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$174+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$443
(American Airlines)

One-way from

$174
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$633

Good one-way deal

$304 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)
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One-way flight from San José del Cabo Los Cabos to Chicago (CHI)
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Highest demand for flights based on searches. 18% potential increase in price ($133 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a one-way flight from San José del Cabo Los Cabos to Chicago (CHI).
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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 April 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Thu 5/13:32 pmSJD - ORD
2 stops23h 28mMultiple Airlines
Mon 5/56:34 pmORD - SJD
2 stops16h 06mMultiple Airlines
Deal found 4/24$361
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Fri 5/28:30 amSJD - ORD
1 stop13h 05mViva
Sat 5/1012:35 pmORD - SJD
1 stop27h 50mViva
Deal found 4/23$378
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 7/912:55 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Wed 7/169:15 amORD - SJD
Nonstop4h 40mAmerican Airlines
Deal found 4/23$443
This Delta deal was found by Cheapflights users on 4/23. 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 7/96:01 amSJD - MDW
2 stops13h 46mDelta
Wed 7/166:00 amMDW - SJD
1 stop7h 30mDelta
Deal found 4/23$446
This Delta deal was found by Cheapflights users on 4/23. 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 5/13:00 pmSJD - ORD
1 stop7h 53mDelta
Sun 5/45:30 amORD - SJD
2 stops13h 57mDelta
Deal found 4/23$446
This United Airlines deal was found by Cheapflights users on 4/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:46 pmSJD - ORD
1 stop8h 29mUnited Airlines
Mon 5/55:15 amORD - SJD
1 stop9h 35mUnited Airlines
Deal found 4/24$448
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/111:53 amSJD - ORD
1 stop10h 22mVolaris
Sun 8/31:55 amORD - SJD
1 stop7h 58mVolaris
Deal found 4/23$486
This Southwest deal was found by Cheapflights users on 4/23. 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 5/11:55 pmSJD - MDW
1 stop7h 40mSouthwest
Sun 5/45:55 amMDW - SJD
1 stop6h 45mSouthwest
Deal found 4/23$497
This Alaska Airlines deal was found by Cheapflights users on 4/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/91:35 pmSJD - ORD
2 stops13h 29mAlaska Airlines
Tue 10/147:55 pmORD - SJD
2 stops19h 57mAlaska Airlines
Deal found 4/23$652
This Aeromexico deal was found by Cheapflights users on 4/23. 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.
Thu 10/912:35 pmSJD - MDW
1 stop27h 23mAeromexico
Tue 10/146:00 amMDW - SJD
1 stop7h 30mAeromexico
Deal found 4/23$777

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 April 24, 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 7/9

12:55 pm-7:20 pm

Nonstop4h 25m

Chicago O'Hare Intl

Wed 7/16

9:15 am-11:55 am

Nonstop4h 40m

$443

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 7/9

6:01 am-9:47 pm

2 stops13h 46m

Chicago Midway

Wed 7/16

6:00 am-11:30 am

1 stop7h 30m

$446

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/9

12:35 pm-11:55 pm

1 stop9h 20m

Chicago O'Hare Intl

Wed 7/16

6:00 am-11:30 am

1 stop7h 30m

$446

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 7/1

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Sun 8/3

1:55 am-7:53 am

1 stop7h 58m

$486

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/9

11:52 am-6:06 pm

Nonstop4h 14m

Chicago O'Hare Intl

Tue 10/14

5:00 am-12:10 pm

1 stop9h 10m

$511

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/9

4:20 pm-11:10 pm

1 stop28h 50m

Chicago O'Hare Intl

Tue 10/14

7:55 pm-1:52 pm

2 stops19h 57m

$583

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 10/9

12:35 pm-5:58 pm

1 stop27h 23m

Chicago Midway

Tue 10/14

6:00 am-11:30 am

1 stop7h 30m

$777

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 6/11

11:53 am-12:15 am

1 stop10h 22m

$174

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/21

9:15 am-11:35 pm

2 stops12h 20m

$195

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sun 6/8

8:10 am-12:15 am

1 stop14h 05m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 23 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on San José del Cabo-Chicago flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 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.

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 April 24, 2025.

It’s typically best to fly out from San José del Cabo to Chicago at noon. Doing so could potentially save you 1% on the flight price compared to flying in the morning, 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 April 24, 2025.

The most flights from SJD to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
To help decide which airline to fly from San José del Cabo to Chicago, see what other customers have to say about Alaska Airlines, Southwest and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Aeromexico
7.5
Good
1,700 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 American Airlines. Our recent data shows that you can find tickets from as low as $443 on this airline. Additional options worth looking into are Delta and Volaris, starting at $446 and $486 round-trip. American Airlines is priced at 23% 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?

    $174 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Viva and American Airlines, with prices starting from $195 and $261, 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 United Airlines (93%), American Airlines (92%) or Emirates (87%) 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 $233. On average you can expect to pay $344. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $313.

  • 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 San José del Cabo?

Book flights to San José del Cabo if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$410Average$685FlexibilityNo cancel feeOn-time69%

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