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Cheap flights from Puerto Rico to Chicago from $58

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 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Puerto Rico to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Puerto Rico to Chicago 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 Puerto Rico to Chicago.

Cheap last minute flights

Planning a quick getaway from Puerto Rico to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$117Spirit Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
$118Frontier
Find Deal
Wed, Dec 11 - Mon, Dec 16
4:49 pm - 2:25 pmSJU-ORD
23h 36m1 stop
5:08 am - 1:44 amORD-SJU
18h 36m1 stop
$122Frontier
Find Deal
Tue, Feb 11 - Mon, Feb 24
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$129Spirit Airlines
Find Deal
Thu, Dec 19 - Tue, Jan 7
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
10:05 am - 12:25 amMDW-SJU
12h 20m2 stops
$210Southwest
Find Deal
Thu, Jan 23 - Mon, Jan 27
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$243United Airlines
Find Deal
Thu, Dec 5 - Sun, Dec 8
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
8:50 am - 10:22 pmORD-SJU
11h 32m1 stop
$290United Airlines
Find Deal
Wed, Jan 15 - Mon, Jan 20
6:10 am - 2:15 pmSJU-MDW
10h 05m1 stop
11:55 am - 12:45 amMDW-SJU
10h 50m2 stops
$325Southwest
Find Deal
Tue, Dec 10 - Mon, Dec 16
6:15 am - 11:59 amSJU-MDW
7h 44m1 stop
12:44 pm - 11:46 pmMDW-SJU
9h 02m1 stop
$334Delta
Find Deal
Thu, Feb 20 - Mon, Feb 24
3:30 pm - 10:20 pmSJU-MDW
8h 50m1 stop
10:57 am - 11:45 pmMDW-SJU
10h 48m1 stop
$399Delta
Find Deal
Wed, Jan 15 - Wed, Jan 22
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$58Spirit Airlines
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Thu, Dec 12
6:00 am - 3:43 pmSJU-MDW
11h 43m1 stop
$61Frontier
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Mon, Jan 27
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$96United Airlines
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Tue, Mar 4
2:05 am - 9:40 amSJU-ORD
9h 35m1 stop
$100United Airlines
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Tue, Jan 28
6:00 am - 4:50 pmSJU-MDW
12h 50m2 stops
$100Southwest
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Wed, Jan 22
6:50 am - 12:20 pmSJU-MDW
7h 30m1 stop
$105Southwest
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Wed, Jan 22
2:02 pm - 10:20 pmSJU-MDW
10h 18m1 stop
$162Delta
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Thu, Jan 16
1:50 pm - 6:50 pmSJU-ORD
7h 00m1 stop
$162Delta
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Thu, Nov 28
3:15 pm - 7:40 pmSJU-ORD
5h 25mnonstop
$188American Airlines
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Wed, Mar 12
3:15 pm - 7:40 pmSJU-ORD
5h 25mnonstop
$189American Airlines
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Thu, Mar 13
5:40 am - 9:04 amSJU-ORD
5h 24mnonstop
6:10 pm - 12:42 amORD-SJU
4h 32mnonstop
$190Spirit Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
5:40 am - 9:04 amSJU-ORD
5h 24mnonstop
6:10 pm - 12:42 amORD-SJU
4h 32mnonstop
$209Spirit Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
3:59 am - 6:26 pmSJU-ORD
16h 27m1 stop
8:21 pm - 10:57 amORD-SJU
12h 36m1 stop
$293Frontier
Find Deal
Thu, Nov 21 - Mon, Nov 25
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
2:36 pm - 12:36 amORD-SJU
8h 00m1 stop
$302United Airlines
Find Deal
Fri, Nov 22 - Mon, Nov 25
7:15 am - 8:05 amSJU-MDW
26h 50m1 stop
8:50 am - 2:52 amMDW-SJU
16h 02m1 stop
$313Frontier
Find Deal
Sat, Nov 23 - Tue, Nov 26
6:05 pm - 11:55 pmSJU-ORD
7h 50m1 stop
10:05 am - 8:53 pmORD-SJU
8h 48m2 stops
$324American Airlines
Find Deal
Sun, Nov 24 - Mon, Nov 25
2:10 pm - 8:07 pmSJU-ORD
7h 57m1 stop
8:50 am - 9:26 pmORD-SJU
10h 36m1 stop
$329United Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
8:00 am - 2:34 pmSJU-MDW
8h 34m1 stop
6:00 am - 5:13 pmMDW-SJU
9h 13m1 stop
$364Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
1:50 pm - 6:46 pmSJU-ORD
6h 56m1 stop
7:05 am - 5:10 pmORD-SJU
8h 05m1 stop
$364Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
7:12 am - 2:15 pmSJU-ORD
9h 03m2 stops
9:46 am - 11:50 pmORD-SJU
12h 04m1 stop
$389American Airlines
Find Deal
Sat, Nov 23 - Wed, Dec 11
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$117Spirit Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$128Spirit Airlines
Find Deal
Tue, Dec 24 - Wed, Jan 1
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$129Spirit Airlines
Find Deal
Thu, Dec 19 - Tue, Jan 7
4:43 pm - 8:13 pmSJU-ORD
5h 30mnonstop
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
$143Spirit Airlines
Find Deal
Sat, Dec 21 - Mon, Jan 6
3:25 pm - 7:40 pmSJU-ORD
5h 15mnonstop
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
$203American Airlines
Find Deal
Thu, May 8 - Sun, May 11
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$211United Airlines
Find Deal
Fri, Dec 6 - Mon, Dec 9
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$238United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
4:15 pm - 7:40 pmSJU-ORD
5h 25mnonstop
8:20 am - 2:00 pmORD-SJU
4h 40mnonstop
$343American Airlines
Find Deal
Thu, Mar 6 - Mon, Mar 10
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
$369American Airlines
Find Deal
Sat, Dec 7 - Wed, Dec 11
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$403United Airlines
Find Deal
Wed, Dec 4 - Sun, Dec 8

Spirit Airlines flights from Puerto Rico to Chicago

Our best Spirit Airlines deals on Puerto Rico to Chicago flight tickets
Spirit Airlines
Dec 24
SJU8:31 pmSan Juan Luis Munoz Marin Intl
5h 27m
ORD11:58 pmChicago O'Hare Intl
Dec 31
ORD1:00 pmChicago O'Hare Intl
4h 36m
SJU7:36 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Dec 19
SJU8:31 pmSan Juan Luis Munoz Marin Intl
5h 27m
ORD11:58 pmChicago O'Hare Intl
Jan 7
ORD1:00 pmChicago O'Hare Intl
4h 36m
SJU7:36 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Dec 12
SJU2:17 pmSan Juan Luis Munoz Marin Intl
5h 30m
ORD5:47 pmChicago O'Hare Intl
Dec 15
ORD1:13 pmChicago O'Hare Intl
11h 39m
1 stop
SJU2:52 amSan Juan Luis Munoz Marin Intl

United Airlines flights from Puerto Rico to Chicago

Our best United Airlines deals on Puerto Rico to Chicago flight tickets
United Airlines
Dec 5
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
ORD8:59 amChicago O'Hare Intl
Dec 8
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
United Airlines
Jan 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
10h 39m
1 stop
ORD10:44 amChicago O'Hare Intl
Jan 20
ORD8:50 amChicago O'Hare Intl
11h 32m
1 stop
SJU10:22 pmSan Juan Luis Munoz Marin Intl
United Airlines
Dec 3
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
ORD9:43 amChicago O'Hare Intl
Dec 9
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl

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 airline that flies to Chicago from Puerto Rico?

Spirit Airlines. Spirit Airlines, Southwest, and Frontier are the most popular carriers operating from Puerto Rico to Chicago

What is the cheapest Puerto Rico to Chicago flight route?

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

How many flights depart from Puerto Rico to Chicago on average per day?

The number of flights available between Puerto Rico and Chicago is 6 per day as of November 2024. The most frequent departure time is 8:00AM, with 47% of daily flights leaving in the afternoon.

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

There are 3 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 1% 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

$58

Fastest flight time

5h 03m

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 $58. The best round-trip flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $117.
The fastest flight from Puerto Rico to Chicago takes 5h 03m
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 $120Free CancellationRating
6.1
3,542 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $148Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
DeltaPriceFrom $182Free CancellationRating
8.0
8,765 reviews
Search Delta flights
United AirlinesPriceFrom $202Free CancellationRating
7.4
9,173 reviews
Search United Airlines flights
SouthwestPriceFrom $220Free CancellationRating
8.1
5,015 reviews
Search Southwest flights
American AirlinesPriceFrom $303Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago