Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Puerto Rico from $76

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 4/8. 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

Discover deals from 900+ travel sites with momondo.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Puerto Rico.
Spirit Airlines Logo
8:45 am - 11:46 pmORD-SJU
14h 01m1 stop
Spirit Airlines Logo
9:30 pm - 8:04 amSJU-ORD
11h 34m1 stop
$180Spirit Airlines
Find Deal
Sun, Apr 13 - Fri, Apr 18
Spirit Airlines Logo
11:53 am - 11:39 pmORD-SJU
10h 46m1 stop
Spirit Airlines Logo
12:54 am - 8:35 amSJU-ORD
8h 41m1 stop
$188Spirit Airlines
Find Deal
Sat, Apr 26 - Fri, May 2
Spirit Airlines Logo
7:00 pm - 8:26 amORD-SJU
12h 26m1 stop
Spirit Airlines Logo
9:30 pm - 8:04 amSJU-ORD
11h 34m1 stop
$196Spirit Airlines
Find Deal
Tue, Apr 15 - Fri, Apr 18
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
$294Frontier
Find Deal
Mon, May 5 - Fri, May 9
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
$296Frontier
Find Deal
Mon, May 5 - Fri, May 9
American Airlines Logo
6:55 pm - 11:10 amORD-SJU
15h 15m1 stop
American Airlines Logo
8:30 am - 7:23 pmSJU-ORD
11h 53m1 stop
$355American Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Southwest Logo
6:35 am - 6:50 pmMDW-SJU
11h 15m1 stop
Southwest Logo
1:00 pm - 5:20 pmSJU-MDW
5h 20mnonstop
$377Southwest
Find Deal
Sat, Apr 26 - Sat, May 3
Southwest Logo
6:35 am - 6:50 pmMDW-SJU
11h 15m1 stop
Southwest Logo
8:00 am - 6:25 pmSJU-MDW
11h 25m1 stop
$381Southwest
Find Deal
Sat, Apr 26 - Tue, Apr 29
United Airlines Logo
11:55 am - 11:09 pmORD-BQN
10h 14m1 stop
United Airlines Logo
12:15 am - 6:41 pmBQN-ORD
19h 26m2 stops
$412United Airlines
Find Deal
Sat, May 3 - Fri, May 9
United Airlines Logo
7:25 am - 11:09 pmORD-BQN
14h 44m2 stops
United Airlines Logo
12:15 am - 7:38 amBQN-ORD
8h 23m1 stop
$531United Airlines
Find Deal
Sun, May 11 - Sat, May 31

Frontier flights from Chicago to Puerto Rico

Our best Frontier deals on Chicago to Puerto Rico flight tickets
Frontier
Apr 9
MDW3:00 pmChicago Midway
6h 53m
1 stop
SJU10:53 pmSan Juan Luis Munoz Marin Intl
Apr 9
SJU2:45 amSan Juan Luis Munoz Marin Intl
7h 39m
1 stop
MDW9:24 amChicago Midway
Frontier
May 5
MDW12:15 pmChicago Midway
12h 35m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
May 9
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 24m
1 stop
MDW12:24 pmChicago Midway
Frontier
May 5
MDW12:15 pmChicago Midway
12h 35m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
May 9
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 24m
1 stop
MDW12:24 pmChicago Midway

JetBlue flights from Chicago to Puerto Rico

Our best JetBlue deals on Chicago to Puerto Rico flight tickets
JetBlue
May 6
ORD8:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
May 9
SJU1:58 pmSan Juan Luis Munoz Marin Intl
8h 56m
1 stop
ORD9:54 pmChicago O'Hare Intl
JetBlue
Apr 30
ORD1:13 pmChicago O'Hare Intl
7h 14m
1 stop
SJU9:27 pmSan Juan Luis Munoz Marin Intl
May 9
SJU1:58 pmSan Juan Luis Munoz Marin Intl
8h 56m
1 stop
ORD9:54 pmChicago O'Hare Intl
JetBlue
Apr 26
ORD1:26 pmChicago O'Hare Intl
7h 36m
1 stop
SJU10:02 pmSan Juan Luis Munoz Marin Intl
Apr 30
SJU3:29 amSan Juan Luis Munoz Marin Intl
9h 44m
1 stop
ORD12:13 pmChicago 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 April to fly from Chicago, when ticket prices are also cheap, with an average price of $312.

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 $365. 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 $421.

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 $298. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $409.

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 5 weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $365 when searching 5 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 $294 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

$76

Fastest flight time

4h 36m

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 $76. The best round-trip flight deal from Chicago to Puerto Rico found on momondo in the last 72 hours is $180.
The fastest flight from Chicago to Puerto Rico takes 4h 36m
Direct flights go from Chicago to Puerto Rico every day.
There is 1 airport near Puerto Rico: 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 $124Free CancellationRating
5.9
3,277 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $144Free CancellationRating
6.3
7,890 reviews
Search Spirit Airlines flights
DeltaPriceFrom $235Free CancellationRating
8.0
7,897 reviews
Search Delta flights
United AirlinesPriceFrom $264Free CancellationRating
7.4
8,619 reviews
Search United Airlines flights
JetBluePriceFrom $293Free CancellationRating
7.3
2,920 reviews
Search JetBlue flights
American AirlinesPriceFrom $327Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $342Free CancellationRating
8.0
4,276 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Wed 4/9
Wed 4/16

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