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Cabo San Lucas

$103+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 33 days in advance, depart on a Tuesday or Monday and return on a Wednesday

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 October 30, 2025.

This Aeromexico deal was found by Cheapflights users on 10/29. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:23 amORD - SJD
1 stop7h 47mAeromexico
Tue 12/26:50 pmSJD - ORD
2 stops20h 52mAeromexico
Deal found 10/29$416
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/16:00 amMDW - SJD
1 stop7h 10mDelta
Sat 12/62:40 pmSJD - MDW
1 stop8h 07mDelta
Deal found 10/29$416
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 amORD - SJD
1 stop8h 32mUnited Airlines
Wed 11/192:11 pmSJD - ORD
1 stop9h 04mUnited Airlines
Deal found 10/28$417
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:00 amORD - SJD
1 stop9h 23mAmerican Airlines
Sat 12/62:02 pmSJD - ORD
1 stop8h 49mAmerican Airlines
Deal found 10/29$418
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/195:25 amMDW - SJD
1 stop7h 45mSouthwest
Wed 12/32:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 10/28$418
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/284:58 pmORD - SJD
1 stop19h 42mMultiple Airlines
Wed 12/33:36 pmSJD - ORD
2 stops29h 39mMultiple Airlines
Deal found 10/27$419
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/28:20 amORD - SJD
3 stops31h 59mMultiple Airlines
Fri 12/54:34 pmSJD - ORD
2 stops17h 45mMultiple Airlines
Deal found 10/28$420
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:03 amORD - SJD
Nonstop5h 00mUnited Airlines
Tue 12/1612:50 pmSJD - ORD
Nonstop4h 11mUnited Airlines
Deal found 10/28$421
This Aeromexico deal was found by Cheapflights users on 10/28. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:23 amORD - SJD
1 stop9h 12mAeromexico
Tue 12/26:50 pmSJD - ORD
2 stops20h 52mAeromexico
Deal found 10/28$423
This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/186:00 amMDW - SJD
1 stop7h 10mDelta
Mon 11/249:32 amSJD - MDW
2 stops13h 08mDelta
Deal found 10/28$423
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:00 amORD - SJD
1 stop7h 43mAmerican Airlines
Mon 11/172:37 pmSJD - ORD
1 stop6h 43mAmerican Airlines
Deal found 10/28$424
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:10 amORD - SJD
Nonstop4h 49mAmerican Airlines
Tue 11/1112:29 pmSJD - ORD
Nonstop4h 21mAmerican Airlines
Deal found 10/29$425

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$415
(Delta)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$576
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
Search Deals
From Chicago (CHI) to Cabo San Lucas
Search Deals
One-way flight from Chicago (CHI) to Cabo San Lucas
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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

MDW - SJD

MDWSJD

Chicago Midway

Wed 11/19

5:25 am-12:10 pm

1 stop7h 45m

San José del Cabo Los Cabos

Wed 12/3

2:05 pm-10:10 pm

1 stop7h 05m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/1

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 12/6

4:50 pm-8:54 am

2 stops15h 04m

$421

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/10

12:49 am-1:51 pm

1 stop14h 02m

San José del Cabo Los Cabos

Sun 2/15

9:40 am-9:56 pm

2 stops11h 16m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 12/14

8:00 am-1:45 pm

1 stop6h 45m

San José del Cabo Los Cabos

Wed 12/24

2:40 pm-5:05 am

2 stops13h 25m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/18

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

Sun 1/25

1:45 pm-10:26 pm

1 stop7h 41m

$423

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/15

8:59 pm-1:15 pm

1 stop17h 16m

San José del Cabo Los Cabos

Tue 11/18

1:09 pm-11:59 pm

1 stop9h 50m

$427

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 1/22

6:17 pm-8:40 am

2 stops15h 23m

San José del Cabo Los Cabos

Thu 1/29

1:45 pm-10:26 pm

1 stop7h 41m

$435

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 2/21

9:00 am-12:28 pm

1 stop28h 28m

San José del Cabo Los Cabos

Sat 2/28

2:30 pm-1:59 pm

2 stops22h 29m

$444

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 12/10

3:05 pm-11:10 am

2 stops21h 05m

San José del Cabo Los Cabos

Sun 12/14

11:40 am-11:50 pm

1 stop11h 10m

$454

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

9:00 am-1:07 pm

1 stop29h 07m

San José del Cabo Los Cabos

Tue 2/3

1:28 pm-11:37 pm

2 stops33h 09m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 39 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 October 24, 2025.

Booking 33 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 $124). Flying from Chicago to Cabo San Lucas in December is currently the most expensive (average of $404). 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 October 30, 2025.

When flying from Chicago to Cabo San Lucas, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 51% versus a flight in the morning.

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 October 30, 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
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
790 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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
6.7
Okay
1,151 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

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 7h 10m. Southwest provides one of the quickest options available for as low as $421. The distance from Chicago to Cabo San Lucas is about 1804 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 $161 on United Airlines. Other airlines that offer cheap prices include Delta from $165 and Southwest from $165 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 United Airlines (91%), American Airlines (90%) and Emirates (82%).

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

    While on average a flight from Chicago to Cabo San Lucas is generally $781, our data shows the cheapest flight currently is $210. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $321 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 $124). Flying from Chicago to Cabo San Lucas in December is currently the most expensive (average of $404). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$267Average$383FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$279Average$398FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$500FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$421Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$448Average$664FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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