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$171+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — CHI
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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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 February 4, 2026.

This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:47 pm
SJD
-
ORD
1 stop8h 05m
Volaris
Fri 4/177:35 am
ORD
-
SJD
1 stop13h 29m
Volaris
Deal found 2/2$337
This Booking.com deal was found by Cheapflights users on 2/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:05 pm
SJD
-
ORD
1 stop28h 40m
Viva
Tue 3/171:15 am
ORD
-
SJD
1 stop17h 10m
Viva
Deal found 2/3$358
This Delta deal was found by Cheapflights users on 2/1. 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.
Thu 2/1910:27 am
SJD
-
ORD
1 stop11h 33m
Delta
Mon 2/237:15 am
ORD
-
SJD
1 stop8h 22m
Delta
Deal found 2/1$370
This Delta deal was found by Cheapflights users on 2/1. 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.
Thu 2/199:35 am
SJD
-
MDW
2 stops11h 56m
Delta
Mon 2/236:00 am
MDW
-
SJD
1 stop9h 09m
Delta
Deal found 2/1$376
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:11 pm
SJD
-
ORD
1 stop16h 35m
United Airlines
Mon 2/235:45 am
ORD
-
SJD
1 stop6h 58m
United Airlines
Deal found 2/1$376
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 3/1211:10 am
SJD
-
ORD
Nonstop4h 09m
United Airlines
Wed 3/187:00 am
ORD
-
SJD
1 stop7h 10m
United Airlines
Deal found 2/3$384
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/194:08 pm
SJD
-
ORD
1 stop11h 28m
Volaris
Thu 3/2611:59 pm
ORD
-
SJD
1 stop13h 31m
Volaris
Deal found 2/3$385
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:32 am
SJD
-
ORD
2 stops23h 18m
Multiple Airlines
Thu 3/2611:59 pm
ORD
-
SJD
1 stop13h 31m
Multiple Airlines
Deal found 2/3$395
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:30 am
SJD
-
ORD
2 stops29h 23m
Multiple Airlines
Mon 2/2311:58 pm
ORD
-
SJD
1 stop16h 22m
Multiple Airlines
Deal found 2/1$397
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1312:50 pm
SJD
-
ORD
Nonstop4h 11m
United Airlines
Mon 2/165:45 am
ORD
-
SJD
1 stop6h 58m
United Airlines
Deal found 2/1$411
This Aeromexico deal was found by Cheapflights users on 2/2. 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.
Fri 2/131:45 pm
SJD
-
MDW
1 stop7h 46m
Aeromexico
Mon 2/166:00 am
MDW
-
SJD
1 stop9h 09m
Aeromexico
Deal found 2/2$417
This Delta deal was found by Cheapflights users on 2/3. 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.
Sat 5/212:36 pm
SJD
-
MDW
1 stop7h 52m
Delta
Tue 5/512:53 pm
MDW
-
SJD
2 stops11h 32m
Delta
Deal found 2/3$425

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$337
(Mytrip)

One-way from

$171
(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.
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 February 2026
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 February 4, 2026.
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

Mon 4/13

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Fri 4/17

7:35 am-7:04 pm

1 stop13h 29m

$337

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Sat 5/2

7:47 pm-5:52 am

1 stop8h 05m

Chicago O'Hare Intl

Mon 5/4

2:19 am-11:29 am

1 stop11h 10m

$337

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 3/12

5:30 pm-12:45 am

2 stops29h 15m

Chicago O'Hare Intl

Tue 3/17

1:15 am-4:25 pm

1 stop17h 10m

$358

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

8:07 pm-1:10 pm

1 stop18h 03m

$370

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

10:27 am-11:00 pm

1 stop11h 33m

Chicago O'Hare Intl

Mon 2/23

6:15 am-3:51 pm

2 stops10h 36m

$370

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/19

4:56 pm-9:06 am

2 stops15h 10m

Chicago Midway

Mon 2/23

6:40 pm-8:40 am

2 stops15h 00m

$376

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 3/12

11:10 am-5:19 pm

Nonstop4h 09m

Chicago O'Hare Intl

Wed 3/18

7:00 am-12:10 pm

1 stop7h 10m

$384

San José del CaboChicago

SJD - ORD

SJDORD

San José del Cabo Los Cabos

Thu 2/19

8:30 am-2:53 pm

2 stops29h 23m

Chicago O'Hare Intl

Mon 2/23

11:58 pm-3:20 pm

1 stop16h 22m

$397

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 5/2

12:36 pm-10:28 pm

1 stop7h 52m

Chicago Midway

Tue 5/5

12:53 pm-10:25 pm

2 stops11h 32m

$425

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/19

2:05 pm-12:25 am

1 stop9h 20m

Chicago Midway

Mon 2/23

8:40 pm-11:40 am

2 stops16h 00m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 34 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 February 4, 2026.

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 February 4, 2026.

The most flights from zzKPG to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 February 4, 2026.
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
9,236 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

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
9,236 reviews
United Airlines
7.4
Good
9,236 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Crew

8.1

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?

    Volaris, Viva, and United Airlines can get you from Los Cabos to Chicago in just under 4h 11m. Your travel time can differ by up to 25h 04m. 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 $207 and $235 on American Airlines and United 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 American Airlines (79%), United Airlines (75%) or Emirates (75%) 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 $233. On average you can expect to pay $838. The most popular route, (San José del Cabo Los Cabos - Chicago O'Hare Intl), can usually be booked for $337.

  • 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

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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$361Average$447FlexibilityNo cancel feeOn-time69%

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