Latest deals
Insights
FAQs
Reviews
Price Alerts

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 11/27. 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 San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:52 pm - 1:42 amMDW-SJU
7h 50m1 stop
Frontier Logo
4:06 pm - 11:25 pmSJU-MDW
9h 19m1 stop
$213Frontier
Find Deal
Wed, Jan 7 - Mon, Jan 12
Frontier Logo
6:15 am - 3:19 pmMDW-SJU
7h 04m1 stop
Frontier Logo
7:11 am - 10:43 pmSJU-MDW
17h 32m2 stops
$214Frontier
Find Deal
Mon, Nov 17 - Thu, Nov 20
Frontier Logo
10:18 am - 2:50 amMDW-SJU
14h 32m1 stop
Frontier Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$215Frontier
Find Deal
Sun, Jan 11 - Thu, Jan 15
Frontier Logo
10:12 am - 2:54 amMDW-SJU
14h 42m1 stop
Frontier Logo
9:30 pm - 4:57 pmSJU-MDW
21h 27m1 stop
$221Frontier
Find Deal
Thu, Nov 13 - Tue, Nov 25
Frontier Logo
6:15 pm - 9:27 amMDW-SJU
37h 12m2 stops
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
$222Frontier
Find Deal
Thu, Nov 27 - Thu, Dec 4
Frontier Logo
3:52 pm - 1:42 amMDW-SJU
7h 50m1 stop
Frontier Logo
3:55 am - 9:13 amSJU-MDW
7h 18m1 stop
$223Frontier
Find Deal
Wed, Jan 7 - Sun, Jan 11
Delta Logo
6:00 am - 2:30 pmMDW-SJU
6h 30m1 stop
Delta Logo
3:55 pm - 10:26 pmSJU-MDW
8h 31m1 stop
$227Delta
Find Deal
Mon, Jan 19 - Wed, Jan 28
Southwest Logo
8:25 am - 5:05 pmMDW-SJU
6h 40m1 stop
Southwest Logo
6:10 am - 1:55 pmSJU-MDW
9h 45m2 stops
$252Southwest
Find Deal
Mon, Jan 12 - Fri, Jan 23
Southwest Logo
1:50 pm - 12:35 amMDW-SJU
8h 45m2 stops
Southwest Logo
6:10 am - 1:55 pmSJU-MDW
9h 45m2 stops
$267Southwest
Find Deal
Sun, Jan 18 - Thu, Jan 22
Multiple Airlines Logo
12:35 pm - 12:35 amMDW-SJU
10h 00m1 stop
Multiple Airlines Logo
7:33 pm - 2:05 pmSJU-MDW
20h 32m1 stop
$286Multiple Airlines
Find Deal
Mon, Dec 8 - Sun, Dec 21

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Jan 7
MDW3:52 pmChicago Midway
7h 50m
1 stop
SJU1:42 amSan Juan Luis Munoz Marin Intl
Jan 12
SJU4:06 pmSan Juan Luis Munoz Marin Intl
9h 19m
1 stop
MDW11:25 pmChicago Midway
$213
Find similar
Frontier
Nov 17
MDW6:15 amChicago Midway
7h 04m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
Nov 20
SJU7:11 amSan Juan Luis Munoz Marin Intl
17h 32m
2 stops
MDW10:43 pmChicago Midway
$214
Find similar
Frontier
Jan 11
MDW10:18 amChicago Midway
14h 32m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
Jan 15
SJU8:00 amSan Juan Luis Munoz Marin Intl
8h 47m
1 stop
MDW2:47 pmChicago Midway
$215
Find similar

Southwest flights from Chicago Midway Airport to San Juan

Our best Southwest deals on Chicago Midway Airport to San Juan flight tickets
Southwest
Jan 12
MDW8:25 amChicago Midway
6h 40m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
$252
Find similar
Southwest
Jan 18
MDW1:50 pmChicago Midway
8h 45m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 22
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
$267
Find similar
Southwest
Jan 21
MDW6:50 amChicago Midway
10h 15m
2 stops
SJU7:05 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU5:30 amSan Juan Luis Munoz Marin Intl
11h 15m
2 stops
MDW2:45 pmChicago Midway
$277
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 October 30, 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

Wed 1/7

3:52 pm-1:42 am

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Mon 1/12

4:06 pm-11:25 pm

1 stop9h 19m

$213

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/17

6:15 am-3:19 pm

1 stop7h 04m

San Juan Luis Munoz Marin Intl

Thu 11/20

7:11 am-10:43 pm

2 stops17h 32m

$214

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/11

10:18 am-2:50 am

1 stop14h 32m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:00 am-2:47 pm

1 stop8h 47m

$215

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/13

10:12 am-2:54 am

1 stop14h 42m

San Juan Luis Munoz Marin Intl

Tue 11/25

9:30 pm-4:57 pm

1 stop21h 27m

$221

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/27

6:15 pm-9:27 am

2 stops37h 12m

San Juan Luis Munoz Marin Intl

Thu 12/4

10:42 am-9:53 pm

1 stop13h 11m

$222

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/7

3:52 pm-1:42 am

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Sun 1/11

3:55 am-9:13 am

1 stop7h 18m

$223

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

6:00 am-2:30 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:26 pm

1 stop8h 31m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/12

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:10 am-1:55 pm

2 stops9h 45m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

1:50 pm-12:35 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

$267

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/8

12:35 pm-12:35 am

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sun 12/21

7:33 pm-2:05 pm

1 stop20h 32m

$286

Flights are sorted by cheapest round-trip flights first.

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

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 November is your next best option. Flight prices from Chicago Midway Airport to San Juan during November average around $342.

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 $392. 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 $449 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 $422 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 $355 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

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 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 30m 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
3,123 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,115 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,996 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,998 reviews
Search Delta flights
SouthwestPriceFrom $380Free CancellationRating
8.0
4,243 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

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
Sat 11/29
Sat 12/6
By creating a price alert you accept our terms of use and privacy policy.

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