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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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$319
(United Airlines)

One-way from

$170
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$362

Good one-way deal

$278 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. 42% potential increase in price ($465 potential increase over avg. RT price).
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Cheapest flight prices on average. 17% potential price decrease ($95 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/9. 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 9/2511:52 amSJD - ORD
Nonstop4h 14mUnited Airlines
Mon 9/298:50 amORD - SJD
Nonstop4h 38mUnited Airlines
Deal found 9/9$319
This United Airlines deal was found by Cheapflights users on 9/9. 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 9/2511:52 amSJD - ORD
Nonstop4h 14mUnited Airlines
Tue 9/307:10 amORD - SJD
1 stop8h 33mUnited Airlines
Deal found 9/9$320
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amSJD - ORD
2 stops14h 14mDelta
Tue 10/75:20 amORD - SJD
2 stops11h 40mDelta
Deal found 9/10$324
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:07 amSJD - ORD
1 stop10h 25mVolaris
Mon 10/61:40 amORD - SJD
1 stop10h 29mVolaris
Deal found 9/10$325
This Aeromexico deal was found by Cheapflights users on 9/10. 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.
Wed 10/18:13 pmSJD - MDW
2 stops23h 23mAeromexico
Tue 10/76:00 amMDW - SJD
2 stops17h 56mAeromexico
Deal found 9/10$326
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:46 pmSJD - ORD
1 stop6h 51mUnited Airlines
Tue 10/77:10 amORD - SJD
1 stop7h 40mUnited Airlines
Deal found 9/10$326
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/301:22 pmSJD - ORD
1 stop8h 37mUnited Airlines
Mon 11/39:30 pmORD - SJD
1 stop18h 12mUnited Airlines
Deal found 9/9$332
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/191:15 pmSJD - MDW
1 stop9h 17mDelta
Mon 1/56:00 amMDW - SJD
1 stop8h 52mDelta
Deal found 9/10$337
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 11/111:53 amSJD - ORD
1 stop10h 22mVolaris
Sat 11/1511:59 pmORD - SJD
1 stop12h 35mVolaris
Deal found 9/11$344
This Flightnetwork deal was found by Cheapflights users on 9/10. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:07 amSJD - ORD
1 stop10h 25mVolaris
Mon 10/61:40 amORD - SJD
1 stop10h 29mVolaris
Deal found 9/10$352
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:55 pmSJD - ORD
1 stop13h 00mViva
Sat 11/18:30 pmORD - SJD
1 stop22h 05mViva
Deal found 9/10$363
This Delta deal was found by Cheapflights users on 9/9. 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 9/1912:35 pmSJD - ORD
1 stop7h 22mDelta
Tue 9/232:45 pmORD - SJD
1 stop9h 15mDelta
Deal found 9/9$366

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 September 11, 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

Thu 9/25

11:52 am-6:06 pm

Nonstop4h 14m

Chicago O'Hare Intl

Mon 9/29

8:50 am-11:28 am

Nonstop4h 38m

$319

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 9/25

11:52 am-6:06 pm

Nonstop4h 14m

Chicago O'Hare Intl

Tue 9/30

7:10 am-1:43 pm

1 stop8h 33m

$320

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 10/1

11:52 am-6:06 pm

Nonstop4h 14m

Chicago O'Hare Intl

Tue 10/7

7:10 am-12:50 pm

1 stop7h 40m

$320

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 10/1

12:30 pm-10:14 pm

1 stop7h 44m

Chicago O'Hare Intl

Tue 10/7

5:20 am-3:00 pm

2 stops11h 40m

$324

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 10/3

12:40 pm-11:54 pm

1 stop9h 14m

Chicago O'Hare Intl

Tue 10/7

5:20 am-3:00 pm

2 stops11h 40m

$324

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 10/3

11:07 am-11:32 pm

1 stop10h 25m

Chicago O'Hare Intl

Tue 10/7

7:25 am-7:54 pm

1 stop14h 29m

$325

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 10/1

8:13 pm-9:36 pm

2 stops23h 23m

Chicago Midway

Tue 10/7

6:00 am-9:56 pm

2 stops17h 56m

$326

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 12/19

1:15 pm-11:32 pm

1 stop9h 17m

Chicago Midway

Mon 1/5

6:00 am-1:52 pm

1 stop8h 52m

$337

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/25

10:40 am-12:05 am

1 stop11h 25m

Chicago Midway

Mon 9/29

7:50 am-12:50 pm

1 stop7h 00m

$379

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 10/1

1:45 pm-11:00 pm

1 stop7h 15m

Chicago Midway

Tue 10/7

5:15 am-10:20 am

1 stop7h 05m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 30 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 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 September 11, 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.

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 September 11, 2025.
Peruse reviews from past customers who have flown with United Airlines from San José del Cabo to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 0 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.

  • How long is the flight from San José del Cabo to Chicago?

    There are many flights that can get you from San José del Cabo to Chicago in 4h 14m. Fly via United Airlines, Aeromexico, or Delta to get the fastest option. San José del Cabo and Chicago are separated by a distance of 1806 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from San José del Cabo to Chicago round-trip?

    Our cheapest airline available from San José del Cabo to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $361 on this airline. United Airlines is priced at 42% lower than the current average price of a flight leaving 3 months from now.

  • 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 Qatar Airways (100%), American Airlines (75%) or Emirates (67%) 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 $160. On average you can expect to pay $278. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $319.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$545FlexibilityNo cancel feeOn-time69%

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