How long is the flight from Chicago to Cabo San Lucas?

A quick flight from Chicago to Cabo San Lucas can take about 8h 40m. Alaska Airlines provides one of the quickest options available for as low as $490. 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 $88 on Viva. Other airlines that offer cheap prices include Volaris from $158 and American Airlines from $178 one-way.

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.

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).

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

While on average a flight from Chicago to Cabo San Lucas is generally $865, our data shows the cheapest flight currently is $162. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $307 for that flight.

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%), Emirates (82%) and American Airlines (54%).

What are the most popular airlines that fly from Chicago to Cabo San Lucas?

American Airlines, United Airlines and Volaris are the most popular airlines when flying from Chicago to Cabo San Lucas.

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.

$100+ Flights from Chicago to Cabo San Lucas

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

Airfare is below average for this route at the moment. Chicago to Cabo San Lucas flights typically cost between $566 and $968 in February. The cheapest round-trip price found within the last 3 days was $377 on Viva (Feb 8-Feb 13).

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Chicago to Cabo San Lucas with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Cabo San Lucas are usually found in September or July, booked 2 days in advance, depart on a Monday or Tuesday and return on a Thursday

Cheap 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 December 18, 2025.

Wed 12/179:03 amORD - SJD

Nonstop5h 00mUnited Airlines

Tue 12/2312:10 pmSJD - ORD

Nonstop4h 09mUnited Airlines

Deal found 12/16

$474

Wed 12/175:30 amORD - SJD

1 stop7h 40mDelta

Wed 12/2411:25 amSJD - ORD

1 stop11h 30mDelta

Deal found 12/17

$478

Wed 12/178:59 pmORD - SJD

1 stop16h 36mMultiple Airlines

Mon 12/222:10 pmSJD - ORD

1 stop28h 35mMultiple Airlines

Deal found 12/16

$484

Wed 12/175:30 amORD - SJD

1 stop7h 40mDelta

Tue 12/239:40 amSJD - ORD

2 stops13h 22mDelta

Deal found 12/16

$493

Mon 12/225:49 amORD - SJD

1 stop6h 54mUnited Airlines

Thu 12/252:22 pmSJD - ORD

1 stop7h 50mUnited Airlines

Deal found 12/15

$504

Tue 12/168:59 pmORD - SJD

1 stop16h 40mAlaska Airlines

Sun 12/2111:44 amSJD - ORD

1 stop11h 15mAlaska Airlines

Deal found 12/15

$513

Wed 12/249:09 amORD - SJD

Nonstop5h 00mUnited Airlines

Sat 12/2712:50 pmSJD - ORD

Nonstop4h 11mUnited Airlines

Deal found 12/17

$519

Wed 12/245:30 amORD - SJD

1 stop8h 17mDelta

Wed 12/311:52 pmSJD - ORD

1 stop9h 10mDelta

Deal found 12/17

$522

Tue 12/306:00 amMDW - SJD

1 stop7h 47mAeromexico

Wed 12/311:52 pmSJD - MDW

1 stop7h 30mAeromexico

Deal found 12/16

$522

Wed 12/247:10 amORD - SJD

1 stop7h 00mUnited Airlines

Mon 12/2912:50 pmSJD - ORD

Nonstop4h 11mUnited Airlines

Deal found 12/16

$523

Tue 12/1610:04 amORD - SJD

Nonstop4h 56mAmerican Airlines

Sun 12/2112:30 pmSJD - ORD

Nonstop4h 27mAmerican Airlines

Deal found 12/15

$524

Mon 12/295:21 amORD - SJD

1 stop12h 03mAmerican Airlines

Wed 1/72:21 pmSJD - ORD

1 stop9h 02mAmerican Airlines

Deal found 12/16

$527

Best flights from Chicago to Cabo San Lucas
Discover carefully curated flight deals from Chicago to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Mon 1/269:00 amORD - SJD

2 stops30h 41mAlaska Airlines

Thu 1/2911:42 amSJD - ORD

1 stop10h 55mAlaska Airlines

Deal found 12/17

$429

Sun 3/16:15 amMDW - SJD

1 stop8h 40mSouthwest

Fri 3/61:35 pmSJD - MDW

Nonstop3h 55mSouthwest

Deal found 12/15

$490

Mon 1/266:00 amMDW - SJD

2 stops12h 36mDelta

Fri 1/306:05 amSJD - MDW

2 stops15h 17mDelta

Deal found 12/15

$500

Thu 2/265:29 pmORD - SJD

1 stop20h 56mAlaska Airlines

Sat 2/281:51 pmSJD - ORD

1 stop9h 08mAlaska Airlines

Deal found 12/17

$434

Fri 2/277:00 amORD - SJD

1 stop10h 10mAlaska Airlines

Sat 3/71:51 pmSJD - ORD

1 stop9h 08mAlaska Airlines

Deal found 12/17

$434

Wed 1/216:00 amMDW - SJD

2 stops12h 41mDelta

Tue 1/276:05 amSJD - MDW

2 stops15h 17mDelta

Deal found 12/16

$500

Fri 1/93:44 pmORD - SJD

2 stops23h 46mAlaska Airlines

Fri 1/1611:42 amSJD - ORD

1 stop10h 55mAlaska Airlines

Deal found 12/17

$434

Mon 3/167:20 pmMDW - SJD

1 stop16h 25mDelta

Wed 3/1812:40 pmSJD - MDW

1 stop7h 49mDelta

Deal found 12/15

$500

Fri 2/207:00 amORD - SJD

1 stop10h 10mAlaska Airlines

Wed 2/251:24 pmSJD - ORD

1 stop22h 47mAlaska Airlines

Deal found 12/17

$438

Tue 3/176:35 pmMDW - SJD

2 stops25h 06mDelta

Tue 3/241:50 pmSJD - MDW

1 stop17h 00mDelta

Deal found 12/15

$500

Sat 2/283:07 pmORD - SJD

2 stops21h 04mAlaska Airlines

Sat 3/71:51 pmSJD - ORD

1 stop9h 08mAlaska Airlines

Deal found 12/17

$439

Tue 3/36:00 amMDW - SJD

2 stops12h 37mDelta

Fri 3/66:05 amSJD - MDW

2 stops15h 37mDelta

Deal found 12/17

$500

Fri 1/233:44 pmORD - SJD

2 stops23h 46mAlaska Airlines

Mon 2/211:42 amSJD - ORD

1 stop10h 55mAlaska Airlines

Deal found 12/17

$439

Tue 3/176:35 pmMDW - SJD

2 stops18h 05mDelta

Fri 3/202:30 pmSJD - MDW

2 stops19h 59mDelta

Deal found 12/15

$505

Thu 1/299:00 amORD - SJD

2 stops30h 41mAlaska Airlines

Sun 2/111:42 amSJD - ORD

1 stop10h 55mAlaska Airlines

Deal found 12/17

$439

Wed 3/116:30 amMDW - SJD

2 stops13h 11mDelta

Tue 3/248:40 amSJD - MDW

2 stops11h 49mDelta

Deal found 12/15

$505

Last-minute flights from Chicago to Cabo San Lucas
Discover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated December 18, 2025 and is based on user searches.

Sat 1/37:00 amORD - SJD

1 stop8h 25mFrontier

Sat 1/1012:20 pmSJD - ORD

1 stop9h 16mFrontier

Deal found 12/16

$380

Wed 1/75:05 amMDW - SJD

1 stop9h 35mSouthwest

Wed 1/1412:35 pmSJD - MDW

1 stop7h 40mSouthwest

Deal found 12/16

$480

Fri 1/912:59 pmORD - SJD

1 stop28h 31mMultiple Airlines

Fri 1/167:55 amSJD - ORD

2 stops33h 45mMultiple Airlines

Deal found 12/17

$398

Tue 1/1312:59 pmORD - SJD

1 stop28h 31mMultiple Airlines

Tue 1/202:15 pmSJD - ORD

2 stops47h 34mMultiple Airlines

Deal found 12/16

$400

Mon 1/1912:55 amORD - SJD

1 stop16h 35mViva

Fri 1/237:55 amSJD - ORD

1 stop14h 30mViva

Deal found 12/17

$399

Sat 1/246:25 amMDW - SJD

1 stop8h 44mMultiple Airlines

Sat 1/313:01 pmSJD - MDW

1 stop19h 44mMultiple Airlines

Deal found 12/14

$470

Tue 1/2712:55 amORD - SJD

1 stop16h 35mViva

Sun 2/85:05 pmSJD - ORD

1 stop29h 20mViva

Deal found 12/17

$383

Tue 1/2711:59 pmORD - SJD

1 stop17h 31mMultiple Airlines

Sat 1/316:30 pmSJD - ORD

2 stops28h 20mMultiple Airlines

Deal found 12/17

$391

Wed 1/281:20 amORD - SJD

1 stop7h 35mViva

Mon 2/25:05 pmSJD - ORD

1 stop29h 20mViva

Deal found 12/16

$390

Sat 1/3111:59 pmORD - SJD

1 stop8h 16mMultiple Airlines

Fri 2/69:00 amSJD - ORD

2 stops13h 50mMultiple Airlines

Deal found 12/16

$381

Sat 1/316:03 amORD - SJD

1 stop8h 33mFrontier

Sat 2/73:01 pmSJD - ORD

2 stops17h 09mFrontier

Deal found 12/17

$382

Sat 1/3111:59 pmORD - SJD

1 stop8h 16mMultiple Airlines

Sat 2/711:20 amSJD - ORD

1 stop22h 59mMultiple Airlines

Deal found 12/15

$394

One-way flights from Chicago to Cabo San Lucas
Search for one-way flight options from Chicago to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

Sun 2/81:20 amORD - SJD

1 stop7h 40mViva

Deal found 12/16

$100

Sun 1/181:20 amORD - SJD

1 stop7h 40mViva

Deal found 12/16

$104

Mon 2/26:23 amORD - SJD

1 stop9h 57mVolaris

Deal found 12/16

$107

Tue 1/2711:59 pmORD - SJD

1 stop12h 31mVolaris

Deal found 12/16

$110

Fri 2/201:20 amORD - SJD

1 stop7h 40mViva

Deal found 12/16

$113

Sat 1/101:10 amORD - SJD

1 stop21h 25mViva

Deal found 12/17

$114

Fri 2/271:20 amORD - SJD

1 stop7h 40mViva

Deal found 12/16

$116

Sun 1/111:20 amORD - SJD

1 stop7h 40mViva

Deal found 12/16

$117

Thu 1/226:23 amORD - SJD

1 stop9h 57mVolaris

Deal found 12/16

$123

Sat 2/149:15 amMDW - SJD

3 stops36h 20mMultiple Airlines

Deal found 12/16

$134

Sat 2/146:00 amMDW - SJD

1 stop8h 20mFrontier

Deal found 12/16

$156

Sun 1/188:19 pmMDW - SJD

3 stops44h 01mMultiple Airlines

Deal found 12/16

$175

Find flight deals from Chicago to Cabo San Lucas

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$377 (CheapOair)
One-way from	$100 (Mytrip)
Popular in	March
Cheapest in	September
Average price	$701

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. 8% potential increase in price ($53 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Cabo San Lucas that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 1/26

9:00 am-2:41 pm

2 stops30h 41m

San José del Cabo Los Cabos

Thu 1/29

11:42 am-11:37 pm

1 stop10h 55m

$429

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/26

5:29 pm-1:25 pm

1 stop20h 56m

San José del Cabo Los Cabos

Sat 2/28

1:51 pm-11:59 pm

1 stop9h 08m

$434

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/27

7:00 am-4:10 pm

1 stop10h 10m

San José del Cabo Los Cabos

Sat 3/7

1:51 pm-11:59 pm

1 stop9h 08m

$434

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/9

3:44 pm-2:30 pm

2 stops23h 46m

San José del Cabo Los Cabos

Fri 1/16

11:42 am-11:37 pm

1 stop10h 55m

$434

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/20

7:00 am-4:10 pm

1 stop10h 10m

San José del Cabo Los Cabos

Wed 2/25

1:24 pm-1:11 pm

1 stop22h 47m

$438

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 2/28

3:07 pm-11:11 am

2 stops21h 04m

San José del Cabo Los Cabos

Sat 3/7

1:51 pm-11:59 pm

1 stop9h 08m

$439

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/23

3:44 pm-2:30 pm

2 stops23h 46m

San José del Cabo Los Cabos

Mon 2/2

11:42 am-11:37 pm

1 stop10h 55m

$439

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 1/29

9:00 am-2:41 pm

2 stops30h 41m

San José del Cabo Los Cabos

Sun 2/1

11:42 am-11:37 pm

1 stop10h 55m

$439

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

6:15 am-1:55 pm

1 stop8h 40m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$490

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/26

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

Fri 1/30

6:05 am-10:22 pm

2 stops15h 17m

$500

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 37 results

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?

Booking 2 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 October is currently the most expensive (average of $392). 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?

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 47% 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

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

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Southwest

7.9

Good

4,250 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

United Airlines

7.4

Good

9,093 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

American Airlines

7.2

Good

11,055 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Viva

7.0

Good

797 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Volaris

6.6

Okay

1,155 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

How long is the flight from Chicago to Cabo San Lucas?
A quick flight from Chicago to Cabo San Lucas can take about 8h 40m. Alaska Airlines provides one of the quickest options available for as low as $490. 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 $88 on Viva. Other airlines that offer cheap prices include Volaris from $158 and American Airlines from $178 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%), Emirates (82%) and American Airlines (54%).
What are the cheapest flights from Chicago to Cabo San Lucas?
While on average a flight from Chicago to Cabo San Lucas is generally $865, our data shows the cheapest flight currently is $162. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $307 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 October is currently the most expensive (average of $392). 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

Alternative routes for Chicago to Cabo San Lucas

O'Hare Intl to San José del Cabo flights

Midway to San José del Cabo flights

St. Louis to San José del Cabo flights

Moline to San José del Cabo flights

O'Hare Intl to La Paz flights

Midway to La Paz flights

O'Hare Intl to Loreto flights

Quincy to San José del Cabo flights

Top 6 airlines flying from Chicago to Cabo San Lucas

Airline	Cheapest	Average	Flexibility	On-time
Viva	Cheapest$263	Average$368	FlexibilityNo cancel fee	On-timeN/A
Volaris	Cheapest$279	Average$392	FlexibilityNo cancel fee	On-time79%
Delta	Cheapest$356	Average$543	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$416	Average$609	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$419	Average$660	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$485	Average$707	FlexibilityNo cancel fee	On-time63%

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$100+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Cabo San Lucas with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Cabo San Lucas are usually found in September or July, booked 2 days in advance, depart on a Monday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to Cabo San Lucas

Cheapest flights from Chicago to Cabo San LucasExplore 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 December 18, 2025.

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 December 18, 2025.

Find 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 December 18, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Cabo San Lucas that are best for you.

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.

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 December 12, 2025.

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

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 December 18, 2025.

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

Reviews of airlines servicing Cabo San Lucas

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.

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?

What are the cheapest airlines to fly from Chicago to Cabo San Lucas one-way?

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

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

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Cabo San Lucas

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Top 6 airlines flying from Chicago to Cabo San Lucas

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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 December 18, 2025.