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C$163 Cheap Flights from Chicago Midway (MDW) to San Juan Luis Munoz Marin (SJU)

Compare Chicago Midway to San Juan Luis Munoz Marin flight deals

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Flight deals from Chicago Midway to San Juan Luis Munoz Marin

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Juan Luis Munoz Marin Airport? If you want to travel next month, return fares start from C$604. Find the lowest prices on one-way and return tickets right here.
San Juan.C$163 per passenger.Departing Tue., Sep. 1.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue., Sep. 1, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$163, select.
San Juan.C$163 per passenger.Departing Fri., Aug. 14.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri., Aug. 14, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$163, select.
San Juan.C$191 per passenger.Departing Wed., Jul. 29.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed., Jul. 29, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$191, select.
San Juan.C$233 per passenger.Departing Fri., May 29.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri., May 29, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$233, select.
San Juan.C$257 per passenger.Departing Sat., Oct. 3.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat., Oct. 3, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$257, select.
San Juan.C$265 per passenger.Departing Sat., Jun. 27.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat., Jun. 27, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$265, select.
San Juan.C$317 per passenger.Departing Fri., Nov. 13.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Midway on Fri., Nov. 13, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$317, select.
San Juan.C$322 per passenger.Departing Mon., Apr. 12.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon., Apr. 12, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$322, select.
San Juan.C$322 per passenger.Departing Mon., Jan. 11.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon., Jan. 11, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$322, select.
San Juan.C$323 per passenger.Departing Wed., Feb. 17.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed., Feb. 17, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$323, select.
San Juan.C$323 per passenger.Departing Tue., Dec. 1.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue., Dec. 1, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$323, select.
San Juan.C$357 per passenger.Departing Sat., Nov. 14.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat., Nov. 14, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$357, select.
San Juan.C$420 per passenger.Departing Sat., Dec. 5.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat., Dec. 5, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$420, select.
San Juan.C$446 per passenger.Departing Mon., Mar. 22.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon., Mar. 22, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$446, select.
San Juan.C$467 per passenger.Departing Sat., Jul. 4.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat., Jul. 4, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$467, select.
San Juan.C$640 per passenger.Departing Sun., Jun. 28.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sun., Jun. 28, arriving in San Juan Luis Munoz Marin.Price includes taxes and charges.From C$640, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Juan Luis Munoz Marin flights are currently cheapest in August.
May
from C$233
Jun.
from C$265
Jul.
from C$191
Aug.
from C$163
Sep.
from C$163
Oct.
from C$257
Nov.
from C$317
Dec.
from C$323
Jan.
from C$322
Feb.
from C$323
Mar.
from C$446
Apr.
from C$322

Which airlines fly from Chicago Midway to San Juan Luis Munoz Marin?

Chicago Midway to San Juan Luis Munoz Marin: Alternative routes

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

San Juan Isla Grande

1km from central San Juan
Closest
Search flights

San Juan Luis Munoz Marin

11km from central San Juan
Cheapest
from C$163
Search flights

Roosevelt Roads

55km from central San Juan
Search flights

Ponce

70km from central San Juan
Search flights

Vieques

82km from central San Juan
Search flights

Culebra

85km from central San Juan
Search flights

Chicago to San Juan: Flight information

The things to know before you go.
Cheapest flight foundC$163
Cheapest month to flyAugust
Average flight time4 hrs, 44 mins
Most popular airlineSouthwest Airlines
Average flights per week2

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

The best price we found for a return flight from Chicago Midway to San Juan Luis Munoz Marin is C$326. 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 44 minutes is the average flight time from Chicago Midway to San Juan Luis Munoz Marin.
Southwest Airlines flies direct from Chicago Midway to San Juan Luis Munoz Marin.
As of May 2026, there are 2 flights per week flying from Chicago Midway to San Juan Luis Munoz Marin.
The cheapest month to fly from Chicago Midway to San Juan Luis Munoz Marin 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 San Juan Luis Munoz Marin Airport on Thursday, September 3, 2026.
Yes – the average flight time is 4 hours and 44 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 San Juan Luis Munoz Marin 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 Juan 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 San Juan Luis Munoz Marin.

Flying from Chicago Midway International Airport (MDW) to Luis Munoz Marin International Airport (SJU): what you need to know

  • 4 hours 39 minutes is the average time for a direct flight from Chicago Midway International Airport to Luis Munoz Marin International Airport. San Juan is 1 hour ahead of Chicago and operates on the UTC-4 timezone.

  • Be prepared for bigger queues during popular months such as July and other peak periods. Arriving up to four hours in advance for international flights and two hours for domestic departures will give you ample time for security and boarding.

  • If you'd like to break up your flight from Chicago Midway International Airport to Luis Munoz Marin International Airport, add a stopover to your trip. Just deselect 'Direct flights only' to find a city that catches your eye. The top stopovers on the MDW - SJU route are:

    • Hartsfield-Jackson Atlanta International Airport

    • Fort Lauderdale-Hollywood International Airport

    • Orlando International Airport

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

  • The lowest price we've found for a one-way ticket from Chicago Midway International Airport to Luis Munoz Marin International Airport is C$163. For a return flight on this route, the best price is C$326. Depending on the availability and when you book, these fares could change.

  • Get cheap flight tickets from MDW to SJU by booking at least 9 months ahead. According to our research, that's the sweet spot for landing a bargain.

  • The cheapest month for flight tickets from Chicago Midway International Airport to Luis Munoz Marin International Airport is May. Use the 'Whole month' tool to see the lowest prices if you have flexible travel dates.

  • Snapping up a cheap ticket from MDW to SJU is easy with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you as soon as there's a better deal.

  • Tailor your flights with filters. Select your ideal departure and arrival times, total journey duration and airlines. You can also sort results by 'Cheapest,' 'Fastest' or 'Best' flights from Chicago Midway International Airport to Luis Munoz Marin International Airport.

Handy information about Chicago Midway International Airport (MDW)

Arriving at Luis Munoz Marin International Airport (SJU)

Getting from Luis Munoz Marin International Airport (SJU) to central San Juan

  • From Luis Munoz Marin International Airport, San Juan is approximately 8 kilometres away. It takes around 11 minutes to get to the center driving.

  • Getting there on public transport takes roughly 56 minutes.

When to fly to Luis Munoz Marin International Airport (SJU)

  • It's time to pick your dates for your flight from Chicago Midway International Airport to Luis Munoz Marin International Airport. July is the busiest month to visit San Juan. If you prefer a more relaxed vibe, go in May.

  • The warmest month in San Juan is September, with the temperature ranging between 23ºC and 33ºC. Book your flights from Chicago Midway International Airport to Luis Munoz Marin International Airport in this month if this is the kind of weather you like.

  • Search for cheap flight tickets from MDW to SJU in February if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between 20ºC and 28ºC on average.

More about San Juan

Complete your San Juan trip with hotels and a car rental

  • Once you've secured your cheap ticket to Luis Munoz Marin International Airport, check out the lowest prices and exclusive rates for hotels. You can also compare a range of car rental companies in one place to find the best car rental price for your San Juan getaway.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.