Cheap flights from Puerto Rico to Chicago (CHI) from $39
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
How far in advance should I book a flight from Puerto Rico to Chicago?
To save up to 85% on this flight, we recommend booking at least 16 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Puerto Rico to Chicago from $238 1-2 weeks out and tickets from $309 for flights departing within the next 72 hours.
What is the cheapest month to fly from Puerto Rico to Chicago?
Our data shows that January tends to be the cheapest month to fly to Chicago from Puerto Rico. Users have commonly found prices around $270 for the month, but tickets can be as low as $122. Due to multiple factors, prepare for potentially higher prices in March.
When is the cheapest time to fly from Puerto Rico to Chicago (PR - CHI)?
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Puerto Rico to Chicago as you normally would.
Cheap Spirit Airlines flights from Puerto Rico to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between Puerto Rico and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Find some of the cheapest Spirit Airlines flights traveling from Puerto Rico to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Cheap Frontier flights from Puerto Rico to Chicago
Explore cheap flight options specifically provided by Frontier for the route between Puerto Rico and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Take a gander at the lowest prices we've found on Frontier flights from Puerto Rico to Chicago. Check back soon if you're not seeing flights that suit your needs.
Cheap Puerto Rico to Chicago flights in May & June 2024
Find cheap flight options from Puerto Rico to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Prices were last updated on May 5, 2024.
Scroll through some of the best deals on flights from Puerto Rico to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Puerto Rico to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Puerto Rico and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Scroll through some of the best deals on flights from Puerto Rico to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Non-stop flights to Chicago from Puerto Rico
Discover non-stop flight options from Puerto Rico to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Take a look at some of the direct flights traveling from Puerto Rico to Chicago in the near future. Users can also choose from other Puerto Rico to Chicago flights by using the search form above.
Puerto Rico to Chicago flights leaving soon
Find last-minute flight options from Puerto Rico to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Have a look at some of the flights available from Puerto Rico to Chicago departing last-minute. To prevent any unwanted surprises, users should verify their flight info before booking.
One-way flights to Chicago from Puerto Rico
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Users traveling one-way from Puerto Rico to Chicago can select one of these great deals. Users can also find round-trip Puerto Rico to Chicago flights by using the search form above.
Find flights from Puerto Rico to Chicago within your budget
Customize your flight search to find flights from Puerto Rico to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Fly from
Fly to
Budget
$129 - $162
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop7h 00m
Chicago O'Hare Intl
Tue 6/18
1 stop10h 29m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 5/29
1 stop13h 48m
Chicago O'Hare Intl
Mon 6/3
1 stop12h 39m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop7h 00m
Chicago O'Hare Intl
Tue 6/11
1 stop17h 23m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
1 stop7h 00m
Chicago O'Hare Intl
Tue 6/11
1 stop16h 01m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop9h 36m
Chicago Midway
Tue 5/21
1 stop12h 38m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 5/25
1 stop9h 00m
Chicago O'Hare Intl
Tue 5/28
1 stop27h 10m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Wed 5/15
1 stop9h 53m
Chicago Midway
Sun 5/19
1 stop29h 02m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop21h 14m
Chicago O'Hare Intl
Tue 5/21
1 stop27h 10m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 5/25
Nonstop5h 10m
Chicago O'Hare Intl
Tue 5/28
1 stop27h 10m
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 5, 2024.
Read reviews from past customers who have flown Spirit Airlines, Frontier and United Airlines from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Overall
Food
Entertainment
Crew
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Overall
Food
Entertainment
Crew
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Overall
Food
Entertainment
Crew
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Overall
Food
Entertainment
Crew
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Overall
Food
Entertainment
Crew
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Overall
Food
Entertainment
Crew
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Puerto Rico to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Puerto Rico to Chicago
Discover the top 6 airlines that operate flights from Puerto Rico to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Search flights from Puerto Rico to Chicago by cabin class
Find flights from Puerto Rico to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Puerto Rico to Chicago
Find hourly flight availability from Puerto Rico to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2024.
| 19%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 0%of flight departures | Morning6 am to noon |
| 81%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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How does Cheapflights help users find flights from Puerto Rico to Chicago?
Deals for Puerto Rico to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Puerto Rico to Chicago?
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Puerto Rico to Chicago for you. Better yet — we are completely free to use.
Can Cheapflights find flights from Puerto Rico to Chicago with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Puerto Rico to Chicago, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Puerto Rico to Chicago become cheaper?
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Puerto Rico today and book when prices fit your budget.