Cheap flights from Chicago Midway Airport to Puerto Rico from $65
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Puerto Rico departing on 9/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to Puerto Rico
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Frontier flights from Chicago Midway Airport to Puerto Rico
Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets
Delta flights from Chicago Midway Airport to Puerto Rico
Our best Delta deals on Chicago Midway Airport to Puerto Rico flight tickets
See travel insights to Puerto Rico from
How to get the cheapest flight ticket from Chicago Midway Airport to Puerto Rico
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Puerto Rico?
If you don’t want to visit Puerto Rico in August, then you should wait until November to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $317.
What is the cheapest day to depart on your flight to Puerto Rico?
On average, the least expensive day to fly to Puerto Rico from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $59. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Saturday, with ticket prices averaging around $456.
What is the cheapest time of day to depart on your flight to Puerto Rico?
Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Chicago Midway Airport to Puerto Rico during this time can be as low as $324. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $456.
What is the cheapest Chicago Midway to Puerto Rico flight route?
Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - Puerto Rico flight prices
How far in advance should I book a flight to Puerto Rico?
You are more likely to see cheaper flights to Puerto Rico from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $410 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago Midway Airport for as low as $309 on momondo.
What cabin class options are available on Chicago Midway to Puerto Rico flights?
There are 1 cabin classes available to choose from on Chicago Midway to Puerto Rico flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago Midway to Puerto Rico?
Frontier, Southwest, and Delta are the most popular carriers operating from Chicago Midway to Puerto Rico
What airlines fly to Puerto Rico?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Puerto Rico from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 5 different airlines that fly to Puerto Rico on a routine basis, so you have a few additional options to choose from.
Cheap Chicago Midway Airport to Puerto Rico flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Puerto Rico
Best Price Found | $65 |
|---|---|
Fastest flight time | 6h 35m |
Direct flights | Mon and Sun |
Airports in Puerto Rico | 1 airport |
When did momondo last update prices for flights from Chicago Midway Airport to Puerto Rico?
Prices for flights from Chicago Midway Airport to Puerto Rico are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Puerto Rico?
As of July 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Puerto Rico.
How old do you have to be to fly from Chicago Midway Airport to Puerto Rico?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Puerto Rico.
What documentation or ID do you need to fly to Puerto Rico?
The necessary travel and health documents for your Puerto Rico trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Puerto Rico?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Puerto Rico is Boeing 737 MAX 8 (24.77% of total bookings). The next most popular plane models are Boeing 737-800 (15.60%), Boeing 737 MAX 9 (14.68%), and Airbus A321neo (12.84%).
Best airlines flying from Chicago Midway Airport to Puerto Rico
Compare and see reviews for airlines that fly from Chicago Midway Airport to Puerto Rico with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $133 | Free Cancellation | Rating 5.9 3,286 reviews | |||
| PriceFrom $149 | Free Cancellation | Rating 6.3 8,086 reviews | |||
| PriceFrom $299 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $325 | Free Cancellation | Rating 8.0 7,982 reviews | |||
| PriceFrom $354 | Free Cancellation | Rating 8.0 4,266 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Puerto Rico?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Puerto Rico from Chicago.
Can I find flights from Chicago to Puerto Rico with flexible booking policies on momondo?
Flights from Chicago to Puerto Rico with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Puerto Rico?
Once all potential Chicago to Puerto Rico flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Puerto Rico right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Puerto Rico, momondo offers a useful price alert feature which will track prices for flights to Puerto Rico from Chicago and alert you when they change.