HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$192+ 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 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Los Cabos to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 22, 2025.

This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:20 amSJD - ORD
1 stop14h 30mViva
Sat 1/34:30 pmORD - SJD
1 stop16h 30mViva
Deal found 12/21$540
This Air Canada deal was found by Cheapflights users on 12/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/292:10 pmSJD - ORD
1 stop28h 35mAir Canada
Fri 1/28:40 pmORD - SJD
1 stop17h 30mAir Canada
Deal found 12/21$550
This Expedia deal was found by Cheapflights users on 12/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/279:02 amSJD - ORD
1 stop12h 27mMultiple Airlines
Sat 1/33:37 pmORD - SJD
2 stops20h 59mMultiple Airlines
Deal found 12/21$658
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/2912:50 pmSJD - ORD
Nonstop4h 11mUnited Airlines
Fri 1/29:23 pmORD - SJD
1 stop15h 20mUnited Airlines
Deal found 12/21$706
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/299:40 amSJD - MDW
2 stops11h 42mDelta
Fri 1/26:00 amMDW - SJD
1 stop7h 47mDelta
Deal found 12/21$712
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/299:40 amSJD - ORD
2 stops13h 22mDelta
Fri 1/25:30 amORD - SJD
2 stops14h 46mDelta
Deal found 12/21$712
This Mytrip deal was found by Cheapflights users on 12/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2110:05 pmSJD - ORD
1 stop15h 55mViva
Sat 12/274:30 pmORD - SJD
1 stop16h 20mViva
Deal found 12/21$735
This Delta deal was found by Cheapflights users on 12/21. 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.
Sat 12/276:04 amSJD - MDW
2 stops15h 18mDelta
Sat 1/36:00 amMDW - SJD
1 stop9h 10mDelta
Deal found 12/21$807
This Mytrip deal was found by Cheapflights users on 12/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2110:05 pmSJD - ORD
3 stops37h 56mMultiple Airlines
Sat 12/274:30 pmORD - SJD
1 stop16h 20mMultiple Airlines
Deal found 12/21$845
This Southwest deal was found by Cheapflights users on 12/21. 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.
Sat 12/271:25 pmSJD - MDW
Nonstop4h 05mSouthwest
Sat 1/38:10 amMDW - SJD
Nonstop4h 50mSouthwest
Deal found 12/21$855
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Sat 12/2712:30 pmSJD - ORD
Nonstop4h 27mAmerican Airlines
Sat 1/39:57 amORD - SJD
Nonstop4h 53mAmerican Airlines
Deal found 12/21$855
This Delta deal was found by Cheapflights users on 12/21. 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.
Sat 12/276:04 amSJD - ORD
2 stops14h 10mDelta
Sat 1/36:45 amORD - SJD
2 stops12h 41mDelta
Deal found 12/21$862

Find 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 December 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$366
(Booking.com)

One-way from

$192
(Mytrip)

Popular in

May

Cheapest in

September

Average price

$653
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago (CHI) flights.
Search Deals
From Los Cabos to Chicago (CHI)
Search Deals
One-way flight from Los Cabos to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 41% potential increase in price ($450 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($93 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 22, 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

Tue 2/3

5:05 pm-11:25 pm

1 stop29h 20m

Chicago O'Hare Intl

Mon 2/9

12:55 am-4:30 pm

1 stop16h 35m

$366

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 2/23

7:10 am-2:42 pm

1 stop8h 32m

$371

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sat 2/28

12:11 pm-10:29 pm

1 stop9h 18m

Chicago O'Hare Intl

Sat 3/7

6:23 am-3:20 pm

1 stop9h 57m

$371

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

6:05 am-11:00 pm

1 stop15h 55m

Chicago O'Hare Intl

Mon 2/23

5:25 am-10:27 pm

2 stops18h 02m

$371

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 2/3

12:50 pm-6:01 pm

Nonstop4h 11m

Chicago O'Hare Intl

Tue 2/10

7:50 pm-11:43 am

1 stop16h 53m

$372

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/19

6:05 am-10:31 pm

2 stops15h 26m

Chicago Midway

Mon 2/23

6:00 am-5:37 pm

2 stops12h 37m

$377

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 1/12

1:45 pm-10:07 pm

1 stop7h 22m

Chicago Midway

Sat 1/17

5:31 pm-8:40 am

2 stops16h 09m

$424

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 2/3

9:35 am-10:22 pm

2 stops11h 47m

Chicago Midway

Tue 2/10

6:00 am-5:37 pm

2 stops12h 37m

$429

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 2/6

8:30 am-11:50 pm

1 stop14h 20m

$208

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 1/22

12:50 pm-6:01 pm

Nonstop4h 11m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 24 results
1
2
3

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 December 22, 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 December 22, 2025.

The most flights from zzKPG to CHI are scheduled on a Friday (8 on average). You will have fewer flight options on Wednesday, 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 December 22, 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
9,102 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

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
9,102 reviews
United Airlines
7.4
Good
9,102 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

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?

    Viva, United Airlines, and Volaris can get you from Los Cabos to Chicago in just under 4h 11m. Your travel time can differ by up to 25h 09m. 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 Volaris. According to our data, you can fly for as low as $158. Users have also found prices from $178 and $207 on Viva and American Airlines, 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 United Airlines (93%), Emirates (85%) or American Airlines (85%) 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 $212. On average you can expect to pay $493. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $371.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$447FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.