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$162+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$336
(Delta)

One-way from

$162
(Trip.com)

Popular in

May

Cheapest in

September

Average price

$530

Good round-trip deal

$446 or less

Good one-way deal

$284 or less
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. 27% potential increase in price ($249 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($84 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from San José del Cabo Los Cabos to Chicago (CHI).
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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 junio 12, 2025.

This Delta deal was found by Cheapflights users on 6/11. 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.
jue. 10/96:01 amSJD - MDW
2 stops13h 43mDelta
mar. 10/146:00 amMDW - SJD
1 stop7h 30mDelta
Deal found 6/11$336
This Delta deal was found by Cheapflights users on 6/12. 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.
jue. 10/96:01 amSJD - ORD
2 stops15h 52mDelta
mar. 10/146:00 amORD - SJD
2 stops14h 01mDelta
Deal found 6/12$336
This American Airlines deal was found by Cheapflights users on 6/11. 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.
mié. 7/912:45 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
mié. 7/169:05 amORD - SJD
Nonstop4h 40mAmerican Airlines
Deal found 6/11$351
This United Airlines deal was found by Cheapflights users on 6/11. 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.
mar. 7/12:50 pmSJD - ORD
1 stop7h 40mUnited Airlines
lun. 8/49:32 pmORD - SJD
1 stop16h 38mUnited Airlines
Deal found 6/11$356
This Mytrip deal was found by Cheapflights users on 6/11. 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.
mar. 6/2411:53 amSJD - ORD
1 stop10h 22mMultiple Airlines
mar. 7/112:25 pmORD - SJD
1 stop10h 10mMultiple Airlines
Deal found 6/11$378
This Southwest deal was found by Cheapflights users on 6/12. 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.
jue. 7/101:05 pmSJD - MDW
1 stop7h 45mSouthwest
mié. 7/165:55 amMDW - SJD
1 stop7h 05mSouthwest
Deal found 6/12$408
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
jue. 7/101:27 pmSJD - ORD
2 stops14h 13mAlaska Airlines
mié. 7/306:00 amORD - SJD
1 stop32h 17mAlaska Airlines
Deal found 6/11$427
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
mar. 6/249:00 amSJD - ORD
2 stops12h 45mViva
mar. 7/112:25 pmORD - SJD
1 stop10h 10mViva
Deal found 6/11$463
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
mié. 7/232:57 pmSJD - ORD
1 stop7h 18mVolaris
mar. 7/291:55 amORD - SJD
1 stop11h 16mVolaris
Deal found 6/11$507
This Aeromexico deal was found by Cheapflights users on 6/11. 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.
vie. 7/46:01 amSJD - ORD
2 stops13h 23mAeromexico
mié. 7/99:50 amORD - SJD
2 stops14h 10mAeromexico
Deal found 6/11$563
This Aeromexico deal was found by Cheapflights users on 6/10. 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.
jue. 7/1012:27 pmSJD - MDW
1 stop25h 10mAeromexico
mié. 7/306:00 amMDW - SJD
1 stop7h 22mAeromexico
Deal found 6/10$566

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 junio 12, 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 - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 10/9

6:01 am-9:44 pm

2 stops13h 43m

Chicago Midway

mar. 10/14

6:00 am-11:30 am

1 stop7h 30m

$336

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

jue. 10/9

6:01 am-11:53 pm

2 stops15h 52m

Chicago O'Hare Intl

mar. 10/14

6:00 am-6:01 pm

2 stops14h 01m

$336

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mié. 7/9

12:45 pm-7:10 pm

Nonstop4h 25m

Chicago O'Hare Intl

mié. 7/16

9:05 am-11:45 am

Nonstop4h 40m

$351

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 7/1

2:50 pm-12:30 am

1 stop7h 40m

Chicago O'Hare Intl

lun. 8/4

9:32 pm-12:10 pm

1 stop16h 38m

$356

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 6/24

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

mar. 7/1

12:25 pm-8:35 pm

1 stop10h 10m

$378

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 7/10

1:05 pm-10:50 pm

1 stop7h 45m

Chicago Midway

mié. 7/16

5:55 am-11:00 am

1 stop7h 05m

$408

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

jue. 7/10

1:27 pm-5:40 am

2 stops14h 13m

Chicago O'Hare Intl

mié. 7/30

6:00 am-12:17 pm

1 stop32h 17m

$427

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 6/24

9:00 am-11:45 pm

2 stops12h 45m

Chicago O'Hare Intl

mar. 7/1

12:25 pm-8:35 pm

1 stop10h 10m

$463

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mié. 7/23

2:57 pm-12:15 am

1 stop7h 18m

Chicago O'Hare Intl

mar. 7/29

1:55 am-11:11 am

1 stop11h 16m

$507

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

vie. 7/4

6:01 am-9:24 pm

2 stops13h 23m

Chicago O'Hare Intl

mié. 7/9

9:50 am-10:00 pm

2 stops14h 10m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 26 results
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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 junio 12, 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 junio 12, 2025.

The most flights from SJD to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 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 junio 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,706 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Delta. Our recent data shows that you can find tickets from as low as $336 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $351 and $356 round-trip. Delta is priced at 49% 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?

    $162 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 Delta, with prices starting from $188 and $205, 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 (97%), United Airlines (97%) or American Airlines (89%) 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 $235. On average you can expect to pay $413. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $336.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$420Average$612FlexibilityNo cancel feeOn-time69%

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