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Cheap flights from Illinois to Puerto Rico from $58

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

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Find the cheapest flights from Illinois to Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:42 pm - 3:26 pm
STL
-
SJU
19h 44m1 stop
Frontier Logo
4:36 pm - 10:23 am
SJU
-
STL
19h 47m1 stop
$116Frontier
Mon, Jan 26 - Thu, Jan 29
Frontier Logo
5:42 pm - 11:59 pm
STL
-
SJU
28h 17m1 stop
Frontier Logo
4:36 pm - 11:33 pm
SJU
-
STL
8h 57m1 stop
$148Frontier
Tue, Feb 3 - Mon, Feb 9
JetBlue Logo
6:45 am - 6:05 pm
ORD
-
SJU
9h 20m1 stop
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
$201JetBlue
Mon, Jan 12 - Tue, Jan 20
JetBlue Logo
7:45 am - 6:05 pm
ORD
-
SJU
8h 20m1 stop
JetBlue Logo
1:20 pm - 7:36 pm
SJU
-
ORD
8h 16m1 stop
$205JetBlue
Sun, Jan 25 - Sat, Jan 31
Multiple Airlines Logo
9:34 am - 2:39 am
ORD
-
SJU
15h 05m2 stops
Multiple Airlines Logo
5:18 pm - 11:46 pm
SJU
-
ORD
8h 28m1 stop
$206Multiple Airlines
Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
9:23 am - 6:58 pm
ORD
-
SJU
7h 35m1 stop
Multiple Airlines Logo
10:47 pm - 8:18 am
SJU
-
ORD
11h 31m1 stop
$207Multiple Airlines
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
5:16 pm - 10:48 am
PIA
-
SJU
15h 32m2 stops
American Airlines Logo
1:24 pm - 10:21 pm
SJU
-
PIA
10h 57m2 stops
$235American Airlines
Sat, Jan 24 - Tue, Jan 27
American Airlines Logo
6:00 am - 11:34 pm
SPI
-
SJU
15h 34m2 stops
American Airlines Logo
11:38 am - 10:14 pm
SJU
-
SPI
12h 36m2 stops
$235American Airlines
Thu, Jan 1 - Wed, Jan 14
United Airlines Logo
1:24 pm - 6:11 am
PIA
-
SJU
14h 47m2 stops
United Airlines Logo
8:35 am - 2:23 pm
SJU
-
PIA
7h 48m1 stop
$290United Airlines
Sat, Jan 24 - Tue, Jan 27
United Airlines Logo
8:30 am - 8:38 pm
PIA
-
SJU
11h 08m2 stops
United Airlines Logo
1:00 am - 10:02 am
SJU
-
PIA
10h 02m2 stops
$325United Airlines
Sat, May 2 - Tue, May 5

Frontier flights from Illinois to Puerto Rico

Our best Frontier deals on Illinois to Puerto Rico flight tickets
Frontier
Jan 26
STL5:42 pmLambert-St Louis
19h 44m
1 stop
SJU3:26 pmSan Juan Luis Munoz Marin Intl
Jan 29
SJU4:36 pmSan Juan Luis Munoz Marin Intl
19h 47m
1 stop
STL10:23 amLambert-St Louis
$116
Find similar
Frontier
Feb 3
STL5:42 pmLambert-St Louis
28h 17m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Feb 9
SJU4:36 pmSan Juan Luis Munoz Marin Intl
8h 57m
1 stop
STL11:33 pmLambert-St Louis
$148
Find similar
Frontier
Jan 24
STL5:42 pmLambert-St Louis
14h 12m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
Jan 31
SJU4:36 pmSan Juan Luis Munoz Marin Intl
8h 57m
1 stop
STL11:33 pmLambert-St Louis
$149
Find similar

JetBlue flights from Illinois to Puerto Rico

Our best JetBlue deals on Illinois to Puerto Rico flight tickets
JetBlue
Jan 12
ORD6:45 amChicago O'Hare Intl
9h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Jan 20
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
$201
Find similar
JetBlue
Jan 25
ORD7:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU1:20 pmSan Juan Luis Munoz Marin Intl
8h 16m
1 stop
ORD7:36 pmChicago O'Hare Intl
$205
Find similar
JetBlue
Feb 6
ORD7:45 amChicago O'Hare Intl
8h 17m
1 stop
SJU6:02 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU5:22 pmSan Juan Luis Munoz Marin Intl
7h 48m
1 stop
ORD11:10 pmChicago O'Hare Intl
$211
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Puerto Rico 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Illinois to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Mon 1/26

5:42 pm-3:26 pm

1 stop19h 44m

San Juan Luis Munoz Marin Intl

Thu 1/29

4:36 pm-10:23 am

1 stop19h 47m

$116

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 2/3

5:42 pm-11:59 pm

1 stop28h 17m

San Juan Luis Munoz Marin Intl

Mon 2/9

4:36 pm-11:33 pm

1 stop8h 57m

$148

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

6:45 am-6:05 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Tue 1/20

11:06 am-7:36 pm

1 stop10h 30m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Sat 1/31

1:20 pm-7:36 pm

1 stop8h 16m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/5

9:34 am-2:39 am

2 stops15h 05m

San Juan Luis Munoz Marin Intl

Fri 1/9

5:18 pm-11:46 pm

1 stop8h 28m

$206

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 1/9

9:23 am-6:58 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Mon 1/12

10:47 pm-8:18 am

1 stop11h 31m

$207

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Sat 1/24

5:16 pm-10:48 am

2 stops15h 32m

San Juan Luis Munoz Marin Intl

Tue 1/27

1:24 pm-10:21 pm

2 stops10h 57m

$235

SpringfieldSan Juan

SPI - SJU

SPISJU

Springfield Capital

Thu 1/1

6:00 am-11:34 pm

2 stops15h 34m

San Juan Luis Munoz Marin Intl

Wed 1/14

11:38 am-10:14 pm

2 stops12h 36m

$235

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Sat 1/24

1:24 pm-6:11 am

2 stops14h 47m

San Juan Luis Munoz Marin Intl

Tue 1/27

8:35 am-2:23 pm

1 stop7h 48m

$290

PeoriaSan Juan

PIA - SJU

PIASJU

Greater Peoria

Sat 5/2

8:30 am-8:38 pm

2 stops11h 08m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-10:02 am

2 stops10h 02m

$325

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Puerto Rico from

How to get the cheapest flight ticket from Illinois to Puerto Rico

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 to Puerto Rico?

If you don’t want to visit Puerto Rico in April, then you should wait until October to fly from Illinois, when ticket prices are also cheap, with an average price of $353.

What is the cheapest day to depart on your flight to Puerto Rico?

On average, the least expensive day to fly to Puerto Rico from Illinois is on a Monday. momondo users have found tickets for Monday departures for as low as $391. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Friday, with ticket prices averaging around $444.

What is the cheapest time of day to depart on your flight to Puerto Rico?

Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Illinois to Puerto Rico during this time can be as low as $318. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $447.

What is the cheapest Illinois to Puerto Rico flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Illinois - Puerto Rico flight prices

How far in advance should I book a flight to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $397 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Illinois for as low as $332 on momondo.

What cabin class options are available on Illinois to Puerto Rico flights?

There are 4 cabin classes available to choose from on Illinois to Puerto Rico flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Illinois to Puerto Rico flights?

You could potentially save up to 44% on your flight if you consider stops on a Illinois to Puerto Rico flight.

Cheap Illinois to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Puerto Rico

Best Price Found

$153

Fastest flight time

4h 20m

Direct flights

Every day

Airports in Puerto Rico

20 airports
The best one-way flight to Puerto Rico from Illinois in the past 72 hours is $153. The best round-trip flight deal from Illinois to Puerto Rico found on momondo in the last 72 hours is $303.
The fastest flight from Illinois to Puerto Rico takes 4h 20m
Direct flights go from Illinois to Puerto Rico every day.
There are 20 airports in Puerto Rico. From Illinois there are direct flights to San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

  • When did momondo last update prices for flights from Illinois to Puerto Rico?

    Prices for flights from Illinois to Puerto Rico are updated daily.

  • How many operators does momondo search for flights from Illinois to Puerto Rico?

  • How old do you have to be to fly from Illinois to Puerto Rico?

    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 Illinois to Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The required travel and health documents for your Puerto Rico trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Puerto Rico. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Illinois to Puerto Rico?

Best airlines flying from Illinois to Puerto Rico

Compare and see reviews for airlines that fly from Illinois to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $107Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $140Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
JetBluePriceFrom $147Free CancellationRating
7.2
2,898 reviews
Search JetBlue flights
DeltaPriceFrom $190Free CancellationRating
7.9
8,008 reviews
Search Delta flights
American AirlinesPriceFrom $225Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
United AirlinesPriceFrom $284Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
SouthwestPriceFrom $381Free CancellationRating
7.9
4,252 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Puerto Rico?

It is quick and easy to find Illinois to Puerto Rico flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Puerto Rico that suits you.

Can I find flights from Illinois to Puerto Rico with flexible booking policies on momondo?

All flight searches from Illinois to Puerto Rico on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Illinois to Puerto Rico?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Illinois to Puerto Rico.

I’m not ready to book a flight from Illinois to Puerto Rico right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Illinois to Puerto Rico flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Puerto Rico

Popular cities in Puerto Rico

Popular flights according to clicks in the last 7 days on momondo
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