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Cheap flights from Chicago to Puerto Rico from $103

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 11/1. 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 Chicago to Puerto Rico

Cheap round-trip flights

Multiple Airlines Logo
3:00 pm - 8:40 pmORD-SJU
4h 40mnonstop
Multiple Airlines Logo
5:51 pm - 2:26 pmSJU-ORD
21h 35m1 stop
$195Multiple Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
Spirit Airlines Logo
8:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
$196Spirit Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
Spirit Airlines Logo
3:00 pm - 8:40 pmORD-SJU
4h 40mnonstop
Spirit Airlines Logo
7:43 pm - 11:57 pmSJU-ORD
5h 14mnonstop
$199Spirit Airlines
Find Deal
Sat, Oct 11 - Fri, Oct 24
Frontier Logo
7:05 am - 12:01 pmORD-SJU
26h 56m1 stop
Frontier Logo
12:11 pm - 8:42 pmSJU-ORD
10h 31m1 stop
$243Frontier
Find Deal
Thu, Nov 6 - Mon, Nov 10
United Airlines Logo
8:55 am - 3:40 pmORD-SJU
4h 45mnonstop
United Airlines Logo
4:52 pm - 8:20 pmSJU-ORD
5h 28mnonstop
$254United Airlines
Find Deal
Mon, Jan 19 - Fri, Jan 23
Delta Logo
1:05 pm - 11:49 pmMDW-SJU
8h 44m1 stop
Delta Logo
7:30 am - 4:25 pmSJU-MDW
10h 55m1 stop
$263Delta
Find Deal
Mon, Jan 19 - Fri, Jan 23
Frontier Logo
6:15 am - 2:28 pmMDW-SJU
7h 13m1 stop
Frontier Logo
3:31 pm - 10:03 pmSJU-MDW
7h 32m1 stop
$272Frontier
Find Deal
Sat, Oct 25 - Thu, Oct 30
Southwest Logo
1:25 pm - 12:05 amMDW-SJU
8h 40m2 stops
Southwest Logo
9:05 am - 6:35 pmSJU-MDW
11h 30m1 stop
$303Southwest
Find Deal
Sun, Jan 25 - Wed, Jan 28
Southwest Logo
12:15 pm - 11:00 pmMDW-SJU
8h 45m1 stop
Southwest Logo
2:20 pm - 11:50 pmSJU-MDW
11h 30m1 stop
$328Southwest
Find Deal
Sat, Jan 31 - Tue, Feb 17
United Airlines Logo
2:30 pm - 11:57 pmORD-BQN
7h 27m1 stop
United Airlines Logo
1:09 am - 8:30 amBQN-ORD
9h 21m1 stop
$485United Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4

Spirit Airlines flights from Chicago to Puerto Rico

Our best Spirit Airlines deals on Chicago to Puerto Rico flight tickets
Spirit Airlines
Oct 31
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
Nov 3
SJU8:43 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:57 pmChicago O'Hare Intl
$196
Find similar
Spirit Airlines
Oct 11
ORD3:00 pmChicago O'Hare Intl
4h 40m
SJU8:40 pmSan Juan Luis Munoz Marin Intl
Oct 24
SJU7:43 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:57 pmChicago O'Hare Intl
$199
Find similar
Spirit Airlines
Oct 29
ORD5:28 pmChicago O'Hare Intl
7h 16m
1 stop
SJU1:44 amSan Juan Luis Munoz Marin Intl
Nov 14
SJU3:41 pmSan Juan Luis Munoz Marin Intl
5h 10m
ORD6:51 pmChicago O'Hare Intl
$200
Find similar

Frontier flights from Chicago to Puerto Rico

Our best Frontier deals on Chicago to Puerto Rico flight tickets
Frontier
Nov 6
ORD7:05 amChicago O'Hare Intl
26h 56m
1 stop
SJU12:01 pmSan Juan Luis Munoz Marin Intl
Nov 10
SJU12:11 pmSan Juan Luis Munoz Marin Intl
10h 31m
1 stop
ORD8:42 pmChicago O'Hare Intl
$243
Find similar
Frontier
Oct 4
MDW6:15 amChicago Midway
6h 56m
1 stop
SJU2:11 pmSan Juan Luis Munoz Marin Intl
Oct 11
SJU4:22 pmSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW10:47 pmChicago Midway
$272
Find similar
Frontier
Nov 7
MDW12:14 pmChicago Midway
10h 27m
1 stop
SJU12:41 amSan Juan Luis Munoz Marin Intl
Nov 14
SJU3:59 amSan Juan Luis Munoz Marin Intl
8h 27m
1 stop
MDW10:26 amChicago Midway
$276
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 September 29, 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

Sat 10/25

3:00 pm-8:40 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Sat 11/1

5:51 pm-2:26 pm

1 stop21h 35m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 10/31

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Mon 11/3

8:43 pm-11:57 pm

Nonstop5h 14m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 10/11

3:00 pm-8:40 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

$199

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 11/6

7:05 am-12:01 pm

1 stop26h 56m

San Juan Luis Munoz Marin Intl

Mon 11/10

12:11 pm-8:42 pm

1 stop10h 31m

$243

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

8:55 am-3:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Fri 1/23

4:52 pm-8:20 pm

Nonstop5h 28m

$254

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

1:05 pm-11:49 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Fri 1/23

7:30 am-4:25 pm

1 stop10h 55m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/25

6:15 am-2:28 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Thu 10/30

3:31 pm-10:03 pm

1 stop7h 32m

$272

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

1:25 pm-12:05 am

2 stops8h 40m

San Juan Luis Munoz Marin Intl

Wed 1/28

9:05 am-6:35 pm

1 stop11h 30m

$303

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

12:15 pm-11:00 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 2/17

2:20 pm-11:50 pm

1 stop11h 30m

$328

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 3/3

2:30 pm-11:57 pm

1 stop7h 27m

Aguadilla Borinquen

Wed 3/4

1:09 am-8:30 am

1 stop9h 21m

$485

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 October, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $357.

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 $395. 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 $445.

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 $447.

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 $390 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 $314 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.

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

You could potentially save up to 11% on your flight if you consider stops on a Chicago to Puerto Rico flight.

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

$169

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 $169. The best round-trip flight deal from Chicago to Puerto Rico found on momondo in the last 72 hours is $343.
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
3,158 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,050 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,964 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,912 reviews
Search JetBlue flights
United AirlinesPriceFrom $273Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
American AirlinesPriceFrom $349Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $376Free CancellationRating
8.0
4,246 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

Popular cities in Puerto Rico

Popular flights according to clicks in the last 7 days on momondo
Flights to San Juanfrom $120
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