HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$169+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Jun 22 — Jun 291
Sun 6/22
Sun 6/29
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

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

Round-trip from

$351
(American Airlines)

One-way from

$169
(Trip.com)

Popular in

May

Cheapest in

September

Average price

$530
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. 27% potential increase in price ($249 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($84 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 17, 2025.

This American Airlines deal was found by Cheapflights users on 6/16. 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 7/912:45 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Wed 7/169:05 amORD - SJD
Nonstop4h 40mAmerican Airlines
Deal found 6/16$351
This Delta deal was found by Cheapflights users on 6/16. 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 7/912:42 pmSJD - ORD
1 stop7h 26mDelta
Wed 7/166:00 amORD - SJD
2 stops15h 13mDelta
Deal found 6/16$355
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/911:52 amSJD - ORD
Nonstop4h 14mUnited Airlines
Tue 10/145:01 amORD - SJD
1 stop10h 42mUnited Airlines
Deal found 6/16$356
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 9/196:00 amSJD - MDW
2 stops13h 44mDelta
Mon 9/226:00 amMDW - SJD
2 stops15h 07mDelta
Deal found 6/16$370
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:17 pmSJD - ORD
3 stops25h 15mMultiple Airlines
Sun 9/212:00 amORD - SJD
1 stop14h 00mMultiple Airlines
Deal found 6/16$402
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2411:15 amSJD - MDW
1 stop9h 35mSouthwest
Mon 7/285:15 amMDW - SJD
1 stop5h 35mSouthwest
Deal found 6/15$408
This Booking.com deal was found by Cheapflights users on 6/17. 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 6/2811:53 amSJD - ORD
1 stop10h 22mVolaris
Mon 6/301:55 amORD - SJD
1 stop11h 16mVolaris
Deal found 6/17$440
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:38 amSJD - ORD
2 stops16h 23mAlaska Airlines
Tue 10/147:59 pmORD - SJD
1 stop16h 36mAlaska Airlines
Deal found 6/15$442
This Hawaiian Airlines deal was found by Cheapflights users on 6/15. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:45 amSJD - ORD
1 stop10h 14mHawaiian Airlines
Sun 10/198:20 amORD - SJD
1 stop9h 05mHawaiian Airlines
Deal found 6/15$475
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 6/288:41 amSJD - MDW
1 stop8h 35mMultiple Airlines
Tue 7/18:39 pmMDW - SJD
1 stop20h 16mMultiple Airlines
Deal found 6/17$477
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/110:05 amSJD - ORD
2 stops9h 25mSouthwest
Wed 7/97:00 amORD - SJD
1 stop7h 20mSouthwest
Deal found 6/15$485
This Aeromexico deal was found by Cheapflights users on 6/15. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:13 pmSJD - ORD
2 stops15h 29mAeromexico
Mon 12/297:05 amORD - SJD
1 stop7h 47mAeromexico
Deal found 6/15$535

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 June 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

Wed 7/9

12:45 pm-7:10 pm

Nonstop4h 25m

Chicago O'Hare Intl

Wed 7/16

9:05 am-11:45 am

Nonstop4h 40m

$351

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/9

12:42 pm-10:08 pm

1 stop7h 26m

Chicago O'Hare Intl

Wed 7/16

6:00 am-7:13 pm

2 stops15h 13m

$355

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/9

11:52 am-6:06 pm

Nonstop4h 14m

Chicago O'Hare Intl

Tue 10/14

5:01 am-1:43 pm

1 stop10h 42m

$356

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 9/19

6:00 am-9:44 pm

2 stops13h 44m

Chicago Midway

Mon 9/22

6:00 am-7:07 pm

2 stops15h 07m

$370

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Fri 9/19

8:17 pm-11:32 pm

3 stops25h 15m

Chicago O'Hare Intl

Sun 9/21

2:00 am-2:00 pm

1 stop14h 00m

$402

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 7/24

11:15 am-10:50 pm

1 stop9h 35m

Chicago Midway

Mon 7/28

5:15 am-8:50 am

1 stop5h 35m

$408

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sat 6/28

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Mon 6/30

1:55 am-11:11 am

1 stop11h 16m

$440

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 10/9

10:38 am-5:01 am

2 stops16h 23m

Chicago O'Hare Intl

Tue 10/14

7:59 pm-10:35 am

1 stop16h 36m

$442

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 10/14

11:45 am-11:59 pm

1 stop10h 14m

Chicago O'Hare Intl

Sun 10/19

8:20 am-3:25 pm

1 stop9h 05m

$475

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 6/28

8:41 am-7:16 pm

1 stop8h 35m

Chicago Midway

Tue 7/1

8:39 pm-2:55 pm

1 stop20h 16m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 31 results
1
2
3
4

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 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.

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 June 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.

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 June 17, 2025.

The most flights from zzKPG to CHI are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, 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 June 17, 2025.
Read through reviews of airlines operating flights from Los Cabos to Chicago, such as Alaska Airlines, Southwest and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,504 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,712 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 $169. Users have also found prices from $195 and $216 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 Emirates (96%), United Airlines (96%) or American Airlines (79%) 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 $235. On average you can expect to pay $381. 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 Los Cabos?

Book flights to Los Cabos if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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 June 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$420Average$612FlexibilityNo 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.