Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Puerto Rico from $57

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 12/9. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Chicago to Puerto Rico

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Puerto Rico that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Puerto Rico.

Cheap last minute flights

Planning a quick getaway from Chicago to Puerto Rico? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Puerto Rico, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Puerto Rico

Find recent round-trip train or bus tickets from Chicago to Puerto Rico.

All round-trip flight deals to Puerto Rico

The cheapest plane tickets to Puerto Rico found on KAYAK recently.
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$117Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$128Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
9:15 pm - 8:24 amSJU-ORD
13h 09m1 stop
$133Frontier
Find Deal
Mon, Dec 9 - Wed, Dec 11
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
5:08 pm - 6:39 amSJU-MDW
15h 31m1 stop
$133Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
1:20 pm - 12:50 amMDW-SJU
9h 30m2 stops
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$210Southwest
Find Deal
Sun, Feb 2 - Wed, Feb 5
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
$216United Airlines
Find Deal
Mon, Dec 9 - Mon, Dec 16
12:53 pm - 12:36 amORD-SJU
9h 43m1 stop
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
$247United Airlines
Find Deal
Mon, Dec 9 - Sun, Dec 15
1:20 pm - 9:40 pmMDW-SJU
6h 20m1 stop
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$275Southwest
Find Deal
Wed, Jan 15 - Thu, Jan 23
12:44 pm - 11:45 pmMDW-SJU
9h 01m1 stop
3:30 pm - 10:20 pmSJU-MDW
8h 50m1 stop
$334Delta
Find Deal
Tue, Jan 28 - Thu, Jan 30
12:44 pm - 11:46 pmMDW-SJU
9h 02m1 stop
6:15 am - 11:59 amSJU-MDW
7h 44m1 stop
$379Delta
Find Deal
Tue, Feb 18 - Tue, Feb 25
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
$57Frontier
Find Deal
Mon, Dec 9
5:28 pm - 2:19 amORD-SJU
6h 51m1 stop
$63Frontier
Find Deal
Mon, Jan 20
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
$64Spirit Airlines
Find Deal
Wed, Jan 1
9:32 pm - 12:01 pmORD-SJU
12h 29m1 stop
$81Spirit Airlines
Find Deal
Fri, Dec 6
5:50 pm - 6:12 amORD-SJU
10h 22m1 stop
$105United Airlines
Find Deal
Sat, Jan 11
7:35 am - 9:46 pmORD-SJU
12h 11m1 stop
$125United Airlines
Find Deal
Tue, Feb 18
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
$167Delta
Find Deal
Tue, Jan 14
8:20 am - 2:00 pmORD-SJU
4h 40mnonstop
$188American Airlines
Find Deal
Sun, Mar 9
1:54 pm - 12:42 amORD-SJU
8h 48m2 stops
$207American Airlines
Find Deal
Mon, Nov 25
7:30 am - 4:20 pmORD-SJU
7h 50m1 stop
$247Delta
Find Deal
Thu, Mar 13
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
2:45 am - 10:56 amSJU-ORD
10h 11m1 stop
$244Spirit Airlines
Find Deal
Thu, Nov 21 - Mon, Nov 25
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
4:00 pm - 7:26 pmSJU-ORD
5h 26mnonstop
$252Spirit Airlines
Find Deal
Thu, Nov 21 - Tue, Dec 3
2:56 pm - 2:20 amMDW-SJU
9h 24m1 stop
8:10 pm - 8:21 amSJU-MDW
14h 11m1 stop
$282Frontier
Find Deal
Sat, Nov 23 - Tue, Dec 31
8:21 pm - 10:57 amORD-SJU
12h 36m1 stop
7:30 am - 1:27 pmSJU-ORD
7h 57m1 stop
$288Frontier
Find Deal
Mon, Nov 25 - Thu, Nov 28
7:35 am - 9:26 pmORD-SJU
11h 51m1 stop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$367United Airlines
Find Deal
Sat, Nov 23 - Wed, Nov 27
7:35 am - 9:26 pmORD-SJU
11h 51m1 stop
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
$402United Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
5:00 am - 3:43 pmORD-SJU
8h 43m2 stops
3:29 pm - 12:16 amSJU-ORD
10h 47m1 stop
$414American Airlines
Find Deal
Sun, Nov 24 - Wed, Nov 27
5:00 am - 3:43 pmORD-SJU
8h 43m2 stops
5:50 am - 2:43 pmSJU-ORD
10h 53m2 stops
$425American Airlines
Find Deal
Mon, Nov 25 - Thu, Nov 28
6:00 am - 2:31 pmMDW-SJU
6h 31m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$479Delta
Find Deal
Fri, Nov 22 - Thu, Nov 28
7:10 am - 5:13 pmORD-SJU
8h 03m1 stop
3:41 pm - 11:59 pmSJU-ORD
10h 18m1 stop
$484Delta
Find Deal
Fri, Nov 22 - Mon, Dec 2
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$117Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$128Spirit Airlines
Find Deal
Tue, Jan 7 - Wed, Jan 15
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$129Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$131Spirit Airlines
Find Deal
Mon, Jan 6 - Wed, Jan 15
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$132Spirit Airlines
Find Deal
Mon, Jan 6 - Wed, Jan 15
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$211United Airlines
Find Deal
Tue, Dec 10 - Fri, Dec 13
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$293United Airlines
Find Deal
Sat, Dec 7 - Fri, Dec 13
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:20 pm - 7:40 pmSJU-ORD
5h 20mnonstop
$346American Airlines
Find Deal
Tue, Apr 8 - Tue, Apr 15
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
$354American Airlines
Find Deal
Wed, Dec 11 - Tue, Dec 17
8:45 am - 3:20 pmMDW-SJU
4h 35mnonstop
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
$1,233Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22

Frontier flights from Chicago to Puerto Rico

Our best Frontier deals on Chicago to Puerto Rico flight tickets
Frontier
Dec 9
ORD4:58 pmChicago O'Hare Intl
7h 04m
1 stop
SJU2:02 amSan Juan Luis Munoz Marin Intl
Dec 11
SJU9:15 pmSan Juan Luis Munoz Marin Intl
13h 09m
1 stop
ORD8:24 amChicago O'Hare Intl
Frontier
Dec 9
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 11
SJU6:20 amSan Juan Luis Munoz Marin Intl
7h 22m
1 stop
MDW11:42 amChicago Midway
Frontier
Jan 13
ORD3:25 pmChicago O'Hare Intl
7h 10m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 15
SJU4:49 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
ORD1:50 pmChicago O'Hare Intl

United Airlines flights from Chicago to Puerto Rico

Our best United Airlines deals on Chicago to Puerto Rico flight tickets
United Airlines
Dec 9
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Dec 16
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
ORD8:59 amChicago O'Hare Intl
United Airlines
Dec 9
ORD12:53 pmChicago O'Hare Intl
9h 43m
1 stop
SJU12:36 amSan Juan Luis Munoz Marin Intl
Dec 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
ORD8:59 amChicago O'Hare Intl
United Airlines
Nov 28
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Dec 3
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
ORD9:43 amChicago O'Hare Intl

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 Chicago to Puerto Rico 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 - Puerto Rico flight prices

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

There are 2 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 10% 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

$57

Fastest flight time

4h 32m

Direct flights

Every day

Airports in Puerto Rico

3 airports
The best one-way flight to Puerto Rico from Chicago in the past 72 hours is $57. The best round-trip flight deal from Chicago to Puerto Rico found on momondo in the last 72 hours is $117.
The fastest flight from Chicago to Puerto Rico takes 4h 32m
Direct flights go from Chicago to Puerto Rico every day.
There are 3 airports near Puerto Rico: Culebra (CPX), Aguadilla Borinquen (BQN), San Juan Luis Munoz Marin Intl (SJU)

  • 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 $119Free CancellationRating
6.1
3,539 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,394 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $162Free CancellationRating
6.3
8,174 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $264Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,014 reviews
Search Southwest flights
DeltaPriceFrom $324Free CancellationRating
8.0
8,756 reviews
Search Delta flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
10,000 reviews
Search American Airlines 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 11/25
Mon 12/2
Email me momondo's favorite deals

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