Cheap flights from Chicago to San Juan from $122

Round-trip
1 adult
Economy
From?
To?
Tue 7/5
Tue 7/12

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

$122

Fastest flight time

4h 35m

Direct flights

None

Airports in San Juan

2 airports
The best one-way flight to San Juan from Chicago in the past 72 hours is $122. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $228.
The fastest flight from Chicago to San Juan takes 4h 35m
There are no direct flights from Chicago to San Juan. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - San Juan Luis Munoz Marin Intl Airport and Chicago Midway Airport - San Juan Luis Munoz Marin Intl Airport.
There are 2 airports near San Juan: San Juan Isla Grande (SIG), 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?

Juneyao Airlines

American Airlines, Delta, and Frontier are the most popular carriers operating from Chicago to San Juan

What is the cheapest Chicago to San Juan flight route?

Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl

Fly from Chicago O'Hare Intl 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

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 ORD — SJU during the month of June with an average price of $228 RT.

Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU)$228
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Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU)$371
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Chicago O'Hare Intl Airport (ORD) to Ponce Mercedita Airport (PSE)$409
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Chicago O'Hare Intl Airport (ORD) to Culebra Airport (CPX)$1,706
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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 three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to San Juan by changing tabs
Spirit Airlines
Sep 20
ORD3:41 pmChicago O'Hare Intl
23h 05m
1 stop
SJU2:46 pmSan Juan Luis Munoz Marin Intl
Sep 27
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl
Multiple Airlines
Sep 3
ORD10:30 amChicago O'Hare Intl
10h 49m
1 stop
SJU9:19 pmSan Juan Luis Munoz Marin Intl
Sep 11
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl
JetBlue
Aug 30
ORD11:57 amChicago O'Hare Intl
8h 25m
1 stop
SJU8:22 pmSan Juan Luis Munoz Marin Intl
Sep 4
SJU1:40 amSan Juan Luis Munoz Marin Intl
10h 32m
1 stop
ORD12:12 pmChicago O'Hare Intl
Frontier
Jul 12
MDW2:30 pmChicago Midway
25h 09m
1 stop
SJU3:39 pmSan Juan Luis Munoz Marin Intl
Aug 16
SJU5:41 amSan Juan Luis Munoz Marin Intl
25h 51m
1 stop
MDW7:32 amChicago Midway
Spirit Airlines
Sep 13
ORD3:41 pmChicago O'Hare Intl
23h 05m
1 stop
SJU2:46 pmSan Juan Luis Munoz Marin Intl
Sep 21
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl
Multiple Airlines
Sep 2
ORD11:57 amChicago O'Hare Intl
9h 25m
1 stop
SJU9:22 pmSan Juan Luis Munoz Marin Intl
Sep 11
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl

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 Delta, JetBlue and Spirit Airlines
Spirit Airlines
Aug 17
ORD3:40 pmChicago O'Hare Intl
17h 54m
1 stop
SJU9:34 amSan Juan Luis Munoz Marin Intl
JetBlue
Aug 24
ORD11:57 amChicago O'Hare Intl
8h 25m
1 stop
SJU8:22 pmSan Juan Luis Munoz Marin Intl
Multiple Airlines
Jul 11
ORD3:41 pmChicago O'Hare Intl
12h 05m
1 stop
SJU3:46 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
Spirit Airlines
Jul 10
ORD1:05 amChicago O'Hare Intl
13h 24m
1 stop
SJU2:29 pmSan Juan Luis Munoz Marin Intl
Aug 15
SJU4:29 pmSan Juan Luis Munoz Marin Intl
14h 08m
1 stop
ORD6:37 amChicago O'Hare Intl
Multiple Airlines
Jul 8
ORD10:30 amChicago O'Hare Intl
10h 49m
1 stop
SJU9:19 pmSan Juan Luis Munoz Marin Intl
Aug 5
SJU4:25 pmSan Juan Luis Munoz Marin Intl
14h 13m
1 stop
ORD6:38 amChicago O'Hare Intl
American Airlines
Jul 6
ORD5:56 amChicago O'Hare Intl
11h 58m
2 stops
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Jul 9
SJU2:00 amSan Juan Luis Munoz Marin Intl
15h 45m
1 stop
ORD5:45 pmChicago O'Hare Intl
Frontier
Jul 9
MDW1:24 pmChicago Midway
7h 03m
1 stop
SJU8:27 pmSan Juan Luis Munoz Marin Intl
Jul 12
SJU5:41 amSan Juan Luis Munoz Marin Intl
25h 51m
1 stop
MDW7:32 amChicago Midway
Spirit Airlines
Jul 9
ORD1:05 amChicago O'Hare Intl
13h 24m
1 stop
SJU2:29 pmSan Juan Luis Munoz Marin Intl
Jul 16
SJU1:10 pmSan Juan Luis Munoz Marin Intl
6h 51m
1 stop
ORD8:01 pmChicago O'Hare Intl
Multiple Airlines
Jul 6
ORD6:30 amChicago O'Hare Intl
11h 24m
2 stops
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Aug 11
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
ORD12:54 pmChicago 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
AirlineRatingFree CancellationPrice
Juneyao AirlinesPriceFrom $11Free CancellationRating
0.0
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Spirit AirlinesPriceFrom $85Free CancellationRating
6.2
6.4

Boarding

5.9

Comfort

7.0

Crew

4.9

Entertainment

5.1

Food

Reviews

I purchased the first two front row seats. They were very comfortable and had plenty of room. It is worth the extra to purchase them. The flight crew coming and going were awsome and kept the time passing.

1 / 10
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JetBluePriceFrom $101Free CancellationRating
6.9
7.1

Boarding

7.3

Comfort

7.7

Crew

7.0

Entertainment

6.5

Food

Reviews

Flight attendants were amazing

1 / 10
Search JetBlue flights
FrontierPriceFrom $111Free CancellationRating
6.2
6.4

Boarding

5.8

Comfort

7.0

Crew

4.7

Entertainment

5.0

Food

Reviews

Received a text saying flight had been delayed by 30 minutes. When I arrived they were boarding at original flight time I was late! No text was sent informing me that original time was the current time.

1 / 10
Search Frontier flights
DeltaPriceFrom $122Free CancellationRating
7.8
7.9

Boarding

8.0

Comfort

8.3

Crew

7.7

Entertainment

7.3

Food

Reviews

This is another disease as if you have the Internet, you are ordinary deceivers!

1 / 10
Search Delta flights
United AirlinesPriceFrom $124Free CancellationRating
7.2
7.5

Boarding

7.1

Comfort

8.0

Crew

6.9

Entertainment

6.5

Food

Reviews

No delays, and everything went smoothly, right on time

1 / 10
Search United Airlines flights
American AirlinesPriceFrom $174Free CancellationRating
7.1
7.4

Boarding

7.1

Comfort

8.0

Crew

6.8

Entertainment

6.4

Food

Reviews

Flight attendant very attentive and great service

1 / 10
Search American Airlines flights
Alaska AirlinesPriceFrom $325Free CancellationRating
7.9
8.2

Boarding

7.9

Comfort

8.5

Crew

7.2

Entertainment

7.1

Food

Reviews

The snacks were great and the landing was pretty concerning.

1 / 10
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Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets
Spirit Airlines
Sep 20
ORD3:41 pmChicago O'Hare Intl
23h 05m
1 stop
SJU2:46 pmSan Juan Luis Munoz Marin Intl
Sep 27
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl
Spirit Airlines
Sep 13
ORD3:41 pmChicago O'Hare Intl
23h 05m
1 stop
SJU2:46 pmSan Juan Luis Munoz Marin Intl
Sep 21
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl
Spirit Airlines
Sep 10
ORD1:05 amChicago O'Hare Intl
13h 18m
1 stop
SJU2:23 pmSan Juan Luis Munoz Marin Intl
Sep 14
SJU4:00 amSan Juan Luis Munoz Marin Intl
8h 53m
1 stop
ORD12:53 pmChicago O'Hare Intl

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Jul 12
MDW2:30 pmChicago Midway
25h 09m
1 stop
SJU3:39 pmSan Juan Luis Munoz Marin Intl
Aug 16
SJU5:41 amSan Juan Luis Munoz Marin Intl
25h 51m
1 stop
MDW7:32 amChicago Midway
Frontier
Jul 12
MDW2:30 pmChicago Midway
25h 09m
1 stop
SJU3:39 pmSan Juan Luis Munoz Marin Intl
Jul 27
SJU5:41 amSan Juan Luis Munoz Marin Intl
25h 54m
1 stop
MDW7:35 amChicago Midway
Frontier
Jul 12
MDW3:53 amChicago Midway
11h 27m
2 stops
SJU3:20 pmSan Juan Luis Munoz Marin Intl
Aug 16
SJU5:41 amSan Juan Luis Munoz Marin Intl
25h 51m
1 stop
MDW7:32 amChicago Midway

  • Are airlines flying from Chicago to San Juan offering flexible cancellation due to COVID-19?

    Some of our partner airlines flying from Chicago to San Juan are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are American Airlines, Frontier, and United Airlines. You can search for the full list of airlines like American Airlines that are offering this flexibility.

  • How far is Chicago to San Juan by plane?

    San Juan is 2052.1 mi away from Chicago. 7h 33m 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 time3h 02m
Cheapest price$295

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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.

momondo provides multiple filters to help you find the best flight to San Juan from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

Yes momondo offers price alerts on flights to San Juan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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