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$194+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1211:11 am
SJD
-
ORD
2 stops35h 39m
Multiple Airlines
Sat 2/2112:59 pm
ORD
-
SJD
1 stop19h 16m
Multiple Airlines
Deal found 1/25$361
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:47 pm
SJD
-
ORD
1 stop8h 05m
Volaris
Mon 4/137:35 am
ORD
-
SJD
1 stop13h 29m
Volaris
Deal found 1/27$364
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:02 pm
SJD
-
ORD
1 stop9h 45m
Volaris
Sun 6/141:40 am
ORD
-
SJD
1 stop10h 29m
Volaris
Deal found 1/27$374
This Booking.com deal was found by Cheapflights users on 1/25. 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 3/185:05 pm
SJD
-
ORD
1 stop29h 20m
Viva
Sat 3/211:55 am
ORD
-
SJD
1 stop16h 30m
Viva
Deal found 1/25$376
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/1312:50 pm
SJD
-
ORD
Nonstop4h 11m
United Airlines
Mon 2/169:03 am
ORD
-
SJD
Nonstop5h 00m
United Airlines
Deal found 1/26$378
This Gotogate deal was found by Cheapflights users on 1/27. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:11 pm
SJD
-
ORD
1 stop10h 28m
Volaris
Sat 4/112:19 am
ORD
-
SJD
1 stop11h 10m
Volaris
Deal found 1/27$379
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:11 am
SJD
-
ORD
2 stops11h 34m
Multiple Airlines
Tue 3/171:55 am
ORD
-
SJD
1 stop16h 30m
Multiple Airlines
Deal found 1/24$381
This Mytrip deal was found by Cheapflights users on 1/24. 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 3/114:08 pm
SJD
-
ORD
1 stop11h 28m
Volaris
Wed 3/187:23 am
ORD
-
SJD
1 stop9h 57m
Volaris
Deal found 1/24$382
This Cheapflightsfares deal was found by Cheapflights users on 1/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:11 pm
SJD
-
ORD
1 stop9h 18m
Volaris
Sat 2/2111:59 pm
ORD
-
SJD
1 stop12h 31m
Volaris
Deal found 1/25$383
This Aeromexico deal was found by Cheapflights users on 1/24. 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.
Fri 2/131:45 pm
SJD
-
MDW
1 stop7h 46m
Aeromexico
Mon 2/166:00 am
MDW
-
SJD
1 stop9h 09m
Aeromexico
Deal found 1/24$384
This Aeromexico deal was found by Cheapflights users on 1/24. 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.
Fri 2/136:05 am
SJD
-
ORD
2 stops16h 51m
Aeromexico
Mon 2/165:25 am
ORD
-
SJD
1 stop8h 15m
Aeromexico
Deal found 1/24$384
This Expedia deal was found by Cheapflights users on 1/26. 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.
Fri 3/134:08 pm
SJD
-
ORD
1 stop11h 28m
Volaris
Fri 3/2011:59 pm
ORD
-
SJD
1 stop13h 31m
Volaris
Deal found 1/26$390

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$361
(Kiwi.com)

One-way from

$194
(Mytrip)

Popular in

May

Cheapest in

September

Average price

$819

Good round-trip deal

$612 or less

Good one-way deal

$389 or less
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago (CHI) flights.
Search Deals
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 ($446 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 January 2026
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).
Search Deals

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 January 27, 2026.
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

Fri 4/10

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Mon 4/13

7:35 am-7:04 pm

1 stop13h 29m

$364

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 6/11

12:02 pm-11:47 pm

1 stop9h 45m

Chicago O'Hare Intl

Sun 6/14

1:40 am-10:09 am

1 stop10h 29m

$374

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 3/18

5:05 pm-12:25 am

1 stop29h 20m

Chicago O'Hare Intl

Sat 3/21

1:55 am-4:25 pm

1 stop16h 30m

$376

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/12

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Sun 2/22

7:35 am-2:32 pm

1 stop7h 57m

$378

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

6:05 am-11:00 pm

1 stop15h 55m

Chicago O'Hare Intl

Mon 2/16

6:15 am-1:45 pm

1 stop8h 30m

$378

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/12

6:05 am-11:00 pm

1 stop15h 55m

Chicago O'Hare Intl

Sat 2/21

1:11 am-9:41 am

1 stop9h 30m

$378

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/13

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 2/16

7:35 am-2:32 pm

1 stop7h 57m

$378

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 2/16

6:00 am-2:09 pm

1 stop9h 09m

$384

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 4/10

3:05 pm-5:00 am

1 stop11h 55m

Chicago Midway

Sun 4/12

7:45 am-1:40 pm

2 stops7h 55m

$541

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 3/12

5:47 pm-6:34 pm

2 stops22h 47m

Chicago Midway

Thu 3/19

7:54 pm-10:29 pm

2 stops28h 35m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José del Cabo-Chicago flight deals on Cheapflights vs. FlightHub >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 Expedia the most. Expedia 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 January 27, 2026.

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 January 27, 2026.
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
9,205 reviews

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

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
9,205 reviews
United Airlines
7.4
Good
9,205 reviews

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.6

Crew

8.1

Entertainment

7.1

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 2 outbound flights 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 4h 11m. Fly via Volaris, Viva, or United Airlines to get the fastest option. San José del Cabo and Chicago are separated by a distance of 1806 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 43% 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?

    $158 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $207 and $232, 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 American Airlines (87%), Emirates (80%) or United Airlines (78%) 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 $238. On average you can expect to pay $866. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $342.

  • 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
Lansing
Merrillville
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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$447FlexibilityNo cancel feeOn-time69%

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