Cheap flights from Chicago (CHI) to Los Cabos

CHI — SJD
May 21 — May 281

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

Find a great deal and save up to 12% by booking at least 31 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Los Cabos within the next two weeks, with the cheapest ticket starting at $540.

What is the cheapest month to fly from Chicago to Los Cabos?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to Los Cabos. Flights to Los Cabos from Chicago in August are about $474 on average during August, but can be found for as low as $314.

When is the cheapest time to fly from Chicago to Los Cabos (CHI - KPG)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Los Cabos as you normally would.

Cheap flights from Chicago to Los Cabos in May, June 2022

The best prices found for CHI to Los Cabos flights for May, June
Jun 3 - Jun 7
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

3 stops

26h 54m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

13h 50m
$382

Multiple Airlines

View Deal

Deal found 14/5/22

Jun 3 - Jun 11
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

3 stops

36h 24m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

15h 49m
$420

Multiple Airlines

View Deal

Deal found 15/5/22

Jun 20 - Jun 24
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

Nonstop

4h 38m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

12h 21m
$427

Multiple Airlines

View Deal

Deal found 14/5/22

Chicago to Los Cabos 2022 flight deals

Cheap flights to Los Cabos from Chicago found for this year
Nov 12 - Nov 16
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

18h 09m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

13h 10m
$267

Volaris

View Deal

Deal found 13/5/22

Nov 7 - Nov 10
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

14h 20m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

8h 10m
$271

VivaAerobus

View Deal

Deal found 15/5/22

Oct 22 - Oct 26
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

16h 40m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

8h 10m
$279

VivaAerobus

View Deal

Deal found 13/5/22

Cheap Volaris flights from Chicago to Los Cabos

Nov 12 - Nov 16
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

18h 09m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

13h 10m
$267

Volaris

View Deal

Deal found 13/5/22

Oct 31 - Nov 9
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

13h 51m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

13h 10m
$282

Volaris

View Deal

Deal found 13/5/22

Oct 31 - Nov 9
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

13h 51m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

13h 10m
$283

Volaris

View Deal

Deal found 14/5/22

Cheap VivaAerobus flights from Chicago to Los Cabos

Nov 7 - Nov 10
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

14h 20m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

8h 10m
$271

VivaAerobus

View Deal

Deal found 15/5/22

Oct 22 - Oct 26
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

16h 40m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

8h 10m
$279

VivaAerobus

View Deal

Deal found 13/5/22

Oct 15 - Oct 18
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

16h 40m
SJD

San José del Cabo Los Cabos

ORD

Chicago O'Hare Intl

1 stop

24h 20m
$285

VivaAerobus

View Deal

Deal found 15/5/22

Last minute flights from Chicago to Los Cabos

Late deals on return flights to Los Cabos from Chicago, departing today and this week
May 24 - May 28
MDW

Chicago Midway

SJD

San José del Cabo Los Cabos

1 stop

15h 29m
SJD

San José del Cabo Los Cabos

MDW

Chicago Midway

1 stop

6h 46m
$738

Volaris

View Deal

Deal found 13/5/22

May 21 - May 28
MDW

Chicago Midway

SJD

San José del Cabo Los Cabos

2 stops

30h 26m
SJD

San José del Cabo Los Cabos

MDW

Chicago Midway

2 stops

11h 19m
$891

Aeromexico

View Deal

Deal found 14/5/22

May 22 - May 29
MDW

Chicago Midway

SJD

San José del Cabo Los Cabos

2 stops

12h 34m
SJD

San José del Cabo Los Cabos

MDW

Chicago Midway

2 stops

11h 24m
$1,064

Aeromexico

View Deal

Deal found 15/5/22

One-way flights to Los Cabos from Chicago

The cheapest one-way flights from Chicago to Los Cabos
Oct 17
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

21h 55m
$109

VivaAerobus

View Deal

Deal found 14/5/22

Oct 31
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

13h 51m
$114

Volaris

View Deal

Deal found 16/5/22

Oct 16
ORD

Chicago O'Hare Intl

SJD

San José del Cabo Los Cabos

1 stop

21h 55m
$115

VivaAerobus

View Deal

Deal found 14/5/22

Related info for your journey

Useful info, stats and facts about Chicago to Los Cabos flights.

Which airlines flying from Chicago to Los Cabos have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Los Cabos that may be offering flexible cancellation policies are American Airlines, United Airlines, and Interjet. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Los Cabos for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Los Cabos for under $300. The cheapest flight booked recently is on Volaris for just $267, but on average you can expect to pay $288.

Are there last-minute flights available from Chicago to Los Cabos for under $800?

There are currently 20+ open flights from Chicago to Los Cabos within the next 7 days for less than $800.

What are the cheapest airlines to fly from Chicago to Los Cabos one-way?

To fly one-way, consider booking your trip with VivaAerobus, which is currently one of the cheapest options available, starting at $109. Volaris flights start at $114 while deals on Spirit Airlines start at $195 one-way.

What are the most popular airlines that fly from Chicago to Los Cabos?

The most popular airlines flying from Chicago to Los Cabos are Interjet, Major Airline and American Airlines. Something to consider prior to booking your flight.

What are the most reliable airlines from Chicago to Los Cabos?

Before booking your flight to Los Cabos from Chicago, check out the most reliable airlines to get you to your destination on time: Qatar Airways (96%), United Airlines (90%), American Airlines( 83%).

What are the cheapest flights from Chicago to Los Cabos?

Looking for the cheapest flight from Chicago to Los Cabos? While on average our users pay $822, our data indicates the cheapest price to be $116. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $279.

Alternative routes for Chicago to Los Cabos

See prices for flight routes from nearby airports that may be better suited for you.

Destination points for flights from Chicago to Los Cabos

Select to see more specific information for flights from Chicago to all places in Los Cabos

Top 5 airlines flying from Chicago to Los Cabos

The chart below displays the airlines Cheapflights users traveling from Chicago to Los Cabos choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$20FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
FrontierCheapest$122Average$183FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
Spirit AirlinesCheapest$129Average$250FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
VolarisCheapest$180Average$333FlexibilityNo cancel feeOn-time79%COVID-19 safety
Search Volaris flights
Alaska AirlinesCheapest$195Average$655FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights

Hourly flight availability from Chicago to Los Cabos

See what time of day planes typically take off from Chicago to Los Cabos
0%of flight departuresEarly morningMidnight to 6 am
70%of flight departuresMorning6 am to noon
30%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM