

6:00 am-2:10 pm

1 stop9h 10m

$448

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 12/29

1:52 pm-10:22 pm

1 stop7h 30m

Chicago Midway

Fri 1/2

6:00 am-12:47 pm

1 stop7h 47m

$448

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 2/14

9:40 am-9:46 pm

2 stops11h 06m

Chicago Midway

Tue 2/17

6:00 am-2:00 pm

1 stop9h 00m

$454

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 3/3

9:40 am-9:46 pm

2 stops11h 06m

Chicago Midway

Tue 3/17

6:00 am-1:00 pm

1 stop9h 00m

$519

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 32 results
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Compare providers for flights from San José del Cabo to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San José del Cabo to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San José del Cabo-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San José del Cabo-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from San José del Cabo-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José del Cabo-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San José del Cabo-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San José del Cabo to Chicago as you normally would.

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 October 30, 2025.
Peruse reviews from past customers who have flown with United Airlines 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.
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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.

  • How long is the flight from San José del Cabo to Chicago?

    There are many flights that can get you from San José del Cabo to Chicago in 7h 30m. Fly via United Airlines, Volaris, or Delta to get the fastest option. San José del Cabo and Chicago are separated by a distance of 1804 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from San José del Cabo to Chicago round-trip?

    Our cheapest airline available from San José del Cabo to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $361 on this airline. United Airlines is priced at 44% lower than the current average price of a flight leaving 3 months from now.

  • 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 Qatar Airways (100%), United Airlines (94%) or American Airlines (93%) 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 $207. On average you can expect to pay $488. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $330.

  • 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.

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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$527FlexibilityNo cancel feeOn-time69%

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