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Cheap flights from Chicago Midway Airport to San Juan from $113

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 San Juan departing on 1/20. 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 San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:56 pm - 9:55 amMDW-SJU
10h 59m1 stop
Frontier Logo
4:11 pm - 11:25 pmSJU-MDW
9h 14m1 stop
$211Frontier
Find Deal
Sun, Mar 1 - Thu, Mar 5
Frontier Logo
6:37 pm - 9:55 amMDW-SJU
13h 18m1 stop
Frontier Logo
4:02 pm - 10:12 pmSJU-MDW
8h 10m1 stop
$216Frontier
Find Deal
Sun, Dec 7 - Sat, Dec 20
Frontier Logo
4:46 pm - 2:54 amMDW-SJU
8h 08m1 stop
Frontier Logo
9:15 am - 1:01 pmSJU-MDW
29h 46m1 stop
$219Frontier
Find Deal
Fri, Nov 28 - Wed, Dec 3
Multiple Airlines Logo
7:23 pm - 12:45 amMDW-SJU
27h 22m2 stops
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
$220Multiple Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Frontier Logo
6:05 am - 12:37 amMDW-SJU
16h 32m2 stops
Frontier Logo
7:10 am - 1:01 pmSJU-MDW
31h 51m1 stop
$221Frontier
Find Deal
Wed, Nov 26 - Wed, Dec 3
Frontier Logo
8:41 pm - 3:05 pmMDW-SJU
16h 24m2 stops
Frontier Logo
9:15 am - 1:01 pmSJU-MDW
29h 46m1 stop
$222Frontier
Find Deal
Fri, Nov 28 - Wed, Dec 3
Frontier Logo
5:30 pm - 2:54 amMDW-SJU
7h 24m1 stop
Frontier Logo
7:10 am - 1:01 pmSJU-MDW
31h 51m1 stop
$223Frontier
Find Deal
Thu, Nov 27 - Wed, Dec 3
Multiple Airlines Logo
8:42 pm - 12:32 pmMDW-SJU
37h 50m2 stops
Multiple Airlines Logo
7:06 pm - 1:59 pmSJU-MDW
20h 53m1 stop
$224Multiple Airlines
Find Deal
Fri, Dec 12 - Sat, Dec 20
Delta Logo
10:53 am - 11:44 pmMDW-SJU
10h 51m1 stop
Delta Logo
3:55 pm - 10:26 pmSJU-MDW
8h 31m1 stop
$225Delta
Find Deal
Tue, Jan 20 - Tue, Jan 27
Frontier Logo
6:30 am - 1:42 amMDW-SJU
17h 12m1 stop
Frontier Logo
2:55 am - 3:33 pmSJU-MDW
14h 38m1 stop
$226Frontier
Find Deal
Thu, Feb 26 - Thu, Mar 5

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Mar 1
MDW8:56 pmChicago Midway
10h 59m
1 stop
SJU9:55 amSan Juan Luis Munoz Marin Intl
Mar 6
SJU3:55 amSan Juan Luis Munoz Marin Intl
11h 52m
1 stop
MDW1:47 pmChicago Midway
$211
Find similar
Frontier
Dec 7
MDW6:37 pmChicago Midway
13h 18m
1 stop
SJU9:55 amSan Juan Luis Munoz Marin Intl
Dec 20
SJU4:02 pmSan Juan Luis Munoz Marin Intl
8h 10m
1 stop
MDW10:12 pmChicago Midway
$216
Find similar
Frontier
Nov 28
MDW4:46 pmChicago Midway
8h 08m
1 stop
SJU2:54 amSan Juan Luis Munoz Marin Intl
Dec 3
SJU9:15 amSan Juan Luis Munoz Marin Intl
29h 46m
1 stop
MDW1:01 pmChicago Midway
$219
Find similar

Delta flights from Chicago Midway Airport to San Juan

Our best Delta deals on Chicago Midway Airport to San Juan flight tickets
Delta
Jan 20
MDW10:53 amChicago Midway
10h 51m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
Jan 27
SJU3:55 pmSan Juan Luis Munoz Marin Intl
8h 31m
1 stop
MDW10:26 pmChicago Midway
$225
Find similar
Delta
Feb 3
MDW10:53 amChicago Midway
8h 04m
1 stop
SJU8:57 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 08m
1 stop
MDW3:23 pmChicago Midway
$227
Find similar
Delta
Nov 27
MDW10:47 amChicago Midway
10h 26m
1 stop
SJU11:13 pmSan Juan Luis Munoz Marin Intl
Dec 5
SJU6:38 pmSan Juan Luis Munoz Marin Intl
7h 09m
1 stop
MDW11:47 pmChicago Midway
$290
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Juan 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 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 3/1

8:56 pm-9:55 am

1 stop10h 59m

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-11:25 pm

1 stop9h 14m

$211

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

6:37 pm-9:55 am

1 stop13h 18m

San Juan Luis Munoz Marin Intl

Sat 12/20

4:02 pm-10:12 pm

1 stop8h 10m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 11/28

4:46 pm-2:54 am

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Wed 12/3

9:15 am-1:01 pm

1 stop29h 46m

$219

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/4

7:23 pm-12:45 am

2 stops27h 22m

San Juan Luis Munoz Marin Intl

Thu 12/11

10:42 am-9:53 pm

1 stop13h 11m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 11/26

6:05 am-12:37 am

2 stops16h 32m

San Juan Luis Munoz Marin Intl

Wed 12/3

7:10 am-1:01 pm

1 stop31h 51m

$221

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 11/28

8:41 pm-3:05 pm

2 stops16h 24m

San Juan Luis Munoz Marin Intl

Wed 12/3

9:15 am-1:01 pm

1 stop29h 46m

$222

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/27

5:30 pm-2:54 am

1 stop7h 24m

San Juan Luis Munoz Marin Intl

Wed 12/3

7:10 am-1:01 pm

1 stop31h 51m

$223

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/12

8:42 pm-12:32 pm

2 stops37h 50m

San Juan Luis Munoz Marin Intl

Sat 12/20

7:06 pm-1:59 pm

1 stop20h 53m

$224

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/20

10:53 am-11:44 pm

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:55 pm-10:26 pm

1 stop8h 31m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/26

6:30 am-1:42 am

1 stop17h 12m

San Juan Luis Munoz Marin Intl

Thu 3/5

2:55 am-3:33 pm

1 stop14h 38m

$226

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 San Juan from

How to get the cheapest flight ticket from Chicago Midway Airport to San Juan

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 typical price of a round-trip flight between Chicago Midway Airport and San Juan?

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in May, then October is your next best option. Flight prices from Chicago Midway Airport to San Juan during October average around $354.

What is the cheapest day to depart on your flight to San Juan?

The cheapest day to depart from Chicago Midway Airport to San Juan is on a Tuesday when prices can be found for as low as $393. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $444.

What is the cheapest time of day to depart on your flight to San Juan?

The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $314. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $450 on average. Flights to San Juan from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago Midway to San Juan flight route?

Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - San Juan flight prices

How far in advance should I book a flight to San Juan?

You are more likely to see cheaper flights to San Juan from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $425 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago Midway Airport for as low as $362 on momondo.

What cabin class options are available on Chicago Midway to San Juan flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Juan 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 San Juan flight deals and tips

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

Fastest flight time

4h 35m

Direct flights

Mon and Sun

Airports in San Juan

1 airport
The fastest flight from Chicago Midway Airport to San Juan takes 4h 35m
Direct flights go from Chicago Midway Airport to San Juan on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

  • How far is Chicago Midway to San Juan by plane?

    The straight-line distance from Chicago Midway to San Juan is 2052.0 mi. 6h 35m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago Midway Airport to San Juan?

    Prices for flights from Chicago Midway Airport to San Juan are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to San Juan?

  • How old do you have to be to fly from Chicago Midway Airport to San Juan?

    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 San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The necessary travel and health documents for your San Juan 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.

Best airlines flying from Chicago Midway Airport to San Juan

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Juan with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $144Free CancellationRating
5.8
3,114 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
8,007 reviews
Search Delta flights
SouthwestPriceFrom $380Free CancellationRating
8.0
4,236 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

It is quick and easy to find Chicago to San Juan 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 San Juan that suits you.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to San Juan from Chicago with this policy.

How can momondo help me find flights from Chicago to San Juan?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San Juan.

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

Price alerts on flights to San Juan from Chicago 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.

An easier way to manage your San Juan trip

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Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan

Airports listed have a maximum distance of 7.1 mi from San Juan
San Juan Isla Grande Airport
San Juan Luis Munoz Marin Intl Airport