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$169+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
ene. 27 — feb. 31
lun. 1/27
lun. 2/3
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 enero 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$268
(Viva)

One-way from

$169
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$612

Good round-trip deal

$493 or less

Good one-way deal

$307 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. 13% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in January 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 enero 22, 2025.

This Viva deal was found by Cheapflights users on 1/20. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/294:00 pmSJD - ORD
1 stop21h 20mViva
dom. 2/23:50 pmORD - SJD
1 stop18h 35mViva
Deal found 1/20$268
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
jue. 3/133:32 pmSJD - ORD
1 stop17h 33mVolaris
sáb. 3/151:45 amORD - SJD
1 stop8h 05mVolaris
Deal found 1/21$348
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
mié. 1/298:45 pmSJD - ORD
2 stops16h 35mMultiple Airlines
dom. 2/25:40 pmORD - SJD
1 stop16h 45mMultiple Airlines
Deal found 1/20$371
This Kiwi.com deal was found by Cheapflights users on 1/20. 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. 1/283:20 pmSJD - MDW
1 stop16h 25mMultiple Airlines
mar. 2/47:50 pmMDW - SJD
1 stop22h 54mMultiple Airlines
Deal found 1/20$428
This United Airlines deal was found by Cheapflights users on 1/21. 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. 3/1111:49 amSJD - ORD
Nonstop4h 09mUnited Airlines
mar. 3/187:30 amORD - SJD
1 stop8h 02mUnited Airlines
Deal found 1/21$469
This American Airlines deal was found by Cheapflights users on 1/20. 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.
mar. 3/1112:10 pmSJD - ORD
Nonstop4h 15mAmerican Airlines
mar. 3/185:00 amORD - SJD
1 stop9h 38mAmerican Airlines
Deal found 1/20$475
This Mytrip deal was found by Cheapflights users on 1/20. 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.
vie. 1/245:08 pmSJD - MDW
1 stop14h 37mVolaris
mar. 1/287:50 pmMDW - SJD
1 stop12h 41mVolaris
Deal found 1/20$480
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 3/1112:42 pmSJD - MDW
1 stop7h 41mDelta
mar. 3/186:00 amMDW - SJD
2 stops10h 47mDelta
Deal found 1/21$500
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 3/114:30 pmSJD - ORD
2 stops14h 48mDelta
mar. 3/185:45 amORD - SJD
2 stops11h 02mDelta
Deal found 1/21$500
This Aeromexico deal was found by Cheapflights users on 1/20. 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.
mar. 3/116:02 amSJD - ORD
2 stops15h 54mAeromexico
mar. 3/187:05 amORD - SJD
2 stops13h 27mAeromexico
Deal found 1/20$501
This Southwest deal was found by Cheapflights users on 1/22. 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.
vie. 4/111:55 pmSJD - MDW
1 stop7h 40mSouthwest
lun. 4/145:40 amMDW - SJD
1 stop7h 00mSouthwest
Deal found 1/22$551
This Alaska Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 2/37:59 pmSJD - ORD
2 stops21h 00mAlaska Airlines
lun. 2/107:45 amORD - SJD
1 stop10h 17mAlaska Airlines
Deal found 1/21$560

Find flights from San José del Cabo to Chicago within your budget

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 enero 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

sáb. 3/1

4:30 pm-2:25 pm

1 stop20h 55m

Chicago O'Hare Intl

sáb. 3/8

3:55 pm-9:30 am

1 stop18h 35m

$285

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

jue. 3/13

3:32 pm-11:05 am

1 stop17h 33m

Chicago O'Hare Intl

sáb. 3/15

1:45 am-7:50 am

1 stop8h 05m

$348

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

dom. 5/25

9:15 am-5:00 pm

1 stop29h 45m

Chicago O'Hare Intl

mar. 6/3

5:05 pm-3:35 pm

2 stops24h 30m

$400

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 3/11

11:49 am-5:58 pm

Nonstop4h 09m

Chicago O'Hare Intl

mar. 3/18

7:30 am-1:32 pm

1 stop8h 02m

$469

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 3/11

12:10 pm-6:25 pm

Nonstop4h 15m

Chicago O'Hare Intl

mar. 3/18

5:00 am-12:38 pm

1 stop9h 38m

$475

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mar. 3/11

12:42 pm-10:23 pm

1 stop7h 41m

Chicago Midway

mar. 3/18

6:00 am-2:47 pm

2 stops10h 47m

$500

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 3/11

4:30 pm-9:18 am

2 stops14h 48m

Chicago O'Hare Intl

mar. 3/18

5:45 am-2:47 pm

2 stops11h 02m

$500

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

mar. 3/11

6:02 am-11:56 pm

2 stops15h 54m

Chicago O'Hare Intl

mar. 3/18

7:05 am-6:32 pm

2 stops13h 27m

$501

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

lun. 2/10

4:10 pm-8:45 am

2 stops15h 35m

Chicago Midway

vie. 2/14

10:41 pm-3:33 pm

3 stops17h 52m

$524

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 3/7

4:10 pm-8:45 am

2 stops15h 35m

Chicago Midway

vie. 3/14

6:34 pm-12:14 pm

2 stops19h 40m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 29 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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 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.

Travel insights for flights from San José del Cabo to Chicago

Get recent, data-driven insights about flights from San José del Cabo to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 enero 22, 2025.

It’s typically best to fly out from San José del Cabo to Chicago at noon. Doing so could potentially save you 45% 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 enero 22, 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 enero 22, 2025.
To help decide which airline to fly from San José del Cabo to Chicago, see what other customers have to say about Volaris, United Airlines and Aeromexico. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,707 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,514 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,848 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,975 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 0 airlines. 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 Viva. Our recent data shows that you can find tickets from as low as $268 on this airline. Additional options worth looking into are Volaris and United Airlines, starting at $348 and $469 round-trip. Viva is priced at 51% 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?

    $169 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 $176 and $180, 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 (89%), Emirates (75%) or United Airlines (75%) 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 $226. On average you can expect to pay $514. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $268.

  • 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 $320). 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

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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
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