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Cabo San Lucas

$111+ Cheap flights from Chicago (CHI) to Cabo San Lucas, Mexico

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Cabo San Lucas are usually found in September or July, booked 17 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from Chicago to Cabo San Lucas

Keep the following information in mind while searching for Chicago to Cabo San Lucas flight deals. Data was last updated September 15, 2025.

Round-trip from

$424
(Kiwi.com)

One-way from

$111
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$502
From Chicago (CHI) to Cabo San Lucas
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One-way flight from Chicago (CHI) to Cabo San Lucas
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Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Cabo San Lucas

Cheapest flights from Chicago to Cabo San Lucas
Explore the most affordable flight options available from Chicago to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Tue 10/71:55 amORD - SJD
1 stop11h 16mVolaris
Mon 10/1311:07 amSJD - ORD
1 stop16h 35mVolaris
Deal found 9/12$424
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 11/1812:59 pmORD - SJD
1 stop23h 35mMultiple Airlines
Mon 11/247:45 pmSJD - ORD
2 stops42h 25mMultiple Airlines
Deal found 9/14$425
This Delta deal was found by Cheapflights users on 9/12. 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 11/142:57 pmORD - SJD
1 stop8h 33mDelta
Fri 11/219:32 amSJD - ORD
1 stop12h 09mDelta
Deal found 9/12$426
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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.
Sat 10/183:50 pmORD - SJD
2 stops24h 28mAlaska Airlines
Wed 10/2211:45 amSJD - ORD
1 stop10h 14mAlaska Airlines
Deal found 9/13$427
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/1012:25 pmORD - SJD
2 stops22h 05mViva
Wed 10/152:15 pmSJD - ORD
2 stops31h 20mViva
Deal found 9/13$428
This Orbitz deal was found by Cheapflights users on 9/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:25 amORD - SJD
1 stop14h 29mMultiple Airlines
Tue 10/285:40 pmSJD - ORD
2 stops23h 19mMultiple Airlines
Deal found 9/13$429
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Thu 11/205:18 amORD - SJD
1 stop12h 08mAmerican Airlines
Tue 11/2512:34 pmSJD - ORD
Nonstop4h 21mAmerican Airlines
Deal found 9/12$430
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/309:00 amORD - SJD
Nonstop4h 45mAmerican Airlines
Thu 11/61:40 pmSJD - ORD
Nonstop4h 30mAmerican Airlines
Deal found 9/14$431
This Delta deal was found by Cheapflights users on 9/13. 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.
Sun 11/162:57 pmORD - SJD
1 stop18h 45mDelta
Fri 11/286:00 amSJD - ORD
1 stop15h 41mDelta
Deal found 9/13$432
This Aeromexico deal was found by Cheapflights users on 9/13. 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.
Wed 12/316:00 amMDW - SJD
1 stop9h 10mAeromexico
Thu 1/81:40 pmSJD - MDW
1 stop7h 06mAeromexico
Deal found 9/13$432
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 10/67:59 pmORD - SJD
2 stops22h 39mAlaska Airlines
Thu 10/94:02 pmSJD - ORD
1 stop29h 57mAlaska Airlines
Deal found 9/15$433
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Fri 10/31:55 amORD - SJD
1 stop11h 16mMultiple Airlines
Sat 10/115:14 pmSJD - ORD
2 stops28h 21mMultiple Airlines
Deal found 9/13$434

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Cabo San Lucas 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to Cabo San Lucas that are best for you.

Fly from

Chicago

Fly to

Cabo San Lucas

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 10/21

6:00 am-4:12 pm

2 stops12h 12m

San José del Cabo Los Cabos

Tue 10/28

2:42 pm-12:24 am

1 stop31h 42m

$424

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 11/18

2:57 pm-10:30 pm

1 stop8h 33m

San José del Cabo Los Cabos

Mon 11/24

9:32 am-10:41 pm

1 stop12h 09m

$426

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/18

6:00 am-2:00 pm

1 stop9h 00m

San José del Cabo Los Cabos

Thu 1/22

6:00 am-9:46 pm

2 stops14h 46m

$432

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/2

5:25 pm-2:40 pm

2 stops22h 15m

San José del Cabo Los Cabos

Fri 3/6

10:54 am-9:56 am

2 stops22h 02m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 11/10

12:33 am-8:42 am

1 stop9h 09m

San José del Cabo Los Cabos

Tue 11/18

9:32 am-10:41 pm

1 stop12h 09m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 11/27

2:57 pm-10:30 pm

1 stop8h 33m

San José del Cabo Los Cabos

Tue 12/2

9:32 am-10:41 pm

1 stop12h 09m

$436

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 11/12

2:57 pm-10:30 pm

1 stop8h 33m

San José del Cabo Los Cabos

Sun 11/16

10:17 am-10:41 pm

1 stop11h 24m

$436

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 11/17

7:52 pm-12:12 pm

1 stop17h 20m

San José del Cabo Los Cabos

Fri 11/28

6:00 am-10:41 pm

1 stop15h 41m

$436

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 11/17

12:33 am-8:42 am

1 stop9h 09m

San José del Cabo Los Cabos

Tue 11/25

9:32 am-9:53 pm

2 stops11h 21m

$442

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 10/14

5:01 am-1:43 pm

1 stop10h 42m

San José del Cabo Los Cabos

Sat 10/25

1:46 pm-10:37 pm

1 stop6h 51m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 42 results
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Best time to book a flight from Chicago to Cabo San Lucas

Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Chicago 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 Chicago to Cabo San Lucas

How far ahead should I book a flight from Chicago to Cabo San Lucas?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Cabo San Lucas. Price data was last updated on September 12, 2025.

Booking 17 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Cabo San Lucas. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Cabo San Lucas?

Currently, January is the cheapest month in which you can book a flight from Chicago to Cabo San Lucas (average of $437). Flying from Chicago to Cabo San Lucas in March is currently the most expensive (average of $549). 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 CHI to C4B?

Find hourly flight availability from Chicago to Cabo San Lucas. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Chicago to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Chicago to Cabo San Lucas?

Reviews of airlines servicing Cabo San Lucas

Get insights into the airlines that provide service to Cabo San Lucas. 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 Cabo San Lucas. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Cabo San Lucas to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Viva
7.0
Good
787 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.6
Okay
1,154 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Cabo San Lucas. 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 Chicago to Cabo San Lucas?

    A quick flight from Chicago to Cabo San Lucas can take about 8h 33m. Alaska Airlines provides one of the quickest options available for as low as $426. The distance from Chicago to Cabo San Lucas 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 Chicago to Cabo San Lucas one-way?

    One-way options have recently been found by users for as low as $158 on United Airlines. Other airlines that offer cheap prices include Volaris from $162 and Southwest from $163 one-way.

  • What are the most reliable airlines from Chicago to Cabo San Lucas?

    The top 3 most reliable airlines when flying from Chicago to Cabo San Lucas are American Airlines (89%), Emirates (89%) and United Airlines (89%).

  • What are the cheapest flights from Chicago to Cabo San Lucas?

    While on average a flight from Chicago to Cabo San Lucas is generally $832, our data shows the cheapest flight currently is $197. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $318 for that flight.

  • Can I find deals for flights from Chicago to Cabo San Lucas that include hotel bookings?

    Yes. In addition to deals on Chicago to Cabo San Lucas flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Cabo San Lucas?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Cabo San Lucas.

  • Can I find deals for business class flights from Chicago to Cabo San Lucas?

    Yes. Cheapflights offers flight deals from Chicago to Cabo San Lucas 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 Chicago to Cabo San Lucas?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Cabo San Lucas (average of $437). Flying from Chicago to Cabo San Lucas in March is currently the most expensive (average of $549). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from Chicago to Cabo San Lucas

Discover the top 6 airlines that operate flights from Chicago to Cabo San Lucas. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$267Average$376FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$418FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$545FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$436Average$630FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$447Average$661FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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