Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Puerto Rico from $92

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 2/23. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
6:25 am - 4:21 pm
MDW
-
SJU
7h 56m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$188Frontier
Sat, Feb 28 - Wed, Mar 4
Multiple Airlines Logo
2:19 pm - 6:58 pm
MDW
-
SJU
26h 39m
2 stops
Multiple Airlines Logo
6:50 pm - 1:41 pm
SJU
-
MDW
20h 51m
1 stop
$189Multiple Airlines
Mon, Mar 2 - Fri, Mar 6
Multiple Airlines Logo
6:00 am - 2:22 pm
MDW
-
SJU
30h 22m
1 stop
Multiple Airlines Logo
6:27 pm - 9:39 pm
SJU
-
MDW
29h 12m
1 stop
$190Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Frontier Logo
8:00 am - 1:27 pm
MDW
-
SJU
27h 27m
1 stop
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$197Frontier
Sat, Feb 28 - Thu, Mar 5
Multiple Airlines Logo
2:19 pm - 6:58 pm
MDW
-
SJU
26h 39m
2 stops
Multiple Airlines Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$199Multiple Airlines
Mon, Mar 2 - Thu, Mar 5
Frontier Logo
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
4:16 pm - 10:37 pm
SJU
-
MDW
8h 21m
1 stop
$202Frontier
Tue, Feb 24 - Fri, Feb 27
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
$204Frontier
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
6:10 am - 6:58 pm
MDW
-
SJU
34h 48m
2 stops
Multiple Airlines Logo
4:16 pm - 10:37 pm
SJU
-
MDW
8h 21m
1 stop
$205Multiple Airlines
Tue, Feb 24 - Fri, Feb 27
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
$207Frontier
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
9:22 pm - 2:53 am
MDW
-
SJU
27h 31m
1 stop
Frontier Logo
10:57 am - 1:08 pm
SJU
-
MDW
28h 11m
1 stop
$211Frontier
Mon, Mar 2 - Thu, Mar 5

Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets
Frontier
Feb 28
MDW6:25 amChicago Midway
7h 56m
1 stop
SJU4:21 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$188
Frontier
Feb 28
MDW8:00 amChicago Midway
27h 27m
1 stop
SJU1:27 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW1:56 pmChicago Midway
$197
Frontier
Feb 24
MDW6:10 amChicago Midway
6h 56m
1 stop
SJU3:06 pmSan Juan Luis Munoz Marin Intl
Feb 27
SJU4:16 pmSan Juan Luis Munoz Marin Intl
8h 21m
1 stop
MDW10:37 pmChicago Midway
$202

Delta flights from Chicago Midway Airport to Puerto Rico

Our best Delta deals on Chicago Midway Airport to Puerto Rico flight tickets
Delta
Apr 21
MDW12:53 pmChicago Midway
6h 31m
1 stop
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Apr 29
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 55m
1 stop
MDW4:25 pmChicago Midway
$246
Delta
Apr 23
MDW12:53 pmChicago Midway
9h 19m
1 stop
SJU11:12 pmSan Juan Luis Munoz Marin Intl
Apr 28
SJU2:34 pmSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
MDW10:28 pmChicago Midway
$256
Delta
Feb 24
MDW12:45 pmChicago Midway
6h 27m
1 stop
SJU9:12 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU7:30 amSan Juan Luis Munoz Marin Intl
6h 29m
1 stop
MDW11:59 amChicago Midway
$266

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 February 10, 2026.
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

Sat 2/28

6:25 am-4:21 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:26 pm

1 stop23h 01m

$188

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

2:19 pm-6:58 pm

2 stops26h 39m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:50 pm-1:41 pm

1 stop20h 51m

$189

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

6:00 am-2:22 pm

1 stop30h 22m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:27 pm-9:39 pm

1 stop29h 12m

$190

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

8:00 am-1:27 pm

1 stop27h 27m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

$197

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

2:19 pm-6:58 pm

2 stops26h 39m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

$199

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/24

6:10 am-3:06 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 2/27

4:16 pm-10:37 pm

1 stop8h 21m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 4/18

6:00 am-2:08 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Sat 4/25

3:18 pm-10:19 pm

1 stop8h 01m

$204

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/24

6:10 am-6:58 pm

2 stops34h 48m

San Juan Luis Munoz Marin Intl

Fri 2/27

4:16 pm-10:37 pm

1 stop8h 21m

$205

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

9:22 pm-9:54 am

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Thu 2/26

3:53 am-2:26 pm

1 stop12h 33m

$207

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

9:22 pm-2:53 am

1 stop27h 31m

San Juan Luis Munoz Marin Intl

Thu 3/5

10:57 am-1:08 pm

1 stop28h 11m

$211

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 February, then you should wait until January to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $304.

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 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 $401 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 $222 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 40m

Direct flights

Mon and Sun

Airports in Puerto Rico

20 airports
The fastest flight from Chicago Midway Airport to Puerto Rico takes 4h 40m
Direct flights go from Chicago Midway Airport to Puerto Rico on Monday and Sunday. There are no airlines offering direct flights.
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
DeltaPriceFrom $132Free CancellationRating
7.9
8,180 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,280 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 3/12
Thu 3/19
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Puerto Rico

Popular cities in Puerto Rico

Popular flights according to clicks in the last 7 days on momondo
Flights to San Juanfrom $92
Flights to Aguadillafrom $137
Flights to Mayagüezfrom $304