Skyscanner home

Cheap Flights from Chicago to Los Cabos International

Compare Chicago to Los Cabos International flight deals

Find the cheapest month or even day of the year to fly to Los Cabos International

Book the best Los Cabos International fare with no extra fees

Flight deals from Chicago to Los Cabos International Airport

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 $580. Find the lowest prices on one-way and return tickets right here.
San Jose del Cabo.$466 per passenger.Departing Mon, 1 Jun, returning Sun, 7 Jun.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 1 Jun, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 7 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $466, select.
San Jose del Cabo.$523 per passenger.Departing Tue, 3 Nov, returning Thu, 5 Nov.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Tue, 3 Nov, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $523, select.
San Jose del Cabo.$527 per passenger.Departing Sat, 3 Oct, returning Sun, 18 Oct.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 3 Oct, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 18 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $527, select.
San Jose del Cabo.$528 per passenger.Departing Tue, 8 Sep, returning Fri, 25 Sep.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Tue, 8 Sep, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Fri, 25 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $528, select.
San Jose del Cabo.$529 per passenger.Departing Mon, 18 May, returning Sun, 7 Jun.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 18 May, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 7 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $529, select.
San Jose del Cabo.$529 per passenger.Departing Wed, 6 May, returning Fri, 22 May.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Wed, 6 May, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Fri, 22 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $529, select.
San Jose del Cabo.$557 per passenger.Departing Thu, 24 Sep, returning Mon, 12 Oct.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Thu, 24 Sep, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Mon, 12 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $557, select.
San Jose del Cabo.$558 per passenger.Departing Mon, 20 Apr, returning Sun, 10 May.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 20 Apr, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 10 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $558, select.
San Jose del Cabo.$569 per passenger.Departing Mon, 19 Oct, returning Thu, 5 Nov.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 19 Oct, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Thu, 5 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $569, select.
San Jose del Cabo.$580 per passenger.Departing Mon, 20 Apr, returning Wed, 22 Apr.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 20 Apr, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Wed, 22 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $580, select.
San Jose del Cabo.$580 per passenger.Departing Fri, 21 Aug, returning Sat, 29 Aug.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 21 Aug, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sat, 29 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $580, select.
San Jose del Cabo.$588 per passenger.Departing Fri, 21 Aug, returning Sun, 6 Sep.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 21 Aug, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 6 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $588, select.
San Jose del Cabo.$610 per passenger.Departing Sat, 20 Jun, returning Mon, 6 Jul.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 20 Jun, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Mon, 6 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $610, select.
San Jose del Cabo.$654 per passenger.Departing Mon, 13 Jul, returning Mon, 20 Jul.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Mon, 13 Jul, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Mon, 20 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $654, select.
San Jose del Cabo.$694 per passenger.Departing Wed, 29 Jul, returning Mon, 17 Aug.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Wed, 29 Jul, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Mon, 17 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $694, select.
San Jose del Cabo.$760 per passenger.Departing Tue, 24 Mar, returning Sun, 12 Apr.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Tue, 24 Mar, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Sun, 12 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $760, 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 June.
Mar
from $796
Apr
from $580
May
from $529
Jun
from $466
Jul
from $654
Aug
from $580
Sep
from $528
Oct
from $527
Nov
from $523
Dec
from $1,476
Jan
from $1,063
Feb
from $2,610

Direct flights 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 $466
Search flights

Chicago to San Jose del Cabo: Flight information

The things to know before you go.
Cheapest flight found$466
Cheapest month to flyJune
Average flight time4 hrs, 52 mins
Most popular airlineAmerican Airlines
Average flights per week30

Check out these San Jose del Cabo hotels

Ready to plan your stay? Other travellers rate these San Jose del Cabo hotels for cleanliness, service and location.
Punto Nima Luxury Condos
2.58 km from city centre
$1,225
Per night
Suites Lomboy & Plaza
8.95 km from city centre
$200
Per night
Flamboyan Hotel & Residences
0.13 km from city centre
$341
Per night
Punto Nima Luxury Condos
2.58 km from city centre
$1,225
Per night
Suites Lomboy & Plaza
8.95 km from city centre
$200
Per night
Flamboyan Hotel & Residences
0.13 km from city centre
$341
Per night
Explore top-rated hotels

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 $466. 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 52 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 March 2026, there are 30 flights per week flying from Chicago to Los Cabos International.
The cheapest month to fly from Chicago to Los Cabos International is usually June.
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 Monday, 1 June 2026.
Yes – the average flight time is 4 hours and 52 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.

Travelling from Chicago to Los Cabos International Airport (SJD): What you need to know

  • Start your holiday planning by considering where you'll take off for your flight from Chicago to Los Cabos International Airport (SJD). Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.

  • Hop on a direct Chicago to Los Cabos International Airport flight and you'll be travelling for around 4 hours 50 minutes.

  • The timezone in San Jose del Cabo is UTC-7, which is one hour behind Chicago. Los Cabos International Airport is located in San Jose del Cabo.

  • The most popular route is from Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD), with 14 direct weekly services. If you're looking to take off without delay, the earliest flight from ORD to SJD is the 7:30am United Airlines option. If you prefer to leave later in the day, the last departure is at 11:20am with United Airlines.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules worth sticking to. Make sure you're at the airport on time to board your flight from Chicago to SJD.

  • Popular months like July or high seasons such as Christmas and New Year will mean bigger queues at check-in and security. Play it safe and get to the airport even earlier. Arriving two hours before domestic flights and up four hours ahead of an international flight is a wise move.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Go straight to your destination from Chicago O'Hare International Airport (ORD). Direct flights from Chicago to Los Cabos International Airport (SJD) operate from here.

  • You'll find a direct flight from Chicago to Los Cabos International Airport with American Airlines. This popular carrier operates departures from ORD.

  • Most travellers choose to book seats with American Airlines between ORD and SJD.

  • Among carriers operating on this route, American Airlines leads the way for on-time arrivals.

  • We make it easy to find cheap flights from Chicago to SJD that include a stopover. To explore your options departing from Chicago O'Hare International Airport (ORD), deselect 'Direct flights only.' Next, select a flight with a stop long enough to tour your chosen city. Top stopovers between ORD and SJD include:

    • Dallas Fort Worth International Airport (DFW)

    • Miguel Hidalgo y Costilla Guadalajara Intl Airport (GDL)

    • St Louis Lambert International Airport (STL)

  • ORD is around 27 kilometres from central Chicago. If you're ride-sharing, catching a taxi or driving from the centre, it'll take 30 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the trip time to be around 45 minutes.

  • Catching an early flight from Chicago to Los Cabos International Airport? Avoid rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels close to Chicago O'Hare International Airport:

  • Of the departures from Chicago O'Hare International Airport, 75% land on time at their destination.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can book a direct Chicago to Los Cabos International Airport (SJD) plane ticket out of Chicago Midway International Airport (MDW). Decide if leaving from MDW is a better fit for your trip.

  • Southwest Airlines operates direct flights from Chicago to SJD out of MDW. Book your favourite window (or aisle) seat and reach your destination without any detours.

  • Southwest Airlines is the top choice for passengers flying from MDW to SJD.

  • Go with Southwest Airlines for the most punctual service. Its flights between Chicago Midway International Airport and Los Cabos International Airport touch down as scheduled 100.0% of the time.

  • Tick a new place off your list or just take a moment to reset with a stopover. If you'd like to split up your flight from Chicago to Los Cabos International Airport, check out these options when heading out from Chicago Midway International Airport:

    • Denver International Airport (DEN)

    • Phoenix Sky Harbour International Airport (PHX)

    • Houston Hobby Airport (HOU)

  • On public transport, you can travel from central Chicago to MDW in around 30 minutes. The airport is roughly 16 kilometres away, and making the trip by car will take approximately 25 minutes.

  • Want to treat yourself to an extra night away before your Chicago to SJD flight? Relax in a hotel near Chicago Midway International Airport before your trip officially starts. These stays are calling your name:

  • 77% of flights departing Chicago Midway International Airport arrive within the expected time frame.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • When booking your plane ticket from Chicago to Los Cabos International Airport (SJD) out of Chicago Rockford International Airport (RFD), you have stopover options to choose from. Make a pit stop at Los Angeles International Airport (LAX), one of the most popular transit hubs on this route.

  • From central Chicago, RFD is around 145 kilometres away. It'll take you roughly 1 hour 40 minutes to reach the airport by car and 2 hours or so on public transport.

  • Make catching an early Chicago to Los Cabos International Airport flight the easiest part of your trip. Stay at one of these accommodation options near Chicago Rockford International Airport and get to your departure gate with plenty of time to spare:

  • Flights that leave from RFD touch down at their destination as scheduled 76% of the time.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Los Cabos International Airport (SJD)

  • If you're arriving on a late flight from Chicago to Los Cabos International Airport, nothing tops the convenience of staying near the terminal. Grab your luggage from the carousel and then be showered and resting soon after at one of these hotels near SJD:

  • Get on the fast track to adventure by picking up a Los Cabos International Airport rental car. Grab your wheels from America, MEX or Europcar to explore San Jose del Cabo and beyond.

  • Lock in the best rate by reserving your vehicle around two weeks ahead of your Chicago to Los Cabos International Airport flight.

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

  • Los Cabos International Airport is around 8 kilometres from the centre of San Jose del Cabo. It takes around 15 minutes or so to drive to the city.

  • It takes around 25 minutes to get there using public transport.

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

  • Currently, $187 is the best price we've found for a one-way ticket from Chicago to Los Cabos International Airport. The cheapest price for a return flight is $466. Keep in mind fares may change due to demand at the time of booking.

  • Book five months before you travel. Pricing trends show that this is the ideal window for finding cheap flights from Chicago to SJD.

  • October is when you're most likely to land a good deal on a Chicago to Los Cabos International Airport ticket. If you need to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • There's no need to check every day to find out if fares have dropped when you create a Price Alert. We'll let you know as soon as a better deal is available on plane tickets from Chicago to SJD.

  • Bag the best deal on a flight from Chicago to Los Cabos International Airport with the help of the filters. Pick your preferred departure and arrival times, number of stops and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest.'

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

  • It's time to work out when to book your flight from Chicago to Los Cabos International Airport (SJD). March is when most people travel to San Jose del Cabo. If you like things a bit more low-key, go in September.

  • The warmest month in San Jose del Cabo is July, with temperatures ranging between 25ºC and 35ºC. Book your Chicago to SJD plane ticket then if you enjoy this type of weather.

  • Look for cheap tickets from Chicago to Los Cabos International Airport in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between 14ºC and 26ºC.

More about San Jose del Cabo

Explore more of Mexico

  • You've seen San Jose del Cabo, now it's time to discover other parts of Mexico. Travel about 129 kilometres northwest to La Paz to tick off its top attractions. From Cabo Adventures Sea of Cortez Adventures to Balandra Beach and Malecon, there's plenty to keep you busy.

  • Around 290 kilometres northwest of San Jose del Cabo, Ciudad Constitucion is another essential stop in Mexico. Experience major highlights starting with Santuario de Nuestra Señora de Guadalupe, Valle Del Paraiso Park and St. Jude Thaddeus Church.

More travel options

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 45 days.