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Cabo San Lucas

$123+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Cabo San Lucas are usually found in July or September, booked 49 days in advance, depart on a Tuesday or Monday and return on a Tuesday

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 junio 12, 2025.

Round-trip from

$396
(American Airlines)

One-way from

$123
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$590
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. 7% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
lun. 10/610:37 amORD - SJD
1 stop6h 58mAmerican Airlines
vie. 10/1012:25 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 6/11$395
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/67:25 amORD - SJD
1 stop14h 39mVolaris
lun. 10/136:41 pmSJD - ORD
1 stop7h 19mVolaris
Deal found 6/11$397
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
mar. 9/21:55 amORD - SJD
1 stop15h 00mMultiple Airlines
dom. 9/79:00 amSJD - ORD
2 stops12h 50mMultiple Airlines
Deal found 6/12$399
This Delta deal was found by Cheapflights users on 6/10. 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.
mar. 7/156:00 amORD - SJD
2 stops14h 15mDelta
mar. 7/2212:42 pmSJD - ORD
1 stop7h 26mDelta
Deal found 6/10$400
This Delta deal was found by Cheapflights users on 6/10. 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.
lun. 8/186:04 amMDW - SJD
1 stop7h 19mDelta
vie. 8/226:02 amSJD - MDW
2 stops13h 47mDelta
Deal found 6/10$400
This Southwest deal was found by Cheapflights users on 6/11. 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.
lun. 6/305:15 amMDW - SJD
1 stop5h 50mSouthwest
mié. 7/91:15 pmSJD - MDW
1 stop9h 40mSouthwest
Deal found 6/11$430
This Alaska Airlines deal was found by Cheapflights users on 6/9. 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.
sáb. 9/132:07 pmORD - SJD
2 stops22h 29mAlaska Airlines
vie. 9/194:20 pmSJD - ORD
1 stop12h 43mAlaska Airlines
Deal found 6/9$431
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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.
jue. 10/97:59 pmORD - SJD
1 stop16h 36mHawaiian Airlines
vie. 10/174:02 pmSJD - ORD
1 stop29h 57mHawaiian Airlines
Deal found 6/10$449
This Mytrip deal was found by Cheapflights users on 6/11. 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.
mié. 6/1812:35 pmORD - SJD
1 stop10h 00mViva
mié. 6/259:15 pmSJD - ORD
1 stop24h 30mViva
Deal found 6/11$462
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
jue. 10/308:39 pmMDW - SJD
1 stop13h 14mMultiple Airlines
dom. 11/28:00 amSJD - MDW
1 stop8h 34mMultiple Airlines
Deal found 6/10$476
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/39:50 pmORD - SJD
1 stop14h 40mUnited Airlines
vie. 8/82:50 pmSJD - ORD
1 stop16h 51mUnited Airlines
Deal found 6/12$490
This Southwest deal was found by Cheapflights users on 6/11. 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.
lun. 6/307:30 amORD - SJD
2 stops8h 55mSouthwest
mié. 7/91:15 pmSJD - ORD
1 stop7h 50mSouthwest
Deal found 6/11$514

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 junio 12, 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

lun. 10/6

10:37 am-3:35 pm

1 stop6h 58m

San José del Cabo Los Cabos

vie. 10/10

12:25 pm-6:50 pm

Nonstop4h 25m

$395

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

lun. 10/6

7:25 am-8:04 pm

1 stop14h 39m

San José del Cabo Los Cabos

lun. 10/13

6:41 pm-4:00 am

1 stop7h 19m

$397

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mar. 9/2

1:55 am-2:55 pm

1 stop15h 00m

San José del Cabo Los Cabos

dom. 9/7

9:00 am-11:50 pm

2 stops12h 50m

$399

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mar. 7/15

6:00 am-6:15 pm

2 stops14h 15m

San José del Cabo Los Cabos

mar. 7/22

12:42 pm-10:08 pm

1 stop7h 26m

$400

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 8/18

6:04 am-11:23 am

1 stop7h 19m

San José del Cabo Los Cabos

vie. 8/22

6:02 am-9:49 pm

2 stops13h 47m

$400

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 6/30

5:15 am-9:05 am

1 stop5h 50m

San José del Cabo Los Cabos

mié. 7/9

1:15 pm-12:55 am

1 stop9h 40m

$430

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 9/13

2:07 pm-10:36 am

2 stops22h 29m

San José del Cabo Los Cabos

vie. 9/19

4:20 pm-7:03 am

1 stop12h 43m

$431

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

jue. 10/9

7:59 pm-10:35 am

1 stop16h 36m

San José del Cabo Los Cabos

vie. 10/17

4:02 pm-11:59 pm

1 stop29h 57m

$449

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

dom. 8/3

9:50 pm-10:30 am

1 stop14h 40m

San José del Cabo Los Cabos

vie. 8/8

2:50 pm-9:41 am

1 stop16h 51m

$490

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 7/5

8:39 pm-2:26 pm

1 stop19h 47m

San José del Cabo Los Cabos

vie. 7/11

8:10 am-7:16 pm

1 stop9h 06m

$500

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 27 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 June 9, 2025.

Booking 49 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 junio 12, 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.

Weekly flight availability from Chicago to Cabo San Lucas

Explore weekly flight availability from Chicago to Cabo San Lucas. 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 junio 12, 2025.

The most flights from CHI to C4B 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 Cabo San Lucas by month

Plan your trip to Cabo San Lucas by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Cabo San Lucas ranges from 0.0 - 4.5 inches per month. September is typically the wettest month, when rainfall can reach 4.5 in. March is typically the driest time to visit Cabo San Lucas when rainfall is around 0.0 in.

Temperature in Cabo San Lucas by month

Plan your trip to Cabo San Lucas by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Cabo San Lucas, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 66.2 F).

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 junio 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Chicago to Cabo San Lucas by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Aeromexico
7.5
Good
1,706 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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.

  • 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 $123 on Viva. Other airlines that offer cheap prices include Volaris from $150 and Delta 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 (90%), Emirates (79%) and United Airlines (79%).

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

    While on average a flight from Chicago to Cabo San Lucas is generally $1,231, our data shows the cheapest flight currently is $148. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $317 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 7 airlines flying from Chicago to Cabo San Lucas

Discover the top 7 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$379FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$413FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$597FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$426Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$454Average$642FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$460Average$683FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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