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$172+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$332
(American Airlines)

One-way from

$166
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$425
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 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. 40% potential increase in price ($445 potential increase over avg. RT price).
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Cheapest flight prices on average. 16% potential price decrease ($93 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 2, 2025.

This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 11/136:00 amSJD - ORD
1 stop15h 41mDelta
Sun 11/166:00 amORD - SJD
2 stops13h 15mDelta
Deal found 11/2$356
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 11/131:15 pmSJD - MDW
1 stop9h 25mDelta
Sun 11/166:00 amMDW - SJD
1 stop7h 10mDelta
Deal found 11/2$362
This United Airlines deal was found by Cheapflights users on 11/2. 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 11/133:46 pmSJD - ORD
1 stop28h 12mUnited Airlines
Sun 11/169:05 amORD - SJD
Nonstop4h 58mUnited Airlines
Deal found 11/2$362
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 11/136:00 amSJD - ORD
1 stop15h 41mDelta
Mon 11/175:23 amORD - SJD
1 stop7h 47mDelta
Deal found 11/2$377
This Delta deal was found by Cheapflights users on 11/2. 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.
Thu 11/131:15 pmSJD - MDW
1 stop9h 25mDelta
Mon 11/176:00 amMDW - SJD
1 stop7h 10mDelta
Deal found 11/2$382
This Delta deal was found by Cheapflights users on 11/1. 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 stop7h 10mDelta
Deal found 11/1$412
This Delta deal was found by Cheapflights users on 11/1. 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 11/112:32 pmSJD - ORD
1 stop7h 11mDelta
Sat 11/155:23 amORD - SJD
2 stops11h 07mDelta
Deal found 11/1$412
This United Airlines deal was found by Cheapflights users on 11/2. 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 11/1312:50 pmSJD - ORD
Nonstop4h 13mUnited Airlines
Mon 11/179:05 amORD - SJD
Nonstop4h 58mUnited Airlines
Deal found 11/2$424
This Aeromexico deal was found by Cheapflights users on 11/2. 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.
Thu 11/136:00 amSJD - ORD
2 stops17h 01mAeromexico
Mon 11/175:23 amORD - SJD
1 stop7h 47mAeromexico
Deal found 11/2$439
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Mon 12/2911:44 amSJD - ORD
1 stop11h 15mHawaiian Airlines
Fri 1/28:39 amORD - SJD
1 stop8h 21mHawaiian Airlines
Deal found 11/2$441
This United Airlines deal was found by Cheapflights users on 11/2. 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 12/2912:10 pmSJD - ORD
Nonstop4h 09mUnited Airlines
Fri 1/29:23 pmORD - SJD
1 stop15h 20mUnited Airlines
Deal found 11/2$443
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 12/291:52 pmSJD - MDW
1 stop7h 30mDelta
Fri 1/26:00 amMDW - SJD
1 stop9h 10mDelta
Deal found 11/1$447

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 November 2, 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 11/13

6:00 am-10:41 pm

1 stop15h 41m

Chicago O'Hare Intl

Sun 11/16

6:00 am-6:15 pm

2 stops13h 15m

$356

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 11/13

3:46 pm-8:58 pm

1 stop28h 12m

Chicago O'Hare Intl

Sun 11/16

9:05 am-1:03 pm

Nonstop4h 58m

$362

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 11/13

6:00 am-10:41 pm

1 stop15h 41m

Chicago O'Hare Intl

Mon 11/17

5:23 am-12:10 pm

1 stop7h 47m

$377

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 11/13

12:50 pm-6:03 pm

Nonstop4h 13m

Chicago O'Hare Intl

Mon 11/17

9:30 pm-1:10 pm

1 stop16h 40m

$377

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 11/13

1:15 pm-11:40 pm

1 stop9h 25m

Chicago Midway

Mon 11/17

6:00 am-12:10 pm

1 stop7h 10m

$382

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 11/13

6:00 am-12:01 am

2 stops17h 01m

Chicago O'Hare Intl

Mon 11/17

5:23 am-12:10 pm

1 stop7h 47m

$439

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 12/29

11:44 am-11:59 pm

1 stop11h 15m

Chicago O'Hare Intl

Fri 1/2

8:58 pm-12:35 pm

1 stop16h 37m

$441

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 12/29

12:10 pm-5:19 pm

Nonstop4h 09m

Chicago O'Hare Intl

Fri 1/2

9:23 pm-11:43 am

1 stop15h 20m

$443

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 12/29

1:52 pm-10:22 pm

1 stop7h 30m

Chicago Midway

Fri 1/2

6:00 am-2:10 pm

1 stop9h 10m

$447

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Mon 12/29

9:40 am-12:02 am

2 stops13h 22m

Chicago O'Hare Intl

Fri 1/2

6:35 am-3:30 pm

2 stops9h 55m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 32 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 November 2, 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.

Weekly flight availability from Los Cabos to Chicago

Explore weekly flight availability from Los Cabos 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 2, 2025.

The most flights from zzKPG 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).

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 2, 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
8,997 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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?

    Delta and United Airlines can get you from Los Cabos to Chicago in just under 15h 41m. Your travel time can differ by up to 12h 31m. 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 cheapest airlines to fly from Los Cabos to Chicago one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $199. Users have also found prices from $205 and $206 on Delta and Southwest, respectively.

  • 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%), United Airlines (94%) or American Airlines (93%) 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 $207. On average you can expect to pay $488. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $386.

  • 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.

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
Porter
Benton Harbor

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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$527FlexibilityNo cancel feeOn-time69%

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