Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to San Juan from $63

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 2/24. 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

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
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.

Find the cheapest flights from Chicago Midway Airport to San Juan

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to San Juan that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to San Juan.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to San Juan? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Juan, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to San Juan

Find recent round-trip train or bus tickets from Chicago Midway Airport to San Juan.

All round-trip flight deals to San Juan

The cheapest plane tickets to San Juan found on KAYAK recently.
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
12:59 am - 1:09 pmSJU-MDW
14h 10m1 stop
$133Frontier
Find Deal
Mon, Dec 9 - Mon, Dec 16
11:33 am - 2:19 amMDW-SJU
12h 46m1 stop
6:00 am - 3:43 pmSJU-MDW
11h 43m1 stop
$138Frontier
Find Deal
Mon, Jan 20 - Mon, Jan 27
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
7:14 pm - 3:12 pmSJU-MDW
21h 58m1 stop
$139Frontier
Find Deal
Mon, Dec 9 - Sat, Dec 14
10:58 am - 2:19 amMDW-SJU
13h 21m1 stop
6:00 am - 3:43 pmSJU-MDW
11h 43m1 stop
$143Frontier
Find Deal
Sun, Jan 26 - Mon, Jan 27
1:20 pm - 12:50 amMDW-SJU
9h 30m2 stops
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$210Southwest
Find Deal
Sun, Feb 2 - Wed, Feb 5
8:15 am - 5:43 pmMDW-SJU
31h 28m2 stops
3:20 am - 10:45 pmSJU-MDW
45h 25m2 stops
Mon, Dec 9 - Sat, Dec 14
8:15 am - 5:43 pmMDW-SJU
31h 28m2 stops
9:32 pm - 10:45 pmSJU-MDW
27h 13m3 stops
Mon, Dec 9 - Sun, Dec 15
1:20 pm - 12:40 amMDW-SJU
9h 20m1 stop
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$275Southwest
Find Deal
Wed, Jan 15 - Thu, Jan 23
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
2:02 pm - 10:20 pmSJU-MDW
10h 18m1 stop
$334Delta
Find Deal
Tue, Jan 28 - Fri, Feb 7
6:00 am - 5:15 pmMDW-SJU
9h 15m1 stop
3:30 pm - 10:06 pmSJU-MDW
8h 36m1 stop
$354Delta
Find Deal
Wed, Dec 11 - Wed, Dec 18
4:20 pm - 1:44 amMDW-SJU
7h 24m1 stop
$63Frontier
Find Deal
Mon, Feb 24
9:59 pm - 10:50 amMDW-SJU
10h 51m1 stop
$64Frontier
Find Deal
Mon, Jan 6
7:45 am - 1:59 amMDW-SJU
16h 14m1 stop
$66Frontier
Find Deal
Mon, Feb 3
9:59 pm - 10:50 amMDW-SJU
10h 51m1 stop
$67Frontier
Find Deal
Mon, Jan 6
10:05 am - 12:25 amMDW-SJU
12h 20m2 stops
$105Southwest
Find Deal
Wed, Jan 22
6:30 am - 5:43 pmMDW-SJU
33h 13m2 stops
Sun, Dec 8
7:15 am - 1:22 pmMDW-SJU
28h 07m2 stops
Sat, Dec 14
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
$162Delta
Find Deal
Tue, Jan 14
12:44 pm - 11:45 pmMDW-SJU
9h 01m1 stop
$167Delta
Find Deal
Tue, Jan 21
5:55 am - 3:10 pmMDW-SJU
7h 15m1 stop
$170Southwest
Find Deal
Sat, Jan 11
8:50 am - 8:36 pmMDW-SJU
9h 46m1 stop
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
$258Frontier
Find Deal
Tue, Nov 26 - Wed, Dec 4
7:42 am - 7:17 pmMDW-SJU
9h 35m1 stop
6:20 am - 5:18 pmSJU-MDW
12h 58m1 stop
$278Frontier
Find Deal
Mon, Nov 25 - Thu, Dec 5
2:56 pm - 2:20 amMDW-SJU
9h 24m1 stop
6:20 am - 5:18 pmSJU-MDW
12h 58m1 stop
$318Frontier
Find Deal
Sat, Nov 23 - Thu, Dec 5
7:42 am - 7:17 pmMDW-SJU
9h 35m1 stop
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
$338Frontier
Find Deal
Mon, Nov 25 - Wed, Dec 4
3:19 pm - 11:22 pmMDW-SJU
6h 03m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$414Delta
Find Deal
Sun, Nov 24 - Wed, Dec 4
11:40 am - 12:40 amMDW-SJU
11h 00m2 stops
3:40 pm - 11:15 pmSJU-MDW
9h 35m1 stop
$444Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
11:40 am - 12:40 amMDW-SJU
11h 00m2 stops
5:35 am - 1:15 pmSJU-MDW
9h 40m2 stops
$465Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
3:19 pm - 11:22 pmMDW-SJU
6h 03m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$514Delta
Find Deal
Sun, Nov 24 - Mon, Dec 2
9:09 pm - 11:40 pmMDW-SJU
24h 31m3 stops
8:05 pm - 8:41 amSJU-MDW
14h 36m1 stop
Fri, Nov 22 - Mon, Nov 25
5:10 am - 7:49 pmMDW-SJU
60h 39m3 stops
11:12 am - 11:10 amSJU-MDW
25h 58m2 stops
Sat, Nov 23 - Sat, Nov 30
8:45 am - 3:20 pmMDW-SJU
4h 35mnonstop
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
$1,233Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Dec 9
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 16
SJU12:59 amSan Juan Luis Munoz Marin Intl
14h 10m
1 stop
MDW1:09 pmChicago Midway
Frontier
Jan 20
MDW11:33 amChicago Midway
12h 46m
1 stop
SJU2:19 amSan Juan Luis Munoz Marin Intl
Jan 27
SJU6:00 amSan Juan Luis Munoz Marin Intl
11h 43m
1 stop
MDW3:43 pmChicago Midway
Frontier
Dec 9
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 14
SJU7:14 pmSan Juan Luis Munoz Marin Intl
21h 58m
1 stop
MDW3:12 pmChicago Midway

Southwest flights from Chicago Midway Airport to San Juan

Our best Southwest deals on Chicago Midway Airport to San Juan flight tickets
Southwest
Feb 2
MDW1:20 pmChicago Midway
9h 30m
2 stops
SJU12:50 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 15
MDW1:20 pmChicago Midway
9h 20m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 23
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 28
MDW10:05 amChicago Midway
12h 20m
2 stops
SJU12:25 amSan Juan Luis Munoz Marin Intl
Feb 3
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 45m
1 stop
MDW11:45 amChicago Midway

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 August, then September is your next best option. Flight prices from Chicago Midway Airport to San Juan during September average around $290.

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 $334. The most expensive day to fly to San Juan is Sunday, with ticket prices averaging around $401.

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 afternoon when flights can be purchased for as low as $292. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $381 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?

We recommend purchasing flights from Chicago Midway Airport to San Juan 9 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to San Juan for $352. However, in the past 72 hours, people saw flights from Chicago Midway Airport for as low as $256.

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

There are 1 cabin classes 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.

Can stopping save me money on Chicago Midway Airport to San Juan flights?

You could potentially save up to 66% on your flight if you consider stops on a Chicago Midway Airport to San Juan flight.

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

Best Price Found

$63

Fastest flight time

4h 35m

Direct flights

Mon and Sun

Airports in San Juan

1 airport
The best one-way flight to San Juan from Chicago Midway Airport in the past 72 hours is $63. The best round-trip flight deal from Chicago Midway Airport to San Juan found on momondo in the last 72 hours is $133.
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. The only airline offering direct flights is Southwest.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)

  • 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 15m 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 $119Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $199Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $374Free CancellationRating
8.0
8,755 reviews
Search Delta 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

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