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$160+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(Kiwi.com)

One-way from

$160
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$620
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. 18% potential increase in price ($129 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
Wed 6/49:00 amSJD - ORD
2 stops12h 45mMultiple Airlines
Tue 6/106:34 pmORD - SJD
2 stops15h 51mMultiple Airlines
Deal found 4/4$311
This eDestinos deal was found by Cheapflights users on 4/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/111:53 amSJD - ORD
1 stop10h 22mVolaris
Mon 8/47:25 amORD - SJD
1 stop14h 29mVolaris
Deal found 4/3$366
This Delta deal was found by Cheapflights users on 4/3. 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 4/1012:20 pmSJD - ORD
1 stop9h 37mDelta
Wed 4/165:30 amORD - SJD
2 stops14h 47mDelta
Deal found 4/3$440
This American Airlines deal was found by Cheapflights users on 4/3. 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 7/912:55 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Wed 7/169:01 amORD - SJD
1 stop8h 19mAmerican Airlines
Deal found 4/3$444
This United Airlines deal was found by Cheapflights users on 4/3. 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 7/911:32 amSJD - ORD
1 stop8h 01mUnited Airlines
Wed 7/169:00 pmORD - SJD
1 stop13h 48mUnited Airlines
Deal found 4/3$445
This Delta deal was found by Cheapflights users on 4/3. 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 4/1012:26 pmSJD - MDW
1 stop7h 55mDelta
Wed 4/166:04 amMDW - SJD
2 stops14h 13mDelta
Deal found 4/3$446
This Southwest deal was found by Cheapflights users on 4/4. 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 6/412:30 pmSJD - MDW
1 stop8h 05mSouthwest
Tue 6/106:15 amMDW - SJD
1 stop9h 10mSouthwest
Deal found 4/4$575
This Alaska Airlines deal was found by Cheapflights users on 4/4. 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.
Wed 7/237:51 pmSJD - ORD
2 stops31h 49mAlaska Airlines
Wed 7/306:00 amORD - SJD
2 stops38h 41mAlaska Airlines
Deal found 4/4$617
This Aeromexico deal was found by Cheapflights users on 4/4. 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 10/912:35 pmSJD - MDW
1 stop27h 23mAeromexico
Tue 10/146:00 amMDW - SJD
1 stop7h 30mAeromexico
Deal found 4/4$809
This Kiwi.com deal was found by Cheapflights users on 4/4. 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.
Thu 4/179:15 amSJD - ORD
2 stops12h 20mViva
Sat 4/191:50 amORD - SJD
2 stops18h 15mViva
Deal found 4/4$854

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 April 4, 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 6/4

9:00 am-11:45 pm

2 stops12h 45m

Chicago O'Hare Intl

Tue 6/10

6:34 pm-8:25 am

2 stops15h 51m

$311

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Tue 7/1

11:53 am-12:15 am

1 stop10h 22m

Chicago O'Hare Intl

Mon 8/4

7:25 am-7:54 pm

1 stop14h 29m

$366

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/9

12:55 pm-7:20 pm

Nonstop4h 25m

Chicago O'Hare Intl

Wed 7/16

9:15 am-11:55 am

Nonstop4h 40m

$440

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/9

11:32 am-9:33 pm

1 stop8h 01m

Chicago O'Hare Intl

Wed 7/16

9:00 pm-8:48 am

1 stop13h 48m

$445

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/17

12:15 pm-10:22 pm

1 stop8h 07m

Chicago Midway

Sun 4/20

6:04 am-11:10 am

1 stop7h 06m

$446

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/17

9:15 am-11:59 pm

2 stops12h 44m

Chicago O'Hare Intl

Sun 4/20

7:25 am-1:55 pm

1 stop8h 30m

$446

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 6/4

12:30 pm-10:35 pm

1 stop8h 05m

Chicago Midway

Tue 6/10

6:15 am-1:25 pm

1 stop9h 10m

$575

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 7/23

7:51 pm-5:40 am

2 stops31h 49m

Chicago O'Hare Intl

Wed 7/30

6:00 am-6:41 pm

2 stops38h 41m

$617

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 4/17

9:15 am-11:35 pm

2 stops12h 20m

Chicago O'Hare Intl

Sat 4/19

1:50 am-6:05 pm

2 stops18h 15m

$854

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Wed 5/7

3:32 pm-12:15 am

1 stop6h 43m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 22 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 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 April 4, 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 April 4, 2025.

The most flights from zzKPG to CHI are scheduled on a Friday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 April 4, 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
9,839 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,839 reviews
Alaska Airlines
8.0
Very good
9,839 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,839 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,900 reviews
Alaska Airlines
8.0
Very good
9,839 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Aeromexico
7.5
Good
1,701 reviews
Alaska Airlines
8.0
Very good
9,839 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,839 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $160. Users have also found prices from $190 and $218 on Viva and Delta, 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 American Airlines (93%), United Airlines (91%) or Emirates (82%) 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 $239. On average you can expect to pay $406. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $302.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$410Average$685FlexibilityNo cancel feeOn-time69%

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