Skyscanner home

185 € Cheap Flights from San Juan Luis Munoz Marin to Chicago Midway

Return selected
Return selected
origin
Enter the city you're flying from, or choose from the options below
Include nearby airports
    selected
    destination
    . Enter your destination, or choose from the options below
    Include nearby airports
      selected
      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare San Juan Luis Munoz Marin to Chicago Midway flight deals

      Find the cheapest month or even day of the year to fly to Chicago Midway

      Book the best Chicago Midway fare with no extra fees

      Flight deals from San Juan Luis Munoz Marin to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from San Juan Luis Munoz Marin Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 185 €. Find the lowest prices on one-way and return tickets right here.
      Chicago.185 € per passenger.Departing Sat, 10 Oct, returning Mon, 19 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Juan Luis Munoz Marin on Sat, 10 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 19 Oct, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 185 €, select.
      Chicago.185 € per passenger.Departing Thu, 10 Dec, returning Mon, 14 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Juan Luis Munoz Marin on Thu, 10 Dec, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 14 Dec, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 185 €, select.
      Chicago.232 € per passenger.Departing Thu, 12 Nov, returning Mon, 16 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Thu, 12 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 16 Nov, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 232 €, select.
      Chicago.254 € per passenger.Departing Thu, 14 Jan, returning Mon, 18 Jan.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Juan Luis Munoz Marin on Thu, 14 Jan, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 18 Jan, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 254 €, select.
      Chicago.272 € per passenger.Departing Tue, 22 Dec, returning Mon, 11 Jan.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Juan Luis Munoz Marin on Tue, 22 Dec, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 11 Jan, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 272 €, select.
      Chicago.274 € per passenger.Departing Thu, 29 Oct, returning Thu, 5 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Thu, 29 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 5 Nov, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 274 €, select.
      Chicago.279 € per passenger.Departing Fri, 25 Sep, returning Mon, 28 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Fri, 25 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 28 Sep, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 279 €, select.
      Chicago.279 € per passenger.Departing Fri, 25 Sep, returning Mon, 5 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Fri, 25 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 5 Oct, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 279 €, select.
      Chicago.340 € per passenger.Departing Wed, 5 May, returning Wed, 12 May.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Wed, 5 May, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 12 May, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 340 €, select.
      Chicago.391 € per passenger.Departing Wed, 21 Apr, returning Sun, 25 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Wed, 21 Apr, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 25 Apr, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 391 €, select.
      Chicago.420 € per passenger.Departing Wed, 13 Jan, returning Wed, 10 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Wed, 13 Jan, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 10 Mar, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 420 €, select.
      Chicago.449 € per passenger.Departing Wed, 24 Mar, returning Tue, 30 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Wed, 24 Mar, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 30 Mar, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 449 €, select.
      Chicago.457 € per passenger.Departing Fri, 27 Nov, returning Wed, 2 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Fri, 27 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 2 Dec, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 457 €, select.
      Chicago.573 € per passenger.Departing Thu, 10 Jun, returning Tue, 15 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from San Juan Luis Munoz Marin on Thu, 10 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 15 Jun, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From 573 €, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from San Juan Luis Munoz Marin to Chicago Midway found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from San Juan Luis Munoz Marin to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Juan Luis Munoz Marin to Chicago Midway flights are currently cheapest in October.
      Sep
      from 279 €
      Oct
      from 185 €
      Nov
      from 232 €
      Dec
      from 185 €
      Jan
      from 254 €
      Feb
      Find prices
      Mar
      from 449 €
      Apr
      from 391 €
      May
      from 340 €
      Jun
      from 573 €
      Jul
      Find prices
      Aug
      Find prices

      Direct flights from San Juan Luis Munoz Marin to Chicago Midway

      Southwest Airlines

      San Juan Luis Munoz Marin to Chicago Midway: Alternative routes

      Compare routes from San Juan Luis Munoz Marin to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

      Chicago Midway

      14km from central Chicago
      Closest
      from 185 €
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from 157 €
      Search flights

      Chicago Rockford

      127km from central Chicago
      from 235 €
      Search flights

      San Juan to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found185 €
      Cheapest month to flyOctober
      Average flight time5 hrs, 12 mins
      Most popular airlineSouthwest Airlines
      Average flights per week2

      Finding cheap flights from San Juan Luis Munoz Marin to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from San Juan Luis Munoz Marin to Chicago Midway is 185 €. 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.
      5 hours and 12 minutes is the average flight time from San Juan Luis Munoz Marin to Chicago Midway.
      Southwest Airlines flies direct from San Juan Luis Munoz Marin to Chicago Midway.
      As of September 2026, there are 2 flights per week flying from San Juan Luis Munoz Marin to Chicago Midway.
      The cheapest month to fly from San Juan Luis Munoz Marin to Chicago Midway is usually October.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Juan Luis Munoz Marin Airport to Chicago Midway Airport on Saturday, 10 October 2026.
      Yes – the average flight time is 5 hours and 12 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 Chicago Midway 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

      Travelling from San Juan Luis Munoz Marin Airport (SJU) to Chicago Midway Airport (MDW): what you need to know

      • The average length of a direct flight from San Juan Luis Munoz Marin Airport to Chicago Midway Airport is 5 hours.

      • Chicago is two hours behind San Juan and observes the UTC-6 timezone.

      • Get to the airport on time so you don't miss your SJU to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

      • During popular months such as July, it's best to get to the airport even earlier. Plan to arrive two hours before domestic departures and four hours ahead for an international flight whenever you're travelling during a high season in general.

      • Jetting into Chicago (and then discovering more of the United States!) is a snap with Southwest Airlines. This popular airline offers direct flights from San Juan Luis Munoz Marin Airport to Chicago Midway Airport.

      • Southwest Airlines has the highest passenger demand on this route.

      • The most punctual carrier that operates SJU to MDW flights is Southwest Airlines. Its services land as planned 66.67% of the time.

      • If you want to split up your journey, just deselect 'Direct flights only' when searching for your ticket from San Juan Luis Munoz Marin Airport to Chicago Midway Airport. These are the most popular stopovers between SJU and MDW:

        • Charlotte Douglas Airport

        • Orlando International Airport

        • Tampa International Airport

      How to find the cheapest flights from San Juan Luis Munoz Marin Airport (SJU) to Chicago Midway Airport (MDW)

      • At the moment, 92 € is the lowest price we've found for a one-way San Juan Luis Munoz Marin Airport to Chicago Midway Airport flight. The best price for a return plane ticket is 185 €. Bear in mind that fares can change due to demand when booking.

      • It's a good idea to book ahead of time if you want to find cheap tickets from SJU to MDW. That's because flight prices are based on demand, which tends to rise closer to the date of departure.

      • May is the cheapest month for flights from San Juan Luis Munoz Marin Airport to Chicago Midway Airport. If you prefer to fly during a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

      • Landing cheap flights from SJU to MDW is a breeze with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch as soon as a new deal comes up.

      • Lock in the ideal flight for you with the help of the filters. To see the 'Fastest,' 'Cheapest' or 'Best' flights from San Juan Luis Munoz Marin Airport to Chicago Midway Airport, use the 'Sort by' function. You can also filter results by arrival and departure times, airline, and journey duration.

      Handy information about San Juan Luis Munoz Marin Airport (SJU)

      • San Juan Luis Munoz Marin Airport scores high marks for its on-time performance. 81% of flights that depart SJU reach their destination on time.

      • Central San Juan to San Juan Luis Munoz Marin Airport is around 11 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're ride-sharing, catching a taxi or driving.

      • The trip when using public transport typically takes 1 hour.

      • Get your trip off to a relaxed start by staying near SJU. Whether you've booked an early flight from San Juan Luis Munoz Marin Airport to Chicago Midway Airport or want to avoid feeling rushed, these hotels have you covered:

      Arriving at Chicago Midway Airport (MDW)

      • If you're landing on a late San Juan Luis Munoz Marin Airport to Chicago Midway Airport flight, few things beat the convenience of being near the terminal. Pick up your bags from the carousel and then be resting soon after at one of these hotels near MDW:

      • Follow your own route with a Chicago Midway Airport rental car. Book your wheels from Dollar, Hertz or Budget and see more of Chicago and beyond.

      • Booking your ride from Chicago Midway Airport about four weeks in advance boosts your odds of scoring a great price.

      When to fly to Chicago Midway Airport (MDW)

      • July is the most popular month for flights from San Juan Luis Munoz Marin Airport to Chicago Midway Airport. To escape the crowds, head to Chicago in December.

      • Before locking in your flight from San Juan Luis Munoz Marin Airport to Chicago Midway Airport, consider the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 16ºC (61ºF) to 28ºC (82ºF).

      • Look for cheap tickets from SJU to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

      Explore more of the United States

      • Columbus is just one of the many cities in the United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in the United States. Get a taste of what this destination has to offer at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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