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Cheap flights from Chicago Midway Airport to Puerto Rico from $117

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 1/11. 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 Chicago Midway Airport to Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:10 pm - 11:16 am
MDW
-
SJU
18h 06m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$201Frontier
lun., ene. 5 - lun., ene. 12
Frontier Logo
6:15 am - 12:39 pm
MDW
-
SJU
28h 24m1 stop
Frontier Logo
11:05 am - 8:32 pm
SJU
-
MDW
11h 27m1 stop
$202Frontier
jue., feb. 26 - lun., mar. 2
Frontier Logo
3:01 pm - 12:35 pm
MDW
-
SJU
19h 34m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$203Frontier
mié., ene. 7 - vie., ene. 9
Frontier Logo
6:15 am - 2:35 am
MDW
-
SJU
18h 20m1 stop
Frontier Logo
5:30 pm - 8:32 pm
SJU
-
MDW
29h 02m1 stop
$204Frontier
jue., feb. 19 - dom., mar. 1
Frontier Logo
12:41 pm - 12:05 am
MDW
-
SJU
9h 24m1 stop
Frontier Logo
9:23 pm - 11:09 pm
SJU
-
MDW
27h 46m1 stop
$211Frontier
jue., ene. 8 - dom., ene. 11
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
Frontier Logo
7:00 am - 5:11 pm
SJU
-
MDW
12h 11m1 stop
$215Frontier
vie., feb. 6 - sáb., feb. 14
Frontier Logo
1:00 pm - 3:26 pm
MDW
-
SJU
24h 26m1 stop
Frontier Logo
8:02 pm - 2:26 pm
SJU
-
MDW
20h 24m1 stop
$216Frontier
vie., feb. 6 - sáb., feb. 14
Frontier Logo
9:32 pm - 2:48 am
MDW
-
SJU
27h 16m1 stop
Frontier Logo
4:25 pm - 2:26 pm
SJU
-
MDW
24h 01m1 stop
$217Frontier
lun., feb. 16 - jue., feb. 19
Frontier Logo
3:10 pm - 8:54 am
MDW
-
SJU
15h 44m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$218Frontier
vie., ene. 2 - lun., ene. 12
Frontier Logo
6:10 am - 4:21 pm
MDW
-
SJU
8h 11m1 stop
Frontier Logo
4:35 pm - 10:19 pm
SJU
-
MDW
7h 44m1 stop
$219Frontier
sáb., ene. 10 - jue., ene. 15

Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets
Frontier
Jan 5
MDW3:10 pmChicago Midway
18h 06m
1 stop
SJU11:16 amSan Juan Luis Munoz Marin Intl
Jan 12
SJU5:45 amSan Juan Luis Munoz Marin Intl
10h 21m
1 stop
MDW2:06 pmChicago Midway
$201
Find similar
Frontier
Feb 26
MDW6:15 amChicago Midway
28h 24m
1 stop
SJU12:39 pmSan Juan Luis Munoz Marin Intl
Mar 2
SJU11:05 amSan Juan Luis Munoz Marin Intl
11h 27m
1 stop
MDW8:32 pmChicago Midway
$202
Find similar
Frontier
Jan 7
MDW3:01 pmChicago Midway
19h 34m
1 stop
SJU12:35 pmSan Juan Luis Munoz Marin Intl
Jan 9
SJU5:45 amSan Juan Luis Munoz Marin Intl
10h 21m
1 stop
MDW2:06 pmChicago Midway
$203
Find similar

Southwest flights from Chicago Midway Airport to Puerto Rico

Our best Southwest deals on Chicago Midway Airport to Puerto Rico flight tickets
Southwest
Jan 25
MDW3:15 pmChicago Midway
7h 25m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU6:10 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW11:35 amChicago Midway
$225
Find similar
Southwest
Jan 26
MDW1:55 pmChicago Midway
8h 40m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
$245
Find similar
Southwest
Dec 16
MDW4:35 pmChicago Midway
6h 00m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Dec 23
SJU6:05 amSan Juan Luis Munoz Marin Intl
11h 05m
1 stop
MDW3:10 pmChicago Midway
$420
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 diciembre 11, 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

lun. 1/5

3:10 pm-11:16 am

1 stop18h 06m

San Juan Luis Munoz Marin Intl

lun. 1/12

5:45 am-2:06 pm

1 stop10h 21m

$201

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 2/26

6:15 am-12:39 pm

1 stop28h 24m

San Juan Luis Munoz Marin Intl

lun. 3/2

11:05 am-8:32 pm

1 stop11h 27m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mié. 1/7

3:01 pm-12:35 pm

1 stop19h 34m

San Juan Luis Munoz Marin Intl

vie. 1/9

5:45 am-2:06 pm

1 stop10h 21m

$203

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 2/19

6:15 am-2:35 am

1 stop18h 20m

San Juan Luis Munoz Marin Intl

dom. 3/1

5:30 pm-8:32 pm

1 stop29h 02m

$204

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 1/8

12:41 pm-12:05 am

1 stop9h 24m

San Juan Luis Munoz Marin Intl

dom. 1/11

9:23 pm-11:09 pm

1 stop27h 46m

$211

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 2/6

1:00 pm-11:59 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

sáb. 2/14

7:00 am-5:11 pm

1 stop12h 11m

$215

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 2/6

1:00 pm-3:26 pm

1 stop24h 26m

San Juan Luis Munoz Marin Intl

sáb. 2/14

8:02 pm-2:26 pm

1 stop20h 24m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 2/16

9:32 pm-2:48 am

1 stop27h 16m

San Juan Luis Munoz Marin Intl

jue. 2/19

4:25 pm-2:26 pm

1 stop24h 01m

$217

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 1/2

3:10 pm-8:54 am

1 stop15h 44m

San Juan Luis Munoz Marin Intl

lun. 1/12

5:45 am-2:06 pm

1 stop10h 21m

$218

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

sáb. 1/10

6:10 am-4:21 pm

1 stop8h 11m

San Juan Luis Munoz Marin Intl

jue. 1/15

4:35 pm-10:19 pm

1 stop7h 44m

$219

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 May, then you should wait until February to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $339.

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 $526.

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 $530.

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 $424 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 $336 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

Fastest flight time

4h 35m

Direct flights

Mon and Sun

Airports in Puerto Rico

20 airports
The fastest flight from Chicago Midway Airport to Puerto Rico takes 4h 35m
Direct flights go from Chicago Midway Airport to Puerto Rico on Monday and Sunday. The only airline offering direct flights is Southwest.
There are 20 airports in Puerto Rico. From Chicago Midway Airport there are direct flights to 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 $142Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
8,008 reviews
Search Delta flights
SouthwestPriceFrom $381Free CancellationRating
7.9
4,252 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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