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$161+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$368
(Trip.com)

One-way from

$161
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$958

Good one-way deal

$318 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 ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1811:53 amSJD - ORD
1 stop10h 22mVolaris
Sun 6/227:25 amORD - SJD
1 stop14h 39mVolaris
Deal found 3/30$368
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/189:00 amSJD - ORD
2 stops12h 45mMultiple Airlines
Sun 6/227:25 amORD - SJD
1 stop14h 39mMultiple Airlines
Deal found 3/30$405
This Delta deal was found by Cheapflights users on 3/31. 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 7/91:42 pmSJD - ORD
1 stop8h 33mDelta
Wed 7/1610:35 amORD - SJD
2 stops13h 25mDelta
Deal found 3/31$440
This American Airlines deal was found by Cheapflights users on 3/31. 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 7/165:00 amORD - SJD
1 stop10h 30mAmerican Airlines
Deal found 3/31$444
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Mon 4/72:50 pmSJD - ORD
1 stop7h 02mUnited Airlines
Mon 4/149:50 pmORD - SJD
1 stop14h 40mUnited Airlines
Deal found 3/31$445
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Mon 4/78:30 amSJD - MDW
2 stops27h 18mMultiple Airlines
Tue 4/158:50 pmMDW - SJD
1 stop16h 30mMultiple Airlines
Deal found 3/31$473
This Aeromexico deal was found by Cheapflights users on 3/31. 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.
Mon 4/712:26 pmSJD - ORD
1 stop9h 33mAeromexico
Mon 4/141:59 amORD - SJD
1 stop8h 25mAeromexico
Deal found 3/31$506
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 6/186:03 amSJD - MDW
2 stops13h 35mDelta
Sun 6/226:00 amMDW - SJD
1 stop7h 30mDelta
Deal found 3/30$550
This Expedia deal was found by Cheapflights users on 3/31. 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 4/712:26 pmSJD - MDW
1 stop7h 55mAeromexico
Tue 4/156:04 amMDW - SJD
1 stop7h 06mAeromexico
Deal found 3/31$604
This Southwest deal was found by Cheapflights users on 3/30. 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.
Wed 6/183:20 pmSJD - MDW
1 stop7h 30mSouthwest
Sun 6/227:35 amMDW - SJD
1 stop7h 50mSouthwest
Deal found 3/30$627
This Alaska Airlines deal was found by Cheapflights users on 3/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/94:15 pmSJD - ORD
1 stop29h 44mAlaska Airlines
Tue 10/149:00 pmORD - SJD
2 stops17h 38mAlaska Airlines
Deal found 3/30$647
This Mytrip deal was found by Cheapflights users on 3/31. 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.
Mon 4/74:15 pmSJD - MDW
2 stops24h 51mVolaris
Tue 4/158:39 pmMDW - SJD
2 stops21h 31mVolaris
Deal found 3/31$852

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 March 31, 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 6/18

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Sun 6/22

7:25 am-8:04 pm

1 stop14h 39m

$368

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 6/18

9:00 am-11:45 pm

2 stops12h 45m

Chicago O'Hare Intl

Sun 6/22

7:25 am-8:04 pm

1 stop14h 39m

$405

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/9

1:42 pm-12:15 am

1 stop8h 33m

Chicago O'Hare Intl

Wed 7/16

10:35 am-10:00 pm

2 stops13h 25m

$440

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

5:00 am-1:30 pm

1 stop10h 30m

$444

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 6/18

6:03 am-9:38 pm

2 stops13h 35m

Chicago Midway

Sun 6/22

6:00 am-11:30 am

1 stop7h 30m

$550

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 6/18

3:20 pm-12:50 am

1 stop7h 30m

Chicago Midway

Sun 6/22

7:35 am-1:25 pm

1 stop7h 50m

$627

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/7

3:32 pm-12:15 am

1 stop6h 43m

$161

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 5/3

10:45 am-8:33 pm

3 stops31h 48m

$190

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/28

8:30 am-11:35 pm

1 stop13h 05m

$191

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 6/2

7:55 pm-5:00 pm

2 stops19h 05m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 21 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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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 FlightHub the most. FlightHub 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 $323). 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 March 31, 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 March 31, 2025.

The most flights from SJD to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 March 31, 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
9,818 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Aeromexico
7.5
Good
1,700 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 3 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 Volaris. Our recent data shows that you can find tickets from as low as $368 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $440 and $444 round-trip. Volaris is priced at 36% 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?

    $161 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 Frontier, with prices starting from $191 and $240, 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%), Emirates (87%) 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 $239. On average you can expect to pay $432. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $302.

  • 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 $323). 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
New Buffalo
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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$410Average$685FlexibilityNo cancel feeOn-time69%
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