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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 1/16. 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.
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$257Viva
Find Deal
Thu, Jan 16 - Thu, Jan 30
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
3:45 pm - 11:30 pmSJD-ORD
6h 45m1 stop
$261Viva
Find Deal
Sat, Jan 18 - Fri, Jan 24
5:40 pm - 8:27 pmORD-SJD
27h 47m2 stops
8:19 pm - 4:00 pmSJD-ORD
18h 41m2 stops
$334Volaris
Find Deal
Wed, Jan 22 - Sun, Jan 26
5:40 pm - 5:12 pmORD-SJD
24h 32m3 stops
8:19 pm - 4:00 pmSJD-ORD
18h 41m2 stops
$344Volaris
Find Deal
Wed, Jan 22 - Sun, Jan 26
5:45 am - 6:25 pmORD-SJD
13h 40m2 stops
6:01 am - 8:48 pmSJD-ORD
13h 47m2 stops
$419Delta
Find Deal
Tue, Jan 21 - Tue, Jan 28
6:00 am - 6:32 pmMDW-SJD
13h 32m2 stops
6:02 am - 10:20 pmSJD-MDW
15h 18m2 stops
$459Delta
Find Deal
Thu, Feb 6 - Tue, Feb 11
6:00 am - 2:11 pmMDW-SJD
9h 11m1 stop
1:41 pm - 10:20 pmSJD-MDW
7h 39m1 stop
$492Aeromexico
Find Deal
Sun, Jan 19 - Thu, Jan 23
6:00 am - 2:11 pmMDW-SJD
9h 11m1 stop
1:41 pm - 10:20 pmSJD-MDW
7h 39m1 stop
$509Aeromexico
Find Deal
Mon, Jan 27 - Thu, Jan 30
6:20 am - 10:40 amMDW-SJD
6h 20m1 stop
12:30 pm - 10:35 pmSJD-MDW
8h 05m1 stop
$539Southwest
Find Deal
Sun, May 4 - Tue, May 6
6:10 am - 1:50 pmMDW-SJD
8h 40m1 stop
12:40 pm - 6:45 pmSJD-MDW
4h 05mnonstop
$587Southwest
Find Deal
Wed, Mar 5 - Sun, Mar 9
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$88Viva
Find Deal
Thu, Jan 16
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$92Viva
Find Deal
Sun, Feb 2
3:55 pm - 9:30 amORD-SJD
18h 35m1 stop
$93Viva
Find Deal
Mon, Mar 3
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$97Viva
Find Deal
Wed, Jan 22
5:40 pm - 12:34 pmORD-SJD
19h 54m2 stops
$112Volaris
Find Deal
Mon, Jan 27
5:40 pm - 12:34 pmORD-SJD
19h 54m2 stops
$121Volaris
Find Deal
Sun, Jan 26
5:45 am - 6:32 pmORD-SJD
13h 47m2 stops
$189Delta
Find Deal
Tue, Feb 18
6:00 am - 6:20 pmMDW-SJD
13h 20m2 stops
$189Delta
Find Deal
Sun, Jan 19
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
$228United Airlines
Find Deal
Tue, Jan 7
8:20 am - 12:15 pmORD-SJD
4h 55mnonstop
$233American Airlines
Find Deal
Tue, Feb 18
1:15 am - 9:25 amORD-SJD
9h 10m1 stop
8:25 pm - 2:15 pmSJD-ORD
16h 50m1 stop
$567Viva
Find Deal
Sun, Dec 22 - Fri, Dec 27
3:45 pm - 9:25 amORD-SJD
18h 40m1 stop
8:25 pm - 2:15 pmSJD-ORD
16h 50m1 stop
$641Viva
Find Deal
Mon, Dec 23 - Fri, Dec 27
5:40 am - 12:21 pmORD-SJD
7h 41m1 stop
6:01 am - 3:23 pmSJD-ORD
8h 22m1 stop
$701Aeromexico
Find Deal
Thu, Dec 19 - Tue, Dec 24
5:40 am - 12:26 pmORD-SJD
7h 46m1 stop
10:40 am - 10:09 pmSJD-ORD
10h 29m1 stop
$736Delta
Find Deal
Fri, Dec 20 - Tue, Dec 31
5:40 am - 12:26 pmORD-SJD
7h 46m1 stop
10:40 am - 9:58 pmSJD-ORD
10h 18m1 stop
$741Delta
Find Deal
Mon, Dec 23 - Mon, Dec 30
11:20 am - 3:13 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$747United Airlines
Find Deal
Thu, Dec 19 - Tue, Dec 24
9:50 am - 1:45 pmORD-SJD
4h 55mnonstop
12:55 pm - 6:15 pmSJD-ORD
4h 20mnonstop
$797American Airlines
Find Deal
Sun, Dec 22 - Thu, Dec 26
7:00 am - 1:28 pmORD-SJD
7h 28m1 stop
12:55 pm - 6:15 pmSJD-ORD
4h 20mnonstop
$801American Airlines
Find Deal
Sun, Dec 22 - Fri, Dec 27
9:40 pm - 1:10 pmORD-SJD
16h 30m1 stop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$841United Airlines
Find Deal
Sat, Dec 21 - Thu, Dec 26
1:13 am - 12:19 pmORD-SJD
12h 06m1 stop
1:08 pm - 12:14 amSJD-ORD
10h 06m1 stop
$3,613Aeromexico
Find Deal
Fri, Dec 20 - Thu, Dec 26
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$405American Airlines
Find Deal
Sun, Feb 2 - Thu, Feb 6
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$468American Airlines
Find Deal
Sun, Jan 19 - Thu, Jan 23
8:20 am - 12:15 pmORD-SJD
4h 55mnonstop
1:15 pm - 6:30 pmSJD-ORD
4h 15mnonstop
$484American Airlines
Find Deal
Fri, Feb 28 - Wed, Mar 5
9:50 am - 1:50 pmORD-SJD
5h 00mnonstop
2:50 pm - 8:10 pmSJD-ORD
4h 20mnonstop
$485American Airlines
Find Deal
Sat, Jan 11 - Sat, Feb 1
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$503United Airlines
Find Deal
Sun, Jan 12 - Fri, Jan 17
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$507United Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$508United Airlines
Find Deal
Wed, Jan 29 - Tue, Feb 4
9:10 am - 12:10 pmMDW-SJD
5h 00mnonstop
12:40 pm - 6:45 pmSJD-MDW
4h 05mnonstop
$955Southwest
Find Deal
Sun, Mar 16 - Sun, Mar 23
9:10 am - 12:10 pmMDW-SJD
5h 00mnonstop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$1,090Southwest
Find Deal
Sun, Mar 16 - Fri, Mar 21
9:10 am - 12:10 pmMDW-SJD
5h 00mnonstop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$1,369Southwest
Find Deal
Sun, Mar 23 - Fri, Mar 28

Delta flights from Chicago to San José del Cabo

Our best Delta deals on Chicago to San José del Cabo flight tickets
Delta
Jan 21
ORD5:45 amChicago O'Hare Intl
13h 40m
2 stops
SJD6:25 pmSan José del Cabo Los Cabos
Jan 28
SJD6:01 amSan José del Cabo Los Cabos
13h 47m
2 stops
ORD8:48 pmChicago O'Hare Intl
Delta
Feb 6
MDW6:00 amChicago Midway
13h 32m
2 stops
SJD6:32 pmSan José del Cabo Los Cabos
Feb 11
SJD6:02 amSan José del Cabo Los Cabos
15h 18m
2 stops
MDW10:20 pmChicago Midway
Delta
Feb 10
MDW6:00 amChicago Midway
13h 32m
2 stops
SJD6:32 pmSan José del Cabo Los Cabos
Feb 15
SJD5:35 pmSan José del Cabo Los Cabos
14h 16m
2 stops
MDW8:51 amChicago Midway

Alaska Airlines flights from Chicago to San José del Cabo

Our best Alaska Airlines deals on Chicago to San José del Cabo flight tickets
Alaska Airlines
Jan 29
ORD6:55 pmChicago O'Hare Intl
24h 54m
2 stops
SJD6:49 pmSan José del Cabo Los Cabos
Feb 4
SJD1:14 pmSan José del Cabo Los Cabos
22h 53m
2 stops
ORD1:07 pmChicago O'Hare Intl
Alaska Airlines
Jan 8
ORD6:55 pmChicago O'Hare Intl
24h 54m
2 stops
SJD6:49 pmSan José del Cabo Los Cabos
Jan 15
SJD1:14 pmSan José del Cabo Los Cabos
22h 53m
2 stops
ORD1:07 pmChicago O'Hare Intl
Alaska Airlines
Mar 25
ORD6:56 pmChicago O'Hare Intl
23h 19m
2 stops
SJD4:15 pmSan José del Cabo Los Cabos
Apr 1
SJD12:57 pmSan José del Cabo Los Cabos
14h 43m
1 stop
ORD5:40 amChicago 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 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 July. Flight prices, which tend to average around $524, 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 $524. 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 $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 $595. 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 49 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 $576. However, in the past 72 hours, people saw flights from Chicago for as low as $439.

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 61% 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 0% more expensive 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 53m

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 $257.
The fastest flight from Chicago to San José del Cabo takes 4h 53m
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
848 reviews
Search Viva flights
VolarisPriceFrom $323Free CancellationRating
6.7
1,267 reviews
Search Volaris flights
AeromexicoPriceFrom $392Free CancellationRating
7.5
1,930 reviews
Search Aeromexico flights
DeltaPriceFrom $400Free CancellationRating
8.0
8,604 reviews
Search Delta flights
United AirlinesPriceFrom $404Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights
American AirlinesPriceFrom $405Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $527Free CancellationRating
8.1
4,848 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 3 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.


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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