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Cheap flights from Chicago to San José del Cabo from $82

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 3/3. 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.
2:42 am - 4:00 pmORD-SJD
14h 18m1 stop
11:22 am - 1:02 amSJD-ORD
12h 40m1 stop
Sat, Mar 1 - Wed, Mar 5
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$243Viva
Find Deal
Sat, Jan 18 - Wed, Jan 22
3:45 am - 11:36 amORD-SJD
9h 51m1 stop
12:24 pm - 1:05 amSJD-ORD
10h 41m1 stop
$260Volaris
Find Deal
Sat, Mar 8 - Fri, Mar 14
12:45 pm - 9:27 amORD-SJD
22h 42m2 stops
12:24 pm - 1:05 amSJD-ORD
10h 41m1 stop
$273Volaris
Find Deal
Sun, Mar 9 - Fri, Mar 14
6:00 am - 12:33 pmMDW-SJD
7h 33m1 stop
1:38 pm - 10:20 pmSJD-MDW
7h 42m1 stop
$491Aeromexico
Find Deal
Mon, Jan 13 - Wed, Jan 15
6:00 am - 2:11 pmMDW-SJD
9h 11m1 stop
5:35 pm - 8:54 amSJD-MDW
14h 19m2 stops
$495Delta
Find Deal
Mon, Jan 13 - Thu, Jan 16
8:35 pm - 11:40 amMDW-SJD
16h 05m2 stops
12:15 pm - 10:55 pmSJD-MDW
9h 40m2 stops
$504Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:00 am - 12:33 pmMDW-SJD
7h 33m1 stop
1:38 pm - 10:20 pmSJD-MDW
7h 42m1 stop
$505Aeromexico
Find Deal
Tue, Jan 14 - Thu, Jan 16
10:10 am - 9:40 pmMDW-SJD
13h 30m2 stops
5:05 pm - 9:23 amSJD-MDW
14h 18m2 stops
$509Delta
Find Deal
Wed, Mar 12 - Tue, Mar 18
9:15 pm - 11:40 amMDW-SJD
15h 25m2 stops
12:35 pm - 11:20 pmSJD-MDW
9h 45m2 stops
$539Southwest
Find Deal
Sat, Mar 1 - Tue, Mar 4
2:42 am - 7:27 pmORD-SJD
17h 45m1 stop
$82Volaris
Find Deal
Mon, Mar 3
5:10 am - 3:15 pmORD-SJD
11h 05m1 stop
Fri, Feb 14
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$87Viva
Find Deal
Fri, Jan 10
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$91Viva
Find Deal
Mon, Jan 20
8:27 am - 12:12 pmORD-SJD
4h 45mnonstop
$161American Airlines
Find Deal
Mon, Dec 16
8:30 pm - 1:29 pmORD-SJD
17h 59m1 stop
$166American Airlines
Find Deal
Sat, Dec 14
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
$215United Airlines
Find Deal
Mon, Jan 13
6:00 am - 6:01 pmORD-SJD
14h 01m2 stops
$225Delta
Find Deal
Sun, May 18
6:00 am - 6:25 pmMDW-SJD
13h 25m2 stops
$225Delta
Find Deal
Mon, Jan 20
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
$236United Airlines
Find Deal
Mon, Dec 16
4:05 pm - 9:20 amORD-SJD
18h 15m1 stop
8:00 am - 11:45 pmSJD-ORD
14h 45m1 stop
$345Viva
Find Deal
Fri, Nov 22 - Sun, Nov 24
1:15 am - 3:15 pmORD-SJD
15h 00m1 stop
3:55 pm - 2:30 pmSJD-ORD
21h 35m1 stop
$385Viva
Find Deal
Mon, Nov 25 - Tue, Dec 3
10:45 am - 5:19 pmMDW-SJD
7h 34m1 stop
8:39 pm - 9:28 amSJD-MDW
11h 49m1 stop
$659Volaris
Find Deal
Fri, Nov 22 - Sun, Nov 24
10:45 am - 5:19 pmMDW-SJD
7h 34m1 stop
1:38 pm - 8:45 amSJD-MDW
18h 07m2 stops
$679Volaris
Find Deal
Fri, Nov 22 - Sun, Nov 24
8:50 pm - 9:45 amORD-SJD
13h 55m1 stop
1:10 pm - 6:20 pmSJD-ORD
4h 10mnonstop
$756American Airlines
Find Deal
Thu, Nov 21 - Thu, Nov 28
6:45 pm - 10:25 amORD-SJD
16h 40m1 stop
1:10 pm - 6:20 pmSJD-ORD
4h 10mnonstop
$824American Airlines
Find Deal
Sat, Nov 23 - Wed, Nov 27
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$891United Airlines
Find Deal
Thu, Nov 21 - Thu, Nov 28
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$1,064United Airlines
Find Deal
Sun, Nov 24 - Fri, Nov 29
1:05 am - 11:54 amORD-SJD
11h 49m1 stop
6:04 am - 11:59 pmSJD-ORD
16h 55m2 stops
$1,269Aeromexico
Find Deal
Mon, Nov 25 - Tue, Dec 3
1:05 am - 11:54 amORD-SJD
11h 49m1 stop
12:53 pm - 11:14 pmSJD-ORD
9h 21m1 stop
$1,304Aeromexico
Find Deal
Mon, Nov 25 - Tue, Dec 3
8:25 am - 12:10 pmORD-SJD
4h 45mnonstop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$459American Airlines
Find Deal
Tue, Dec 3 - Fri, Dec 13
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$471United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 24
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$476United Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$485United Airlines
Find Deal
Sun, Mar 2 - Wed, Mar 5
8:20 am - 11:09 amORD-SJD
4h 49mnonstop
12:41 pm - 6:55 pmSJD-ORD
4h 14mnonstop
$490American Airlines
Find Deal
Wed, Mar 12 - Tue, Mar 18
8:27 am - 12:12 pmORD-SJD
4h 45mnonstop
12:55 pm - 6:15 pmSJD-ORD
4h 20mnonstop
$492American Airlines
Find Deal
Sat, Dec 14 - Thu, Dec 19
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$493United Airlines
Find Deal
Sun, Mar 2 - Thu, Mar 6
9:00 am - 12:00 pmMDW-SJD
5h 00mnonstop
12:40 pm - 6:45 pmSJD-MDW
4h 05mnonstop
$579Southwest
Find Deal
Mon, Mar 10 - Sun, Mar 16
9:00 am - 1:00 pmMDW-SJD
5h 00mnonstop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$604Southwest
Find Deal
Fri, Mar 7 - Mon, Mar 10
9:00 am - 12:00 pmMDW-SJD
5h 00mnonstop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$781Southwest
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
Jan 18
ORD3:50 pmChicago O'Hare Intl
18h 35m
1 stop
SJD9:25 amSan José del Cabo Los Cabos
Jan 22
SJD4:00 pmSan José del Cabo Los Cabos
21h 20m
1 stop
ORD2:20 pmChicago O'Hare Intl
Viva
Feb 7
ORD1:00 amChicago O'Hare Intl
14h 50m
1 stop
SJD2:50 pmSan José del Cabo Los Cabos
Feb 11
SJD3:20 pmSan José del Cabo Los Cabos
7h 10m
1 stop
ORD11:30 pmChicago O'Hare Intl
Viva
May 9
ORD5:00 pmChicago O'Hare Intl
17h 00m
1 stop
SJD8:00 amSan José del Cabo Los Cabos
May 16
SJD8:05 amSan José del Cabo Los Cabos
8h 10m
1 stop
ORD6:15 pmChicago O'Hare Intl

Volaris flights from Chicago to San José del Cabo

Our best Volaris deals on Chicago to San José del Cabo flight tickets
Volaris
Mar 8
ORD3:45 amChicago O'Hare Intl
9h 51m
1 stop
SJD11:36 amSan José del Cabo Los Cabos
Mar 14
SJD12:24 pmSan José del Cabo Los Cabos
10h 41m
1 stop
ORD1:05 amChicago O'Hare Intl
Volaris
Mar 9
ORD12:45 pmChicago O'Hare Intl
22h 42m
2 stops
SJD9:27 amSan José del Cabo Los Cabos
Mar 14
SJD12:24 pmSan José del Cabo Los Cabos
10h 41m
1 stop
ORD1:05 amChicago O'Hare Intl
Volaris
May 15
ORD7:25 amChicago O'Hare Intl
14h 03m
1 stop
SJD7:28 pmSan José del Cabo Los Cabos
May 18
SJD8:21 pmSan José del Cabo Los Cabos
7h 23m
1 stop
ORD5:44 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 cheapest month to fly from Chicago to San José del Cabo?

July. The cheapest time of year to fly to San José del Cabo from Chicago is July. Most expensive is December

What is the cheapest day to depart Chicago for San José del Cabo?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Thursday

When is the cheapest time to fly from Chicago to San José del Cabo?

In the afternoon. Chicago to San José del Cabo flights are approximately 42% more expensive in the morning than in the afternoon

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

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

How far in advance should you book Chicago to San José del Cabo flights?

34 days before. The cheapest time to buy a flight from Chicago to San José del Cabo is approximately 34 days to departure

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

There are 2 cabin classes available to choose from on Chicago to San José del Cabo 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 49% 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 November 2024, prices for Chicago to San José del Cabo flights are approximately 21% 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

$82

Fastest flight time

4h 45m

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 $82. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $226.
The fastest flight from Chicago to San José del Cabo takes 4h 45m
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 $272Free CancellationRating
6.9
854 reviews
Search Viva flights
VolarisPriceFrom $324Free CancellationRating
6.6
1,287 reviews
Search Volaris flights
DeltaPriceFrom $367Free CancellationRating
8.0
8,756 reviews
Search Delta flights
AeromexicoPriceFrom $392Free CancellationRating
7.5
2,004 reviews
Search Aeromexico flights
United AirlinesPriceFrom $402Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
American AirlinesPriceFrom $403Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • United Airlines Flights From Chicago to San José del Cabo

    United Airlines flight deals from Chicago to San José del Cabo start from $402 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $657 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 7 flights from Chicago to San José del Cabo in any given week. The average American Airlines airfare for this route is around $574, with deals from around $403 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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