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Cheap flights from Chicago to Puerto Rico from $108

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 Puerto Rico departing on 11/17. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:40 am - 5:54 pmORD-SJU
10h 14m1 stop
Frontier Logo
1:59 am - 11:52 amSJU-ORD
10h 53m1 stop
$201Frontier
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Wed, Oct 29 - Sat, Nov 1
Frontier Logo
6:30 pm - 8:45 amORD-SJU
36h 15m2 stops
Frontier Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
$202Frontier
Find Deal
Fri, Nov 7 - Wed, Nov 12
Spirit Airlines Logo
8:41 am - 3:17 pmORD-SJU
4h 36mnonstop
Spirit Airlines Logo
9:47 pm - 12:59 amSJU-ORD
5h 12mnonstop
$217Spirit Airlines
Find Deal
Tue, Dec 2 - Sun, Dec 7
Spirit Airlines Logo
5:55 am - 12:36 pmORD-SJU
4h 41mnonstop
Spirit Airlines Logo
7:08 pm - 10:30 pmSJU-ORD
5h 22mnonstop
$218Spirit Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 16
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
8:35 am - 11:57 amSJU-ORD
5h 22mnonstop
$254United Airlines
Find Deal
Mon, Jan 12 - Fri, Jan 16
Southwest Logo
12:50 pm - 11:00 pmMDW-SJU
8h 10m2 stops
Southwest Logo
3:00 pm - 6:20 pmSJU-MDW
5h 20mnonstop
$259Southwest
Find Deal
Sat, Jan 24 - Sat, Jan 31
Southwest Logo
7:10 am - 9:30 pmMDW-SJU
12h 20m1 stop
Southwest Logo
10:50 am - 4:10 pmSJU-MDW
7h 20m1 stop
$263Southwest
Find Deal
Tue, Dec 9 - Thu, Feb 26
JetBlue Logo
7:00 am - 10:42 pmORD-BQN
13h 42m2 stops
JetBlue Logo
5:05 am - 9:33 pmBQN-ORD
17h 28m2 stops
$366JetBlue
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Sun, Mar 1 - Wed, Mar 18
JetBlue Logo
8:45 am - 10:30 pmORD-BQN
11h 45m1 stop
JetBlue Logo
6:15 am - 1:10 pmBQN-ORD
8h 55m1 stop
$391JetBlue
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Thu, Jan 29 - Fri, Feb 6
United Airlines Logo
1:00 pm - 11:57 pmORD-BQN
8h 57m1 stop
United Airlines Logo
1:09 am - 7:54 amBQN-ORD
8h 45m1 stop
$395United Airlines
Find Deal
Thu, Feb 5 - Sat, Feb 7

Spirit Airlines flights from Chicago to Puerto Rico

Our best Spirit Airlines deals on Chicago to Puerto Rico flight tickets
Spirit Airlines
Dec 2
ORD8:41 amChicago O'Hare Intl
4h 36m
SJU3:17 pmSan Juan Luis Munoz Marin Intl
Dec 7
SJU9:47 pmSan Juan Luis Munoz Marin Intl
5h 12m
ORD12:59 amChicago O'Hare Intl
$217
Find similar
Spirit Airlines
Dec 6
ORD5:55 amChicago O'Hare Intl
4h 41m
SJU12:36 pmSan Juan Luis Munoz Marin Intl
Dec 16
SJU7:08 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD10:30 pmChicago O'Hare Intl
$218
Find similar
Spirit Airlines
Dec 8
ORD5:55 amChicago O'Hare Intl
4h 41m
SJU12:36 pmSan Juan Luis Munoz Marin Intl
Dec 17
SJU7:08 pmSan Juan Luis Munoz Marin Intl
5h 22m
ORD10:30 pmChicago O'Hare Intl
$231
Find similar

Southwest flights from Chicago to Puerto Rico

Our best Southwest deals on Chicago to Puerto Rico flight tickets
Southwest
Jan 24
MDW12:50 pmChicago Midway
8h 10m
2 stops
SJU11:00 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU3:00 pmSan Juan Luis Munoz Marin Intl
5h 20m
MDW6:20 pmChicago Midway
$259
Find similar
Southwest
Dec 9
MDW7:10 amChicago Midway
12h 20m
1 stop
SJU9:30 pmSan Juan Luis Munoz Marin Intl
Feb 26
SJU10:50 amSan Juan Luis Munoz Marin Intl
7h 20m
1 stop
MDW4:10 pmChicago Midway
$263
Find similar
Southwest
Dec 3
MDW4:35 pmChicago Midway
6h 00m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Dec 8
SJU11:20 amSan Juan Luis Munoz Marin Intl
7h 15m
1 stop
MDW4:35 pmChicago Midway
$289
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 October 16, 2025.
Use the filters below to find and compare flights from Chicago to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

6:40 am-5:54 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Sat 11/1

1:59 am-11:52 am

1 stop10h 53m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 11/7

6:30 pm-8:45 am

2 stops36h 15m

San Juan Luis Munoz Marin Intl

Wed 11/12

9:00 am-12:45 pm

1 stop29h 45m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/2

8:41 am-3:17 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Sun 12/7

9:47 pm-12:59 am

Nonstop5h 12m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/6

5:55 am-12:36 pm

Nonstop4h 41m

San Juan Luis Munoz Marin Intl

Tue 12/16

7:08 pm-10:30 pm

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/12

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/16

8:35 am-11:57 am

Nonstop5h 22m

$254

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/24

12:50 pm-11:00 pm

2 stops8h 10m

San Juan Luis Munoz Marin Intl

Sat 1/31

3:00 pm-6:20 pm

Nonstop5h 20m

$259

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 12/9

7:10 am-9:30 pm

1 stop12h 20m

San Juan Luis Munoz Marin Intl

Thu 2/26

10:50 am-4:10 pm

1 stop7h 20m

$263

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 3/1

7:00 am-10:42 pm

2 stops13h 42m

Aguadilla Borinquen

Wed 3/18

5:05 am-9:33 pm

2 stops17h 28m

$366

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 1/29

8:45 am-10:30 pm

1 stop11h 45m

Aguadilla Borinquen

Fri 2/6

6:15 am-1:10 pm

1 stop8h 55m

$391

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 2/5

1:00 pm-11:57 pm

1 stop8h 57m

Aguadilla Borinquen

Sat 2/7

1:09 am-7:54 am

1 stop8h 45m

$395

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 Chicago 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 Chicago, 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 Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $393. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Thursday, with ticket prices averaging around $443.

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 Chicago to Puerto Rico during this time can be as low as $306. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $448.

What is the cheapest Chicago to Puerto Rico flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - 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 Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago for as low as $319 on momondo.

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

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

Cheap Chicago to Puerto Rico flight deals and tips

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

Best Price Found

$186

Fastest flight time

4h 24m

Direct flights

Every day

Airports in Puerto Rico

1 airport
The best one-way flight to Puerto Rico from Chicago in the past 72 hours is $186. The best round-trip flight deal from Chicago to Puerto Rico found on momondo in the last 72 hours is $328.
The fastest flight from Chicago to Puerto Rico takes 4h 24m
Direct flights go from Chicago to Puerto Rico every day.
There is 1 airport near Puerto Rico: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

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

    Prices for flights from Chicago to Puerto Rico refresh daily.

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

  • How old do you have to be to fly from Chicago 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 Chicago to Puerto Rico.

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

    The travel and health documents required for your trip to Puerto Rico 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 Puerto Rico. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Chicago to Puerto Rico

Compare and see reviews for airlines that fly from Chicago to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.8
3,137 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,099 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,982 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
United AirlinesPriceFrom $271Free CancellationRating
7.4
8,982 reviews
Search United Airlines flights
American AirlinesPriceFrom $358Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Why use momondo?

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

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 Chicago to Puerto Rico for you.

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

momondo does allow users to show only those flights to Puerto Rico from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Chicago and Puerto Rico by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Puerto Rico from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to Puerto Rico

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