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Cheap flights from Chicago to San José del Cabo from $88

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 1/11. 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

These are some of the best round-trip flight deals from Chicago to San José del Cabo that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to San José del Cabo.

Cheap last minute flights

Planning a quick getaway from Chicago to San José del Cabo? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San José del Cabo, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to San José del Cabo

Find recent round-trip train or bus tickets from Chicago to San José del Cabo.

All round-trip flight deals to San José del Cabo

The cheapest plane tickets to San José del Cabo found on KAYAK recently.
4:25 pm - 7:30 amORD-SJD
16h 05m1 stop
3:45 pm - 11:52 pmSJD-ORD
7h 07m1 stop
Sat, Jan 18 - Wed, Jan 22
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$257Viva
Find Deal
Sat, Feb 8 - Wed, Feb 12
4:25 pm - 3:33 pmORD-SJD
24h 08m2 stops
8:15 am - 1:02 amSJD-ORD
15h 47m1 stop
$278Volaris
Find Deal
Sat, Jan 18 - Wed, Jan 22
8:39 pm - 11:36 amMDW-SJD
16h 57m1 stop
8:13 am - 7:14 pmSJD-MDW
9h 01m1 stop
$309Volaris
Find Deal
Thu, Mar 27 - Thu, Apr 3
6:00 am - 6:32 pmMDW-SJD
13h 32m2 stops
5:30 pm - 9:39 amSJD-MDW
15h 09m2 stops
$504Delta
Find Deal
Thu, Feb 20 - Mon, Feb 24
10:35 pm - 11:40 amMDW-SJD
14h 05m1 stop
11:40 am - 9:55 pmSJD-MDW
9h 15m1 stop
$513Southwest
Find Deal
Sun, Mar 2 - Thu, Mar 6
6:00 am - 11:30 amMDW-SJD
7h 30m1 stop
6:00 am - 10:27 pmSJD-MDW
14h 27m2 stops
$517Aeromexico
Find Deal
Wed, Mar 12 - Tue, Mar 18
9:15 pm - 11:40 amMDW-SJD
15h 25m2 stops
2:45 pm - 10:10 pmSJD-MDW
6h 25m1 stop
$522Southwest
Find Deal
Sun, Jan 12 - Thu, Feb 13
6:00 am - 6:32 pmMDW-SJD
13h 32m2 stops
6:02 am - 10:20 pmSJD-MDW
15h 18m2 stops
$527Delta
Find Deal
Tue, Feb 18 - Wed, Feb 26
6:00 am - 2:02 pmMDW-SJD
9h 02m1 stop
1:41 pm - 10:20 pmSJD-MDW
7h 39m1 stop
$585Aeromexico
Find Deal
Fri, Jan 3 - Sat, Jan 11
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$88Viva
Find Deal
Sat, Jan 11
1:55 am - 2:51 pmORD-SJD
14h 56m1 stop
$91Volaris
Find Deal
Wed, Mar 26
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$92Viva
Find Deal
Fri, Jan 24
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
$184American Airlines
Find Deal
Mon, Jan 13
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
$224American Airlines
Find Deal
Fri, Jan 10
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
$233United Airlines
Find Deal
Sun, Jan 12
6:00 am - 6:01 pmMDW-SJD
14h 01m2 stops
$234Delta
Find Deal
Sun, Apr 20
6:00 am - 1:00 pmMDW-SJD
9h 00m1 stop
$238Aeromexico
Find Deal
Wed, Mar 12
6:00 am - 2:11 pmMDW-SJD
9h 11m1 stop
$243Delta
Find Deal
Mon, Jan 13
6:00 am - 12:36 pmMDW-SJD
7h 36m1 stop
$279Aeromexico
Find Deal
Tue, Jan 7
3:45 pm - 9:25 amORD-SJD
18h 40m1 stop
3:55 pm - 2:30 pmSJD-ORD
21h 35m1 stop
$509Viva
Find Deal
Sat, Dec 14 - Tue, Dec 17
5:40 pm - 9:25 amORD-SJD
16h 45m1 stop
3:55 pm - 4:00 pmSJD-ORD
23h 05m1 stop
Fri, Dec 13 - Tue, Dec 17
8:27 am - 12:12 pmORD-SJD
4h 45mnonstop
12:55 pm - 6:15 pmSJD-ORD
4h 20mnonstop
$682American Airlines
Find Deal
Sun, Dec 15 - Wed, Dec 25
5:40 am - 12:26 pmORD-SJD
7h 46m1 stop
8:35 am - 9:58 pmSJD-ORD
12h 23m1 stop
$686Aeromexico
Find Deal
Sun, Dec 15 - Wed, Dec 25
8:27 am - 12:12 pmORD-SJD
4h 45mnonstop
2:45 pm - 8:01 pmSJD-ORD
4h 16mnonstop
$697American Airlines
Find Deal
Sun, Dec 15 - Fri, Dec 20
5:40 am - 12:26 pmORD-SJD
7h 46m1 stop
8:35 am - 9:17 pmSJD-ORD
11h 42m2 stops
$711Aeromexico
Find Deal
Sun, Dec 15 - Wed, Dec 25
7:30 am - 2:40 pmORD-SJD
8h 10m1 stop
3:07 pm - 11:53 pmSJD-ORD
7h 46m1 stop
$751Delta
Find Deal
Wed, Dec 11 - Sat, Dec 21
6:00 am - 12:26 pmMDW-SJD
7h 26m1 stop
6:04 am - 10:06 pmSJD-MDW
15h 02m2 stops
$751Delta
Find Deal
Wed, Dec 11 - Sun, Dec 15
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$835United Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:37 pm - 11:59 pmSJD-ORD
10h 22m1 stop
$943United Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$479American Airlines
Find Deal
Sun, Jan 12 - Wed, Jan 29
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:15 pm - 6:30 pmSJD-ORD
4h 15mnonstop
$503American Airlines
Find Deal
Sun, Jan 12 - Thu, Feb 13
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$513American Airlines
Find Deal
Sun, Jan 12 - Thu, Jan 16
8:05 am - 10:35 amORD-SJD
4h 30mnonstop
12:30 pm - 6:50 pmSJD-ORD
4h 20mnonstop
$518American Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 25
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$533United Airlines
Find Deal
Mon, Jan 20 - Sat, Jan 25
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$593United Airlines
Find Deal
Wed, Feb 5 - Thu, Feb 13
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$598United Airlines
Find Deal
Wed, Jan 29 - Tue, Feb 4
9:00 am - 1:00 pmMDW-SJD
5h 00mnonstop
11:35 am - 5:40 pmSJD-MDW
4h 05mnonstop
$628Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
9:00 am - 1:00 pmMDW-SJD
5h 00mnonstop
11:35 am - 5:40 pmSJD-MDW
4h 05mnonstop
$653Southwest
Find Deal
Sat, Mar 8 - Sat, Mar 15
9:00 am - 12:00 pmMDW-SJD
5h 00mnonstop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$734Southwest
Find Deal
Fri, Mar 14 - Wed, Mar 19

Viva flights from Chicago to San José del Cabo

Our best Viva deals on Chicago to San José del Cabo flight tickets
Viva
Feb 8
ORD3:50 pmChicago O'Hare Intl
18h 35m
1 stop
SJD9:25 amSan José del Cabo Los Cabos
Feb 12
SJD4:00 pmSan José del Cabo Los Cabos
21h 20m
1 stop
ORD2:20 pmChicago O'Hare Intl
Viva
Jan 12
ORD3:50 pmChicago O'Hare Intl
18h 35m
1 stop
SJD9:25 amSan José del Cabo Los Cabos
Feb 13
SJD4:00 pmSan José del Cabo Los Cabos
21h 20m
1 stop
ORD2:20 pmChicago O'Hare Intl
Viva
Jan 18
ORD3:50 pmChicago O'Hare Intl
18h 35m
1 stop
SJD9:25 amSan José del Cabo Los Cabos
Jan 29
SJD3:45 pmSan José del Cabo Los Cabos
6h 45m
1 stop
ORD11:30 pmChicago O'Hare Intl

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
Dec 16
ORD8:27 amChicago O'Hare Intl
4h 45m
SJD12:12 pmSan José del Cabo Los Cabos
Dec 23
SJD2:45 pmSan José del Cabo Los Cabos
4h 16m
ORD8:01 pmChicago O'Hare Intl
American Airlines
Dec 16
ORD6:47 amChicago O'Hare Intl
7h 53m
1 stop
SJD1:40 pmSan José del Cabo Los Cabos
Dec 23
SJD2:45 pmSan José del Cabo Los Cabos
4h 16m
ORD8:01 pmChicago O'Hare Intl
American Airlines
Dec 23
ORD7:09 amChicago O'Hare Intl
8h 26m
1 stop
SJD2:35 pmSan José del Cabo Los Cabos
Dec 29
SJD2:45 pmSan José del Cabo Los Cabos
4h 16m
ORD8:01 pmChicago O'Hare Intl

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 cheapest month to fly to San José del Cabo?

The cheapest month to fly to San José del Cabo from Chicago is in July. Flight prices, which tend to average around $523, 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 July, then August is your next best option. Flight prices from Chicago to San José del Cabo during August average around $525.

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 $522. 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 $648.

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 $329 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 $587. 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?

Most flyers found that booking tickets 34 days in advance of their planned departure date is the best time to get cheap flights to San José del Cabo. During this timeframe, flight prices are around $584. However, in the past 72 hours, people saw flights from Chicago for as low as $455.

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 52% 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 December 2024, prices for Chicago to San José del Cabo flights are approximately 1% 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

$88

Fastest flight time

4h 50m

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 $88. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $256.
The fastest flight from Chicago to San José del Cabo takes 4h 50m
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)

  • 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 5h 00m.

  • 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 $271Free CancellationRating
6.9
849 reviews
Search Viva flights
VolarisPriceFrom $323Free CancellationRating
6.6
1,269 reviews
Search Volaris flights
AeromexicoPriceFrom $392Free CancellationRating
7.5
1,945 reviews
Search Aeromexico flights
DeltaPriceFrom $400Free CancellationRating
8.0
8,656 reviews
Search Delta flights
United AirlinesPriceFrom $404Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
American AirlinesPriceFrom $405Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $527Free CancellationRating
8.1
4,895 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 $404 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $658 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 10,000 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 $586, with deals from around $405 rare but found on momondo. Referenced prices are for round-trip Chicago to San José del Cabo flight searches in the last 72 hours.


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.


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