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Cheap flights from Chicago Midway Airport to San Juan from $87

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 4/9. 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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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.
4:40 pm - 8:33 amMDW-SJU
14h 53m1 stop
2:12 pm - 7:35 pmSJU-MDW
30h 23m1 stop
$178Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
4:40 pm - 1:50 amMDW-SJU
8h 10m1 stop
2:55 am - 7:35 pmSJU-MDW
17h 40m1 stop
$180Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
12:46 pm - 1:50 amMDW-SJU
12h 04m1 stop
5:30 am - 11:43 amSJU-MDW
7h 13m1 stop
$183Frontier
Find Deal
Wed, Apr 9 - Thu, Apr 10
4:00 pm - 11:15 pmMDW-SJU
6h 15m1 stop
12:50 pm - 10:22 pmSJU-MDW
10h 32m1 stop
$271Delta
Find Deal
Sat, Apr 26 - Sat, May 3
4:00 pm - 11:15 pmMDW-SJU
6h 15m1 stop
7:15 am - 5:59 pmSJU-MDW
11h 44m1 stop
$296Delta
Find Deal
Sat, Apr 26 - Sat, May 3
4:00 pm - 11:15 pmMDW-SJU
6h 15m1 stop
12:50 pm - 10:22 pmSJU-MDW
10h 32m1 stop
$326Delta
Find Deal
Sat, Apr 26 - Wed, Apr 30
8:35 am - 2:15 pmMDW-SJU
4h 40mnonstop
8:00 am - 6:25 pmSJU-MDW
11h 25m1 stop
$377Southwest
Find Deal
Sat, Apr 26 - Tue, Apr 29
6:05 am - 3:10 pmMDW-SJU
8h 05m1 stop
7:20 am - 7:10 pmSJU-MDW
12h 50m2 stops
$381Southwest
Find Deal
Fri, Sep 5 - Tue, Sep 9
9:40 am - 9:50 pmMDW-SJU
11h 10m1 stop
11:15 am - 8:25 pmSJU-MDW
10h 10m1 stop
$389Southwest
Find Deal
Tue, May 6 - Tue, May 13
9:05 am - 10:05 pmMDW-SJU
12h 00m2 stops
11:15 am - 8:25 pmSJU-MDW
10h 10m1 stop
$390Southwest
Find Deal
Fri, May 9 - Wed, May 14

Southwest flights from Chicago Midway Airport to San Juan

Our best Southwest deals on Chicago Midway Airport to San Juan flight tickets
Southwest
Apr 26
MDW8:35 amChicago Midway
4h 40m
SJU2:15 pmSan Juan Luis Munoz Marin Intl
Apr 29
SJU8:00 amSan Juan Luis Munoz Marin Intl
11h 25m
1 stop
MDW6:25 pmChicago Midway
Southwest
Sep 5
MDW6:05 amChicago Midway
8h 05m
1 stop
SJU3:10 pmSan Juan Luis Munoz Marin Intl
Sep 9
SJU7:20 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW7:10 pmChicago Midway
Southwest
May 6
MDW9:40 amChicago Midway
11h 10m
1 stop
SJU9:50 pmSan Juan Luis Munoz Marin Intl
May 13
SJU11:15 amSan Juan Luis Munoz Marin Intl
10h 10m
1 stop
MDW8:25 pmChicago Midway

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Apr 1
MDW4:40 pmChicago Midway
14h 53m
1 stop
SJU8:33 amSan Juan Luis Munoz Marin Intl
Apr 8
SJU2:12 pmSan Juan Luis Munoz Marin Intl
30h 23m
1 stop
MDW7:35 pmChicago Midway
Frontier
Apr 1
MDW4:40 pmChicago Midway
8h 10m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
Apr 8
SJU2:55 amSan Juan Luis Munoz Marin Intl
17h 40m
1 stop
MDW7:35 pmChicago Midway
Frontier
Mar 26
MDW3:14 pmChicago Midway
8h 21m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Mar 27
SJU5:30 amSan Juan Luis Munoz Marin Intl
7h 10m
1 stop
MDW11:40 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 May, then September is your next best option. Flight prices from Chicago Midway Airport to San Juan during September 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 Tuesday when prices can be found for as low as $361. The most expensive day to fly to San Juan is Sunday, with ticket prices averaging around $424.

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 $306. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $410 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 6 weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $396 when searching 6 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 $287 on momondo.

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.

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

$87

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 $87. The best round-trip flight deal from Chicago Midway Airport to San Juan found on momondo in the last 72 hours is $178.
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. 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
FrontierPriceFrom $133Free CancellationRating
6.0
3,292 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $174Free CancellationRating
6.3
7,896 reviews
Search Spirit Airlines flights
DeltaPriceFrom $325Free CancellationRating
8.0
7,944 reviews
Search Delta flights
SouthwestPriceFrom $337Free CancellationRating
8.0
4,292 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