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.

Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU)$173
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Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU)$147
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Chicago O'Hare Intl Airport (ORD) to Ponce Mercedita Airport (PSE)$334
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Chicago O'Hare Intl Airport (ORD) to Culebra Airport (CPX)$472
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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
Aug 30
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
Sep 5
SJU12:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW5:19 pmChicago Midway
United Airlines
Sep 12
ORD4:45 amChicago O'Hare Intl
4h 50m
SJU9:35 amSan Juan Luis Munoz Marin Intl
Sep 19
SJU11:41 amSan Juan Luis Munoz Marin Intl
5h 03m
ORD4:44 pmChicago O'Hare Intl
Undisclosed Carrier
Sep 5
ORD2:30 amChicago O'Hare Intl
9h 28m
1 stop
SJU11:58 amSan Juan Luis Munoz Marin Intl
Sep 23
SJU3:55 amSan Juan Luis Munoz Marin Intl
5h 12m
ORD9:07 amChicago O'Hare Intl
Multiple Airlines
Jul 5
MDW5:20 amChicago Midway
4h 39m
SJU9:59 amSan Juan Luis Munoz Marin Intl
Jul 11
SJU9:39 pmSan Juan Luis Munoz Marin Intl
16h 03m
1 stop
MDW1:42 pmChicago Midway
Frontier
Nov 3
MDW1:33 pmChicago Midway
4h 39m
SJU6:12 pmSan Juan Luis Munoz Marin Intl
Nov 15
SJU1:00 amSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:06 amChicago Midway
Frontier
Aug 22
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
Aug 25
SJU12:01 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW5:07 pmChicago 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
Frontier
Aug 9
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
Undisclosed Carrier
Jun 27
ORD11:30 pmChicago O'Hare Intl
4h 45m
SJU4:15 amSan Juan Luis Munoz Marin Intl
United Airlines
Aug 26
ORD5:22 amChicago O'Hare Intl
4h 47m
SJU10:09 amSan Juan Luis Munoz Marin Intl

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
May 31
MDW6:41 amChicago Midway
4h 33m
SJU11:14 amSan Juan Luis Munoz Marin Intl
Jun 5
SJU1:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:19 pmChicago Midway
Undisclosed Carrier
May 30
ORD12:00 amChicago O'Hare Intl
4h 40m
SJU4:40 amSan Juan Luis Munoz Marin Intl
Jun 13
SJU2:50 amSan Juan Luis Munoz Marin Intl
12h 04m
1 stop
ORD2:54 pmChicago O'Hare Intl
Multiple Airlines
May 31
ORD9:36 amChicago O'Hare Intl
9h 59m
1 stop
SJU7:35 pmSan Juan Luis Munoz Marin Intl
Jun 8
SJU11:46 amSan Juan Luis Munoz Marin Intl
18h 11m
2 stops
ORD5:57 amChicago O'Hare Intl
Spirit Airlines
May 30
ORD2:50 amChicago O'Hare Intl
17h 09m
1 stop
SJU7:59 pmSan Juan Luis Munoz Marin Intl
Jun 13
SJU4:57 pmSan Juan Luis Munoz Marin Intl
23h 22m
2 stops
ORD4:19 pmChicago O'Hare Intl
American Airlines
Jun 2
ORD9:50 amChicago O'Hare Intl
7h 34m
1 stop
SJU5:24 pmSan Juan Luis Munoz Marin Intl
Jun 5
SJU2:30 amSan Juan Luis Munoz Marin Intl
5h 09m
ORD7:39 amChicago O'Hare Intl
Frontier
May 31
MDW6:41 amChicago Midway
4h 33m
SJU11:14 amSan Juan Luis Munoz Marin Intl
Jun 5
SJU1:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:19 pmChicago Midway

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
FrontierPriceFrom $106Free CancellationRating
6.1
846 reviews
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JetBluePriceFrom $134Free CancellationRating
7.0
938 reviews
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DeltaPriceFrom $156Free CancellationRating
7.8
1,240 reviews
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Spirit AirlinesPriceFrom $156Free CancellationRating
6.1
2,141 reviews
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United AirlinesPriceFrom $236Free CancellationRating
7.2
2,104 reviews
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American AirlinesPriceFrom $258Free CancellationRating
7.2
2,191 reviews
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Alaska AirlinesPriceFrom $303Free CancellationRating
7.9
1,943 reviews
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Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Aug 30
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
Sep 5
SJU12:13 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW5:19 pmChicago Midway
Frontier
Nov 3
MDW1:33 pmChicago Midway
4h 39m
SJU6:12 pmSan Juan Luis Munoz Marin Intl
Nov 15
SJU1:00 amSan Juan Luis Munoz Marin Intl
5h 06m
MDW6:06 amChicago Midway
Frontier
Aug 22
MDW6:41 amChicago Midway
4h 39m
SJU11:20 amSan Juan Luis Munoz Marin Intl
Aug 25
SJU12:01 pmSan Juan Luis Munoz Marin Intl
5h 06m
MDW5:07 pmChicago Midway

United Airlines flights from Chicago to San Juan

Our best United Airlines deals on Chicago to San Juan flight tickets
United Airlines
Sep 12
ORD4:45 amChicago O'Hare Intl
4h 50m
SJU9:35 amSan Juan Luis Munoz Marin Intl
Sep 19
SJU11:41 amSan Juan Luis Munoz Marin Intl
5h 03m
ORD4:44 pmChicago O'Hare Intl
United Airlines
Aug 29
ORD6:35 amChicago O'Hare Intl
12h 13m
1 stop
SJU6:48 pmSan Juan Luis Munoz Marin Intl
Sep 12
SJU11:41 amSan Juan Luis Munoz Marin Intl
5h 03m
ORD4:44 pmChicago O'Hare Intl
United Airlines
Sep 18
ORD4:45 amChicago O'Hare Intl
4h 50m
SJU9:35 amSan Juan Luis Munoz Marin Intl
Sep 22
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

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
St. Louis to San Juan Flights
Fastest flight time2h 02m
Cheapest price$282

Similar Chicago to San Juan flights

Flexible with your destination? Broaden your search and find flights similar to your Chicago to San Juan route

Flights to other cities in Puerto Rico

Lost the lust for San Juan? Check out some flights to other cities in Puerto Rico

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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