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Cheap flights from Chicago Midway Airport to Puerto Rico from $120

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 Midway Airport to Puerto Rico departing on 10/6. 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 Chicago Midway Airport to Puerto Rico

Cheap round-trip flights

Frontier Logo
4:56 pm - 9:52 amMDW-SJU
15h 56m2 stops
Frontier Logo
9:26 pm - 1:38 pmSJU-MDW
17h 12m2 stops
$220Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
12:13 pm - 12:29 amMDW-SJU
11h 16m1 stop
Frontier Logo
11:48 am - 11:20 pmSJU-MDW
12h 32m2 stops
$226Frontier
Find Deal
Fri, Oct 17 - Fri, Oct 24
Frontier Logo
4:56 pm - 9:56 amMDW-SJU
16h 00m2 stops
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
$233Frontier
Find Deal
Thu, Sep 25 - Sat, Sep 27
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
Frontier Logo
6:22 am - 11:20 pmSJU-MDW
17h 58m2 stops
$240Frontier
Find Deal
Fri, Oct 3 - Tue, Oct 7
Frontier Logo
5:15 pm - 11:59 pmMDW-SJU
29h 44m2 stops
Frontier Logo
4:51 pm - 3:58 pmSJU-MDW
24h 07m2 stops
$242Frontier
Find Deal
Fri, Sep 26 - Tue, Sep 30
Frontier Logo
5:15 pm - 9:56 amMDW-SJU
15h 41m2 stops
Frontier Logo
10:57 am - 11:41 pmSJU-MDW
13h 44m2 stops
$243Frontier
Find Deal
Mon, Sep 29 - Fri, Oct 3
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
Frontier Logo
9:26 pm - 3:58 pmSJU-MDW
19h 32m2 stops
$244Frontier
Find Deal
Fri, Sep 26 - Wed, Oct 1
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
Frontier Logo
10:57 am - 11:41 pmSJU-MDW
13h 44m2 stops
$245Frontier
Find Deal
Sun, Sep 28 - Thu, Oct 2
Frontier Logo
6:15 am - 11:23 pmMDW-SJU
16h 08m2 stops
Frontier Logo
9:26 pm - 3:58 pmSJU-MDW
19h 32m2 stops
$246Frontier
Find Deal
Sat, Sep 20 - Tue, Sep 23
Frontier Logo
4:56 pm - 9:56 amMDW-SJU
16h 00m2 stops
Frontier Logo
7:50 pm - 4:25 pmSJU-MDW
21h 35m2 stops
$248Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5

Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets
Frontier
Oct 2
MDW4:56 pmChicago Midway
15h 56m
2 stops
SJU9:52 amSan Juan Luis Munoz Marin Intl
Oct 6
SJU9:26 pmSan Juan Luis Munoz Marin Intl
17h 12m
2 stops
MDW1:38 pmChicago Midway
$220
Find similar
Frontier
Oct 17
MDW12:13 pmChicago Midway
11h 16m
1 stop
SJU12:29 amSan Juan Luis Munoz Marin Intl
Oct 24
SJU11:48 amSan Juan Luis Munoz Marin Intl
12h 32m
2 stops
MDW11:20 pmChicago Midway
$226
Find similar
Frontier
Sep 25
MDW4:56 pmChicago Midway
16h 00m
2 stops
SJU9:56 amSan Juan Luis Munoz Marin Intl
Sep 27
SJU12:28 amSan Juan Luis Munoz Marin Intl
7h 43m
1 stop
MDW7:11 amChicago Midway
$233
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Puerto Rico 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 September 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/2

4:56 pm-9:52 am

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Mon 10/6

9:26 pm-1:38 pm

2 stops17h 12m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/17

12:13 pm-12:29 am

1 stop11h 16m

San Juan Luis Munoz Marin Intl

Fri 10/24

11:48 am-11:20 pm

2 stops12h 32m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 9/25

4:56 pm-9:56 am

2 stops16h 00m

San Juan Luis Munoz Marin Intl

Sat 9/27

12:28 am-7:11 am

1 stop7h 43m

$233

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/3

6:21 am-3:22 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Tue 10/7

6:22 am-11:20 pm

2 stops17h 58m

$240

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/26

5:15 pm-11:59 pm

2 stops29h 44m

San Juan Luis Munoz Marin Intl

Tue 9/30

4:51 pm-3:58 pm

2 stops24h 07m

$242

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/29

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Fri 10/3

10:57 am-11:41 pm

2 stops13h 44m

$243

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/26

6:21 am-3:22 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Wed 10/1

9:26 pm-3:58 pm

2 stops19h 32m

$244

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 9/28

6:21 am-3:22 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Thu 10/2

10:57 am-11:41 pm

2 stops13h 44m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/20

6:15 am-11:23 pm

2 stops16h 08m

San Juan Luis Munoz Marin Intl

Tue 9/23

9:26 pm-3:58 pm

2 stops19h 32m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/2

4:56 pm-9:56 am

2 stops16h 00m

San Juan Luis Munoz Marin Intl

Sun 10/5

7:50 pm-4:25 pm

2 stops21h 35m

$248

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 Puerto Rico from

How to get the cheapest flight ticket from Chicago Midway Airport 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 November, then you should wait until May to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $328.

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 Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $59. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Saturday, with ticket prices averaging around $510.

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 Midway Airport to Puerto Rico during this time can be as low as $324. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $510.

What is the cheapest Chicago Midway to Puerto Rico flight route?

Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - 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 Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $419 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago Midway Airport for as low as $326 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway 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 Midway Airport to Puerto Rico flight deals and tips

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

Best Price Found

$476

Fastest flight time

4h 40m

Direct flights

Sun

Airports in Puerto Rico

1 airport
The best flight deal from Chicago Midway Airport to Puerto Rico found on momondo in the last 72 hours is $476
The fastest flight from Chicago Midway Airport to Puerto Rico takes 4h 40m
Direct flights go from Chicago Midway Airport to Puerto Rico on Sunday. There are no airlines offering direct flights.
There is 1 airport near Puerto Rico: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

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

    Prices for flights from Chicago Midway Airport to Puerto Rico are refreshed on a daily basis.

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

  • How old do you have to be to fly from Chicago Midway Airport 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 Midway Airport to Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The necessary travel and health documents for your Puerto Rico 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 Chicago Midway Airport to Puerto Rico?

Best airlines flying from Chicago Midway Airport to Puerto Rico

Compare and see reviews for airlines that fly from Chicago Midway Airport to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $133Free CancellationRating
5.8
3,194 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,016 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,977 reviews
Search Delta flights
SouthwestPriceFrom $361Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Puerto Rico from Chicago.

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

Flights from Chicago to Puerto Rico 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 Chicago to Puerto Rico?

Once all potential Chicago to Puerto Rico flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Puerto Rico, momondo offers a useful price alert feature which will track prices for flights to Puerto Rico from Chicago and alert you when they change.

An easier way to manage your Puerto Rico trip

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