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Cheap flights from Chicago to San José del Cabo from $89

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 2/16. 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 from Chicago to San José del Cabo

The cheapest plane tickets from Chicago 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
$259Viva
Find Deal
Mon, Feb 10 - Fri, Feb 14
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$260Viva
Find Deal
Sat, Feb 8 - Thu, Feb 13
6:23 am - 4:55 pmORD-SJD
11h 32m1 stop
5:08 pm - 1:02 amSJD-ORD
6h 54m1 stop
$352Volaris
Find Deal
Tue, Feb 4 - Fri, Feb 14
5:40 pm - 4:23 pmORD-SJD
23h 43m2 stops
8:19 pm - 4:37 amSJD-ORD
7h 18m1 stop
$374Volaris
Find Deal
Fri, Feb 28 - Fri, Mar 7
6:00 am - 12:36 pmMDW-SJD
7h 36m1 stop
1:41 pm - 10:20 pmSJD-MDW
7h 39m1 stop
$515Aeromexico
Find Deal
Mon, Feb 10 - Fri, Feb 14
6:00 am - 5:27 pmMDW-SJD
12h 27m2 stops
6:02 am - 10:20 pmSJD-MDW
15h 18m2 stops
$538Delta
Find Deal
Sun, Feb 23 - Thu, Feb 27
6:00 am - 3:20 pmMDW-SJD
11h 20m2 stops
4:30 pm - 8:45 amSJD-MDW
14h 15m2 stops
$542Delta
Find Deal
Wed, Mar 12 - Tue, Mar 18
5:25 am - 12:50 pmMDW-SJD
9h 25m1 stop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$548Southwest
Find Deal
Sun, Mar 30 - Wed, Apr 2
6:00 am - 12:35 pmMDW-SJD
8h 35m1 stop
6:01 am - 10:29 pmSJD-MDW
14h 28m2 stops
$558Aeromexico
Find Deal
Tue, Apr 29 - Fri, May 2
5:20 am - 11:40 amMDW-SJD
7h 20m1 stop
2:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$573Southwest
Find Deal
Mon, Mar 3 - Fri, Mar 7
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$89Viva
Find Deal
Sun, Feb 16
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
$92Viva
Find Deal
Sat, Feb 22
3:50 pm - 9:30 amORD-SJD
18h 40m1 stop
$93Viva
Find Deal
Fri, Feb 28
1:45 am - 10:13 amORD-SJD
10h 28m1 stop
$123Volaris
Find Deal
Fri, Apr 4
7:25 am - 4:34 pmORD-SJD
11h 09m1 stop
$132Volaris
Find Deal
Wed, May 21
1:59 am - 12:04 pmORD-SJD
12h 05m1 stop
$246Delta
Find Deal
Tue, Apr 15
6:15 am - 6:37 pmORD-SJD
13h 22m2 stops
$251Aeromexico
Find Deal
Tue, Feb 18
6:00 am - 11:33 amMDW-SJD
7h 33m1 stop
$251Delta
Find Deal
Tue, Mar 18
9:00 am - 12:00 pmMDW-SJD
5h 00mnonstop
$266Southwest
Find Deal
Wed, Mar 19
5:50 am - 10:40 amMDW-SJD
6h 50m1 stop
$291Southwest
Find Deal
Fri, Mar 21
3:50 pm - 9:25 amORD-SJD
18h 35m1 stop
4:00 pm - 2:20 pmSJD-ORD
21h 20m1 stop
$260Viva
Find Deal
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
$263Viva
Find Deal
Sun, Jan 19 - Tue, Jan 21
7:50 pm - 7:31 amMDW-SJD
12h 41m1 stop
4:10 pm - 8:45 amSJD-MDW
15h 35m2 stops
$421Volaris
Find Deal
Tue, Jan 21 - Wed, Jan 29
5:40 pm - 12:34 pmORD-SJD
19h 54m2 stops
8:19 pm - 4:00 pmSJD-ORD
18h 41m3 stops
$457Volaris
Find Deal
Sun, Jan 19 - Thu, Jan 23
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$717American Airlines
Find Deal
Sun, Jan 19 - Thu, Jan 23
6:45 pm - 10:18 amORD-SJD
16h 33m1 stop
1:12 pm - 6:32 pmSJD-ORD
4h 20mnonstop
$722American Airlines
Find Deal
Sat, Jan 18 - Wed, Jan 22
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$757United Airlines
Find Deal
Mon, Jan 20 - Sat, Jan 25
5:45 am - 11:41 amORD-SJD
6h 56m1 stop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$762United Airlines
Find Deal
Mon, Jan 20 - Sat, Jan 25
1:03 am - 9:59 amORD-SJD
9h 56m1 stop
6:01 am - 9:15 pmSJD-ORD
14h 14m2 stops
$793Aeromexico
Find Deal
Sun, Jan 19 - Sat, Jan 25
6:15 am - 2:40 pmORD-SJD
9h 25m1 stop
7:13 pm - 3:45 pmSJD-ORD
19h 32m2 stops
$1,081Aeromexico
Find Deal
Sat, Jan 18 - Tue, Jan 21
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:15 pm - 6:30 pmSJD-ORD
4h 15mnonstop
$486American Airlines
Find Deal
Mon, Feb 10 - Fri, Feb 14
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$523United Airlines
Find Deal
Sun, Feb 9 - Thu, Feb 13
8:19 am - 11:04 amORD-SJD
4h 45mnonstop
12:04 pm - 6:19 pmSJD-ORD
4h 15mnonstop
$538American Airlines
Find Deal
Sun, Mar 30 - Wed, Apr 2
8:20 am - 12:10 pmORD-SJD
4h 50mnonstop
1:55 pm - 7:10 pmSJD-ORD
4h 15mnonstop
$553American Airlines
Find Deal
Mon, Feb 10 - Sat, Feb 15
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$557United Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
8:45 am - 11:28 amORD-SJD
4h 43mnonstop
11:52 am - 6:10 pmSJD-ORD
4h 18mnonstop
$558United Airlines
Find Deal
Thu, Apr 10 - Tue, Apr 15
8:05 am - 10:35 amORD-SJD
4h 30mnonstop
12:35 pm - 6:50 pmSJD-ORD
4h 15mnonstop
$563American Airlines
Find Deal
Wed, May 28 - Mon, Jun 2
9:00 am - 1:00 pmMDW-SJD
5h 00mnonstop
1:00 pm - 7:00 pmSJD-MDW
4h 00mnonstop
$628Southwest
Find Deal
Fri, Mar 7 - Mon, Mar 10
9:00 am - 12:00 pmMDW-SJD
5h 00mnonstop
12:40 pm - 6:45 pmSJD-MDW
4h 05mnonstop
$658Southwest
Find Deal
Mon, Mar 31 - Sun, Apr 6
9:04 am - 12:57 pmORD-SJD
4h 53mnonstop
12:49 pm - 5:58 pmSJD-ORD
4h 09mnonstop
$700Austrian Airlines
Find Deal
Sat, Feb 1 - Fri, Feb 28

Viva flights from Chicago to San José del Cabo

Our best Viva deals on Chicago to San José del Cabo flight tickets
Viva
Feb 10
ORD3:50 pmChicago O'Hare Intl
18h 35m
1 stop
SJD9:25 amSan José del Cabo Los Cabos
Feb 14
SJD4:00 pmSan José del Cabo Los Cabos
21h 20m
1 stop
ORD2:20 pmChicago O'Hare Intl
Viva
Feb 8
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
Feb 15
ORD3:50 pmChicago O'Hare Intl
18h 35m
1 stop
SJD9:25 amSan José del Cabo Los Cabos
Feb 22
SJD4:00 pmSan José del Cabo Los Cabos
21h 20m
1 stop
ORD2:20 pmChicago O'Hare Intl

Delta flights from Chicago to San José del Cabo

Our best Delta deals on Chicago to San José del Cabo flight tickets
Delta
Feb 23
MDW6:00 amChicago Midway
12h 27m
2 stops
SJD5:27 pmSan José del Cabo Los Cabos
Feb 27
SJD6:02 amSan José del Cabo Los Cabos
15h 18m
2 stops
MDW10:20 pmChicago Midway
Delta
Mar 12
MDW6:00 amChicago Midway
11h 20m
2 stops
SJD3:20 pmSan José del Cabo Los Cabos
Mar 18
SJD4:30 pmSan José del Cabo Los Cabos
14h 15m
2 stops
MDW8:45 amChicago Midway
Delta
Mar 16
MDW6:00 amChicago Midway
13h 27m
2 stops
SJD5:27 pmSan José del Cabo Los Cabos
Mar 21
SJD4:30 pmSan José del Cabo Los Cabos
14h 15m
2 stops
MDW8:45 amChicago Midway

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 August. Flight prices, which tend to average around $526, 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 August, then July is your next best option. Flight prices from Chicago to San José del Cabo during July average around $530.

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?

You are more likely to see cheaper flights to San José del Cabo from Chicago when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to San José del Cabo for around $580 when searching 6 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 $531 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.

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

As of January 2025, prices for Chicago to San José del Cabo flights are approximately 31% 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

$89

Fastest flight time

5h 00m

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 $89. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $259.
The fastest flight from Chicago to San José del Cabo takes 5h 00m
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 6h 50m.

  • 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
833 reviews
Search Viva flights
VolarisPriceFrom $323Free CancellationRating
6.6
1,249 reviews
Search Volaris flights
DeltaPriceFrom $400Free CancellationRating
8.0
8,511 reviews
Search Delta flights
American AirlinesPriceFrom $404Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $404Free CancellationRating
7.4
8,965 reviews
Search United Airlines flights
AeromexicoPriceFrom $426Free CancellationRating
7.5
1,849 reviews
Search Aeromexico flights
SouthwestPriceFrom $563Free CancellationRating
8.1
4,659 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 $651 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 $597, with deals from around $404 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
Cabo San Lucas
Los Barriles
Todos Santos

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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