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Cheap flights from Chicago to San José del Cabo from $112

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 9/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to San José del Cabo

Cheap round-trip flights

Volaris Logo
1:40 am - 10:09 amORD-SJD
10h 29m1 stop
Volaris Logo
11:07 am - 5:42 amSJD-ORD
16h 35m1 stop
$283Volaris
Find Deal
Mon, Aug 11 - Fri, Aug 22
 Logo
6:55 am - 11:11 amORD-SJD
30h 16m1 stop
 Logo
2:57 pm - 12:15 amSJD-ORD
7h 18m1 stop
Mon, Aug 25 - Fri, Aug 29
Volaris Logo
7:25 am - 7:54 pmORD-SJD
14h 29m1 stop
Volaris Logo
8:37 pm - 12:15 amSJD-ORD
25h 38m2 stops
$290Volaris
Find Deal
Mon, Aug 25 - Fri, Aug 29
 Logo
2:00 am - 11:11 amORD-SJD
11h 11m1 stop
 Logo
8:37 pm - 5:42 amSJD-ORD
31h 05m1 stop
Sat, Aug 16 - Wed, Aug 20
Volaris Logo
1:40 am - 10:09 amORD-SJD
10h 29m1 stop
Volaris Logo
8:37 pm - 5:42 amSJD-ORD
31h 05m1 stop
$312Volaris
Find Deal
Sat, Aug 16 - Wed, Aug 20
Delta Logo
6:04 am - 11:23 amMDW-SJD
7h 19m1 stop
Delta Logo
6:10 am - 9:44 pmSJD-MDW
13h 34m2 stops
$400Delta
Find Deal
Mon, Aug 18 - Fri, Aug 22
Delta Logo
6:04 am - 11:23 amMDW-SJD
7h 19m1 stop
Delta Logo
6:10 am - 9:44 pmSJD-MDW
13h 34m2 stops
$401Delta
Find Deal
Wed, Aug 13 - Wed, Aug 20
Southwest Logo
5:15 am - 8:50 amMDW-SJD
5h 35m1 stop
Southwest Logo
11:55 am - 12:50 amSJD-MDW
10h 55m1 stop
$431Southwest
Find Deal
Mon, Jul 14 - Wed, Jul 16
Southwest Logo
6:50 am - 1:10 pmMDW-SJD
8h 20m2 stops
Southwest Logo
12:40 pm - 12:05 amSJD-MDW
9h 25m1 stop
$436Southwest
Find Deal
Sun, Aug 10 - Fri, Aug 15
Aeromexico Logo
6:00 am - 10:30 pmMDW-SJD
18h 30m2 stops
Aeromexico Logo
7:55 pm - 9:36 pmSJD-MDW
23h 41m2 stops
$546Aeromexico
Find Deal
Fri, Sep 19 - Mon, Sep 22

Delta flights from Chicago to San José del Cabo

Our best Delta deals on Chicago to San José del Cabo flight tickets
Delta
Aug 18
MDW6:04 amChicago Midway
7h 19m
1 stop
SJD11:23 amSan José del Cabo Los Cabos
Aug 22
SJD6:10 amSan José del Cabo Los Cabos
13h 34m
2 stops
MDW9:44 pmChicago Midway
Delta
Aug 13
MDW6:04 amChicago Midway
7h 19m
1 stop
SJD11:23 amSan José del Cabo Los Cabos
Aug 20
SJD6:10 amSan José del Cabo Los Cabos
13h 34m
2 stops
MDW9:44 pmChicago Midway
Delta
Oct 7
MDW6:00 amChicago Midway
10h 49m
2 stops
SJD2:49 pmSan José del Cabo Los Cabos
Oct 14
SJD6:00 amSan José del Cabo Los Cabos
13h 44m
2 stops
MDW9:44 pmChicago Midway

Southwest flights from Chicago to San José del Cabo

Our best Southwest deals on Chicago to San José del Cabo flight tickets
Southwest
Jul 14
MDW5:15 amChicago Midway
5h 35m
1 stop
SJD8:50 amSan José del Cabo Los Cabos
Jul 16
SJD11:55 amSan José del Cabo Los Cabos
10h 55m
1 stop
MDW12:50 amChicago Midway
Southwest
Aug 10
MDW6:50 amChicago Midway
8h 20m
2 stops
SJD1:10 pmSan José del Cabo Los Cabos
Aug 15
SJD12:40 pmSan José del Cabo Los Cabos
9h 25m
1 stop
MDW12:05 amChicago Midway
Southwest
Sep 27
MDW7:40 amChicago Midway
7h 30m
1 stop
SJD1:10 pmSan José del Cabo Los Cabos
Oct 1
SJD12:40 pmSan José del Cabo Los Cabos
8h 40m
1 stop
MDW11:20 pmChicago 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 July. Flight prices, which tend to average around $532, 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 January is your next best option. Flight prices from Chicago to San José del Cabo during January average around $560.

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 $714.

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 $654. 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 $612 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 $552 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?

No. A direct flight is the cheapest option for a flight between Chicago to San José del Cabo.

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

As of July 2025, prices for Chicago to San José del Cabo flights are approximately 35% 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

$112

Fastest flight time

5h 35m

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 $112. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $283.
The fastest flight from Chicago to San José del Cabo takes 5h 35m
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 35m.

  • 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
788 reviews
Search Viva flights
VolarisPriceFrom $311Free CancellationRating
6.7
1,171 reviews
Search Volaris flights
DeltaPriceFrom $356Free CancellationRating
8.0
7,983 reviews
Search Delta flights
American AirlinesPriceFrom $447Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $461Free CancellationRating
7.4
8,861 reviews
Search United Airlines flights
SouthwestPriceFrom $543Free CancellationRating
8.0
4,270 reviews
Search Southwest flights
  • American Airlines Flights From Chicago to San José del Cabo

    American Airlines flight deals from Chicago to San José del Cabo start from $447 round-trip. Over the 1 American Airlines flight for this route in a normal week, average airfare is usually $643 round-trip - but some users have found much cheaper deals with momondo.


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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1 adult
Tue 7/8
Tue 7/15

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