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Cheap flights from Chicago to San Juan from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Juan departing on 8/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Tue 7/16
Tue 7/23

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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
Spirit Airlines
Sep 7
ORD7:05 amChicago O'Hare Intl
12h 54m
1 stop
SJU8:59 pmSan Juan Luis Munoz Marin Intl
Sep 10
SJU6:20 pmSan Juan Luis Munoz Marin Intl
16h 13m
1 stop
ORD9:33 amChicago O'Hare Intl
Multiple Airlines
Sep 14
ORD7:00 amChicago O'Hare Intl
13h 56m
1 stop
SJU9:56 pmSan Juan Luis Munoz Marin Intl
Sep 16
SJU1:25 amSan Juan Luis Munoz Marin Intl
10h 08m
1 stop
ORD10:33 amChicago O'Hare Intl
Frontier
Sep 4
MDW4:46 pmChicago Midway
10h 35m
1 stop
SJU4:21 amSan Juan Luis Munoz Marin Intl
Sep 20
SJU3:08 amSan Juan Luis Munoz Marin Intl
7h 05m
1 stop
MDW9:13 amChicago Midway
Spirit Airlines
Sep 23
ORD7:05 amChicago O'Hare Intl
11h 03m
1 stop
SJU7:08 pmSan Juan Luis Munoz Marin Intl
Sep 30
SJU9:45 pmSan Juan Luis Munoz Marin Intl
12h 48m
1 stop
ORD9:33 amChicago O'Hare Intl
Spirit Airlines
Sep 7
ORD5:05 amChicago O'Hare Intl
14h 54m
1 stop
SJU8:59 pmSan Juan Luis Munoz Marin Intl
Sep 10
SJU3:16 pmSan Juan Luis Munoz Marin Intl
30h 43m
2 stops
ORD8:59 pmChicago O'Hare Intl
Multiple Airlines
Sep 23
ORD5:05 amChicago O'Hare Intl
14h 54m
1 stop
SJU8:59 pmSan Juan Luis Munoz Marin Intl
Sep 29
SJU1:25 amSan Juan Luis Munoz Marin Intl
10h 08m
1 stop
ORD10:33 amChicago 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 American Airlines, Frontier and Spirit Airlines
Spirit Airlines
Aug 13
ORD9:15 pmChicago O'Hare Intl
16h 23m
1 stop
SJU2:38 pmSan Juan Luis Munoz Marin Intl
Frontier
Sep 9
MDW3:28 pmChicago Midway
8h 57m
1 stop
SJU1:25 amSan Juan Luis Munoz Marin Intl
Multiple Airlines
Aug 12
ORD9:33 pmChicago O'Hare Intl
34h 12m
2 stops
SJU8:45 amSan Juan Luis Munoz Marin Intl

Find the cheapest direct flights from Chicago to San Juan

Spirit Airlines
Aug 20
ORD2:10 pmChicago O'Hare Intl
4h 47m
SJU7:57 pmSan Juan Luis Munoz Marin Intl
Aug 23
SJU8:50 pmSan Juan Luis Munoz Marin Intl
4h 59m
ORD12:49 amChicago O'Hare Intl
United Airlines
Nov 3
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Nov 7
SJU8:35 amSan Juan Luis Munoz Marin Intl
5h 19m
ORD11:54 amChicago O'Hare Intl
Spirit Airlines
Aug 27
ORD2:10 pmChicago O'Hare Intl
4h 47m
SJU7:57 pmSan Juan Luis Munoz Marin Intl
Sep 3
SJU8:50 pmSan Juan Luis Munoz Marin Intl
4h 59m
ORD12:49 amChicago O'Hare Intl
American Airlines
Dec 10
ORD8:20 amChicago O'Hare Intl
4h 32m
SJU2:52 pmSan Juan Luis Munoz Marin Intl
Dec 16
SJU4:15 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD7:40 pmChicago O'Hare Intl
Spirit Airlines
Aug 10
ORD10:26 pmChicago O'Hare Intl
4h 45m
SJU4:11 amSan Juan Luis Munoz Marin Intl
Aug 20
SJU8:50 pmSan Juan Luis Munoz Marin Intl
4h 59m
ORD12:49 amChicago O'Hare Intl
Spirit Airlines
Aug 27
ORD2:10 pmChicago O'Hare Intl
4h 47m
SJU7:57 pmSan Juan Luis Munoz Marin Intl
Sep 9
SJU3:07 pmSan Juan Luis Munoz Marin Intl
5h 19m
ORD7:26 pmChicago O'Hare 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 20
ORD10:26 pmChicago O'Hare Intl
4h 45m
SJU4:11 amSan Juan Luis Munoz Marin Intl
Jul 28
SJU9:15 pmSan Juan Luis Munoz Marin Intl
12h 48m
1 stop
ORD9:03 amChicago O'Hare Intl
Frontier
Jul 17
MDW9:31 amChicago Midway
16h 41m
1 stop
SJU3:12 amSan Juan Luis Munoz Marin Intl
Aug 8
SJU5:27 amSan Juan Luis Munoz Marin Intl
10h 23m
1 stop
MDW2:50 pmChicago Midway
Multiple Airlines
Jul 16
ORD11:48 amChicago O'Hare Intl
4h 47m
SJU5:35 pmSan Juan Luis Munoz Marin Intl
Aug 5
SJU3:08 amSan Juan Luis Munoz Marin Intl
22h 21m
1 stop
ORD12:29 amChicago O'Hare Intl
Spirit Airlines
Jul 19
ORD5:42 pmChicago O'Hare Intl
7h 54m
1 stop
SJU2:36 amSan Juan Luis Munoz Marin Intl
Jul 28
SJU9:15 pmSan Juan Luis Munoz Marin Intl
12h 48m
1 stop
ORD9:03 amChicago O'Hare Intl
Frontier
Jul 20
MDW11:51 amChicago Midway
13h 10m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
Jul 25
SJU8:41 pmSan Juan Luis Munoz Marin Intl
12h 55m
1 stop
MDW8:36 amChicago Midway
Spirit Airlines
Jul 18
ORD12:28 pmChicago O'Hare Intl
4h 45m
SJU6:13 pmSan Juan Luis Munoz Marin Intl
Jul 25
SJU11:08 pmSan Juan Luis Munoz Marin Intl
11h 06m
1 stop
ORD9:14 amChicago O'Hare Intl

Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets
Spirit Airlines
Sep 7
ORD7:05 amChicago O'Hare Intl
12h 54m
1 stop
SJU8:59 pmSan Juan Luis Munoz Marin Intl
Sep 10
SJU6:20 pmSan Juan Luis Munoz Marin Intl
16h 13m
1 stop
ORD9:33 amChicago O'Hare Intl
Spirit Airlines
Sep 23
ORD7:05 amChicago O'Hare Intl
11h 03m
1 stop
SJU7:08 pmSan Juan Luis Munoz Marin Intl
Sep 30
SJU9:45 pmSan Juan Luis Munoz Marin Intl
12h 48m
1 stop
ORD9:33 amChicago O'Hare Intl
Spirit Airlines
Sep 7
ORD5:05 amChicago O'Hare Intl
14h 54m
1 stop
SJU8:59 pmSan Juan Luis Munoz Marin Intl
Sep 10
SJU3:16 pmSan Juan Luis Munoz Marin Intl
30h 43m
2 stops
ORD8:59 pmChicago O'Hare Intl

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Sep 4
MDW4:46 pmChicago Midway
10h 35m
1 stop
SJU4:21 amSan Juan Luis Munoz Marin Intl
Sep 20
SJU3:08 amSan Juan Luis Munoz Marin Intl
7h 05m
1 stop
MDW9:13 amChicago Midway
Frontier
Sep 4
MDW4:46 pmChicago Midway
10h 35m
1 stop
SJU4:21 amSan Juan Luis Munoz Marin Intl
Sep 21
SJU9:42 amSan Juan Luis Munoz Marin Intl
10h 36m
1 stop
MDW7:18 pmChicago Midway
Frontier
Sep 23
MDW7:59 pmChicago Midway
12h 11m
1 stop
SJU9:10 amSan Juan Luis Munoz Marin Intl
Sep 30
SJU10:16 amSan Juan Luis Munoz Marin Intl
9h 57m
1 stop
MDW7:13 pmChicago Midway

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?

October. The cheapest time of year to fly to San Juan from Chicago is October. Most expensive is March

What is the cheapest day to depart Chicago for San Juan?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Chicago to San Juan?

In the afternoon. Chicago to San Juan flights are approximately 33% more expensive in the evening than in the afternoon

What is the cheapest airline that flies to San Juan from Chicago?

Frontier. Frontier, Spirit Airlines, and JetBlue 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?

31 days before. The cheapest time to buy a flight from Chicago to San Juan is approximately 31 days to departure

How many flights depart from Chicago to San Juan on average per day?

7 flights are operational weekly from Chicago to San Juan as of July 2024. The most popular departure time for this route is 7:00AM, with 100% of flights per day taking off at noon.

How many flights depart from Chicago to San Juan on average per week?

As of July 2024, there are 50 flights per week flying from Chicago to San Juan. The most common day of the week flights depart is Saturday, with 20% of flights taking off on this day.

Can stopping save me money on Chicago to San Juan flights?

You could potentially save up to 27% on your flight if you consider stops on a Chicago to San Juan flight.

Cheap Chicago to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan

Best Price Found

$55

Fastest flight time

4h 32m

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 $55. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $119.
The fastest flight from Chicago to San Juan takes 4h 32m
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 far is Chicago to San Juan by plane?

    San Juan is 2052.1 mi away from Chicago. 4h 45m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to San Juan?

    Prices for flights from Chicago to San Juan refresh daily.

  • How many operators does momondo search for flights from Chicago to San Juan?

  • How old do you have to be to fly from Chicago to San Juan?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The travel and health documents required for your trip to San Juan can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Juan. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


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 $90Free CancellationRating
6.2
3,868 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $133Free CancellationRating
6.3
8,440 reviews
Search Spirit Airlines flights
JetBluePriceFrom $136Free CancellationRating
7.6
4,082 reviews
Search JetBlue flights
DeltaPriceFrom $158Free CancellationRating
8.0
9,842 reviews
Search Delta flights
United AirlinesPriceFrom $173Free CancellationRating
7.4
10,000 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $301Free CancellationRating
8.0
9,367 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $315Free CancellationRating
7.3
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

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.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

Yes. All flights to San Juan from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to San Juan?

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.

I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?

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.


An easier way to manage your San Juan trip

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1 adult
From?
To?
Tue 7/16
Tue 7/23
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Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan
Airports listed have a maximum distance of 7.1 mi from San Juan