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Cabo San Lucas

$108+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 49 days in advance, depart on a Monday or Tuesday and return on a Saturday

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 July 31, 2025.

Round-trip from

$401
(Mytrip)

One-way from

$109
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$553
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 ($49 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 July 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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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 8/126:40 amMDW - SJD
1 stop8h 10mSouthwest
Fri 8/1510:40 amSJD - MDW
1 stop11h 25mSouthwest
Deal found 7/29$401
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Sun 9/211:55 amORD - SJD
1 stop11h 16mVolaris
Fri 9/268:17 pmSJD - ORD
2 stops25h 15mVolaris
Deal found 7/29$401
This Hawaiian Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 10/2510:00 amORD - SJD
1 stop31h 20mHawaiian Airlines
Tue 10/2812:09 pmSJD - ORD
1 stop9h 50mHawaiian Airlines
Deal found 7/31$403
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 11/611:59 pmORD - SJD
1 stop15h 57mMultiple Airlines
Thu 11/1312:11 pmSJD - ORD
1 stop10h 14mMultiple Airlines
Deal found 7/30$404
This Delta deal was found by Cheapflights users on 7/28. 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 8/316:00 amMDW - SJD
1 stop7h 23mDelta
Thu 9/46:01 amSJD - MDW
2 stops13h 25mDelta
Deal found 7/28$406
This Delta deal was found by Cheapflights users on 7/30. 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 8/315:45 amORD - SJD
1 stop7h 38mDelta
Thu 9/412:28 pmSJD - ORD
1 stop8h 09mDelta
Deal found 7/30$406
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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 11/159:20 amORD - SJD
1 stop28h 55mAlaska Airlines
Tue 11/186:40 pmSJD - ORD
2 stops23h 19mAlaska Airlines
Deal found 7/31$407
This Booking.com deal was found by Cheapflights users on 7/29. 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 8/2812:25 pmORD - SJD
1 stop10h 10mViva
Thu 9/48:30 amSJD - ORD
1 stop13h 20mViva
Deal found 7/29$419
This Aeromexico deal was found by Cheapflights users on 7/31. 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.
Tue 9/95:45 amORD - SJD
2 stops11h 10mAeromexico
Mon 9/153:50 pmSJD - ORD
1 stop18h 12mAeromexico
Deal found 7/31$420
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 8/255:00 amORD - SJD
1 stop8h 13mAmerican Airlines
Sat 8/3010:55 amSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 7/30$436
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/238:50 amORD - SJD
Nonstop4h 38mUnited Airlines
Wed 8/271:12 pmSJD - ORD
1 stop7h 30mUnited Airlines
Deal found 7/30$442
This Aeromexico deal was found by Cheapflights users on 7/31. 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 10/66:00 amMDW - SJD
1 stop7h 41mAeromexico
Thu 10/912:46 pmSJD - MDW
1 stop7h 28mAeromexico
Deal found 7/31$476

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 July 31, 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

Sun 9/21

8:01 pm-3:35 pm

2 stops21h 34m

San José del Cabo Los Cabos

Fri 9/26

12:54 pm-11:32 pm

3 stops32h 38m

$401

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 8/12

6:40 am-12:50 pm

1 stop8h 10m

San José del Cabo Los Cabos

Fri 8/15

10:40 am-12:05 am

1 stop11h 25m

$401

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 9/3

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

Tue 9/9

11:53 am-12:15 am

1 stop10h 22m

$402

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 10/25

10:00 am-3:20 pm

1 stop31h 20m

San José del Cabo Los Cabos

Tue 10/28

12:09 pm-11:59 pm

1 stop9h 50m

$403

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 8/31

5:45 am-11:23 am

1 stop7h 38m

San José del Cabo Los Cabos

Thu 9/4

6:01 am-10:37 pm

2 stops14h 36m

$406

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 8/31

6:00 am-11:23 am

1 stop7h 23m

San José del Cabo Los Cabos

Thu 9/4

6:01 am-9:26 pm

2 stops13h 25m

$406

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 10/18

3:50 pm-10:35 am

1 stop20h 45m

San José del Cabo Los Cabos

Sat 10/25

1:31 pm-11:59 pm

1 stop8h 28m

$413

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 8/28

12:25 pm-8:35 pm

1 stop10h 10m

San José del Cabo Los Cabos

Thu 9/4

8:30 am-11:50 pm

1 stop13h 20m

$419

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 9/9

5:45 am-2:55 pm

2 stops11h 10m

San José del Cabo Los Cabos

Mon 9/15

3:50 pm-12:02 pm

1 stop18h 12m

$420

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 8/25

5:00 am-11:13 am

1 stop8h 13m

San José del Cabo Los Cabos

Sat 8/30

10:55 am-5:20 pm

Nonstop4h 25m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 22 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 July 25, 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 July 31, 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 July 31, 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).

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 July 31, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Aeromexico
7.5
Good
1,721 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 $109 on Volaris. Other airlines that offer cheap prices include Viva from $136 and Aeromexico from $162 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 Emirates (100%), United Airlines (100%) and American Airlines (91%).

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

    While on average a flight from Chicago to Cabo San Lucas is generally $465, 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 $301 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

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$375FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$413FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$576FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$439Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$454Average$678FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$543Average$707FlexibilityNo cancel feeOn-time63%

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