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$167+ Cheap flights from Los Cabos 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Los Cabos to Chicago

Keep the following information in mind while searching for Los Cabos to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$321
(United Airlines)

One-way from

$167
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$383
From Los Cabos to Chicago (CHI)
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One-way flight from Los Cabos to Chicago (CHI)
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Highest demand for flights based on searches. 41% potential increase in price ($456 potential increase over avg. RT price).
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Cheapest flight prices on average. 17% potential price decrease ($94 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Los Cabos to Chicago

Cheapest flights from Los Cabos to Chicago
Explore the most affordable flight options available from Los Cabos to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:53 amSJD - ORD
1 stop10h 22mVolaris
Thu 11/66:23 amORD - SJD
1 stop10h 02mVolaris
Deal found 9/15$362
This Booking.com deal was found by Cheapflights users on 9/14. 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 10/3111:53 amSJD - ORD
1 stop10h 22mVolaris
Thu 11/66:23 amORD - SJD
1 stop10h 02mVolaris
Deal found 9/14$373
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:00 pmSJD - ORD
1 stop17h 12mMultiple Airlines
Wed 11/512:55 amORD - SJD
1 stop16h 40mMultiple Airlines
Deal found 9/15$395
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/312:15 pmSJD - ORD
2 stops31h 15mMultiple Airlines
Thu 11/611:59 pmORD - SJD
1 stop15h 57mMultiple Airlines
Deal found 9/14$396
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 9/15$398
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/3012:45 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Thu 11/68:45 pmORD - SJD
1 stop14h 49mAmerican Airlines
Deal found 9/15$401
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/2612:34 pmSJD - ORD
Nonstop4h 21mAmerican Airlines
Sat 11/2910:05 pmORD - SJD
1 stop13h 18mAmerican Airlines
Deal found 9/16$403
This Delta deal was found by Cheapflights users on 9/16. 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 11/269:42 amSJD - MDW
2 stops12h 50mDelta
Sat 11/296:00 amMDW - SJD
1 stop8h 36mDelta
Deal found 9/16$405
This Delta deal was found by Cheapflights users on 9/16. 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 11/269:42 amSJD - ORD
2 stops13h 20mDelta
Sat 11/296:40 amORD - SJD
1 stop7h 56mDelta
Deal found 9/16$405
This Booking.com deal was found by Cheapflights users on 9/14. 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 10/312:40 pmSJD - ORD
1 stop6h 55mViva
Wed 11/512:55 amORD - SJD
1 stop16h 40mViva
Deal found 9/14$422
This Southwest deal was found by Cheapflights users on 9/16. 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 11/2612:35 pmSJD - MDW
1 stop10h 35mSouthwest
Sat 11/295:30 amMDW - SJD
1 stop11h 05mSouthwest
Deal found 9/16$460
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 11/112:47 pmSJD - MDW
1 stop7h 27mDelta
Sat 11/156:00 amMDW - SJD
1 stop8h 36mDelta
Deal found 9/15$494

Cheapflights Fare Finder

 
Customize your flight search to find flights from Los Cabos 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 17, 2025.
Use the filters below to find and compare flights from Los Cabos to Chicago that are best for you.

Fly from

Los Cabos

Fly to

Chicago

Route

Depart

Return

Price

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/30

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Thu 11/6

6:23 am-3:25 pm

1 stop10h 02m

$362

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 10/31

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Thu 11/6

6:23 am-3:25 pm

1 stop10h 02m

$373

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 10/31

2:15 pm-11:30 pm

2 stops31h 15m

Chicago O'Hare Intl

Thu 11/6

11:59 pm-2:56 pm

1 stop15h 57m

$396

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sat 11/1

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Sat 11/15

11:59 pm-11:34 am

1 stop12h 35m

$400

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/30

12:45 pm-7:10 pm

Nonstop4h 25m

Chicago O'Hare Intl

Thu 11/6

8:45 pm-10:34 am

1 stop14h 49m

$401

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 11/26

12:34 pm-5:55 pm

Nonstop4h 21m

Chicago O'Hare Intl

Sat 11/29

10:05 pm-10:23 am

1 stop13h 18m

$403

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 11/26

9:42 am-11:32 pm

2 stops12h 50m

Chicago Midway

Sat 11/29

6:00 am-1:36 pm

1 stop8h 36m

$405

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 11/26

9:42 am-12:02 am

2 stops13h 20m

Chicago O'Hare Intl

Sat 11/29

6:40 am-1:36 pm

1 stop7h 56m

$405

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 10/31

2:40 pm-11:35 pm

1 stop6h 55m

Chicago O'Hare Intl

Wed 11/5

12:55 am-4:35 pm

1 stop16h 40m

$422

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/30

6:00 am-11:58 pm

2 stops15h 58m

Chicago O'Hare Intl

Thu 11/6

8:59 pm-4:20 pm

1 stop20h 21m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 30 results
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Best time to book a flight from Los Cabos to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Los Cabos 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 Los Cabos to Chicago

What is the cheapest time of day to fly from KPG to CHI?

Find hourly flight availability from Los Cabos 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 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Los Cabos to Chicago as you normally would.

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 17, 2025.
Peruse reviews from past customers who have flown with United Airlines from Los Cabos to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,926 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

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
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

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 Los Cabos to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Los Cabos to Chicago?

    Volaris, American Airlines, and Delta can get you from Los Cabos to Chicago in just under 4h 25m. Your travel time can differ by up to 8h 25m. The distance from Los Cabos to Chicago is about 1806 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Los Cabos to Chicago?

    No one likes to see their flight delayed. When booking a flight from Los Cabos to Chicago consider choosing Qatar Airways (100%), American Airlines (88%) or Emirates (67%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Los Cabos to Chicago?

    The cheapest flight price from Los Cabos to Chicago is $160. On average you can expect to pay $313. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $355.

  • Can I find deals for flights from Los Cabos to Chicago that include hotel bookings?

    Yes. In addition to deals on Los Cabos to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Los Cabos to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Los Cabos to Chicago.

  • Can I find deals for business class flights from Los Cabos to Chicago?

    Yes. Cheapflights offers flight deals from Los Cabos 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 Los Cabos to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Los Cabos to Chicago (average of $245). Flying from Los Cabos 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 Los Cabos 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 Los Cabos to Chicago

Discover the top airline that operate flights from Los Cabos 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$540FlexibilityNo cancel feeOn-time69%

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