Cheap flights from Chicago to San Juan from $66
Round-trip
1 adult
Economy
From?
To?
Tue 5/30
Tue 6/6
Deals available from 900+ travel sites.
Flight information for Chicago to San Juan
Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan
Best Price Found | $66 |
|---|---|
Fastest flight time | 3h 40m |
Direct flights | Every day |
Airports in San Juan | 1 airport |
The best one-way flight to San Juan from Chicago in the past 72 hours is $66. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $165.
The fastest flight from Chicago to San Juan takes 3h 40m
Direct flights go from Chicago to San Juan every day.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)
How to get the cheapest flight ticket from Chicago to San Juan
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 from Chicago to San Juan?
September. The cheapest time of year to fly to San Juan from Chicago is September. Most expensive is December
What is the cheapest airline that flies to San Juan from Chicago?
Frontier. Alaska Airlines, American Airlines, and Delta are the most popular carriers operating from Chicago to San Juan
What is the cheapest Chicago to San Juan flight route?
Chicago Midway - San Juan Luis Munoz Marin Intl. Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices
How far in advance should you book Chicago to San Juan flights?
60 days before. The cheapest time to buy a flight from Chicago to San Juan is approximately 60 days to departure
Can stopping save me money on Chicago to San Juan flights?
No. A direct flight is the cheapest option for a flight between Chicago to San Juan.
If you are looking to fly from Chicago to San Juan, you are most likely going to fly from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport, the most popular airports on that route. You may be looking for an airport near Chicago O'Hare Intl Airport to depart from when traveling to San Juan and Chicago Midway Airport, located in Chicago is a great option. When traveling from Chicago, it is helpful to have an alternative airport to fly into when you land in San Juan. Good options for arrival airports in San Juan, you can try Ponce Mercedita Airport (in Ponce) or Culebra Airport (in Culebra). The least expensive flight option from Chicago to San Juan will typically be MDW — SJU during the month of May with an average price of $147 RT.
Easily compare round-trip flights from Chicago to San Juan
Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to San Juan by changing tabs
Frontier![Frontier]()
Aug 30![Frontier]()
Sep 5
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
SJU12:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW5:19 pmChicago Midway
United Airlines![United Airlines]()
Sep 12![United Airlines]()
Sep 19
ORD4:45 amChicago O'Hare Intl
4h 50m
SJU9:35 amSan Juan Luis Munoz Marin Intl
SJU11:41 amSan Juan Luis Munoz Marin Intl
5h 03m
ORD4:44 pmChicago O'Hare Intl
Undisclosed Carrier![Undisclosed Carrier]()
Sep 5![Undisclosed Carrier]()
Sep 23
ORD2:30 amChicago O'Hare Intl
9h 28m
1 stop
SJU11:58 amSan Juan Luis Munoz Marin Intl
SJU3:55 amSan Juan Luis Munoz Marin Intl
5h 12m
ORD9:07 amChicago O'Hare Intl
Multiple Airlines![Multiple Airlines]()
Jul 5![Multiple Airlines]()
Jul 11
MDW5:20 amChicago Midway
4h 39m
SJU9:59 amSan Juan Luis Munoz Marin Intl
SJU9:39 pmSan Juan Luis Munoz Marin Intl
16h 03m
1 stop
MDW1:42 pmChicago Midway
Frontier![Frontier]()
Nov 3![Frontier]()
Nov 15
MDW1:33 pmChicago Midway
4h 39m
SJU6:12 pmSan Juan Luis Munoz Marin Intl
SJU1:00 amSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:06 amChicago Midway
Find the cheapest one-way flights from Chicago to San Juan
If you're looking for one-way flights from Chicago to San Juan, view some of our deals below provided by Frontier, Undisclosed Carrier and United Airlines
Search last-minute flights to San Juan from Chicago
Find and compare round-trip flight prices for your last-minute flight from Chicago to San Juan
Frontier![Frontier]()
May 31![Frontier]()
Jun 5
MDW6:41 amChicago Midway
4h 33m
SJU11:14 amSan Juan Luis Munoz Marin Intl
SJU1:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:19 pmChicago Midway
Undisclosed Carrier![Undisclosed Carrier]()
May 30![Undisclosed Carrier]()
Jun 13
ORD12:00 amChicago O'Hare Intl
4h 40m
SJU4:40 amSan Juan Luis Munoz Marin Intl
SJU2:50 amSan Juan Luis Munoz Marin Intl
12h 04m
1 stop
ORD2:54 pmChicago O'Hare Intl
Multiple Airlines![Multiple Airlines]()
May 31![Multiple Airlines]()
Jun 8
ORD9:36 amChicago O'Hare Intl
9h 59m
1 stop
SJU7:35 pmSan Juan Luis Munoz Marin Intl
SJU11:46 amSan Juan Luis Munoz Marin Intl
18h 11m
2 stops
ORD5:57 amChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
May 30![Spirit Airlines]()
Jun 13
ORD2:50 amChicago O'Hare Intl
17h 09m
1 stop
SJU7:59 pmSan Juan Luis Munoz Marin Intl
SJU4:57 pmSan Juan Luis Munoz Marin Intl
23h 22m
2 stops
ORD4:19 pmChicago O'Hare Intl
American Airlines![American Airlines]()
Jun 2![American Airlines]()
Jun 5
ORD9:50 amChicago O'Hare Intl
7h 34m
1 stop
SJU5:24 pmSan Juan Luis Munoz Marin Intl
SJU2:30 amSan Juan Luis Munoz Marin Intl
5h 09m
ORD7:39 amChicago O'Hare Intl
Best airlines flying from Chicago to San Juan
Compare and see reviews for airlines that fly from Chicago to San Juan with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $106 | Free Cancellation | Rating 6.1 846 reviews | |||
| PriceFrom $134 | Free Cancellation | Rating 7.0 938 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 7.8 1,240 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 6.1 2,141 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 7.2 2,104 reviews | |||
| PriceFrom $258 | Free Cancellation | Rating 7.2 2,191 reviews | |||
| PriceFrom $303 | Free Cancellation | Rating 7.9 1,943 reviews |
Frontier flights from Chicago to San Juan
Our best Frontier deals on Chicago to San Juan flight tickets
Frontier![Frontier]()
Aug 30![Frontier]()
Sep 5
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
SJU12:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW5:19 pmChicago Midway
Frontier![Frontier]()
Nov 3![Frontier]()
Nov 15
MDW1:33 pmChicago Midway
4h 39m
SJU6:12 pmSan Juan Luis Munoz Marin Intl
SJU1:00 amSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:06 amChicago Midway
United Airlines flights from Chicago to San Juan
Our best United Airlines deals on Chicago to San Juan flight tickets
United Airlines![United Airlines]()
Sep 12![United Airlines]()
Sep 19
ORD4:45 amChicago O'Hare Intl
4h 50m
SJU9:35 amSan Juan Luis Munoz Marin Intl
SJU11:41 amSan Juan Luis Munoz Marin Intl
5h 03m
ORD4:44 pmChicago O'Hare Intl
United Airlines![United Airlines]()
Aug 29![United Airlines]()
Sep 12
ORD6:35 amChicago O'Hare Intl
12h 13m
1 stop
SJU6:48 pmSan Juan Luis Munoz Marin Intl
SJU11:41 amSan Juan Luis Munoz Marin Intl
5h 03m
ORD4:44 pmChicago O'Hare Intl
How far is Chicago to San Juan by plane?
San Juan is 2052.1 mi away from Chicago. 4h 34m is a normal flight duration for this route.
Alternative routes for Chicago to San Juan
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Why use momondo?
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 San Juan from Chicago.
Yes. All flights to San Juan from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
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