Cheap flights from Puerto Rico to Chicago from $108

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 12/4. 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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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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:22 pm - 4:37 pmSJU-ORD
5h 15mnonstop
Multiple Airlines Logo
8:51 pm - 9:25 amORD-SJU
10h 34m1 stop
$183Multiple Airlines
Find Deal
Fri, Jan 16 - Sun, Jan 18
Multiple Airlines Logo
7:00 am - 11:05 amSJU-ORD
30h 05m1 stop
Multiple Airlines Logo
7:10 am - 12:45 amORD-SJU
15h 35m1 stop
$184Multiple Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
4:31 pm - 10:24 pmSJU-ORD
7h 53m1 stop
Multiple Airlines Logo
3:26 pm - 12:45 amORD-SJU
7h 19m1 stop
$185Multiple Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
5:40 am - 12:21 pmORD-SJU
4h 41mnonstop
$187Spirit Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
Spirit Airlines Logo
5:40 am - 12:21 pmORD-SJU
4h 41mnonstop
$188Spirit Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
6:14 pm - 1:59 pmSJU-MDW
21h 45m2 stops
Multiple Airlines Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$189Multiple Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
7:10 am - 1:01 pmSJU-MDW
31h 51m1 stop
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$194Frontier
Find Deal
Wed, Dec 3 - Sun, Dec 7
Frontier Logo
9:15 am - 1:59 pmSJU-MDW
30h 44m2 stops
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$195Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
United Airlines Logo
1:09 am - 7:45 amBQN-ORD
8h 36m1 stop
United Airlines Logo
12:45 pm - 11:57 pmORD-BQN
9h 12m1 stop
$485United Airlines
Find Deal
Wed, Feb 18 - Mon, Feb 23
United Airlines Logo
1:09 am - 8:03 amBQN-ORD
32h 54m3 stops
United Airlines Logo
12:45 pm - 11:57 pmORD-BQN
9h 12m1 stop
$494United Airlines
Find Deal
Wed, Feb 18 - Mon, Feb 23

Spirit Airlines flights from Puerto Rico to Chicago

Our best Spirit Airlines deals on Puerto Rico to Chicago flight tickets
Spirit Airlines
Dec 11
SJU8:45 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:59 pmChicago O'Hare Intl
Dec 15
ORD5:40 amChicago O'Hare Intl
4h 41m
SJU12:21 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Dec 12
SJU8:45 pmSan Juan Luis Munoz Marin Intl
5h 14m
ORD11:59 pmChicago O'Hare Intl
Dec 15
ORD5:40 amChicago O'Hare Intl
4h 41m
SJU12:21 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Dec 12
SJU6:14 pmSan Juan Luis Munoz Marin Intl
7h 55m
1 stop
ORD12:09 amChicago O'Hare Intl
Dec 15
ORD5:40 amChicago O'Hare Intl
4h 41m
SJU12:21 pmSan Juan Luis Munoz Marin Intl

American Airlines flights from Puerto Rico to Chicago

Our best American Airlines deals on Puerto Rico to Chicago flight tickets
American Airlines
Jan 23
SJU6:00 amSan Juan Luis Munoz Marin Intl
5h 35m
ORD9:35 amChicago O'Hare Intl
Jan 25
ORD3:00 pmChicago O'Hare Intl
4h 39m
SJU9:39 pmSan Juan Luis Munoz Marin Intl
American Airlines
Dec 20
SJU2:35 pmSan Juan Luis Munoz Marin Intl
12h 08m
1 stop
ORD12:43 amChicago O'Hare Intl
Jan 3
ORD7:11 amChicago O'Hare Intl
12h 54m
1 stop
SJU10:05 pmSan Juan Luis Munoz Marin Intl
American Airlines
Dec 24
SJU6:00 amSan Juan Luis Munoz Marin Intl
5h 29m
ORD9:29 amChicago O'Hare Intl
Jan 3
ORD7:11 amChicago O'Hare Intl
7h 06m
1 stop
SJU4:17 pmSan Juan Luis Munoz Marin Intl

momondo Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 17, 2025.
Use the filters below to find and compare flights from Puerto Rico to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 1/16

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Sun 1/18

8:51 pm-9:25 am

1 stop10h 34m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/4

7:00 am-11:05 am

1 stop30h 05m

Chicago O'Hare Intl

Mon 12/8

7:10 am-12:45 am

1 stop15h 35m

$184

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/12

4:31 pm-10:24 pm

1 stop7h 53m

Chicago O'Hare Intl

Mon 12/15

3:26 pm-12:45 am

1 stop7h 19m

$185

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/11

8:45 pm-11:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

Mon 12/15

5:40 am-12:21 pm

Nonstop4h 41m

$187

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/12

8:45 pm-11:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

Mon 12/15

5:40 am-12:21 pm

Nonstop4h 41m

$188

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

6:14 pm-1:59 pm

2 stops21h 45m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$189

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/3

7:10 am-1:01 pm

1 stop31h 51m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$194

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

9:15 am-1:59 pm

2 stops30h 44m

Chicago Midway

Sun 12/7

2:59 pm-9:37 am

1 stop16h 38m

$195

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 2/18

1:09 am-7:45 am

1 stop8h 36m

Chicago O'Hare Intl

Mon 2/23

12:45 pm-11:57 pm

1 stop9h 12m

$485

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Wed 2/18

1:09 am-8:03 am

3 stops32h 54m

Chicago O'Hare Intl

Mon 2/23

12:45 pm-11:57 pm

1 stop9h 12m

$494

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $265. 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 $271.

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 $381. 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 $518.

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 $254. 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 $337 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 $276 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?

No. A direct flight is the cheapest option for a flight between Puerto Rico to Chicago.

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

$179

Fastest flight time

5h 05m

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 $179. The best round-trip flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $339.
The fastest flight from Puerto Rico to Chicago takes 5h 05m
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
Spirit AirlinesPriceFrom $137Free CancellationRating
6.3
8,144 reviews
Search Spirit Airlines flights
FrontierPriceFrom $139Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
DeltaPriceFrom $162Free CancellationRating
7.9
8,006 reviews
Search Delta flights
United AirlinesPriceFrom $290Free CancellationRating
7.4
9,014 reviews
Search United Airlines flights
American AirlinesPriceFrom $334Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
SouthwestPriceFrom $384Free CancellationRating
8.0
4,244 reviews
Search Southwest 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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
Wed 12/17
Wed 12/24

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