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Cheap flights from Puerto Rico to Illinois from $112

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Puerto Rico to Illinois departing on 5/21. 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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Find the cheapest flights from Puerto Rico to Illinois

Recent round-trip flight deals from Puerto Rico to Illinois

Enter your travel dates to find the best prices.
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
$220Frontier
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
12:59 am - 5:00 am
SJU
-
ORD
5h 01mnonstop
American Airlines Logo
5:00 am - 1:43 pm
ORD
-
SJU
7h 43m
1 stop
$222American Airlines
Wed, Sep 2 - Tue, Sep 8
Frontier Logo
9:00 am - 12:25 pm
SJU
-
ORD
28h 25m
2 stops
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$223Frontier
Mon, Aug 3 - Sat, Aug 8
American Airlines Logo
7:14 pm - 9:00 am
SJU
-
ORD
14h 46m
1 stop
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
$232American Airlines
Tue, Aug 11 - Tue, Aug 25
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
5:00 am - 1:00 pm
MDW
-
SJU
7h 00m
1 stop
$286Southwest
Fri, Aug 14 - Sun, Aug 16
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
2:45 pm - 12:30 am
MDW
-
SJU
8h 45m
2 stops
$331Southwest
Fri, Aug 14 - Sun, Aug 16
JetBlue Logo
2:20 pm - 11:44 pm
BQN
-
ORD
10h 24m
1 stop
JetBlue Logo
1:00 pm - 10:39 pm
ORD
-
BQN
8h 39m
1 stop
$372JetBlue
Tue, Sep 22 - Sat, Sep 26
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
JetBlue Logo
1:00 pm - 10:39 pm
ORD
-
BQN
8h 39m
1 stop
$381JetBlue
Tue, Sep 22 - Sat, Sep 26
United Airlines Logo
1:19 pm - 8:15 pm
MAZ
-
ORD
7h 56m
1 stop
United Airlines Logo
5:00 am - 4:11 pm
ORD
-
MAZ
10h 11m
2 stops
$1,554United Airlines
Thu, Jun 11 - Wed, Jun 17
United Airlines Logo
10:48 am - 9:00 pm
CPX
-
ORD
11h 12m
2 stops
United Airlines Logo
8:55 am - 5:21 pm
ORD
-
CPX
7h 26m
1 stop
$1,558United Airlines
Tue, Oct 20 - Sat, Oct 24

Frontier flights from Puerto Rico to Illinois

Our best Frontier deals on Puerto Rico to Illinois flight tickets
Frontier
Sep 3
SJU6:11 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD10:26 pmChicago O'Hare Intl
Sep 7
ORD12:29 amChicago O'Hare Intl
4h 57m
SJU6:26 amSan Juan Luis Munoz Marin Intl
$220
Frontier
Aug 3
SJU9:00 amSan Juan Luis Munoz Marin Intl
28h 25m
2 stops
ORD12:25 pmChicago O'Hare Intl
Aug 8
ORD12:44 amChicago O'Hare Intl
5h 00m
SJU6:44 amSan Juan Luis Munoz Marin Intl
$223
Frontier
Aug 20
SJU6:11 pmSan Juan Luis Munoz Marin Intl
5h 15m
ORD10:26 pmChicago O'Hare Intl
Aug 24
ORD12:29 amChicago O'Hare Intl
4h 57m
SJU6:26 amSan Juan Luis Munoz Marin Intl
$224

United Airlines flights from Puerto Rico to Illinois

Our best United Airlines deals on Puerto Rico to Illinois flight tickets
United Airlines
Jul 28
BQN12:15 amAguadilla Borinquen
8h 27m
1 stop
ORD7:42 amChicago O'Hare Intl
Aug 3
ORD9:05 amChicago O'Hare Intl
13h 04m
2 stops
BQN11:09 pmAguadilla Borinquen
$581
United Airlines
May 19
SJU3:56 pmSan Juan Luis Munoz Marin Intl
8h 00m
1 stop
STL10:56 pmLambert-St Louis
May 28
STL9:14 amLambert-St Louis
10h 20m
1 stop
SJU8:34 pmSan Juan Luis Munoz Marin Intl
$701
United Airlines
May 29
SJU1:00 amSan Juan Luis Munoz Marin Intl
12h 07m
2 stops
STL12:07 pmLambert-St Louis
Jun 2
STL5:29 pmLambert-St Louis
11h 00m
2 stops
SJU5:29 amSan Juan Luis Munoz Marin Intl
$716

momondo Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Illinois 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 May 16, 2026.
Use the filters below to find and compare flights from Puerto Rico to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/3

6:11 pm-10:26 pm

Nonstop5h 15m

Chicago O'Hare Intl

Mon 9/7

12:29 am-6:26 am

Nonstop4h 57m

$220

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 9/2

12:59 am-5:00 am

Nonstop5h 01m

Chicago O'Hare Intl

Tue 9/8

5:00 am-1:43 pm

1 stop7h 43m

$222

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 8/3

9:00 am-12:25 pm

2 stops28h 25m

Chicago O'Hare Intl

Sat 8/8

12:44 am-6:44 am

Nonstop5h 00m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/11

7:14 pm-9:00 am

1 stop14h 46m

Chicago O'Hare Intl

Tue 8/25

5:14 pm-11:07 pm

Nonstop4h 53m

$232

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Sun 8/16

5:00 am-1:00 pm

1 stop7h 00m

$286

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Sun 8/16

2:45 pm-12:30 am

2 stops8h 45m

$331

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Tue 9/22

2:20 pm-11:44 pm

1 stop10h 24m

Chicago O'Hare Intl

Sat 9/26

1:00 pm-10:39 pm

1 stop8h 39m

$372

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Tue 9/22

5:01 am-1:39 pm

1 stop9h 38m

Chicago O'Hare Intl

Sat 9/26

1:00 pm-10:39 pm

1 stop8h 39m

$381

MayagüezChicago

MAZ - ORD

MAZORD

Mayagüez Eugenio M De Hostos

Thu 6/11

1:19 pm-8:15 pm

1 stop7h 56m

Chicago O'Hare Intl

Wed 6/17

5:00 am-4:11 pm

2 stops10h 11m

$1,554

CulebraChicago

CPX - ORD

CPXORD

Culebra

Tue 10/20

10:48 am-9:00 pm

2 stops11h 12m

Chicago O'Hare Intl

Sat 10/24

8:55 am-5:21 pm

1 stop7h 26m

$1,558

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 Illinois from

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

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 Illinois?

The cheapest month to fly to Illinois from Puerto Rico is in May. Flight prices, which tend to average around $64, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of May, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $75.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Puerto Rico to Illinois is on a Friday when prices can be found for as low as $392. Flights from Puerto Rico to Illinois on a Sunday will generally be more expensive and average around $565. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Puerto Rico to Illinois during this time can be as low as $289. Flights in the afternoon are often more expensive with an average ticket price of $478.

What is the cheapest Puerto Rico to Illinois flight route?

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

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

You are more likely to see cheaper flights to Illinois from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $324 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Puerto Rico for as low as $270 on momondo.

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

No. A direct flight is the cheapest option for a flight between Puerto Rico to Illinois.

Cheap Puerto Rico to Illinois flight deals and tips

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

Best Price Found

$158

Fastest flight time

4h 35m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Puerto Rico in the past 72 hours is $158. The best round-trip flight deal from Puerto Rico to Illinois found on momondo in the last 72 hours is $295.
The fastest flight from Puerto Rico to Illinois takes 4h 35m
Direct flights go from Puerto Rico to Illinois every day.
There are 98 airports in Illinois. From Puerto Rico there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Lambert-St Louis (STL).
Search flight deals

Frequently asked questions about flying from Puerto Rico to Illinois

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

    Prices for flights from Puerto Rico to Illinois were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Puerto Rico to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The travel and health documents you'll need for your trip to Illinois may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Illinois. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Puerto Rico to Illinois

Compare and see reviews for airlines that fly from Puerto Rico to Illinois with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $116Free CancellationRating
7.9
8,454 reviews
Search Delta flights
FrontierPriceFrom $119Free CancellationRating
5.6
2,949 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $120Free CancellationRating
6.2
8,625 reviews
Search Spirit Airlines flights
JetBluePriceFrom $131Free CancellationRating
7.1
2,977 reviews
Search JetBlue flights
United AirlinesPriceFrom $256Free CancellationRating
7.4
9,729 reviews
Search United Airlines flights
American AirlinesPriceFrom $257Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights
SouthwestPriceFrom $292Free CancellationRating
8.0
4,294 reviews
Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Puerto Rico to Illinois for you.

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

Flights from Puerto Rico to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Puerto Rico to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Puerto Rico to Illinois flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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