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$170+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$293
(Viva)

One-way from

$170
(Kiwi.com)
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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High demand for flights, 42% potential price rise
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Best time to find cheap flights, 34% potential price drop
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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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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 November 21, 2024.

This Viva deal was found by Cheapflights users on 11/20. 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.
Thu 11/218:40 pmSJD - ORD
1 stop16h 55mViva
Sun 11/241:15 amORD - SJD
1 stop9h 05mViva
Deal found 11/20$303
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Thu 11/2111:22 amSJD - ORD
1 stop12h 40mVolaris
Mon 11/255:40 pmORD - SJD
2 stops18h 02mVolaris
Deal found 11/20$334
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 11/218:40 pmSJD - ORD
1 stop16h 55mMultiple Airlines
Mon 11/255:40 pmORD - SJD
1 stop16h 40mMultiple Airlines
Deal found 11/20$345
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/172:00 pmSJD - ORD
1 stop20h 12mUnited Airlines
Tue 12/3111:20 amORD - SJD
Nonstop4h 53mUnited Airlines
Deal found 11/20$449
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/181:35 pmSJD - MDW
1 stop7h 31mDelta
Tue 12/316:00 amMDW - SJD
1 stop9h 02mDelta
Deal found 11/20$457
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Thu 11/215:08 pmSJD - MDW
1 stop14h 37mVolaris
Mon 11/257:55 pmMDW - SJD
1 stop15h 47mVolaris
Deal found 11/20$458
This Kiwi.com deal was found by Cheapflights users on 11/21. 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.
Sat 11/305:57 pmSJD - MDW
1 stop14h 31mMultiple Airlines
Thu 12/54:27 pmMDW - SJD
2 stops16h 03mMultiple Airlines
Deal found 11/21$514
This American Airlines deal was found by Cheapflights users on 11/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2912:55 pmSJD - ORD
Nonstop4h 20mAmerican Airlines
Thu 1/28:05 amORD - SJD
Nonstop4h 50mAmerican Airlines
Deal found 11/21$578
This Southwest deal was found by Cheapflights users on 11/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2911:50 amSJD - MDW
2 stops11h 30mSouthwest
Thu 1/210:40 pmMDW - SJD
1 stop14h 00mSouthwest
Deal found 11/21$672
This Delta deal was found by Cheapflights users on 11/21. 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.
Fri 11/226:04 amSJD - ORD
2 stops15h 10mDelta
Sun 12/16:17 amORD - SJD
2 stops14h 11mDelta
Deal found 11/21$806
This Aeromexico deal was found by Cheapflights users on 11/21. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/226:04 amSJD - ORD
2 stops16h 55mAeromexico
Sat 11/301:00 amORD - SJD
1 stop21h 35mAeromexico
Deal found 11/21$923
This Aeromexico deal was found by Cheapflights users on 11/21. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/221:35 pmSJD - MDW
1 stop7h 11mAeromexico
Sun 12/112:43 pmMDW - SJD
1 stop24h 47mAeromexico
Deal found 11/21$1,123

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 2,612,795 searches. Data last updated November 21, 2024.

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Fly to

Any airport

Route

Depart

Return

Price

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/14

8:30 am-3:30 pm

1 stop29h 00m

Chicago O'Hare Intl

Wed 5/28

6:35 am-2:50 pm

1 stop10h 15m

$293

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 5/13

3:31 pm-1:05 am

1 stop7h 34m

Chicago O'Hare Intl

Wed 5/28

6:35 am-2:50 pm

1 stop10h 15m

$401

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 12/17

2:00 pm-11:12 am

1 stop20h 12m

Chicago O'Hare Intl

Tue 12/31

11:20 am-3:13 pm

Nonstop4h 53m

$449

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 12/18

1:35 pm-10:06 pm

1 stop7h 31m

Chicago Midway

Tue 12/31

6:00 am-2:02 pm

1 stop9h 02m

$457

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/14

10:54 am-12:29 am

1 stop11h 35m

Chicago O'Hare Intl

Wed 5/28

6:00 am-4:01 pm

2 stops12h 01m

$466

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/14

12:40 pm-6:55 pm

Nonstop4h 15m

Chicago O'Hare Intl

Wed 5/28

8:05 am-10:35 am

Nonstop4h 30m

$503

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 5/13

7:42 am-7:14 pm

1 stop9h 32m

Chicago Midway

Thu 5/29

8:39 pm-7:02 am

1 stop12h 23m

$516

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 5/14

2:20 pm-11:35 pm

1 stop7h 15m

Chicago Midway

Wed 5/28

5:35 am-10:40 am

1 stop7h 05m

$579

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sun 12/29

4:10 pm-4:00 pm

3 stops22h 50m

Chicago O'Hare Intl

Wed 1/1

2:42 am-7:31 am

1 stop29h 49m

$729

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sun 12/29

2:05 pm-11:30 am

2 stops20h 25m

Chicago O'Hare Intl

Thu 1/2

6:15 am-3:35 pm

2 stops10h 20m

$923

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 28 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 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, September is the cheapest month in which you can book a flight from San José del Cabo to Chicago (average of $232). Flying from San José del Cabo to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

It’s typically best to fly out from San José del Cabo to Chicago at noon. Doing so could potentially save you 23% 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 November 21, 2024.

The most flights from SJD to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, 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 November 21, 2024.
To help decide which airline to fly from San José del Cabo to Chicago, see what other customers have to say about American Airlines, Delta and Volaris. 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
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Aeromexico
7.5
Good
2,004 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Viva. Our recent data shows that you can find tickets from as low as $293 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $449 and $457 round-trip. Viva is priced at 47% 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?

    $170 is the cheapest one-way deal found within the past few days, from Viva. You may also be able to find cheap deals on Volaris and Frontier, with prices starting from $174 and $222, 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 (91%), Emirates (90%) or United Airlines (90%) 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 $153. On average you can expect to pay $318. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $293.

  • 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, September is the cheapest month in which you can book a flight from San José del Cabo to Chicago (average of $232). Flying from San José del Cabo to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$410Average$520FlexibilityNo cancel feeOn-time71%
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