Cheap Flights from Chicago Midway to Aguadilla

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Flight deals from Chicago Midway Airport to Aguadilla Airport

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Aguadilla Airport? If you want to travel next month, return fares start from $660. Find the lowest prices on one-way and return tickets right here.

Aguadilla.$506 per passenger.Departing Tue, 31 Mar, returning Thu, 9 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 31 Mar, arriving in Aguadilla.Inbound indirect flight with Frontier Airlines, departs from Aguadilla on Thu, 9 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $506, select.

Aguadilla.$660 per passenger.Departing Mon, 20 Apr, returning Sun, 26 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 20 Apr, arriving in Aguadilla.Inbound indirect flight with Frontier Airlines, departs from Aguadilla on Sun, 26 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $660, select.

Aguadilla.$713 per passenger.Departing Sun, 8 Mar, returning Sun, 15 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 8 Mar, arriving in Aguadilla.Inbound indirect flight with Frontier Airlines, departs from Aguadilla on Sun, 15 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $713, select.

Aguadilla.$723 per passenger.Departing Fri, 26 Jun, returning Sun, 28 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 26 Jun, arriving in Aguadilla.Inbound indirect flight with Frontier Airlines, departs from Aguadilla on Sun, 28 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $723, select.

Find the cheapest month to fly from Chicago Midway to Aguadilla

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Aguadilla flights are currently cheapest in April.

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Chicago Midway to Aguadilla: Alternative routes

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

Chicago to Aguadilla: Flight information

The things to know before you go.

Cheapest flight found	$506
Cheapest month to fly	March

Finding cheap flights from Chicago Midway to Aguadilla: Frequently asked questions

How much are return flights from Chicago Midway to Aguadilla?

The best price we found for a return flight from Chicago Midway to Aguadilla is $506. 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.

Which airlines fly direct from Chicago Midway to Aguadilla?

Currently, there are no airlines that fly direct from Chicago Midway to Aguadilla. But we found flights with one or more stops from $506.

How many flights are there a week from Chicago Midway to Aguadilla?

As of March 2026, there are no flights flying from Chicago Midway to Aguadilla.

When is the cheapest time to fly from Chicago Midway to Aguadilla?

The cheapest month to fly from Chicago Midway to Aguadilla is usually March.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Aguadilla Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Aguadilla Airport on Tuesday, 31 March 2026.

Can I get a direct flight from Chicago Midway Airport to Aguadilla Airport?

No airlines currently offer direct flights between Chicago Midway Airport and Aguadilla Airport. Most routes have one or more stops.

How can I find the best flight deal to Aguadilla?

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 Aguadilla 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.

When is the best time to book flights to Aguadilla?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Aguadilla is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Chicago Midway Airport to Aguadilla with?

Currently, Frontier Airlines offers the cheapest flight tickets to Aguadilla.

Flying from Chicago Midway International Airport (MDW) to Rafael Hernandez Airport (BQN): what you need to know

Aguadilla's timezone is UTC-4, making Aguadilla one hour ahead of Chicago.
To ensure you catch your MDW to BQN flight, leave enough time to check in and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the general travel rule.
Flying during a peak month such as July? School holidays and other popular seasons can result in longer queues at security. Play things extra safe and arrive up to four hours ahead of international flights and two hours before domestic departures.
Pick a stopover if you want to break up your flight. Simply deselect 'Direct flights only' to look at your options for tickets from Chicago Midway International Airport to Rafael Hernandez Airport. Orlando International Airport is a popular stopover on the MDW to BQN route.

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Rafael Hernandez Airport (BQN)

$171 is the lowest price for a one-way Chicago Midway International Airport to Rafael Hernandez Airport flight. Return flights start at $506. These fares may change based on availability.
Don't leave everything to the last minute. You're more likely to find cheap tickets from MDW to BQN if you book ahead. Airlines often have some great early bird rates.
Getting cheap flights from Chicago Midway International Airport to Rafael Hernandez Airport is easier if you're flexible with your travel dates. Use the 'Whole month' search tool to see the lowest prices throughout the month and snap up a great deal.
You won't have to check every day to see if fares have gone down when you set up a Price Alert. We'll update you the moment the price changes on cheap flights from MDW to BQN.
Tailor your flights with filters. Select your preferred departure and arrival times, airlines and total journey duration. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway International Airport to Rafael Hernandez Airport.

Handy information about Chicago Midway International Airport (MDW)

You'll find MDW at 5700 South Cicero.
Of all flights departing from Chicago Midway International Airport, 77.88% land on schedule at their destination.
Central Chicago to Chicago Midway International Airport is around 19 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're catching a cab, ride-sharing or driving.
Expect a trip time of about 45 minutes when using public transport.
Looking for a handy hotel near MDW? If you're catching an early flight from Chicago Midway International Airport to Rafael Hernandez Airport, these accommodation options will have you moments from your departure gate:

Arriving at Rafael Hernandez Airport (BQN)

The last thing you need is a lengthy journey to your hotel if you're arriving on a late Chicago Midway International Airport to Rafael Hernandez Airport flight. Reserve one of these accommodation options near BQN instead:
Travel at your own speed with a Rafael Hernandez Airport rental car. Book your wheels from Sixt, Final Rentals or Ace Rent a Car and find adventure across Aguadilla and beyond.
Lock in the lowest price by booking your ride from Rafael Hernandez Airport around three weeks in advance of your trip.

Getting from Rafael Hernandez Airport (BQN) to central Aguadilla

Rafael Hernandez Airport to the centre of Aguadilla has a drive time of about 20 minutes. It's approximately 10 kilometres away.

When to fly to Rafael Hernandez Airport (BQN)

The quietest month for a flight from Chicago Midway International Airport to Rafael Hernandez Airport is May, while April is the most popular. Pick the ideal time to go to Aguadilla based on whether you prefer a laid-back vibe or a more bustling atmosphere.
The warmest month in Aguadilla is August, with the temperature ranging between 25ºC and 31ºC. Lock in your flights from Chicago Midway International Airport to Rafael Hernandez Airport in this month if this is the kind of weather you like.
March sees average temperatures of between 20ºC and 29ºC. Search for cheap tickets from MDW to BQN sometime then if you want to travel in cooler conditions.

Explore more of Puerto Rico

Aguadilla has its own special appeal, but there are so many other corners of Puerto Rico just waiting to be discovered. About 113 kilometres east of Aguadilla, a visit to San Juan will keep you busy. Check out popular attractions like Castillo San Felipe del Morro, La Garita del morro de san juan bahia and Fortaleza Street.
Bayamon is another favourite destination in Puerto Rico and is around 105 kilometres east of Aguadilla. No journey is complete without visiting Plazoleta Ignacio Zorrilla, La Plaza de la Bomba Puertorriqueña, Monumento a los Trovadores and Parque Palm Court.