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Cheap flights from Chicago Midway Airport to San Juan 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 San Juan 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.
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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.
Multiple Airlines Logo
6:00 am - 2:22 pm
MDW
-
SJU
30h 22m
1 stop
Multiple Airlines Logo
6:27 pm - 6:38 pm
SJU
-
MDW
26h 11m
1 stop
$188Multiple Airlines
Mon, Feb 23 - Thu, Feb 26
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
Multiple Airlines Logo
6:00 am - 2:22 pm
MDW
-
SJU
30h 22m
1 stop
Multiple Airlines Logo
4:06 pm - 4:16 pm
SJU
-
MDW
26h 10m
1 stop
$191Multiple Airlines
Mon, Feb 23 - Wed, Feb 25
Multiple Airlines Logo
6:10 am - 6:58 pm
MDW
-
SJU
34h 48m
2 stops
Multiple Airlines Logo
6:27 pm - 6:38 pm
SJU
-
MDW
26h 11m
1 stop
$196Multiple Airlines
Tue, Feb 24 - Thu, Feb 26
Multiple Airlines Logo
6:00 am - 6:58 pm
MDW
-
SJU
34h 58m
2 stops
Multiple Airlines Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$198Multiple Airlines
Mon, Mar 2 - Thu, Mar 5
Frontier Logo
2:56 pm - 12:14 am
MDW
-
SJU
8h 18m
1 stop
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
$202Frontier
Sat, Apr 11 - Fri, Apr 17
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
$203Frontier
Mon, Apr 20 - Thu, Apr 23
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
Multiple Airlines Logo
2:19 pm - 3:31 pm
MDW
-
SJU
23h 12m
2 stops
Multiple Airlines Logo
6:27 pm - 4:16 pm
SJU
-
MDW
23h 49m
1 stop
$209Multiple Airlines
Mon, Mar 2 - Wed, Mar 4
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$211Frontier
Mon, Mar 2 - 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
Apr 11
MDW2:56 pmChicago Midway
8h 18m
1 stop
SJU12:14 amSan Juan Luis Munoz Marin Intl
Apr 17
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
$202
Frontier
Apr 20
MDW6:00 amChicago Midway
7h 08m
1 stop
SJU2:08 pmSan Juan Luis Munoz Marin Intl
Apr 23
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
$203
Frontier
Mar 2
MDW9:22 pmChicago Midway
10h 32m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
Mar 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW1:56 pmChicago Midway
$211

Delta flights from Chicago Midway Airport to San Juan

Our best Delta deals on Chicago Midway Airport to San Juan flight tickets
Delta
Apr 19
MDW6:00 amChicago Midway
6h 14m
1 stop
SJU1:14 pmSan Juan Luis Munoz Marin Intl
Apr 29
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 55m
1 stop
MDW4:25 pmChicago Midway
$256
Delta
Feb 25
MDW10:49 amChicago Midway
11h 09m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Mar 3
SJU6:15 amSan Juan Luis Munoz Marin Intl
7h 44m
1 stop
MDW11:59 amChicago Midway
$276
Delta
Feb 23
MDW10:49 amChicago Midway
8h 23m
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
$286

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 February 13, 2026.
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

Mon 2/23

6:00 am-2:22 pm

1 stop30h 22m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:27 pm-6:38 pm

1 stop26h 11m

$188

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

Mon 2/23

6:00 am-2:22 pm

1 stop30h 22m

San Juan Luis Munoz Marin Intl

Wed 2/25

4:06 pm-4:16 pm

1 stop26h 10m

$191

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

Thu 2/26

6:27 pm-6:38 pm

1 stop26h 11m

$196

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

6:00 am-6:58 pm

2 stops34h 58m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

$198

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 4/11

2:56 pm-12:14 am

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:18 pm-10:19 pm

1 stop8h 01m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/20

6:00 am-2:08 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Thu 4/23

3:18 pm-10:19 pm

1 stop8h 01m

$203

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 3/2

2:19 pm-3:31 pm

2 stops23h 12m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:27 pm-4:16 pm

1 stop23h 49m

$209

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

$211

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 cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in February, then January is your next best option. Flight prices from Chicago Midway Airport to San Juan during January average around $304.

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 Monday when prices can be found for as low as $381. The most expensive day to fly to San Juan is Saturday, with ticket prices averaging around $446.

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 $326. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $479 on average. Flights to San Juan from Chicago Midway Airport at noon 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 $401 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 $222 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

2 airports
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 are 2 airports in San Juan. From Chicago Midway Airport there are direct flights to 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. 4h 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
DeltaPriceFrom $132Free CancellationRating
7.9
8,192 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,283 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.

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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