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Cheap flights from Puerto Rico to Chicago 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 Puerto Rico to Chicago departing on 10/12. 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 Puerto Rico to Chicago

Recent round-trip flight deals from Puerto Rico to Chicago

Frontier Logo
8:15 am - 7:36 pmSJU-MDW
12h 21m1 stop
Frontier Logo
6:15 am - 2:26 pmMDW-SJU
7h 11m1 stop
$143Frontier
Find Deal
Wed, Aug 6 - Mon, Aug 25
Frontier Logo
7:25 am - 6:28 pmSJU-ORD
12h 03m1 stop
Frontier Logo
5:10 am - 2:26 pmORD-SJU
8h 16m1 stop
$143Frontier
Find Deal
Thu, Aug 21 - Sun, Aug 24
Frontier Logo
3:16 pm - 11:20 pmSJU-MDW
9h 04m1 stop
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
$148Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
Spirit Airlines Logo
4:43 pm - 7:04 amSJU-ORD
15h 21m1 stop
Spirit Airlines Logo
5:05 am - 3:30 pmORD-SJU
9h 25m1 stop
$195Spirit Airlines
Find Deal
Tue, Aug 5 - Tue, Aug 12
Spirit Airlines Logo
3:50 pm - 7:04 amSJU-ORD
16h 14m1 stop
Spirit Airlines Logo
6:23 pm - 12:06 amORD-SJU
4h 43mnonstop
$208Spirit Airlines
Find Deal
Fri, Jul 18 - Mon, Jul 21
Delta Logo
12:50 pm - 9:44 pmSJU-MDW
9h 54m1 stop
Delta Logo
6:00 am - 4:36 pmMDW-SJU
9h 36m1 stop
$347Delta
Find Deal
Fri, Aug 29 - Tue, Sep 2
Southwest Logo
7:35 am - 3:45 pmSJU-MDW
9h 10m2 stops
Southwest Logo
12:30 pm - 10:45 pmMDW-SJU
9h 15m1 stop
$369Southwest
Find Deal
Sat, Oct 4 - Wed, Oct 8
Southwest Logo
5:30 am - 1:55 pmSJU-MDW
9h 25m1 stop
Southwest Logo
2:10 pm - 11:10 pmMDW-SJU
8h 00m1 stop
$372Southwest
Find Deal
Mon, Jul 14 - Fri, Jul 18
United Airlines Logo
12:15 am - 2:54 pmBQN-ORD
15h 39m2 stops
United Airlines Logo
7:25 am - 11:09 pmORD-BQN
14h 44m2 stops
$437United Airlines
Find Deal
Mon, Sep 22 - Wed, Oct 1
United Airlines Logo
12:15 am - 9:38 amBQN-ORD
10h 23m1 stop
United Airlines Logo
7:25 am - 11:09 pmORD-BQN
14h 44m2 stops
$464United Airlines
Find Deal
Mon, Sep 22 - Wed, Oct 1

United Airlines flights from Puerto Rico to Chicago

Our best United Airlines deals on Puerto Rico to Chicago flight tickets
United Airlines
Sep 22
BQN12:15 amAguadilla Borinquen
15h 39m
2 stops
ORD2:54 pmChicago O'Hare Intl
Oct 1
ORD7:25 amChicago O'Hare Intl
14h 44m
2 stops
BQN11:09 pmAguadilla Borinquen
United Airlines
Sep 22
BQN12:15 amAguadilla Borinquen
10h 23m
1 stop
ORD9:38 amChicago O'Hare Intl
Oct 1
ORD7:25 amChicago O'Hare Intl
14h 44m
2 stops
BQN11:09 pmAguadilla Borinquen
United Airlines
Aug 26
BQN12:15 amAguadilla Borinquen
10h 23m
1 stop
ORD9:38 amChicago O'Hare Intl
Sep 3
ORD7:25 amChicago O'Hare Intl
14h 44m
2 stops
BQN11:09 pmAguadilla Borinquen

Spirit Airlines flights from Puerto Rico to Chicago

Our best Spirit Airlines deals on Puerto Rico to Chicago flight tickets
Spirit Airlines
Aug 5
SJU4:43 pmSan Juan Luis Munoz Marin Intl
15h 21m
1 stop
ORD7:04 amChicago O'Hare Intl
Aug 12
ORD5:05 amChicago O'Hare Intl
9h 25m
1 stop
SJU3:30 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Jul 18
SJU3:50 pmSan Juan Luis Munoz Marin Intl
16h 14m
1 stop
ORD7:04 amChicago O'Hare Intl
Jul 21
ORD6:23 pmChicago O'Hare Intl
4h 43m
SJU12:06 amSan Juan Luis Munoz Marin Intl
Spirit Airlines
Jul 14
SJU6:00 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD10:16 amChicago O'Hare Intl
Jul 20
ORD5:05 amChicago O'Hare Intl
15h 04m
1 stop
SJU9:09 pmSan Juan Luis Munoz Marin Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Puerto Rico to Chicago

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 Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $232. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Puerto Rico to Chicago during May average around $270.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $341. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Puerto Rico to Chicago for around $482.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Puerto Rico to Chicago during this time can be as low as $243. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $480.

What is the cheapest Puerto Rico to Chicago flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Puerto Rico - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Puerto Rico for as low as $244 on momondo.

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

There are 4 cabin classes available to choose from on Puerto Rico to Chicago 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 Puerto Rico to Chicago flights?

You could potentially save up to 22% on your flight if you consider stops on a Puerto Rico to Chicago flight.

Cheap Puerto Rico to Chicago flight deals and tips

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

Best Price Found

$76

Fastest flight time

4h 58m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Puerto Rico in the past 72 hours is $76. The best round-trip flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $143.
The fastest flight from Puerto Rico to Chicago takes 4h 58m
Direct flights go from Puerto Rico to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

    Prices for flights from Puerto Rico to Chicago were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Puerto Rico to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Puerto Rico to Chicago

Compare and see reviews for airlines that fly from Puerto Rico to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $130Free CancellationRating
5.9
3,293 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $136Free CancellationRating
6.3
8,096 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $160Free CancellationRating
7.4
8,852 reviews
Search United Airlines flights
DeltaPriceFrom $172Free CancellationRating
8.0
7,969 reviews
Search Delta flights
SouthwestPriceFrom $257Free CancellationRating
8.0
4,278 reviews
Search Southwest flights
American AirlinesPriceFrom $329Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Puerto Rico to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Puerto Rico to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Puerto Rico to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Chicago from Puerto Rico 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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1 adult
Sat 7/5
Sat 7/12

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago