What are the cheapest airlines flying from Chicago to San José del Cabo round-trip?

Our cheapest airline available from Chicago to San José del Cabo is Delta. Our recent data shows that you can find tickets from as low as $387 on this airline. Additional options worth looking into are Aeromexico and Volaris, starting at $388 and $392 round-trip. Delta is 37% cheaper than the average price of flights available within the next 90 days to this destination.

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

$112 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $168 and $179, respectively.

What is the cheapest day to fly from Chicago to San José del Cabo?

Travelers seeking maximum savings on their Chicago to San José del Cabo flight should consider departing on Saturday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in San José del Cabo 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 San José del Cabo when rainfall is around 0.0 in.

If weather is an important factor for your trip to San José del Cabo, 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 San José del Cabo?

While on average a flight from Chicago to San José del Cabo is generally $421, our data shows the cheapest flight currently is $173. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $313 for that flight.

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

Before booking your flight to San José del Cabo from Chicago, check out the most reliable airlines to get you to your destination on time: Emirates (100%), United Airlines (100%), American Airlines( 89%).

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

American Airlines, Delta and United Airlines are the most popular airlines when flying from Chicago to San José del Cabo.

What is the cheapest day to fly round-trip from Chicago to San José del Cabo?

Leaving on a Monday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 21% on the overall cost on flights from Chicago to San José del Cabo.

How far in advance should I book a flight from Chicago to San José del Cabo?

Find a great deal and save up to 39% by booking at least 50 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to San José del Cabo within the next two weeks, with the cheapest ticket starting at $561.

What is the cheapest month to fly from Chicago to San José del Cabo?

July can be a great time to fly to San José del Cabo from Chicago with a flight ticket averaging about $615. Cheapflights users have found deals in the month of July for as cheap as $348. The most expensive prices can be found in the month of December.

What airport do you fly into for flights to San José del Cabo from Chicago?

If you book a flight to San José del Cabo from Chicago, you will be flying to Los Cabos, which is the city’s only airport. San José del Cabo Los Cabos (SJD) is located 6.6 mi from the center of San José del Cabo. There are 0 flights from Chicago to Los Cabos per day from 6 different airlines.

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

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

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

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

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

Yes. Cheapflights offers flight deals from Chicago to San José del Cabo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$112+ Flights from Chicago to San José del Cabo

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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

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Cheapflights Tip: The best prices from Chicago to San José del Cabo Los Cabos are usually found in July or January, booked 49 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap flight deals from Chicago to San José del Cabo

Round-trip from	$387 (Delta)
One-way from	$112 (Mytrip)
Popular in	December
Cheapest in	July
Average price	$532
Good round-trip deal	$467 or less
Good one-way deal	$197 or less

From Chicago (CHI) to San José del Cabo Los Cabos

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One-way flight from Chicago (CHI) to San José del Cabo Los Cabos

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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 ($21 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Price to beat on a round-trip flight from Chicago (CHI) to San José del Cabo Los Cabos.

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Price to beat on a one-way flight from Chicago (CHI) to San José del Cabo Los Cabos.

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Find flight deals from Chicago to San José del Cabo

Cheapest flights from Chicago to San José del Cabo
Explore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 3, 2025.

sáb. 11/1512:55 amORD - SJD

1 stop7h 30mMultiple Airlines

sáb. 11/2212:11 pmSJD - ORD

1 stop9h 18mMultiple Airlines

Deal found 7/2

$386

dom. 8/177:02 amORD - SJD

1 stop12h 43mDelta

mié. 8/206:10 amSJD - ORD

1 stop15h 48mDelta

Deal found 7/3

$387

sáb. 8/236:00 pmORD - SJD

2 stops29h 50mAeromexico

jue. 8/287:25 pmSJD - ORD

1 stop17h 05mAeromexico

Deal found 7/1

$388

sáb. 11/1511:59 pmORD - SJD

1 stop12h 35mVolaris

mar. 11/183:39 pmSJD - ORD

1 stop11h 58mVolaris

Deal found 7/3

$389

lun. 8/186:04 amMDW - SJD

1 stop7h 19mDelta

vie. 8/226:10 amSJD - MDW

2 stops13h 34mDelta

Deal found 7/1

$400

mar. 9/96:00 amORD - SJD

1 stop7h 25mAmerican Airlines

mar. 9/1611:40 amSJD - ORD

1 stop8h 44mAmerican Airlines

Deal found 7/3

$406

mar. 8/128:39 pmMDW - SJD

1 stop16h 32mMultiple Airlines

vie. 8/157:25 amSJD - MDW

1 stop9h 51mMultiple Airlines

Deal found 7/3

$423

lun. 7/145:15 amMDW - SJD

1 stop5h 35mSouthwest

mié. 7/1611:55 amSJD - MDW

1 stop10h 55mSouthwest

Deal found 7/1

$431

mar. 9/161:01 pmORD - SJD

2 stops23h 35mAlaska Airlines

vie. 9/2611:46 amSJD - ORD

2 stops17h 17mAlaska Airlines

Deal found 7/3

$432

vie. 9/196:00 amMDW - SJD

2 stops18h 30mAeromexico

lun. 9/227:55 pmSJD - MDW

2 stops23h 41mAeromexico

Deal found 7/2

$546

Best flights from Chicago to San José del Cabo
Discover carefully curated flight deals from Chicago to San José del Cabo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated julio 3, 2025.

dom. 8/177:02 amORD - SJD

1 stop12h 43mDelta

mié. 8/206:10 amSJD - ORD

1 stop15h 48mDelta

Deal found 7/3

$387

sáb. 8/236:00 pmORD - SJD

2 stops29h 50mAeromexico

jue. 8/287:25 pmSJD - ORD

1 stop17h 05mAeromexico

Deal found 7/1

$388

sáb. 8/912:25 pmORD - SJD

3 stops29h 10mMultiple Airlines

sáb. 8/1612:54 pmSJD - ORD

3 stops28h 48mMultiple Airlines

Deal found 7/3

$389

vie. 8/151:40 amORD - SJD

1 stop10h 29mVolaris

sáb. 8/2311:53 amSJD - ORD

1 stop10h 22mVolaris

Deal found 7/2

$392

mar. 7/159:05 amORD - SJD

Nonstop4h 40mAmerican Airlines

mar. 7/2212:45 pmSJD - ORD

Nonstop4h 25mAmerican Airlines

Deal found 7/3

$417

lun. 7/145:15 amMDW - SJD

1 stop5h 35mSouthwest

mié. 7/1611:55 amSJD - MDW

1 stop10h 55mSouthwest

Deal found 7/1

$431

sáb. 9/207:15 amORD - SJD

1 stop6h 55mUnited Airlines

vie. 9/2611:52 amSJD - ORD

Nonstop4h 14mUnited Airlines

Deal found 7/1

$436

lun. 8/186:04 amMDW - SJD

1 stop7h 19mDelta

vie. 8/226:10 amSJD - MDW

2 stops13h 34mDelta

Deal found 7/1

$400

mar. 8/128:39 pmMDW - SJD

1 stop16h 32mMultiple Airlines

vie. 8/157:25 amSJD - MDW

1 stop9h 51mMultiple Airlines

Deal found 7/3

$423

vie. 9/196:00 amMDW - SJD

2 stops18h 30mAeromexico

lun. 9/227:55 pmSJD - MDW

2 stops23h 41mAeromexico

Deal found 7/2

$546

Last-minute flights from Chicago to San José del Cabo
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated julio 3, 2025 and is based on user searches.

mar. 7/87:25 amORD - SJD

1 stop14h 29mVolaris

sáb. 7/1212:06 pmSJD - ORD

1 stop10h 04mVolaris

Deal found 7/3

$520

vie. 7/116:00 amORD - SJD

2 stops12h 25mDelta

vie. 7/1812:42 pmSJD - ORD

1 stop7h 26mDelta

Deal found 7/3

$471

vie. 7/1112:43 pmMDW - SJD

2 stops11h 17mDelta

vie. 7/186:01 amSJD - MDW

2 stops13h 41mDelta

Deal found 7/1

$884

sáb. 7/1210:05 pmORD - SJD

1 stop11h 48mAmerican Airlines

mar. 7/1512:45 pmSJD - ORD

Nonstop4h 25mAmerican Airlines

Deal found 6/30

$420

sáb. 7/128:45 amORD - SJD

Nonstop4h 43mUnited Airlines

sáb. 7/1911:52 amSJD - ORD

Nonstop4h 18mUnited Airlines

Deal found 7/3

$497

sáb. 7/125:20 amMDW - SJD

1 stop10h 10mSouthwest

sáb. 7/1911:55 amSJD - MDW

1 stop7h 05mSouthwest

Deal found 7/3

$511

sáb. 7/128:39 pmMDW - SJD

1 stop16h 32mVolaris

sáb. 7/194:50 pmSJD - MDW

2 stops24h 26mVolaris

Deal found 7/3

$881

dom. 7/131:55 amORD - SJD

1 stop12h 45mMultiple Airlines

mar. 7/227:51 pmSJD - ORD

2 stops16h 22mMultiple Airlines

Deal found 6/30

$428

dom. 7/136:00 amORD - SJD

2 stops18h 00mAeromexico

vie. 7/1812:27 pmSJD - ORD

1 stop9h 42mAeromexico

Deal found 6/30

$430

lun. 7/145:15 amMDW - SJD

1 stop5h 35mSouthwest

mié. 7/1611:55 amSJD - MDW

1 stop10h 55mSouthwest

Deal found 7/1

$431

mié. 7/309:05 amORD - SJD

Nonstop4h 40mAmerican Airlines

mié. 8/61:16 pmSJD - ORD

1 stop14h 45mAmerican Airlines

Deal found 7/1

$396

mié. 7/306:00 amMDW - SJD

1 stop7h 22mAeromexico

mié. 8/612:27 pmSJD - MDW

1 stop27h 20mAeromexico

Deal found 7/1

$612

One-way flights from Chicago to San José del Cabo
Search for one-way flight options from Chicago to San José del Cabo. Find affordable one-way fares based on user searches. Data last updated julio 3, 2025.

dom. 9/147:25 amORD - SJD

1 stop14h 29mVolaris

Deal found 7/1

$112

sáb. 8/231:55 amORD - SJD

1 stop15h 00mMultiple Airlines

Deal found 7/2

$130

lun. 9/17:45 amMDW - SJD

2 stops32h 15mMultiple Airlines

Deal found 7/1

$148

vie. 8/1512:35 pmMDW - SJD

1 stop24h 00mFrontier

Deal found 7/3

$168

lun. 8/118:39 pmMDW - SJD

1 stop16h 32mVolaris

Deal found 7/3

$170

mar. 9/236:00 amMDW - SJD

1 stop7h 25mDelta

Deal found 7/3

$179

sáb. 9/2011:00 amMDW - SJD

2 stops26h 30mAeromexico

Deal found 7/2

$185

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

dom. 8/17

7:02 am-5:45 pm

1 stop12h 43m

San José del Cabo Los Cabos

mié. 8/20

6:10 am-11:58 pm

1 stop15h 48m

$387

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 8/23

6:00 pm-9:50 pm

2 stops29h 50m

San José del Cabo Los Cabos

jue. 8/28

7:25 pm-2:30 pm

1 stop17h 05m

$388

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 8/9

12:25 pm-3:35 pm

3 stops29h 10m

San José del Cabo Los Cabos

sáb. 8/16

12:54 pm-7:42 pm

3 stops28h 48m

$389

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

vie. 8/15

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

sáb. 8/23

11:53 am-12:15 am

1 stop10h 22m

$392

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

6:10 am-9:44 pm

2 stops13h 34m

$400

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mar. 7/15

9:05 am-11:45 am

Nonstop4h 40m

San José del Cabo Los Cabos

mar. 7/22

12:45 pm-7:10 pm

Nonstop4h 25m

$417

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 8/12

8:39 pm-11:11 am

1 stop16h 32m

San José del Cabo Los Cabos

vie. 8/15

7:25 am-7:16 pm

1 stop9h 51m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 7/14

5:15 am-8:50 am

1 stop5h 35m

San José del Cabo Los Cabos

mié. 7/16

11:55 am-12:50 am

1 stop10h 55m

$431

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mar. 9/16

1:01 pm-10:36 am

2 stops23h 35m

San José del Cabo Los Cabos

vie. 9/26

11:46 am-7:03 am

2 stops17h 17m

$432

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 9/19

6:00 am-10:30 pm

2 stops18h 30m

San José del Cabo Los Cabos

lun. 9/22

7:55 pm-9:36 pm

2 stops23h 41m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 19 results

Best time to book a flight from Chicago to San José del Cabo

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo 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 San José del Cabo

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

Booking 49 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San José del Cabo. 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 San José del Cabo?

Currently, January is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $437). Flying from Chicago to San José del Cabo 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 SJD?

It’s optimal to fly from Chicago to San José del Cabo in the afternoon. By choosing this option you can save up to 53% on the cost of your flight, compared to a flight in the morning.

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

Reviews of airlines servicing San José del Cabo

Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico from Chicago to San José del Cabo 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

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,270 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,970 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Aeromexico

7.5

Good

1,718 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

United Airlines

7.4

Good

8,845 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,270 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What airport do you fly into for flights to San José del Cabo from Chicago?
If you book a flight to San José del Cabo from Chicago, you will be flying to Los Cabos, which is the city’s only airport. San José del Cabo Los Cabos (SJD) is located 6.6 mi from the center of San José del Cabo. There are 0 flights from Chicago to Los Cabos per day from 6 different airlines.
What are the cheapest airlines flying from Chicago to San José del Cabo round-trip?
Our cheapest airline available from Chicago to San José del Cabo is Delta. Our recent data shows that you can find tickets from as low as $387 on this airline. Additional options worth looking into are Aeromexico and Volaris, starting at $388 and $392 round-trip. Delta is 37% cheaper than the average price of flights available within the next 90 days to this destination.
What are the cheapest airlines to fly from Chicago to San José del Cabo one-way?
$112 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $168 and $179, respectively.
What are the most reliable airlines from Chicago to San José del Cabo?
Before booking your flight to San José del Cabo from Chicago, check out the most reliable airlines to get you to your destination on time: Emirates (100%), United Airlines (100%), American Airlines( 89%).
What are the cheapest flights from Chicago to San José del Cabo?
While on average a flight from Chicago to San José del Cabo is generally $421, our data shows the cheapest flight currently is $173. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $313 for that flight.
Can I find deals for flights from Chicago to San José del Cabo that include hotel bookings?
Yes. In addition to deals on Chicago to San José del Cabo flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to San José del Cabo?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San José del Cabo.
Can I find deals for business class flights from Chicago to San José del Cabo?
Yes. Cheapflights offers flight deals from Chicago to San José del Cabo 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 San José del Cabo?
Currently, January is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $437). Flying from Chicago to San José del Cabo 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

Top 6 airlines flying from Chicago to San José del Cabo

Airline	Cheapest	Average	Flexibility	On-time
Viva	Cheapest$268	Average$343	FlexibilityNo cancel fee	On-timeN/A
Volaris	Cheapest$311	Average$397	FlexibilityNo cancel fee	On-time79%
Delta	Cheapest$356	Average$597	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$447	Average$643	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$461	Average$690	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$543	Average$714	FlexibilityNo cancel fee	On-time63%

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$112+ Cheap flights from Chicago (CHI) to San José del Cabo (SJD)

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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to San José del Cabo with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to San José del Cabo Los Cabos are usually found in July or January, booked 49 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap flight deals from Chicago to San José del Cabo

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Chicago to San José del Cabo

Cheapest flights from Chicago to San José del CaboExplore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 3, 2025.

Explore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 3, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Chicago to San José del Cabo

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San José del Cabo

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San José del Cabo. Price data was last updated on June 27, 2025.

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

What is the cheapest time of day to fly from CHI to SJD?

Find hourly flight availability from Chicago to San José del Cabo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 3, 2025.

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

Reviews of airlines servicing San José del Cabo

Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico from Chicago to San José del Cabo 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 San José del Cabo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to San José del Cabo from Chicago?

What are the cheapest airlines flying from Chicago to San José del Cabo round-trip?

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

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

What are the cheapest flights from Chicago to San José del Cabo?

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

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

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

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

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 San José del Cabo

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chicago to San José del Cabo

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Cheapest flights from Chicago to San José del Cabo
Explore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 3, 2025.