Cheap Flights from San Juan to Chicago Midway

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? Find the lowest prices on one-way and return tickets right here.

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 April.

Direct flights from San Juan to Chicago Midway

San Juan to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,615
Cheapest month to flyApril
Average flight time5 hrs, 6 mins
Most popular airlineSouthwest Airlines
Average flights per week2

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 R 3,230. 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 6 minutes is the average flight time from San Juan to Chicago Midway.
Southwest Airlines flies direct from San Juan to Chicago Midway.
As of March 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 April.
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 Thursday, 16 April 2026.
Yes – the average flight time is 5 hours and 6 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 Frontier Airlines .

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

  • Planning your trip starts with working out where you'll fly out of in San Juan. Luis Munoz Marin International Airport (SJU) is the city's main base, so check out your options for booking a flight from San Juan to Chicago Midway International Airport (MDW) jetting off from here.

  • Expect to be travelling for 5 hours 10 minutes. That's the average time for a direct San Juan to Chicago Midway International Airport flight.

  • Chicago is one hour behind San Juan. Chicago Midway International Airport is located in Chicago, which runs on the UTC-5 timezone.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport on time to board your flight from San Juan to MDW.

  • Peak season means busier airports, so show up even earlier. Give yourself at least two hours before a domestic flight and four hours for an international journey to keep to your schedule.

Airports in San Juan

Luis Munoz Marin International Airport (SJU)

  • Luis Munoz Marin International Airport (SJU) makes it easy to travel directly to your destination. Nonstop flights from San Juan to Chicago Midway International Airport (MDW) depart from this terminal.

  • You'll find a direct flight from San Juan to Chicago Midway International Airport with Southwest Airlines. This well-known airline operates services from SJU.

  • The airline with the highest booking numbers between SJU and MDW is Southwest Airlines.

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

  • Stopovers are the ideal opportunity to take a travel break and perhaps even explore a different city. When browsing cheap flights from San Juan to MDW departing from Luis Munoz Marin International Airport (SJU), deselect the 'Direct flights only' box to get ideas for where to visit along the way. Here's where you could connect through:

    • Charlotte Douglas International Airport (CLT)

    • Orlando International Airport (MCO)

    • Tampa International Airport (TPA)

  • Located around 8 kilometres from the centre of San Juan, SJU can be reached in about 10 minutes by car (depending on traffic). The journey on public transport takes roughly 55 minutes.

  • Catching an early flight from San Juan to Chicago Midway International Airport? Avoid the last-minute rush to the terminal (and enjoy a little extra shut-eye) by staying at one of these stays close to Luis Munoz Marin International Airport:

  • Of all flights leaving Luis Munoz Marin International Airport, 73.65% land on schedule at their destination.

Fernando Luis Ribas Dominicci Airport (SIG)

About Chicago Midway International Airport (MDW)

  • If you're coming in on a late flight from San Juan to Chicago Midway International Airport, few things top the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and relaxing not long after at one of these hotels near MDW:

  • Travel at your own speed with a Chicago Midway International Airport rental car. Book your wheels from Dollar, Hertz or Budget and experience more of Chicago and beyond.

  • To get the best deal, reserve your vehicle around four weeks ahead of your San Juan to Chicago Midway International Airport flight.

  • MDW is located at 5700 South Cicero.

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

  • Central Chicago is around 14 kilometres from Chicago Midway International Airport. Journey times by car hire or cab will vary depending on traffic conditions and time of day, so do a little research ahead of your trip.

  • Travelling on public transport takes around 45 minutes.

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

  • Currently, R 1,615 is the lowest price we've found for a one-way ticket from San Juan to Chicago Midway International Airport. The cheapest price for a return flight is R 3,230. Keep in mind fares can change due to demand at the time of booking.

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

  • If you can be flexible with your travel plans, use the 'Whole month' tool. It'll give you the cheapest price in each month when searching for your San Juan to Chicago Midway International Airport ticket.

  • You don't need to check every day to find out if prices have dropped when you create a Price Alert. We'll let you know as soon as a new deal shows up on plane tickets from San Juan to MDW.

  • Hunt for savings on a flight from San Juan to Chicago Midway International Airport with the help of the filters. Pick your ideal departure and arrival times, number of stops and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest.'

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

  • July is the most popular month for flights from San Juan to Chicago Midway International Airport (MDW). Plan your visit to Chicago in May if you prefer a quieter experience.

  • Before locking in your San Juan to MDW plane ticket, consider the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January has temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from San Juan to Chicago Midway International Airport around that time if you want to travel when it's cooler.

More about Chicago

Explore more of the United States

  • Indianapolis is just one of the many places in the United States waiting to be discovered once you've seen Chicago. Around 257 kilometres away to the south-east, well-known attractions include 9-11 Memorial, Lucas Oil Stadium and Eiteljorg Museum.

  • Around 137 kilometres north of Chicago, Milwaukee is another essential stop in the United States. Experience this destination's highlights firsthand at Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

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