Cheap flights from Puerto Rico to Chicago from $137
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Puerto Rico to Chicago departing on 6/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Puerto Rico to Chicago Midway Airport
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How to get the cheapest flight ticket from Puerto Rico to Chicago Midway Airport
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 Chicago Midway Airport?
The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Puerto Rico, with most prices found around $252. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Puerto Rico during the month August is also very affordable. Most momondo users find prices during this month for around $270.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Puerto Rico. The lowest ticket price found for a Friday departure recently was $154. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Puerto Rico because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $610.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Puerto Rico in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $614. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Puerto Rico to Chicago Midway flight route?
Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best Puerto Rico - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Puerto Rico when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $365 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Puerto Rico for as low as $241 on momondo.
What cabin class options are available on Puerto Rico to Chicago Midway flights?
There are 1 cabin classes available to choose from on Puerto Rico to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How long does it take to fly to Chicago Midway Airport?
On average, it takes 4h 58m to fly from Puerto Rico to Chicago Midway Airport if you fly out of San Juan (the most popular airport in Puerto Rico) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Aguadilla and into Chicago O'Hare Intl Airport, then the flight time is around 8h 12m.
Cheap Puerto Rico to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago Midway Airport
When did momondo last update prices for flights from Puerto Rico to Chicago Midway Airport?
Prices for flights from Puerto Rico to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Puerto Rico to Chicago Midway Airport?
The number of operators available for flights from Puerto Rico to Chicago Midway Airport is 2 as of April 2025.
How old do you have to be to fly from Puerto Rico to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Puerto Rico to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Puerto Rico to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Puerto Rico to Chicago Midway Airport is Boeing 737-800, representing 31.58% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 21.05%, Airbus A320neo at 15.79%, and Airbus A321neo at 7.89%.
Best airlines flying from Puerto Rico to Chicago Midway Airport
Compare and see reviews for airlines that fly from Puerto Rico to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $148 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $312 | Free Cancellation | Rating 8.0 4,294 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Puerto Rico to Chicago?
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 Chicago from Puerto Rico.
Can I find flights from Puerto Rico to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Puerto Rico on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Puerto Rico to Chicago?
momondo helps you find the best flight between Puerto Rico and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Puerto Rico to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Puerto Rico to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.