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434 € Cheap Flights from Chicago Midway to Los Cabos International

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      Travellers and cabin class, 1 Adult, Economy

      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

      Book the best Los Cabos International fare with no extra fees

      Flight deals from Chicago Midway to Los Cabos International

      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 506 €. Find the lowest prices on one-way and return tickets right here.
      San Jose del Cabo.434 € per passenger.Departing Sun, 13 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 13 Sep, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 434 €, select.
      San Jose del Cabo.434 € per passenger.Departing Sun, 13 Sep, returning Fri, 18 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 13 Sep, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Fri, 18 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 434 €, select.
      San Jose del Cabo.469 € per passenger.Departing Fri, 23 Oct, returning Tue, 27 Oct.Return flight with Volaris and Viva.Outbound indirect flight with Volaris, departs from Chicago Midway on Fri, 23 Oct, arriving in Los Cabos International.Inbound indirect flight with Viva, departs from Los Cabos International on Tue, 27 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 469 €, select.
      San Jose del Cabo.490 € per passenger.Departing Wed, 29 Jul, returning Sat, 15 Aug.Return flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago Midway on Wed, 29 Jul, arriving in Los Cabos International.Inbound indirect flight with Volaris, departs from Los Cabos International on Sat, 15 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 490 €, select.
      San Jose del Cabo.497 € per passenger.Departing Tue, 25 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 25 Aug, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 497 €, select.
      San Jose del Cabo.499 € per passenger.Departing Tue, 17 Nov, returning Tue, 24 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 17 Nov, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Tue, 24 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 499 €, select.
      San Jose del Cabo.504 € per passenger.Departing Sat, 18 Jul, returning Sat, 25 Jul.Return flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago Midway on Sat, 18 Jul, arriving in Los Cabos International.Inbound indirect flight with Volaris, departs from Los Cabos International on Sat, 25 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 504 €, select.
      San Jose del Cabo.506 € per passenger.Departing Sun, 9 Aug, returning Thu, 27 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 9 Aug, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Thu, 27 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 506 €, select.
      San Jose del Cabo.526 € per passenger.Departing Thu, 3 Dec, returning Wed, 9 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 3 Dec, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Wed, 9 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 526 €, select.
      San Jose del Cabo.547 € per passenger.Departing Sun, 14 Mar, returning Thu, 18 Mar.Return flight with Volaris.Outbound indirect flight with Volaris, departs from Chicago Midway on Sun, 14 Mar, arriving in Los Cabos International.Inbound indirect flight with Volaris, departs from Los Cabos International on Thu, 18 Mar, arriving in Chicago Midway.Price includes taxes and charges.From 547 €, select.
      San Jose del Cabo.562 € per passenger.Departing Wed, 20 Jan, returning Wed, 27 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 20 Jan, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Wed, 27 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 562 €, select.
      San Jose del Cabo.581 € per passenger.Departing Mon, 3 May, returning Fri, 7 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 3 May, arriving in Los Cabos International.Inbound indirect flight with Delta, departs from Los Cabos International on Fri, 7 May, arriving in Chicago Midway.Price includes taxes and charges.From 581 €, select.
      San Jose del Cabo.603 € per passenger.Departing Wed, 24 Feb, returning Mon, 1 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 24 Feb, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Mon, 1 Mar, arriving in Chicago Midway.Price includes taxes and charges.From 603 €, select.
      San Jose del Cabo.607 € per passenger.Departing Sat, 20 Feb, returning Sat, 27 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 20 Feb, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Sat, 27 Feb, arriving in Chicago Midway.Price includes taxes and charges.From 607 €, select.
      San Jose del Cabo.607 € per passenger.Departing Fri, 30 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 30 Oct, arriving in Los Cabos International.Inbound indirect flight with Southwest Airlines, departs from Los Cabos International on Mon, 2 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 607 €, select.
      San Jose del Cabo.642 € per passenger.Departing Thu, 25 Mar, returning Thu, 8 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 25 Mar, arriving in Los Cabos International.Inbound indirect flight with Delta, departs from Los Cabos International on Thu, 8 Apr, arriving in Chicago Midway.Price includes taxes and charges.From 642 €, 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 September.
      Jul
      from 504 €
      Aug
      from 506 €
      Sep
      from 434 €
      Oct
      from 469 €
      Nov
      from 499 €
      Dec
      from 526 €
      Jan
      from 562 €
      Feb
      from 607 €
      Mar
      from 547 €
      Apr
      from 3.590 €
      May
      from 581 €
      Jun
      Find prices

      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 434 €
      Search flights

      Chicago to San Jose del Cabo: Flight information

      The things to know before you go.
      Cheapest flight found434 €
      Cheapest month to flySeptember

      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 434 €. 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.
      Currently, there are no airlines that fly direct from Chicago Midway to Los Cabos International. But we found flights with one or more stops from 434 €.
      As of July 2026, there are no flights flying from Chicago Midway to Los Cabos International.
      The cheapest month to fly from Chicago Midway to Los Cabos International is usually September.
      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 Sunday, 13 September 2026.
      No airlines currently offer direct flights between Chicago Midway Airport and Los Cabos International Airport. Most routes have one or more stops.
      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, Southwest Airlines offers the cheapest flight tickets to Los Cabos International.

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

      • Around 4 hours 55 minutes is how long you can expect to be in the air on a direct flight from Chicago Midway Airport to Los Cabos International Airport.

      • San Jose del Cabo is one hour behind Chicago and observes the UTC-7 timezone.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Get to the airport on time to board your MDW to SJD flight.

      • Flying during a peak month like July? School holidays and other popular periods can lead to longer queues and delays at security. Be extra cautious and get there up to four hours before international flights and two hours before domestic departures.

      • Southwest Airlines is your gateway to discovering San Jose del Cabo (and perhaps some other exciting parts of Mexico!). Check out the direct flights from Chicago Midway Airport to Los Cabos International Airport offered by this carrier.

      • The airline with the highest number of bookings on this route is Southwest Airlines.

      • The carrier with the most consistent on-time arrival rate for MDW to SJD flights is Southwest Airlines.

      • If you'd like to explore another city along the way, simply deselect 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Los Cabos International Airport. These are the top stopovers between MDW and SJD:

        • Denver International Airport

        • Phoenix Sky Harbour Airport

        • Houston Hobby Airport

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

      • At the moment, 172 € is the lowest price we've seen for a one-way Chicago Midway Airport to Los Cabos International Airport flight. The best price for a return ticket is 434 €. Keep in mind that fares can change due to availability at the time of booking.

      • To secure cheap tickets from MDW to SJD, book your trip four months ahead of your departure date.

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

      • Snapping up cheap flights from MDW to SJD is a cinch with Price Alerts. Simply create one of these automatic alerts and we'll get in touch when a new discounted fare appears.

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

      Handy information about Chicago Midway Airport (MDW)

      • MDW's address is 5700 South Cicero.

      • When it comes to Chicago Midway Airport's on-time performance, 76% of flights meet their scheduled arrival time.

      • Central Chicago to Chicago Midway Airport is approximately 16 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're driving, catching a taxi or ride-sharing.

      • Taking public transport? Expect a trip time of around 30 minutes.

      • Searching for a convenient hotel near MDW? If you're catching an early flight from Chicago Midway Airport to Los Cabos International Airport, these accommodation options will have you moments from your departure gate:

      Arriving at Los Cabos International Airport (SJD)

      • The last thing you need is a long journey to your hotel if you're arriving on a late Chicago Midway Airport to Los Cabos International Airport flight. Stay at one of these accommodation options near SJD instead:

      • Follow your own route with a Los Cabos International Airport rental car. Pick up a set of wheels from America, MEX or Europcar and discover more of San Jose del Cabo and beyond.

      • To lock in the lowest price, book your vehicle from Los Cabos International Airport around two weeks before travelling.

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

      • Los Cabos International Airport is approximately 8 kilometres from the centre of San Jose del Cabo. The drive time takes around 15 minutes.

      • It'll take around 25 minutes if you're travelling by public transport.

      When to fly to Los Cabos International Airport (SJD)

      • April is the busiest month for flights from Chicago Midway Airport to Los Cabos International Airport. For smaller crowds, travel to San Jose del Cabo in September.

      • The warmest month in San Jose del Cabo is August, with the temperature ranging between 23ºC (73ºF) and 35ºC (95ºF). Lock in your flights from Chicago Midway Airport to Los Cabos International Airport in this month if this is the type of weather you like.

      • Look for cheap tickets from MDW to SJD in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between 11ºC (52ºF) and 26ºC (79ºF) on average.

      Explore more of Mexico

      • You've visited San Jose del Cabo, now it's time to explore other corners of Mexico. Travel about 306 kilometres north-east to Culiacan to tick off its top attractions. From paseo del río Sinaloa Park to Jardin Botanico Culiacan and Reserva Ecologica, you've got a jam-packed schedule ahead.

      • Mazatlan is another sought-after destination in Mexico and is around 338 kilometres east of San Jose del Cabo. No trip is complete without a visit to Malecón, Malecon and Playa Las Gaviotas.

      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.