How long is the flight from Chicago to San José del Cabo?

United Airlines, Alaska Airlines, and Delta can get you from Chicago to San José del Cabo in just under 4h 58m. Your travel time can differ by up to 11h 28m. Airlines will cover a distance of 1806 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 flying from Chicago to San José del Cabo round-trip?

Our cheapest airline available from Chicago to San José del Cabo is Viva. Our recent data shows that you can find tickets from as low as $267 on this airline. Additional options worth looking into are Volaris and Delta, starting at $308 and $356 round-trip. Viva is 56% 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?

$158 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $163 and $163, 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 $832, 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 $315 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: American Airlines (89%), Emirates (89%), United 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 16% 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 1% by booking at least 18 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 $485.

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

September can be a great time to fly to San José del Cabo from Chicago with a flight ticket averaging about $607. Cheapflights users have found deals in the month of September for as cheap as $371. 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.

$111+ Cheap Flights from Chicago to San José del Cabo

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

Airfare is below average for this route at the moment. Chicago to San José del Cabo flights typically cost between $446 and $631 in October. The cheapest round-trip price found within the last 3 days was $423 on Multiple Airlines (Oct 26-Nov 1).

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Find cheap flights from Chicago to San José del Cabo 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 San José del Cabo Los Cabos are usually found in September or July, booked 17 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from Chicago to San José del Cabo

Round-trip from	$423 (Kiwi.com)
One-way from	$111 (Mytrip)
Popular in	December
Cheapest in	September
Average price	$502
Good round-trip deal	$500 or less
Good one-way deal	$219 or less

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

Search Deals

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

Search Deals

Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 2025

Search Deals

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

Search Deals

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 September 14, 2025.

Sun 10/2612:45 pmORD - SJD

1 stop28h 10mMultiple Airlines

Sat 11/111:11 amSJD - ORD

2 stops10h 19mMultiple Airlines

Deal found 9/12

$423

Thu 10/306:45 amORD - SJD

1 stop8h 50mAmerican Airlines

Thu 11/63:41 pmSJD - ORD

1 stop16h 03mAmerican Airlines

Deal found 9/12

$424

Mon 9/291:55 amORD - SJD

1 stop11h 16mMultiple Airlines

Fri 10/38:17 pmSJD - ORD

2 stops25h 18mMultiple Airlines

Deal found 9/12

$425

Tue 11/185:32 amORD - SJD

1 stop7h 40mDelta

Fri 11/286:00 amSJD - ORD

1 stop15h 41mDelta

Deal found 9/12

$426

Fri 10/319:20 amORD - SJD

1 stop8h 00mAlaska Airlines

Wed 11/512:18 pmSJD - ORD

1 stop11h 06mAlaska Airlines

Deal found 9/12

$427

Fri 10/1012:25 pmORD - SJD

2 stops22h 05mViva

Wed 10/152:15 pmSJD - ORD

2 stops31h 20mViva

Deal found 9/13

$428

Thu 10/307:59 pmORD - SJD

1 stop18h 16mHawaiian Airlines

Thu 11/611:40 amSJD - ORD

1 stop11h 19mHawaiian Airlines

Deal found 9/13

$429

Tue 11/185:32 amORD - SJD

1 stop7h 40mDelta

Sun 11/2310:17 amSJD - ORD

1 stop11h 24mDelta

Deal found 9/12

$430

Sun 11/1612:33 amORD - SJD

1 stop18h 37mDelta

Wed 11/266:00 amSJD - ORD

1 stop15h 41mDelta

Deal found 9/13

$432

Wed 12/316:00 amMDW - SJD

1 stop9h 10mAeromexico

Thu 1/81:40 pmSJD - MDW

1 stop7h 06mAeromexico

Deal found 9/13

$432

Mon 10/207:59 pmORD - SJD

2 stops22h 39mAlaska Airlines

Fri 10/2411:45 amSJD - ORD

1 stop25h 05mAlaska Airlines

Deal found 9/13

$433

Fri 10/31:55 amORD - SJD

1 stop11h 16mMultiple Airlines

Sat 10/114:50 pmSJD - ORD

2 stops28h 45mMultiple Airlines

Deal found 9/14

$434

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 September 14, 2025.

Tue 11/189:05 amORD - SJD

Nonstop4h 58mUnited Airlines

Mon 11/2412:50 pmSJD - ORD

Nonstop4h 13mUnited Airlines

Deal found 9/12

$426

Fri 11/149:20 amORD - SJD

1 stop8h 00mAlaska Airlines

Fri 11/212:17 pmSJD - ORD

1 stop8h 15mAlaska Airlines

Deal found 9/11

$427

Sat 11/1512:33 amORD - SJD

1 stop16h 26mDelta

Fri 11/286:00 amSJD - ORD

1 stop15h 41mDelta

Deal found 9/13

$432

Thu 12/47:59 pmORD - SJD

1 stop17h 40mHawaiian Airlines

Wed 12/101:49 pmSJD - ORD

1 stop9h 01mHawaiian Airlines

Deal found 9/14

$449

Fri 11/149:40 pmMDW - SJD

2 stops17h 40mSouthwest

Tue 11/1811:50 amSJD - MDW

1 stop9h 20mSouthwest

Deal found 9/14

$455

Sat 10/186:00 amMDW - SJD

2 stops17h 56mAeromexico

Sat 10/256:00 amSJD - MDW

2 stops14h 14mAeromexico

Deal found 9/13

$583

Tue 10/216:00 amORD - SJD

2 stops12h 12mAlaska Airlines

Tue 10/285:40 pmSJD - ORD

2 stops23h 19mAlaska Airlines

Deal found 9/12

$432

Sun 11/1612:33 amORD - SJD

1 stop18h 37mDelta

Wed 11/266:00 amSJD - ORD

1 stop15h 41mDelta

Deal found 9/13

$432

Sat 11/225:25 amMDW - SJD

1 stop10h 30mSouthwest

Thu 11/2712:15 pmSJD - MDW

1 stop6h 50mSouthwest

Deal found 9/14

$461

Sat 11/156:22 pmORD - SJD

2 stops20h 38mDelta

Sun 11/236:00 amSJD - ORD

1 stop15h 41mDelta

Deal found 9/12

$435

Fri 10/319:20 amORD - SJD

1 stop8h 00mAlaska Airlines

Wed 11/512:18 pmSJD - ORD

1 stop11h 06mAlaska Airlines

Deal found 9/13

$437

Fri 11/142:57 pmORD - SJD

1 stop8h 33mDelta

Fri 11/219:32 amSJD - ORD

1 stop12h 09mDelta

Deal found 9/13

$436

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 September 14, 2025 and is based on user searches.

Sat 9/205:30 amORD - SJD

2 stops18h 30mDelta

Fri 9/262:18 pmSJD - ORD

2 stops16h 22mDelta

Deal found 9/12

$480

Sat 9/202:00 amORD - SJD

1 stop14h 55mViva

Wed 9/247:55 pmSJD - ORD

1 stop13h 00mViva

Deal found 9/11

$488

Sat 9/207:00 amORD - SJD

1 stop7h 50mUnited Airlines

Sat 9/2711:08 amSJD - ORD

Nonstop4h 15mUnited Airlines

Deal found 9/12

$493

Sat 9/207:00 amORD - SJD

1 stop10h 10mMultiple Airlines

Sat 9/274:50 pmSJD - ORD

2 stops29h 00mMultiple Airlines

Deal found 9/12

$505

Sun 9/215:00 amORD - SJD

1 stop9h 10mUnited Airlines

Sat 9/2711:08 amSJD - ORD

Nonstop4h 15mUnited Airlines

Deal found 9/12

$448

Sun 9/212:00 amORD - SJD

1 stop13h 40mViva

Sat 9/278:30 amSJD - ORD

1 stop13h 20mViva

Deal found 9/14

$468

Sun 9/216:30 amORD - SJD

1 stop10h 40mMultiple Airlines

Sat 9/274:50 pmSJD - ORD

2 stops29h 00mMultiple Airlines

Deal found 9/12

$474

Sun 9/216:30 amORD - SJD

1 stop10h 40mMultiple Airlines

Fri 9/262:05 pmSJD - ORD

2 stops31h 45mMultiple Airlines

Deal found 9/12

$491

Sun 9/216:31 amORD - SJD

1 stop13h 29mMultiple Airlines

Wed 9/242:05 pmSJD - ORD

2 stops31h 45mMultiple Airlines

Deal found 9/11

$500

Mon 9/225:00 amORD - SJD

1 stop9h 10mUnited Airlines

Sat 9/271:12 pmSJD - ORD

1 stop8h 47mUnited Airlines

Deal found 9/12

$458

Mon 9/226:15 amORD - SJD

2 stops30h 56mMultiple Airlines

Sat 9/277:55 pmSJD - ORD

1 stop7h 47mMultiple Airlines

Deal found 9/12

$466

Sat 10/186:00 amMDW - SJD

2 stops10h 30mDelta

Sat 10/2512:47 pmSJD - MDW

1 stop7h 27mDelta

Deal found 9/14

$463

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 September 14, 2025.

Sat 10/181:40 amORD - SJD

1 stop10h 29mVolaris

Deal found 9/13

$111

Mon 11/106:23 amORD - SJD

1 stop10h 02mVolaris

Deal found 9/12

$113

Mon 2/166:23 amORD - SJD

1 stop10h 02mVolaris

Deal found 9/13

$117

Sun 11/164:40 pmORD - SJD

1 stop16h 10mViva

Deal found 9/12

$118

Tue 10/217:25 amORD - SJD

1 stop14h 29mVolaris

Deal found 9/13

$119

Sat 11/11:05 amORD - SJD

1 stop22h 15mViva

Deal found 9/14

$121

Sun 1/111:20 amORD - SJD

1 stop7h 40mViva

Deal found 9/14

$127

Sun 1/1111:59 pmORD - SJD

1 stop12h 35mVolaris

Deal found 9/13

$128

Tue 10/286:25 amMDW - SJD

1 stop9h 15mSouthwest

Deal found 9/14

$163

Mon 10/2710:35 amMDW - SJD

2 stops28h 45mAeromexico

Deal found 9/13

$169

Sun 11/96:30 amMDW - SJD

2 stops35h 05mMultiple Airlines

Deal found 9/14

$170

Sun 11/165:30 amMDW - SJD

1 stop7h 10mSouthwest

Deal found 9/14

$179

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

Tue 11/18

9:05 am-1:03 pm

Nonstop4h 58m

San José del Cabo Los Cabos

Mon 11/24

12:50 pm-6:03 pm

Nonstop4h 13m

$426

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 11/14

9:20 am-4:20 pm

1 stop8h 00m

San José del Cabo Los Cabos

Fri 11/21

2:17 pm-11:32 pm

1 stop8h 15m

$427

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/15

12:33 am-3:59 pm

1 stop16h 26m

San José del Cabo Los Cabos

Fri 11/28

6:00 am-10:41 pm

1 stop15h 41m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 10/21

6:00 am-4:12 pm

2 stops12h 12m

San José del Cabo Los Cabos

Tue 10/28

5:40 pm-6:59 pm

2 stops23h 19m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 11/16

12:33 am-6:10 pm

1 stop18h 37m

San José del Cabo Los Cabos

Wed 11/26

6:00 am-10:41 pm

1 stop15h 41m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/15

6:22 pm-2:00 pm

2 stops20h 38m

San José del Cabo Los Cabos

Sun 11/23

6:00 am-10:41 pm

1 stop15h 41m

$435

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 11/14

2:57 pm-10:30 pm

1 stop8h 33m

San José del Cabo Los Cabos

Fri 11/21

9:32 am-10:41 pm

1 stop12h 09m

$436

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 10/31

9:20 am-3:20 pm

1 stop8h 00m

San José del Cabo Los Cabos

Wed 11/5

12:18 pm-12:24 am

1 stop11h 06m

$437

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 11/17

2:54 pm-11:08 am

2 stops21h 14m

San José del Cabo Los Cabos

Mon 11/24

11:39 am-11:32 pm

1 stop10h 53m

$442

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/15

6:22 pm-2:00 pm

2 stops20h 38m

San José del Cabo Los Cabos

Mon 11/24

9:32 am-10:41 pm

1 stop12h 09m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 40 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 17 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 52% 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?

What’s the top layover airport for flights from Chicago to San José del Cabo?

Guadalajara (GDL) – chosen by Cheapflights users on 45% of 1-stop itineraries from Chicago to San José del Cabo on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San José del Cabo?

Monterrey (MTY) is the most affordable 1-stop option, with an average round-trip price of $318.

What’s the fastest layover option from Chicago to San José del Cabo?

Flights via Houston (IAH) have the shortest average one-way travel time for 1-stop routes: 6h 30m.

Which airport typically offers the quickest layover for flights from Chicago to San José del Cabo?

Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 09m.

Reviews of airlines servicing San José del Cabo

Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines 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

4,245 reviews

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

4,245 reviews

Southwest

8.0

Very good

4,245 reviews

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

8,931 reviews

Southwest

8.0

Very good

4,245 reviews

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

10,000 reviews

Southwest

8.0

Very good

4,245 reviews

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

788 reviews

Southwest

8.0

Very good

4,245 reviews

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

6.6

Okay

1,155 reviews

Southwest

8.0

Very good

4,245 reviews

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

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.
How long is the flight from Chicago to San José del Cabo?
United Airlines, Alaska Airlines, and Delta can get you from Chicago to San José del Cabo in just under 4h 58m. Your travel time can differ by up to 11h 28m. Airlines will cover a distance of 1806 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 flying from Chicago to San José del Cabo round-trip?
Our cheapest airline available from Chicago to San José del Cabo is Viva. Our recent data shows that you can find tickets from as low as $267 on this airline. Additional options worth looking into are Volaris and Delta, starting at $308 and $356 round-trip. Viva is 56% 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?
$158 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $163 and $163, 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: American Airlines (89%), Emirates (89%), United 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 $832, 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 $315 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$267	Average$346	FlexibilityNo cancel fee	On-timeN/A
Volaris	Cheapest$308	Average$402	FlexibilityNo cancel fee	On-time79%
Delta	Cheapest$356	Average$545	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$437	Average$630	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$448	Average$662	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$545	Average$720	FlexibilityNo cancel fee	On-time63%

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$111+ 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 10/18. 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

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 San José del Cabo Los Cabos are usually found in September or July, booked 17 days in advance, depart on a Tuesday or Monday and return on a Friday

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 September 14, 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 September 14, 2025.

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

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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 September 12, 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 September 14, 2025.

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

What’s the top layover airport for flights from Chicago to San José del Cabo?

Share of 1-stop round-trip flights from Chicago to San José del Cabo chosen by Cheapflights users in the past 12 months, using the same layover each way.

What’s the cheapest layover airport for flights from Chicago to San José del Cabo?

Average round-trip fare for 1-stop flights from Chicago to San José del Cabo, chosen by Cheapflights users in the past 12 months, with the same layover each way.

What’s the fastest layover option from Chicago to San José del Cabo?

Shortest average travel time for 1-stop one-way flights from Chicago to San José del Cabo, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Which airport typically offers the quickest layover for flights from Chicago to San José del Cabo?

Average layover duration for 1-stop one-way flights from Chicago to San José del Cabo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Reviews of airlines servicing San José del Cabo

Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines 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?

How long is the flight from Chicago to San José del Cabo?

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?

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Alternative routes for Chicago to San José del Cabo

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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 September 14, 2025.