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Cheap flights from Chicago to San José del Cabo from $101

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San José del Cabo departing on 2/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to San José del Cabo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Volaris Logo
11:59 pm - 11:34 amORD-SJD
13h 35m1 stop
Volaris Logo
4:43 pm - 5:37 amSJD-ORD
10h 54m1 stop
$415Volaris
Find Deal
sáb., mar. 21 - sáb., mar. 28
Multiple Airlines Logo
12:59 pm - 4:30 pmORD-SJD
28h 31m1 stop
Multiple Airlines Logo
4:34 pm - 11:19 amSJD-ORD
17h 45m2 stops
$416Multiple Airlines
Find Deal
mié., ene. 14 - lun., ene. 19
American Airlines Logo
5:00 am - 11:50 amORD-SJD
7h 50m1 stop
American Airlines Logo
12:50 pm - 12:23 amSJD-ORD
10h 33m1 stop
$417American Airlines
Find Deal
mié., ene. 14 - dom., ene. 18
American Airlines Logo
5:00 am - 11:43 amORD-SJD
7h 43m1 stop
American Airlines Logo
4:23 pm - 12:31 amSJD-ORD
7h 08m1 stop
$418American Airlines
Find Deal
vie., nov. 28 - sáb., dic. 6
Southwest Logo
5:30 am - 11:40 amMDW-SJD
7h 10m1 stop
Southwest Logo
1:05 pm - 8:55 pmSJD-MDW
6h 50m1 stop
$418Southwest
Find Deal
vie., nov. 28 - mié., dic. 3
Southwest Logo
8:25 am - 2:20 pmMDW-SJD
6h 55m1 stop
Southwest Logo
2:40 pm - 10:55 pmSJD-MDW
7h 15m1 stop
$419Southwest
Find Deal
sáb., nov. 15 - mié., nov. 19
Viva Logo
1:20 am - 8:00 amORD-SJD
7h 40m1 stop
Viva Logo
11:20 am - 11:25 pmSJD-ORD
11h 05m1 stop
$425Viva
Find Deal
vie., ene. 30 - sáb., feb. 7
Viva Logo
12:55 am - 4:30 pmORD-SJD
16h 35m1 stop
Viva Logo
8:40 am - 11:45 pmSJD-ORD
14h 05m1 stop
$430Viva
Find Deal
jue., feb. 26 - lun., mar. 2
Delta Logo
5:20 am - 6:10 pmORD-SJD
13h 50m2 stops
Delta Logo
6:00 am - 10:41 pmSJD-ORD
15h 41m1 stop
$455Delta
Find Deal
vie., nov. 7 - mar., nov. 11
Delta Logo
6:00 am - 11:42 amMDW-SJD
7h 42m1 stop
Delta Logo
1:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
$505Delta
Find Deal
vie., oct. 31 - vie., nov. 7

Hawaiian Airlines flights from Chicago to San José del Cabo

Our best Hawaiian Airlines deals on Chicago to San José del Cabo flight tickets
Hawaiian Airlines
Nov 3
ORD6:00 amChicago O'Hare Intl
32h 09m
1 stop
SJD1:09 pmSan José del Cabo Los Cabos
Nov 7
SJD11:40 amSan José del Cabo Los Cabos
11h 19m
1 stop
ORD11:59 pmChicago O'Hare Intl
$435
Find similar
Hawaiian Airlines
Jan 1
ORD8:39 amChicago O'Hare Intl
8h 21m
1 stop
SJD4:00 pmSan José del Cabo Los Cabos
Jan 6
SJD11:44 amSan José del Cabo Los Cabos
11h 15m
1 stop
ORD11:59 pmChicago O'Hare Intl
$440
Find similar

American Airlines flights from Chicago to San José del Cabo

Our best American Airlines deals on Chicago to San José del Cabo flight tickets
American Airlines
Jan 14
ORD5:00 amChicago O'Hare Intl
7h 50m
1 stop
SJD11:50 amSan José del Cabo Los Cabos
Jan 18
SJD12:50 pmSan José del Cabo Los Cabos
10h 33m
1 stop
ORD12:23 amChicago O'Hare Intl
$417
Find similar
American Airlines
Nov 28
ORD5:00 amChicago O'Hare Intl
7h 43m
1 stop
SJD11:43 amSan José del Cabo Los Cabos
Dec 6
SJD4:23 pmSan José del Cabo Los Cabos
7h 08m
1 stop
ORD12:31 amChicago O'Hare Intl
$418
Find similar
American Airlines
Nov 15
ORD10:10 amChicago O'Hare Intl
4h 49m
SJD1:59 pmSan José del Cabo Los Cabos
Nov 17
SJD4:23 pmSan José del Cabo Los Cabos
17h 13m
1 stop
ORD10:36 amChicago O'Hare Intl
$420
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San José del Cabo 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, momondo users made 832,500 searches. Data last updated octubre 22, 2025.
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

sáb. 3/21

11:59 pm-11:34 am

1 stop13h 35m

San José del Cabo Los Cabos

sáb. 3/28

4:43 pm-5:37 am

1 stop10h 54m

$415

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mié. 1/14

12:59 pm-4:30 pm

1 stop28h 31m

San José del Cabo Los Cabos

lun. 1/19

4:34 pm-11:19 am

2 stops17h 45m

$416

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mié. 1/14

5:00 am-11:50 am

1 stop7h 50m

San José del Cabo Los Cabos

dom. 1/18

12:50 pm-12:23 am

1 stop10h 33m

$417

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

vie. 11/28

5:00 am-11:43 am

1 stop7h 43m

San José del Cabo Los Cabos

sáb. 12/6

4:23 pm-12:31 am

1 stop7h 08m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 11/28

5:30 am-11:40 am

1 stop7h 10m

San José del Cabo Los Cabos

mié. 12/3

1:05 pm-8:55 pm

1 stop6h 50m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 11/15

8:25 am-2:20 pm

1 stop6h 55m

San José del Cabo Los Cabos

mié. 11/19

2:40 pm-10:55 pm

1 stop7h 15m

$419

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

vie. 1/30

1:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

sáb. 2/7

11:20 am-11:25 pm

1 stop11h 05m

$425

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

jue. 2/26

12:55 am-4:30 pm

1 stop16h 35m

San José del Cabo Los Cabos

lun. 3/2

8:40 am-11:45 pm

1 stop14h 05m

$430

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

vie. 11/7

5:20 am-6:10 pm

2 stops13h 50m

San José del Cabo Los Cabos

mar. 11/11

6:00 am-10:41 pm

1 stop15h 41m

$455

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 10/31

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

vie. 11/7

1:47 pm-10:14 pm

1 stop7h 27m

$505

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José del Cabo from

How to get the cheapest flight ticket from Chicago to San José del Cabo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and San José del Cabo?

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

The cheapest month to fly to San José del Cabo from Chicago is in September. Flight prices, which tend to average around $482, are often lower during this time because this is during the off-season. If you’re not able to fly to San José del Cabo in September, then July is your next best option. Flight prices from Chicago to San José del Cabo during July average around $540.

What is the cheapest day to depart on your flight to San José del Cabo?

According to our data, Tuesday is the cheapest day to fly to San José del Cabo from Chicago. The lowest ticket price found for a Tuesday departure recently was $588. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $703.

What is the cheapest time of day to depart on your flight to San José del Cabo?

Flying to San José del Cabo from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $313 when looking at flights departing in the afternoon. Flights to San José del Cabo are more costly in the morning, with an average ticket price of $644. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to San José del Cabo Los Cabos flight route?

Fly from Chicago O'Hare Intl to San José del Cabo Los Cabos for the best Chicago - San José del Cabo Los Cabos flight prices

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

You are more likely to see cheaper flights to San José del Cabo from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José del Cabo for around $607 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José del Cabo from Chicago for as low as $522 on momondo.

What cabin class options are available on Chicago to San José del Cabo Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago to San José del Cabo Los Cabos flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to San José del Cabo flights?

You could potentially save up to 4% on your flight if you consider stops on a Chicago to San José del Cabo flight.

How have Chicago to San José del Cabo flight prices changed over time?

As of October 2025, prices for Chicago to San José del Cabo flights are approximately 38% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San José del Cabo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San José del Cabo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to San José del Cabo (CHI to SJD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San José del Cabo

Best Price Found

$255

Fastest flight time

4h 37m

Direct flights

Every day

Airports in San José del Cabo

1 airport
The best one-way flight to San José del Cabo from Chicago in the past 72 hours is $255. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $470.
The fastest flight from Chicago to San José del Cabo takes 4h 37m
Direct flights go from Chicago to San José del Cabo every day.
There is 1 airport near San José del Cabo: San José del Cabo Los Cabos (SJD)
Search flight deals

  • How far is Chicago to San José del Cabo Los Cabos by plane?

    There are 1817.1 mi between Chicago and San José del Cabo Los Cabos. By plane, this route typically takes 4h 42m.

  • When did momondo last update prices for flights from Chicago to San José del Cabo Los Cabos Airport?

    Prices for flights from Chicago to San José del Cabo Los Cabos Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to San José del Cabo Los Cabos Airport?

  • How old do you have to be to fly from Chicago to San José del Cabo Los Cabos Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San José del Cabo Los Cabos Airport.

  • What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?

    The travel and health documents required for your trip to San José del Cabo Los Cabos Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José del Cabo Los Cabos Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to San José del Cabo?

  • What is the most popular airline from Chicago to San José del Cabo?

Best airlines flying from Chicago to San José del Cabo

Compare and see reviews for airlines that fly from Chicago to San José del Cabo with momondo
Airline
Rating
Free Cancellation
Price
VivaPriceFrom $268Free CancellationRating
7.0
790 reviews
Search Viva flights
VolarisPriceFrom $310Free CancellationRating
6.7
1,152 reviews
Search Volaris flights
DeltaPriceFrom $356Free CancellationRating
7.9
7,977 reviews
Search Delta flights
American AirlinesPriceFrom $424Free CancellationRating
7.2
11,028 reviews
Search American Airlines flights
United AirlinesPriceFrom $448Free CancellationRating
7.4
8,988 reviews
Search United Airlines flights
SouthwestPriceFrom $545Free CancellationRating
8.0
4,237 reviews
Search Southwest flights

  • United Airlines Flights From Chicago to San José del Cabo

    United Airlines flight deals from Chicago to San José del Cabo start from $448 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $665 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to San José del Cabo

    American Airlines (7.2/10 from 11,028 reviews) operates around 5 flights from Chicago to San José del Cabo in any given week. The average American Airlines airfare for this route is around $622, with deals from around $424 rare but found on momondo. Referenced prices are for round-trip Chicago to San José del Cabo flight searches in the last 72 hours.

Traveling to a place near San José del Cabo?

Book flights to San José del Cabo if you plan to visit one of these locations
Todos Santos
Los Barriles

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José del Cabo?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San José del Cabo. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to San José del Cabo with flexible booking policies on momondo?

Flights from Chicago to San José del Cabo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to San José del Cabo?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to San José del Cabo from Chicago.

I’m not ready to book a flight from Chicago to San José del Cabo right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to San José del Cabo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your San José del Cabo trip

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