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C$114 Cheap Flights from Chicago (CHIA) to Los Cabos International (SJD)

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Flight deals from Chicago to Los Cabos International

Looking for a cheap last-minute deal or the best return flight from Chicago to Los Cabos International Airport? If you want to travel next month, return fares start from C$489. Find the lowest prices on one-way and return tickets right here.
San Jose del Cabo.C$114 per passenger.Departing Sun., Jan. 31.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago O'Hare International on Sun., Jan. 31, arriving in Los Cabos International.Price includes taxes and charges.From C$114, select.
San Jose del Cabo.C$132 per passenger.Departing Fri., Aug. 28.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago O'Hare International on Fri., Aug. 28, arriving in Los Cabos International.Price includes taxes and charges.From C$132, select.
San Jose del Cabo.C$132 per passenger.Departing Wed., Oct. 28.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago O'Hare International on Wed., Oct. 28, arriving in Los Cabos International.Price includes taxes and charges.From C$132, select.
San Jose del Cabo.C$133 per passenger.Departing Mon., Sep. 14.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago O'Hare International on Mon., Sep. 14, arriving in Los Cabos International.Price includes taxes and charges.From C$133, select.
San Jose del Cabo.C$154 per passenger.Departing Sun., Nov. 8.One-way flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sun., Nov. 8, arriving in Los Cabos International.Price includes taxes and charges.From C$154, select.
San Jose del Cabo.C$160 per passenger.Departing Tue., Feb. 2.One-way flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Tue., Feb. 2, arriving in Los Cabos International.Price includes taxes and charges.From C$160, select.
San Jose del Cabo.C$169 per passenger.Departing Wed., Jul. 1.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago O'Hare International on Wed., Jul. 1, arriving in Los Cabos International.Price includes taxes and charges.From C$169, select.
San Jose del Cabo.C$174 per passenger.Departing Wed., Jun. 24.One-way flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago O'Hare International on Wed., Jun. 24, arriving in Los Cabos International.Price includes taxes and charges.From C$174, select.
San Jose del Cabo.C$194 per passenger.Departing Thu., Dec. 3.One-way flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Thu., Dec. 3, arriving in Los Cabos International.Price includes taxes and charges.From C$194, select.
San Jose del Cabo.C$297 per passenger.Departing Mon., Sep. 28.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon., Sep. 28, arriving in Los Cabos International.Price includes taxes and charges.From C$297, select.
San Jose del Cabo.C$413 per passenger.Departing Sun., Nov. 15.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun., Nov. 15, arriving in Los Cabos International.Price includes taxes and charges.From C$413, select.
San Jose del Cabo.C$413 per passenger.Departing Mon., Oct. 5.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon., Oct. 5, arriving in Los Cabos International.Price includes taxes and charges.From C$413, select.
San Jose del Cabo.C$443 per passenger.Departing Sat., Aug. 1.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat., Aug. 1, arriving in Los Cabos International.Price includes taxes and charges.From C$443, select.
San Jose del Cabo.C$448 per passenger.Departing Sat., Dec. 5.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat., Dec. 5, arriving in Los Cabos International.Price includes taxes and charges.From C$448, select.
San Jose del Cabo.C$489 per passenger.Departing Fri., Jan. 15.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri., Jan. 15, arriving in Los Cabos International.Price includes taxes and charges.From C$489, select.
San Jose del Cabo.C$490 per passenger.Departing Thu., Feb. 25.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu., Feb. 25, arriving in Los Cabos International.Price includes taxes and charges.From C$490, select.

Find the cheapest month to fly from Chicago to Los Cabos International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Los Cabos International flights are currently cheapest in January.
Jun.
from C$174
Jul.
from C$169
Aug.
from C$132
Sep.
from C$133
Oct.
from C$132
Nov.
from C$154
Dec.
from C$194
Jan.
from C$114
Feb.
from C$160
Mar.
Find prices
Apr.
Find prices
May
Find prices

Which airlines fly from Chicago to Los Cabos International?

Chicago to Los Cabos International: Alternative routes

Compare routes from Chicago to San Jose del Cabo below. You may find an airport to fly into that's cheaper, faster, or easier than Los Cabos International.

Los Cabos International

12km from central San Jose del Cabo
ClosestCheapest
from C$114
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Chicago to San Jose del Cabo: Flight information

The things to know before you go.
Cheapest flight foundC$114
Cheapest month to flyJanuary
Average flight time4 hrs, 48 mins
Most popular airlineAmerican Airlines
Average flights per week69

Finding cheap flights from Chicago to Los Cabos International: Frequently asked questions

The best price we found for a return flight from Chicago to Los Cabos International is C$358. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 48 minutes is the average flight time from Chicago to Los Cabos International.
American Airlines, United and Emirates fly direct from Chicago to Los Cabos International.
As of June 2026, there are 46 flights per week flying from Chicago to Los Cabos International.
The cheapest month to fly from Chicago to Los Cabos International is usually January.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Los Cabos International Airport on Thursday, January 28, 2027.
Yes – the average flight time is 4 hours and 48 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Los Cabos International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Jose del Cabo is around 40 days in advance, so don’t leave your flight to the last minute.

Flying from Chicago to Los Cabos International Airport (SJD): what you need to know

  • Get your vacation planning started by considering the departure point for your flight from Chicago to Los Cabos International Airport (SJD). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are Chicago's main airports.

  • Jump on a direct flight from Chicago to Los Cabos International Airport and you'll be travelling for around 4 hours 44 minutes.

  • San Jose Cabo is 2 hours behind Chicago. Los Cabos International Airport is located in San Jose Cabo, which operates on the UTC-7 timezone.

  • O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) is the most popular route. There are 16 direct flights a week to choose from. If you prefer a later start to the day, hop on the last flight with United at 11:20. Go for the first ORD to SJD departure with United at 07:21 if you want to get going earlier.

  • Leave enough time to get on your flight from Chicago to SJD. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • Peak months like August or vacation periods such as Thanksgiving and Christmas will mean longer queues at check-in and security. Travelling then? Play it safe and get to the terminal even earlier. Arriving two hours before domestic flights and up four hours ahead of international flights is wise.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) provides a hassle-free way to reach your destination. Nonstop flights from Chicago to Los Cabos International Airport (SJD) operate out of this terminal.

  • You can lock in a direct flight from Chicago to Los Cabos International Airport with American Airlines. This top carrier offers services from ORD.

  • Think about adding a stopover to potentially save money on your flight from Chicago to SJD. Simply deselect 'Direct flights only' when browsing departures from O'Hare International Airport (ORD). Take a pause at one of these popular airports:

    • Lambert-St. Louis International Airport (STL)

    • Dallas/Fort Worth International Airport (DFW)

    • Miguel Hidalgo y Costilla International Airport (GDL)

  • ORD is approximately 40 kilometres from central Chicago. To work out how to get there, use Google Maps. This essential travel app will give you the fastest route and your public transport options.

  • Want a hassle-free start to your break? Stay near O'Hare International Airport. Whether you're catching an early flight from Chicago to Los Cabos International Airport or just don't want to be rushed, these hotels are just the thing:

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) operates direct flights from Chicago to Los Cabos International Airport (SJD).

  • From MDW, direct flights from Chicago to SJD can be booked with American Airlines.

  • Get the most out of your vacation with a stopover on your flight from Chicago to Los Cabos International Airport. Visit friends or family or tick a new city off your list. Whatever your plans, check out these options between Chicago Midway International Airport and SJD:

    • Kansas City International Airport (MCI)

    • Dallas/Fort Worth International Airport (DFW)

    • Phoenix Sky Harbour International Airport (PHX)

  • You can reach MDW from central Chicago in about 21 minutes by car, depending on traffic conditions. The journey by public transport will take roughly 46 minutes to travel the 19 kilometres or so.

  • Get your vacation started early with an additional night away from home. Before catching your flight from Chicago to SJD, unwind in one of these hotels near Chicago Midway International Airport:

About Los Cabos International Airport (SJD)

Getting from Los Cabos International Airport (SJD) to central San Jose Cabo

  • Los Cabos International Airport to the centre of San Jose Cabo takes about 21 minutes in a car. It's approximately 13 kilometres away. See what options are available, such as cabs, car rentals or ride-sharing.

How to find the cheapest flights from Chicago to Los Cabos International Airport (SJD)

  • C$114 is the lowest price we've found for a one-way ticket from Chicago to Los Cabos International Airport. Return flights start from C$358. Prices may vary depending on availability at the time of booking.

  • 1 month is how far you'll want to book ahead to find flight tickets from Chicago to SJD.

  • Organize your trip for October. That's the cheapest month for tickets from Chicago to Los Cabos International Airport. If you're flexible with your travel dates, use the 'Whole month' tool to find the lowest price across each month.

  • Sign into your online account or use the app to create a Price Alert. We'll get in touch straight away if there's a deal you won't want to miss. It doesn't take long, and it'll save you the hassle of looking for flight tickets from Chicago to SJD every day.

  • Customize your trip with filters. Choose the total duration, number of stops, and departure and arrival times to find the ideal flight from Chicago to Los Cabos International Airport. You can also sort the results to see the 'Fastest,' 'Cheapest' or 'Best' options first.

The best time to fly from Chicago to Los Cabos International Airport (SJD)

  • It's time to pick your dates for your flight from Chicago to Los Cabos International Airport. July is the most popular month to visit San Jose Cabo. If you like a quieter vibe, go in May.

  • The warmest month in San Jose Cabo is July, with the temperature ranging between 25ºC and 35ºC. Book your flights from Chicago to SJD in this month if this is the type of weather you enjoy.

  • January sees average temperatures of between 14ºC and 26ºC. Search for cheap flights from Chicago to Los Cabos International Airport sometime around then if you'd rather travel in cooler conditions.

More about San Jose Cabo

Complete your San Jose Cabo trip with a car rental

  • Shut down all those tabs and let us do the hard work for you. We've also got amazing deals on car rentals in San Jose Cabo once you've booked your hotel and cheap flight from Chicago to Los Cabos International Airport. Instantly compare prices all in one place and drive away with the lowest rate in town.

Plan the rest of your trip from Chicago to San Jose del Cabo

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.