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Cheap Flights from San Juan (SJUA) to Chicago (MDW)

Compare San Juan 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 to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from San Juan to Chicago Midway Airport? If you want to travel next month, return fares start from $363. Find the lowest prices on one-way and return tickets right here.
Chicago.$363 per passenger.Departing Fri, 11 Sep, returning Sun, 13 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Fri, 11 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 13 Sep, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $363, select.
Chicago.$391 per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Sat, 29 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 5 Sep, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $391, select.
Chicago.$392 per passenger.Departing Fri, 28 Aug, returning Mon, 31 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Fri, 28 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 31 Aug, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $392, select.
Chicago.$393 per passenger.Departing Wed, 4 Nov, returning Mon, 9 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Wed, 4 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 9 Nov, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $393, select.
Chicago.$397 per passenger.Departing Tue, 20 Oct, returning Tue, 27 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Tue, 20 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 27 Oct, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $397, select.
Chicago.$504 per passenger.Departing Tue, 22 Dec, returning Mon, 11 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Tue, 22 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 11 Jan, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $504, select.
Chicago.$981 per passenger.Departing Thu, 7 Jan, returning Mon, 11 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Thu, 7 Jan, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 11 Jan, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $981, select.
Chicago.$1,117 per passenger.Departing Sat, 20 Mar, returning Wed, 24 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from San Juan Luis Munoz Marin on Sat, 20 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 24 Mar, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $1,117, select.
Chicago.$1,190 per passenger.Departing Sat, 3 Apr, returning Sun, 11 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from San Juan Luis Munoz Marin on Sat, 3 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 11 Apr, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $1,190, select.
Chicago.$1,376 per passenger.Departing Sat, 27 Mar, returning Sun, 4 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Sat, 27 Mar, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 4 Apr, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $1,376, select.
Chicago.$1,757 per passenger.Departing Fri, 25 Dec, returning Thu, 31 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from San Juan Luis Munoz Marin on Fri, 25 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 31 Dec, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $1,757, select.
Chicago.$1,909 per passenger.Departing Mon, 14 Jun, returning Thu, 17 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from San Juan Luis Munoz Marin on Mon, 14 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Thu, 17 Jun, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $1,909, select.
Chicago.$3,635 per passenger.Departing Mon, 24 May, returning Sun, 30 May.Return flight with Delta.Outbound indirect flight with Delta, departs from San Juan Luis Munoz Marin on Mon, 24 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 30 May, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From $3,635, select.

Find the cheapest month to fly from San Juan 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 to Chicago Midway flights are currently cheapest in September.
Aug
from $392
Sep
from $363
Oct
from $397
Nov
from $393
Dec
from $1,757
Jan
from $981
Feb
Find prices
Mar
from $1,117
Apr
from $1,190
May
from $3,635
Jun
from $1,909
Jul
Find prices

Direct flights from San Juan to Chicago Midway

San Juan to Chicago Midway: Alternative routes

Compare routes from San Juan 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 $363
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $247
Search flights

Chicago Rockford

127km from central Chicago
Search flights

San Juan to Chicago: Flight information

The things to know before you go.
Cheapest flight found$363
Cheapest month to flySeptember
Average flight time5 hrs, 12 mins
Most popular airlineSouthwest Airlines
Average flights per week4

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

The best price we found for a return flight from San Juan to Chicago Midway is $363. 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 to Chicago Midway.
Southwest Airlines flies direct from San Juan to Chicago Midway.
As of August 2026, there are 2 flights per week flying from San Juan to Chicago Midway.
The cheapest month to fly from San Juan to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Juan to Chicago Midway Airport on Friday, 11 September 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.

The cheapest airline that flies to Chicago Midway is Southwest Airlines .

Travelling from San Juan to Chicago Midway International Airport (MDW): What you need to know

  • Planning your trip begins with working out where you'll leave from in San Juan. Luis Munoz Marin International Airport (SJU) is the city's main airport, so explore your options for reserving a flight from San Juan to Chicago Midway International Airport (MDW) taking off from here.

  • 5 hours 5 minutes is the average duration of a direct San Juan to Chicago Midway International Airport flight.

  • Chicago is two hours behind San Juan. Chicago Midway International Airport is located in Chicago, which operates on the UTC-6 timezone.

  • Your flight from San Juan to MDW won't wait if you're running late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • Flying during a peak month such as March? School holidays and other popular seasons can lead to longer lines at security. Play things extra safe and arrive up to four hours before international flights and two hours before a domestic departure.

Airports in San Juan

Luis Munoz Marin International Airport (SJU)

  • Luis Munoz Marin International Airport (SJU) is a convenient option for travelling directly to your destination. Nonstop flights from San Juan to Chicago Midway International Airport (MDW) take off from this terminal.

  • Southwest Airlines is a well-known airline that offers direct flights from San Juan to Chicago Midway International Airport leaving from SJU.

  • Southwest Airlines is the airline with the highest number of bookings for flights from SJU to MDW.

  • The carrier with the best on-time performance on this route is Southwest Airlines. Its services land as scheduled 66.67% of the time.

  • We make it simple to book cheap flights from San Juan to MDW that include a stopover. To explore all your options leaving from Luis Munoz Marin International Airport (SJU), deselect 'Direct flights only.' Then, simply pick a flight that has a stop long enough to tour the city of your choice. Major stopovers between SJU and MDW include:

    • Charlotte Douglas International Airport (CLT)

    • Orlando International Airport (MCO)

    • Tampa International Airport (TPA)

  • Travelling from central San Juan to SJU takes around 1 hour by public transport. If you ride-share, drive or get a taxi, you'll cover the 11 kilometres in 20 minutes or so, depending on traffic.

  • Planning to catch an early flight from San Juan to Chicago Midway International Airport? Avoid the last-minute rush to the terminal (and get some extra shut-eye) by picking one of these hotels near Luis Munoz Marin International Airport:

  • Luis Munoz Marin International Airport gets high marks for on-time performance. 81% of flights that take off from SJU reach their destination on time.

About Chicago Midway International Airport (MDW)

  • If you're arriving on a late flight from San Juan to Chicago Midway International Airport, few things beat the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and relaxing soon after at one of these options near MDW:

  • Booking your ride around four weeks in advance of your San Juan to Chicago Midway International Airport flight can help you get the lowest rate.

  • You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport is around 16 kilometres from the centre of Chicago. It takes around 25 minutes or so to drive to the city.

  • It takes around 30 minutes if you're using public transport.

How to find the cheapest flights from San Juan to Chicago Midway International Airport (MDW)

  • The lowest price we've found for a one-way ticket from San Juan to Chicago Midway International Airport is $182. For a return flight on this route, the best price is $363. Depending on the availability when you book, these fares may change.

  • To find cheap flights from San Juan to MDW, book in advance. Airlines typically offer lower prices when tickets are first released.

  • Affordable San Juan to Chicago Midway International Airport tickets are easier to find when your travel dates are flexible. Use the 'Whole month' tool to compare fares throughout the month and then fly out on the cheapest day.

  • Locking in a cheap plane ticket from San Juan to MDW couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch as soon as there's a price drop.

  • Save on your flight from San Juan to Chicago Midway International Airport by using filters. Select your preferred departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from San Juan to Chicago Midway International Airport (MDW)

  • November is the quietest month for flights from San Juan to Chicago Midway International Airport (MDW), while July is the most popular. Figure out the best time to go to Chicago based on whether you like a laid-back vibe or a more bustling atmosphere.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your San Juan to MDW plane ticket then if you enjoy this type of weather.

  • If you like travelling in cooler conditions, look for a cheap ticket from San Juan to Chicago Midway International Airport in January when temperatures are between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • Chicago has loads to offer, but there are so many other parts of the United States you'll want to see. About 257 kilometres southeast of Chicago, a trip to Indianapolis will keep you on the move. Check out popular attractions like Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

  • Milwaukee is another must-experience destination in the United States and is around 137 kilometres north of Chicago. No trip is complete without a visit to Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Plan smart, explore more

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Plan the rest of your trip from San Juan to Chicago

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