Cheap flights from San Juan to Chicago (CHI) from $104
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.
The best prices from San Juan to Chicago are usually found in January or August, booked 15 days in advance, depart on a Friday or Thursday and return on a Tuesday
Cheap flight deals from San Juan to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 6, 2024.
Popular in | March |
|---|---|
Cheapest in | January |
Round-trip from | $223 |
One-way from | $137 |
What is the cheapest day to fly round-trip from San Juan to Chicago?
Users have found that flying from San Juan to Chicago on a Friday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.
How far in advance should I book a flight from San Juan to Chicago?
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 16 days in advance, which can save you up to 85% on flights from San Juan to Chicago compared to booking the week you need them. Waiting 16 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $238. For sooner than that we have options available in the next 3 days from $309.
What is the cheapest month to fly from San Juan to Chicago?
The best pricing can be found in the month of January. Prices to Chicago from San Juan average $270. You can even find prices in January for less than $270, as users have found deals to Chicago from as low as $122. The month of March appears to be one of the more expensive times to travel to Chicago from San Juan. Flying in the targeted month can save you up to 34%.
When is the cheapest time to fly from San Juan to Chicago (SJU - CHI)?
When flying from San Juan to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 14% versus a flight in the afternoon.
Cheap Spirit Airlines flights from San Juan to Chicago
Explore cheap flight options specifically provided by Spirit Airlines for the route between San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
Check out some of the cheapest Spirit Airlines flights we've come across from San Juan to Chicago. It's recommended that users confirm their flight details before booking.
Cheap American Airlines flights from San Juan to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
Take a gander at the lowest prices we've found on American Airlines flights from San Juan to Chicago. Make sure to examine the flight information before completing your reservation.
Cheap San Juan to Chicago flights in May & June 2024
Find cheap flight options from San Juan 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 2,719,943 searches. Prices were last updated on May 6, 2024.
These are some of the most attractive deals on flights from San Juan to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
San Juan to Chicago 2024 flight deals
Discover exclusive flight deals for travel between San Juan and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,719,943 searches. Data last updated May 6, 2024.
These are some of the most attractive deals on flights from San Juan 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 San Juan
Discover non-stop flight options from San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
For a shorter flight, select one of these non-stop flights from San Juan to Chicago. If you're looking for other options for flights from San Juan to Chicago, make sure to update the search form at the top of page.
San Juan to Chicago flights leaving soon
Find last-minute flight options from San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
Users seeking a last-minute flight from San Juan to Chicago should consider booking one of these fares. Tip: verify your flight details before completing your reservation.
One-way flights to Chicago from San Juan
Search for one-way flight options from San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
Users traveling one-way from San Juan to Chicago can select one of these great deals. Users in need of a round-trip flight from San Juan to Chicago instead should update the search form at the top of page.
Find flights from San Juan to Chicago within your budget
Customize your flight search to find flights from San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
Fly from
Fly to
Budget
$178 - $263
Route
Depart
Return
Price
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop10h 03m
Chicago Midway
Mon 5/20
1 stop12h 21m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop27h 43m
Chicago O'Hare Intl
Mon 5/20
1 stop7h 02m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/9
Nonstop5h 10m
Chicago O'Hare Intl
Tue 5/14
3 stops27h 24m
San Juan Luis Munoz Marin IntlChicago Midway
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Sat 5/18
1 stop7h 31m
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
Thu 6/6
1 stop12h 49m
Chicago O'Hare Intl
Mon 6/10
Nonstop4h 48m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 6/5
Nonstop5h 09m
Chicago O'Hare Intl
Sat 6/8
Nonstop4h 47m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop22h 43m
Chicago O'Hare Intl
Tue 5/21
1 stop11h 28m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/17
1 stop17h 10m
Chicago O'Hare Intl
Mon 5/20
1 stop7h 02m
San Juan Luis Munoz Marin IntlChicago O'Hare Intl
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 5/8
1 stop8h 46m
Chicago O'Hare Intl
Wed 5/15
1 stop9h 20m
When is the best time to book a flight from San Juan to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San Juan to Chicago. Price data was last updated on May 3, 2024.
To ensure you get the cheapest price possible for a flight from San Juan to Chicago, you should look to book at least 15 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
When is the cheapest time to fly from San Juan to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Juan to Chicago. Price data was last updated on April 28, 2024.
Average price of flights to Chicago by month
Plan your trip from San Juan to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from San Juan to Chicago is currently $110 while a round-trip flight costs $191. Price data was last updated on April 28, 2024.
Currently, February is the cheapest month in which you can book a flight from San Juan to Chicago (average of $245). Flying from San Juan to Chicago in June is currently the most expensive (average of $354). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$245
March
$280
April
$267
May
$279
June
$354
July
$334
August
$274
September
$258
October
$248
November
$270
December
$248
Temperature and rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.
CHI Temperature | 23 - 73.4 °F |
|---|
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 6, 2024.
To help decide which airline to fly from San Juan to Chicago, see what other customers have to say about Spirit Airlines, American Airlines and Frontier. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Crew
Comfort
Food
Boarding
Overall
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.
Entertainment
Crew
Comfort
Food
Boarding
Overall
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.
Entertainment
Crew
Comfort
Food
Boarding
Overall
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.
Entertainment
Crew
Comfort
Food
Boarding
Overall
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.
Entertainment
Crew
Comfort
Food
Boarding
Overall
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.
Entertainment
Crew
Comfort
Food
Boarding
Overall
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 San Juan 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 San Juan 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 San Juan to Chicago
Discover the top 6 airlines that operate flights from San Juan 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 2,719,943 searches. Data last updated May 6, 2024.
Search flights from San Juan to Chicago by cabin class
Find flights from San Juan to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from San Juan to Chicago
Find hourly flight availability from San Juan 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 6, 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 |
Weekly flight availability from San Juan to Chicago
Explore weekly flight availability from San Juan to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 6, 2024.
| Sunday | 11daily flights |
|---|---|
| Monday | 7daily flights |
| Tuesday | 7daily flights |
| Wednesday | 7daily flights |
| Thursday | 7daily flights |
| Friday | 7daily flights |
| Saturday | 11daily flights |
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 San Juan to Chicago?
Cheapflights makes it easy to find San Juan to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from San Juan to Chicago?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from San Juan.
Can Cheapflights find flights from San Juan to Chicago with no change fees?
Yes! Cheapflights helps users easily find flights from San Juan to Chicago with no change fees.
Can Cheapflights notify me if prices for flights from San Juan to Chicago become cheaper?
Yes! Start tracking prices for San Juan to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.