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Cheap flights from Chicago to San Juan from $108

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 to San Juan departing on 12/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:47 pm - 1:12 amMDW-SJU
7h 25m1 stop
Frontier Logo
7:00 am - 2:05 pmSJU-MDW
9h 05m1 stop
$200Frontier
Find Deal
Wed, Nov 26 - Thu, Dec 11
Frontier Logo
6:40 am - 5:54 pmORD-SJU
10h 14m1 stop
Frontier Logo
4:31 pm - 12:11 amSJU-ORD
9h 40m1 stop
$201Frontier
Find Deal
Wed, Oct 29 - Thu, Nov 13
Spirit Airlines Logo
5:28 pm - 1:44 amORD-SJU
7h 16m1 stop
Spirit Airlines Logo
3:41 pm - 6:51 pmSJU-ORD
5h 10mnonstop
$207Spirit Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3
Frontier Logo
6:40 am - 5:54 pmORD-SJU
9h 14m1 stop
Frontier Logo
1:59 am - 7:26 amSJU-ORD
7h 27m1 stop
$208Frontier
Find Deal
Mon, Nov 10 - Wed, Nov 12
Spirit Airlines Logo
8:41 am - 3:17 pmORD-SJU
4h 36mnonstop
Spirit Airlines Logo
9:47 pm - 12:59 amSJU-ORD
5h 12mnonstop
$217Spirit Airlines
Find Deal
Tue, Dec 2 - Sun, Dec 7
JetBlue Logo
6:45 am - 9:54 pmORD-SJU
13h 09m1 stop
JetBlue Logo
9:30 am - 8:52 pmSJU-ORD
13h 22m1 stop
$260JetBlue
Find Deal
Wed, Nov 12 - Tue, Nov 18
JetBlue Logo
8:20 am - 6:10 pmORD-SJU
7h 50m1 stop
JetBlue Logo
2:23 pm - 10:31 pmSJU-ORD
10h 08m1 stop
$262JetBlue
Find Deal
Fri, Nov 21 - Sun, Nov 30
Southwest Logo
10:40 am - 10:05 pmMDW-SJU
9h 25m1 stop
Southwest Logo
5:45 am - 1:45 pmSJU-MDW
10h 00m2 stops
$263Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
1:10 pm - 10:05 pmMDW-SJU
6h 55m1 stop
Southwest Logo
6:40 am - 2:10 pmSJU-MDW
9h 30m2 stops
$289Southwest
Find Deal
Thu, Dec 11 - Sun, Dec 14
Delta Logo
6:00 am - 5:19 pmMDW-SJU
9h 19m1 stop
Delta Logo
6:15 am - 12:01 pmSJU-MDW
7h 46m1 stop
$321Delta
Find Deal
Mon, Jan 19 - Fri, Jan 23

Frontier flights from Chicago to San Juan Luis Munoz Marin Intl Airport

Our best Frontier deals on Chicago to San Juan Luis Munoz Marin Intl Airport flight tickets
Frontier
Nov 26
MDW3:47 pmChicago Midway
7h 25m
1 stop
SJU1:12 amSan Juan Luis Munoz Marin Intl
Dec 11
SJU7:00 amSan Juan Luis Munoz Marin Intl
9h 05m
1 stop
MDW2:05 pmChicago Midway
$200
Find similar
Frontier
Oct 29
ORD6:40 amChicago O'Hare Intl
10h 14m
1 stop
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Nov 13
SJU4:31 pmSan Juan Luis Munoz Marin Intl
9h 40m
1 stop
ORD12:11 amChicago O'Hare Intl
$201
Find similar
Frontier
Nov 10
ORD6:40 amChicago O'Hare Intl
9h 14m
1 stop
SJU5:54 pmSan Juan Luis Munoz Marin Intl
Nov 12
SJU1:59 amSan Juan Luis Munoz Marin Intl
7h 27m
1 stop
ORD7:26 amChicago O'Hare Intl
$208
Find similar

Spirit Airlines flights from Chicago to San Juan Luis Munoz Marin Intl Airport

Our best Spirit Airlines deals on Chicago to San Juan Luis Munoz Marin Intl Airport flight tickets
Spirit Airlines
Oct 29
ORD5:28 pmChicago O'Hare Intl
7h 16m
1 stop
SJU1:44 amSan Juan Luis Munoz Marin Intl
Nov 3
SJU3:41 pmSan Juan Luis Munoz Marin Intl
5h 10m
ORD6:51 pmChicago O'Hare Intl
$207
Find similar
Spirit Airlines
Oct 28
ORD5:28 pmChicago O'Hare Intl
7h 16m
1 stop
SJU1:44 amSan Juan Luis Munoz Marin Intl
Nov 3
SJU3:41 pmSan Juan Luis Munoz Marin Intl
5h 10m
ORD6:51 pmChicago O'Hare Intl
$212
Find similar
Spirit Airlines
Dec 2
ORD8:41 amChicago O'Hare Intl
4h 36m
SJU3:17 pmSan Juan Luis Munoz Marin Intl
Dec 7
SJU9:47 pmSan Juan Luis Munoz Marin Intl
5h 12m
ORD12:59 amChicago O'Hare Intl
$217
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to San Juan Luis Munoz Marin Intl Airport 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 14, 2025.
Use the filters below to find and compare flights from Chicago to San Juan Luis Munoz Marin Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 11/26

3:47 pm-1:12 am

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Thu 12/11

7:00 am-2:05 pm

1 stop9h 05m

$200

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

6:40 am-5:54 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Thu 11/13

4:31 pm-12:11 am

1 stop9h 40m

$201

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 10/29

5:28 pm-1:44 am

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Mon 11/3

3:41 pm-6:51 pm

Nonstop5h 10m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 11/10

6:40 am-5:54 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

Wed 11/12

1:59 am-7:26 am

1 stop7h 27m

$208

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/2

8:41 am-3:17 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Sun 12/7

9:47 pm-12:59 am

Nonstop5h 12m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 11/12

6:45 am-9:54 pm

1 stop13h 09m

San Juan Luis Munoz Marin Intl

Tue 11/18

9:30 am-8:52 pm

1 stop13h 22m

$260

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 11/21

8:20 am-6:10 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Sun 11/30

2:23 pm-10:31 pm

1 stop10h 08m

$262

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 12/3

10:40 am-10:05 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Wed 12/10

5:45 am-1:45 pm

2 stops10h 00m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 12/11

1:10 pm-10:05 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:40 am-2:10 pm

2 stops9h 30m

$289

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

6:00 am-5:19 pm

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-12:01 pm

1 stop7h 46m

$321

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago to San Juan Luis Munoz Marin Intl Airport

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 and San Juan Luis Munoz Marin Intl Airport?

What is the cheapest month to fly to San Juan Luis Munoz Marin Intl Airport?

If you aren’t able to travel to San Juan Luis Munoz Marin Intl Airport during the month of April, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $353.

What is the cheapest day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

On average, the least expensive day to fly to San Juan Luis Munoz Marin Intl Airport from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $393. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $443.

What is the cheapest time of day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

The cheapest time of day to fly to San Juan Luis Munoz Marin Intl Airport is in the evening when flights can be purchased for as low as $306. Flights in the morning are often more expensive with an average ticket price of $448.

What is the cheapest Chicago to San Juan Luis Munoz Marin Intl flight route?

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

How far in advance should I book a flight to San Juan Luis Munoz Marin Intl Airport?

You are more likely to see cheaper flights to San Juan Luis Munoz Marin Intl Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan Luis Munoz Marin Intl Airport for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan Luis Munoz Marin Intl Airport from Chicago for as low as $319 on momondo.

What cabin class options are available on Chicago to San Juan Luis Munoz Marin Intl flights?

There are 4 cabin classes available to choose from on Chicago to San Juan Luis Munoz Marin Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to San Juan Luis Munoz Marin Intl Airport flight prices changed over time?

As of October 2025, prices for Chicago to San Juan Luis Munoz Marin Intl Airport flights are approximately 114% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to San Juan Luis Munoz Marin Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San Juan Luis Munoz Marin Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to San Juan Luis Munoz Marin Intl Airport (CHI to SJU) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan Luis Munoz Marin Intl Airport

Best Price Found

$186

Fastest flight time

4h 35m

Direct flights

Every day
The best one-way flight to San Juan Luis Munoz Marin Intl Airport from Chicago in the past 72 hours is $186. The best round-trip flight deal from Chicago to San Juan Luis Munoz Marin Intl Airport found on momondo in the last 72 hours is $328.
The fastest flight from Chicago to San Juan Luis Munoz Marin Intl Airport takes 4h 35m
Direct flights go from Chicago to San Juan Luis Munoz Marin Intl Airport every day.
Search flight deals

  • How far is Chicago to San Juan Luis Munoz Marin Intl by plane?

    There are 2057.4 mi between Chicago and San Juan Luis Munoz Marin Intl. Typically, this will take 4h 36m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Prices for flights from Chicago to San Juan Luis Munoz Marin Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

  • How old do you have to be to fly from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan Luis Munoz Marin Intl Airport.

  • What documentation or ID do you need to fly to San Juan Luis Munoz Marin Intl Airport?

    The travel and health documents required for your trip to San Juan Luis Munoz Marin Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Juan Luis Munoz Marin Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to San Juan Luis Munoz Marin Intl Airport?

  • What is the most popular airline from Chicago to San Juan Luis Munoz Marin Intl Airport?

Best airlines flying from Chicago to San Juan Luis Munoz Marin Intl Airport

Compare and see reviews for airlines that fly from Chicago to San Juan Luis Munoz Marin Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.8
3,135 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,096 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,975 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,905 reviews
Search JetBlue flights
United AirlinesPriceFrom $271Free CancellationRating
7.4
8,976 reviews
Search United Airlines flights
American AirlinesPriceFrom $358Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

  • United Airlines Flights From Chicago to San Juan Luis Munoz Marin Intl Airport

    United Airlines flight deals from Chicago to San Juan Luis Munoz Marin Intl Airport start from $271 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $488 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to San Juan Luis Munoz Marin Intl Airport

    Across 11,042 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to San Juan Luis Munoz Marin Intl Airport about 7 times each week, with ticket deals ranging from $358 to $525. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near San Juan?

Book flights to San Juan if you plan to visit one of these locations
Carolina
Fajardo
Dorado
Luquillo
Caguas
Humacao
Rio Grande
Bayamón

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San Juan. Millions of users trust and use momondo every year so you are in good hands.

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 provides multiple filters to help you find the best flight to San Juan from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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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