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Cheap flights from Chicago to Puerto Rico from $62

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 3/4. 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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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
$126Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
5:28 pm - 2:19 amORD-SJU
6h 51m1 stop
6:35 am - 2:25 pmSJU-ORD
9h 50m1 stop
$127Frontier
Find Deal
Mon, Feb 10 - Wed, Feb 12
3:16 pm - 12:39 amORD-SJU
7h 23m1 stop
9:49 pm - 9:52 amSJU-ORD
14h 03m1 stop
$128Frontier
Find Deal
Mon, Feb 3 - Thu, Feb 6
11:15 am - 10:22 pmORD-SJU
9h 07m1 stop
2:05 am - 9:40 amSJU-ORD
9h 35m1 stop
$234United Airlines
Find Deal
Sun, Jan 12 - Wed, Jan 22
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
$258United Airlines
Find Deal
Fri, Jan 24 - Thu, Jan 30
12:25 pm - 9:38 pmORD-SJU
7h 13m1 stop
6:00 am - 12:14 pmSJU-ORD
8h 14m1 stop
$264American Airlines
Find Deal
Mon, Jan 27 - Sat, Feb 1
10:05 am - 12:25 amMDW-SJU
12h 20m2 stops
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$279Southwest
Find Deal
Mon, Jan 27 - Wed, Feb 5
10:05 am - 12:25 amMDW-SJU
12h 20m2 stops
6:00 am - 4:50 pmSJU-MDW
12h 50m2 stops
$304Southwest
Find Deal
Mon, Jan 27 - Fri, Jan 31
12:44 pm - 11:46 pmMDW-SJU
9h 02m1 stop
4:15 pm - 10:20 pmSJU-MDW
8h 05m1 stop
$384Delta
Find Deal
Tue, Jan 28 - Fri, Feb 7
10:57 am - 9:06 pmMDW-SJU
8h 09m1 stop
6:15 am - 2:53 pmSJU-MDW
10h 38m1 stop
$394Delta
Find Deal
Sat, Jan 11 - Sat, Jan 18
8:47 am - 5:49 pmMDW-SJU
7h 02m1 stop
$62Frontier
Find Deal
Tue, Mar 4
7:18 pm - 9:35 amORD-SJU
12h 17m1 stop
$63Frontier
Find Deal
Wed, Mar 5
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$65Spirit Airlines
Find Deal
Sun, Jan 12
3:56 pm - 9:21 amORD-SJU
15h 25m1 stop
$72Spirit Airlines
Find Deal
Tue, Jan 14
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
$113United Airlines
Find Deal
Mon, Mar 3
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$141United Airlines
Find Deal
Fri, Jan 24
1:05 pm - 10:11 pmMDW-SJU
8h 06m1 stop
$197Delta
Find Deal
Sat, Apr 26
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
$208American Airlines
Find Deal
Fri, Apr 11
10:05 am - 12:26 amORD-SJU
12h 21m1 stop
$212American Airlines
Find Deal
Mon, Dec 30
10:57 am - 11:46 pmMDW-SJU
10h 49m1 stop
$312Delta
Find Deal
Wed, Jan 15
9:05 am - 3:48 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$454Spirit Airlines
Find Deal
Mon, Dec 23 - Sat, Jan 25
9:05 am - 3:48 pmORD-SJU
4h 43mnonstop
9:15 pm - 9:52 amSJU-ORD
14h 37m1 stop
Mon, Dec 23 - Sat, Jan 25
2:19 pm - 12:41 amORD-SJU
8h 22m1 stop
3:54 am - 10:04 amSJU-ORD
8h 10m1 stop
$458Frontier
Find Deal
Sun, Dec 22 - Wed, Dec 25
2:19 pm - 12:41 amORD-SJU
8h 22m1 stop
3:54 am - 9:24 amSJU-ORD
7h 30m1 stop
$461Frontier
Find Deal
Sun, Dec 22 - Tue, Dec 24
6:37 am - 8:18 pmORD-SJU
11h 41m1 stop
7:05 am - 2:00 pmSJU-ORD
8h 55m1 stop
$468American Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 23
6:37 am - 8:18 pmORD-SJU
11h 41m1 stop
4:00 pm - 7:25 pmSJU-ORD
5h 25mnonstop
$470American Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 23
5:00 am - 6:12 amORD-SJU
23h 12m1 stop
2:05 am - 9:35 amSJU-ORD
9h 30m1 stop
$627United Airlines
Find Deal
Mon, Dec 23 - Fri, Jan 24
7:25 am - 11:57 pmORD-BQN
14h 32m2 stops
1:09 am - 8:49 amBQN-ORD
9h 40m1 stop
$1,002United Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 23
12:10 pm - 9:12 pmMDW-SJU
7h 02m1 stop
6:30 am - 11:21 amSJU-MDW
6h 51m1 stop
$1,253Delta
Find Deal
Mon, Dec 23 - Thu, Dec 26
12:10 pm - 9:12 pmMDW-SJU
7h 02m1 stop
7:30 am - 4:17 pmSJU-MDW
10h 47m1 stop
$1,490Delta
Find Deal
Sun, Dec 22 - Sun, Dec 29
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$126Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$138Spirit Airlines
Find Deal
Mon, Jan 27 - Fri, Jan 31
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$139Spirit Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$141Spirit Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$147Spirit Airlines
Find Deal
Tue, Jan 7 - Fri, Jan 17
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:10 pm - 7:25 pmSJU-ORD
5h 15mnonstop
$225American Airlines
Find Deal
Tue, May 6 - Thu, May 8
6:03 pm - 11:54 pmORD-SJU
4h 51mnonstop
7:45 am - 11:55 amSJU-ORD
5h 10mnonstop
$318United Airlines
Find Deal
Fri, Apr 25 - Thu, May 1
6:03 pm - 11:54 pmORD-SJU
4h 51mnonstop
7:45 am - 11:55 amSJU-ORD
5h 10mnonstop
$320United Airlines
Find Deal
Mon, Mar 31 - Fri, Apr 4
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:10 pm - 7:25 pmSJU-ORD
5h 15mnonstop
$415American Airlines
Find Deal
Wed, May 14 - Thu, May 29
8:55 am - 3:30 pmMDW-SJU
4h 35mnonstop
2:55 pm - 6:10 pmSJU-MDW
5h 15mnonstop
$953Southwest
Find Deal
Sat, Jan 18 - Sat, Feb 1

Frontier flights from Chicago to Puerto Rico

Our best Frontier deals on Chicago to Puerto Rico flight tickets
Frontier
Feb 10
ORD5:28 pmChicago O'Hare Intl
6h 51m
1 stop
SJU2:19 amSan Juan Luis Munoz Marin Intl
Feb 12
SJU6:35 amSan Juan Luis Munoz Marin Intl
9h 50m
1 stop
ORD2:25 pmChicago O'Hare Intl
Frontier
Feb 3
ORD3:16 pmChicago O'Hare Intl
7h 23m
1 stop
SJU12:39 amSan Juan Luis Munoz Marin Intl
Feb 6
SJU9:49 pmSan Juan Luis Munoz Marin Intl
14h 03m
1 stop
ORD9:52 amChicago O'Hare Intl
Frontier
Jan 23
ORD10:33 amChicago O'Hare Intl
13h 46m
1 stop
SJU2:19 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU6:55 pmSan Juan Luis Munoz Marin Intl
16h 57m
1 stop
ORD9:52 amChicago O'Hare Intl

Spirit Airlines flights from Chicago to Puerto Rico

Our best Spirit Airlines deals on Chicago to Puerto Rico flight tickets
Spirit Airlines
Jan 21
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Jan 29
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 25
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Feb 1
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Feb 1
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Feb 8
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 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 month to fly to Puerto Rico?

If you don’t want to visit Puerto Rico in August, then you should wait until May to fly from Chicago, when ticket prices are also cheap, with an average price of $313.

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 $352. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Sunday, with ticket prices averaging around $413.

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 afternoon. 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 $389.

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?

The best time to book a flight to Puerto Rico from Chicago is 59 days out, which is when prices tend to be around $360. However, in the past 72 hours, people saw flights from Chicago for as low as $268.

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 4% 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

$62

Fastest flight time

4h 31m

Direct flights

Every day

Airports in Puerto Rico

2 airports
The best one-way flight to Puerto Rico from Chicago in the past 72 hours is $62. The best round-trip flight deal from Chicago to Puerto Rico found on momondo in the last 72 hours is $126.
The fastest flight from Chicago to Puerto Rico takes 4h 31m
Direct flights go from Chicago to Puerto Rico every day.
There are 2 airports near Puerto Rico: 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
3,478 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,274 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $159Free CancellationRating
6.3
8,120 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
9,048 reviews
Search United Airlines flights
SouthwestPriceFrom $304Free CancellationRating
8.1
4,836 reviews
Search Southwest flights
DeltaPriceFrom $307Free CancellationRating
8.0
8,600 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.


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