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Cheap Flights from Chicago Midway to Los Cabos International

Compare Chicago Midway to Los Cabos International flight deals

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

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Flight deals from Chicago Midway Airport to Los Cabos International Airport

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Los Cabos International Airport? If you want to travel next month, return fares start from R 8,026. Find the lowest prices on one-way and return tickets right here.
San Jose del Cabo.R 3,418 per passenger.Departing Tue, 5 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 5 May, arriving in Los Cabos International.Price includes taxes and charges.From R 3,418, select.
San Jose del Cabo.R 3,601 per passenger.Departing Wed, 15 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 15 Apr, arriving in Los Cabos International.Price includes taxes and charges.From R 3,601, select.
San Jose del Cabo.R 4,392 per passenger.Departing Wed, 19 Aug.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 19 Aug, arriving in Los Cabos International.Price includes taxes and charges.From R 4,392, select.
San Jose del Cabo.R 4,636 per passenger.Departing Mon, 23 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 23 Mar, arriving in Los Cabos International.Price includes taxes and charges.From R 4,636, select.
San Jose del Cabo.R 5,058 per passenger.Departing Sun, 5 Jul.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 5 Jul, arriving in Los Cabos International.Price includes taxes and charges.From R 5,058, select.
San Jose del Cabo.R 5,480 per passenger.Departing Thu, 18 Jun.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 18 Jun, arriving in Los Cabos International.Price includes taxes and charges.From R 5,480, select.
San Jose del Cabo.R 5,999 per passenger.Departing Sun, 22 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 22 Mar, arriving in Los Cabos International.Price includes taxes and charges.From R 5,999, select.
San Jose del Cabo.R 6,582 per passenger.Departing Fri, 5 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 5 Feb, arriving in Los Cabos International.Price includes taxes and charges.From R 6,582, select.
San Jose del Cabo.R 7,744 per passenger.Departing Fri, 4 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 4 Dec, arriving in Los Cabos International.Price includes taxes and charges.From R 7,744, select.
San Jose del Cabo.R 13,503 per passenger.Departing Thu, 15 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 15 Oct, arriving in Los Cabos International.Price includes taxes and charges.From R 13,503, select.

Find the cheapest month to fly from Chicago Midway 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 Midway to Los Cabos International flights are currently cheapest in May.
Mar
from R 4,646
Apr
from R 3,608
May
from R 3,424
Jun
from R 5,490
Jul
from R 5,068
Aug
from R 4,401
Sep
Find prices
Oct
from R 13,530
Nov
Find prices
Dec
from R 7,760
Jan
Find prices
Feb
from R 6,595

Direct flights from Chicago Midway to Los Cabos International

Chicago Midway to Los Cabos International: Alternative routes

Compare routes from Chicago Midway 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 R 3,424
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Chicago to San Jose del Cabo: Flight information

The things to know before you go.
Cheapest flight foundR 3,418
Cheapest month to flyMay
Average flight time4 hrs, 56 mins
Most popular airlineSouthwest Airlines
Average flights per week6

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

The best price we found for a return flight from Chicago Midway to Los Cabos International is R 8,026. 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 56 minutes is the average flight time from Chicago Midway to Los Cabos International.
Southwest Airlines flies direct from Chicago Midway to Los Cabos International.
As of March 2026, there are 6 flights per week flying from Chicago Midway to Los Cabos International.
The cheapest month to fly from Chicago Midway to Los Cabos International is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Los Cabos International Airport on Wednesday, 15 April 2026.
Yes – the average flight time is 4 hours and 56 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.
Currently, Delta and Southwest Airlines offer the cheapest flight tickets to Los Cabos International.

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

  • The average duration of a direct flight from Chicago Midway International Airport to Los Cabos International Airport is 5 hours 5 minutes.

  • The timezone in San Jose Cabo is UTC-7, which is two hours behind Chicago.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This way, you can comfortably board your MDW to SJD flight.

  • Flying during a peak time such as July? Public holidays and other high seasons can mean longer queues at security. Be extra cautious and get there up to four hours ahead of an international flight and two hours before a domestic departure.

  • Southwest Airlines offers direct flights from Chicago Midway International Airport to Los Cabos International Airport. Book with this popular carrier, then get ready to check out the sights in San Jose Cabo — and maybe even more of Mexico if you have time.

  • The airline with the highest booking volume on this route is Southwest Airlines.

  • Among carriers operating MDW to SJD flights, Southwest Airlines has the best track record for timely arrivals.

  • Think about adding a stopover when booking your ticket from Chicago Midway International Airport to Los Cabos International Airport. Just uncheck 'Direct flights only' to break up your journey, or even explore someplace new along the way. Check out these options between MDW and SJD:

    • William P. Hobby Airport

    • Denver International Airport

    • Phoenix Sky Harbour International Airport

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

  • The lowest price we've found for a one-way Chicago Midway International Airport to Los Cabos International Airport flight is R 3,424. A return ticket is currently R 8,026. Depending on the availability when you book, these fares could change.

  • To score cheap tickets from MDW to SJD, reserve your journey ten months before your departure date.

  • The cheapest month for flights from Chicago Midway International Airport to Los Cabos International Airport is September. Use the 'Whole month' tool to find the lowest prices if you have a flexible schedule.

  • Picking up cheap flights from MDW to SJD is a piece of cake with Price Alerts. Simply set up one of these automatic alerts and we'll get in touch as soon as a new deal comes up.

  • Pick your preferred departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to see the best deals on flights from Chicago Midway International Airport to Los Cabos International Airport.

Handy information about Chicago Midway International Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway International Airport, data shows 77.88% of flights meet their scheduled arrival time.

  • To get to Chicago Midway International Airport from central Chicago, it takes around 20 minutes if you're going by car. Of course, this depends on traffic conditions. It's approximately 19 kilometres from the airport to the city centre.

  • The trip when using public transport typically takes 45 minutes.

  • Catching an early flight from Chicago Midway International Airport to Los Cabos International Airport? Avoid the stress of rushing to the terminal (and catch some extra z's) by choosing one of these hotels close to MDW:

Arriving at 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 has a drive time of around 20 minutes. It's approximately 13 kilometres away.

When to fly to Los Cabos International Airport (SJD)

  • It's time to pick your trip dates for your flight from Chicago Midway International Airport to Los Cabos International Airport. January is the busiest month to head to San Jose Cabo. If you're after a quieter vibe, go in May.

  • When booking your flight from Chicago Midway International Airport to Los Cabos International Airport, think about the kind of weather you like. July is the warmest month in San Jose Cabo, with the temperature ranging from 25ºC (77ºF) to 35ºC (95ºF).

  • January has average temperatures of between 14ºC (57ºF) and 26ºC (79ºF). Look for cheap tickets from MDW to SJD sometime around then if you like travelling in cooler conditions.

Explore more of Mexico

  • Culiacan is just one of the many places in Mexico waiting to be explored once you've seen the sights of San Jose Cabo. Around 306 kilometres away to the north-east, its top attractions include Catedral Basilica De Nuestra Senora Del Rosario, Tren turistico Parque las riberas and MASIN Museo de Arte de Sinaloa.

  • If there's time to check out another great destination in Mexico, consider Mazatlan, about 338 kilometres east of San Jose Cabo. Malecon, El Faro Lighthouse and Immaculate Conception Cathedral are key reasons to visit.

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.