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Cheap flights from Chicago to Los Cabos from $104

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 Los Cabos departing on 1/18. 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 Los Cabos

Cheap round-trip flights

Enter your travel dates to find the best prices.
Volaris Logo
6:23 am - 3:20 pm
ORD
-
SJD
9h 57m1 stop
Volaris Logo
4:08 pm - 4:36 am
SJD
-
ORD
11h 28m1 stop
$382Volaris
Fri, Feb 6 - Wed, Feb 11
Viva Logo
12:55 am - 4:30 pm
ORD
-
SJD
16h 35m1 stop
Viva Logo
5:05 pm - 11:25 pm
SJD
-
ORD
29h 20m1 stop
$383Viva
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
11:59 pm - 11:30 am
ORD
-
SJD
12h 31m1 stop
Multiple Airlines Logo
8:30 am - 2:53 pm
SJD
-
ORD
29h 23m2 stops
$384Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Viva Logo
1:20 am - 8:00 am
ORD
-
SJD
7h 40m1 stop
Viva Logo
8:30 am - 11:50 pm
SJD
-
ORD
14h 20m1 stop
$387Viva
Fri, Jan 9 - Wed, Jan 21
Volaris Logo
6:23 am - 3:20 pm
ORD
-
SJD
9h 57m1 stop
Volaris Logo
4:08 pm - 4:36 am
SJD
-
ORD
11h 28m1 stop
$388Volaris
Tue, Jan 20 - Sun, Jan 25
Delta Logo
6:00 am - 5:36 pm
MDW
-
SJD
12h 36m2 stops
Delta Logo
6:05 am - 10:22 pm
SJD
-
MDW
15h 17m2 stops
$430Delta
Mon, Jan 26 - Fri, Jan 30
Aeromexico Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m1 stop
Aeromexico Logo
6:05 am - 10:22 pm
SJD
-
MDW
15h 17m2 stops
$434Aeromexico
Sun, Jan 25 - Wed, Jan 28
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m2 stops
Delta Logo
4:56 pm - 9:06 am
SJD
-
MDW
15h 10m2 stops
$435Delta
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
6:15 am - 1:10 pm
MDW
-
SJD
7h 55m1 stop
Southwest Logo
2:35 pm - 10:55 pm
SJD
-
MDW
7h 20m1 stop
$442Southwest
Tue, Feb 24 - Tue, Mar 3
Aeromexico Logo
6:25 am - 1:14 pm
MDW
-
SJD
8h 49m1 stop
Aeromexico Logo
6:05 am - 10:31 pm
SJD
-
MDW
14h 26m2 stops
$455Aeromexico
Wed, Mar 11 - Thu, Mar 12

Alaska Airlines flights from Chicago to Los Cabos

Our best Alaska Airlines deals on Chicago to Los Cabos flight tickets
Alaska Airlines
Jan 26
ORD2:06 pmChicago O'Hare Intl
23h 09m
1 stop
SJD12:15 pmSan José del Cabo Los Cabos
Jan 29
SJD11:42 amSan José del Cabo Los Cabos
10h 55m
1 stop
ORD11:37 pmChicago O'Hare Intl
$406
Find similar
Alaska Airlines
Jan 18
ORD3:44 pmChicago O'Hare Intl
22h 22m
1 stop
SJD1:06 pmSan José del Cabo Los Cabos
Jan 22
SJD11:42 amSan José del Cabo Los Cabos
10h 55m
1 stop
ORD11:37 pmChicago O'Hare Intl
$408
Find similar
Alaska Airlines
Jan 18
ORD3:44 pmChicago O'Hare Intl
22h 22m
1 stop
SJD1:06 pmSan José del Cabo Los Cabos
Jan 25
SJD11:42 amSan José del Cabo Los Cabos
10h 55m
1 stop
ORD11:37 pmChicago O'Hare Intl
$409
Find similar

United Airlines flights from Chicago to Los Cabos

Our best United Airlines deals on Chicago to Los Cabos flight tickets
United Airlines
Feb 4
ORD9:05 amChicago O'Hare Intl
4h 58m
SJD1:03 pmSan José del Cabo Los Cabos
Feb 10
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
$415
Find similar
United Airlines
Jan 10
ORD9:11 amChicago O'Hare Intl
4h 58m
SJD1:09 pmSan José del Cabo Los Cabos
Jan 21
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
$500
Find similar
United Airlines
Jan 10
ORD9:11 amChicago O'Hare Intl
4h 58m
SJD1:09 pmSan José del Cabo Los Cabos
Jan 17
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
$545
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Los Cabos that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 28, 2025.
Use the filters below to find and compare flights from Chicago to Los Cabos that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/6

6:23 am-3:20 pm

1 stop9h 57m

San José del Cabo Los Cabos

Wed 2/11

4:08 pm-4:36 am

1 stop11h 28m

$382

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/5

12:55 am-4:30 pm

1 stop16h 35m

San José del Cabo Los Cabos

Sun 2/8

5:05 pm-11:25 pm

1 stop29h 20m

$383

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/17

11:59 pm-11:30 am

1 stop12h 31m

San José del Cabo Los Cabos

Sat 1/24

8:30 am-2:53 pm

2 stops29h 23m

$384

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/9

1:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

Wed 1/21

8:30 am-11:50 pm

1 stop14h 20m

$387

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/20

6:23 am-3:20 pm

1 stop9h 57m

San José del Cabo Los Cabos

Sun 1/25

4:08 pm-4:36 am

1 stop11h 28m

$388

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/26

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

Fri 1/30

6:05 am-10:22 pm

2 stops15h 17m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Wed 1/28

6:05 am-10:22 pm

2 stops15h 17m

$434

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/17

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 2/24

4:56 pm-9:06 am

2 stops15h 10m

$435

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

6:15 am-1:10 pm

1 stop7h 55m

San José del Cabo Los Cabos

Tue 3/3

2:35 pm-10:55 pm

1 stop7h 20m

$442

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 3/11

6:25 am-1:14 pm

1 stop8h 49m

San José del Cabo Los Cabos

Thu 3/12

6:05 am-10:31 pm

2 stops14h 26m

$455

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Los Cabos from

How to get the cheapest flight ticket from Chicago to Los Cabos

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 Los Cabos?

The month of September is, on average, the cheapest month to fly to Los Cabos from Chicago, with most prices found around $482. The month of August is another great option to travel to Los Cabos, with average flight prices from Chicago averaging around $543.

What is the cheapest day to depart on your flight to Los Cabos?

The cheapest day to depart from Chicago to Los Cabos is on a Tuesday. Travelers who choose to depart for Los Cabos on a Tuesday will often find tickets for as low as $586. 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 $690.

What is the cheapest Chicago to Los Cabos flight route?

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

How far in advance should I book a flight to Los Cabos?

You are more likely to see cheaper flights to Los Cabos from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Los Cabos for around $601 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Los Cabos from Chicago for as low as $548 on momondo.

What cabin class options are available on Chicago to Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago to 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 Los Cabos flights?

No. A direct flight is the cheapest option for a flight between Chicago to Los Cabos.

Cheap Chicago to Los Cabos flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Los Cabos

Fastest flight time

4h 36m

Direct flights

Every day

Airports in Los Cabos

2 airports
The fastest flight from Chicago to Los Cabos takes 4h 36m
Direct flights go from Chicago to Los Cabos every day.
There are 2 airports in Los Cabos. From Chicago there are direct flights to San José del Cabo Los Cabos (SJD).
Search flight deals

  • When did momondo last update prices for flights from Chicago to Los Cabos?

    Prices for flights from Chicago to Los Cabos are updated daily.

  • How many operators does momondo search for flights from Chicago to Los Cabos?

  • How old do you have to be to fly from Chicago to Los Cabos?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Los Cabos.

  • What documentation or ID do you need to fly to Los Cabos?

    The necessary travel and health documents for your Los Cabos trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Los Cabos?

Best airlines flying from Chicago to Los Cabos

Compare and see reviews for airlines that fly from Chicago to Los Cabos with momondo
Airline
Rating
Free Cancellation
Price
VivaPriceFrom $268Free CancellationRating
7.0
803 reviews
Search Viva flights
VolarisPriceFrom $289Free CancellationRating
6.6
1,166 reviews
Search Volaris flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,016 reviews
Search Delta flights
American AirlinesPriceFrom $417Free CancellationRating
7.2
11,071 reviews
Search American Airlines flights
United AirlinesPriceFrom $421Free CancellationRating
7.4
9,114 reviews
Search United Airlines flights
SouthwestPriceFrom $485Free CancellationRating
8.0
4,250 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Los Cabos?

Finding the right flight to Los Cabos from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Los Cabos quick and easy, saving you time and money.

Can I find flights from Chicago to Los Cabos with flexible booking policies on momondo?

Yes. All flights to Los Cabos from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Los Cabos?

momondo provides multiple filters to help you find the best flight to Los Cabos from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Los Cabos right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Los Cabos flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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