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Cheap flights from Chicago to San Juan from $107

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 1/8. 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 to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:50 am - 4:21 pm
ORD
-
SJU
8h 31m1 stop
Multiple Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$192Multiple Airlines
Sat, Jan 10 - Tue, Jan 13
Multiple Airlines Logo
6:57 pm - 3:06 pm
ORD
-
SJU
18h 09m1 stop
Multiple Airlines Logo
8:53 pm - 9:39 am
SJU
-
ORD
14h 46m1 stop
$193Multiple Airlines
Sun, Feb 8 - Sat, Feb 21
Spirit Airlines Logo
9:23 am - 6:58 pm
ORD
-
SJU
7h 35m1 stop
Spirit Airlines Logo
11:52 am - 6:16 pm
SJU
-
ORD
8h 24m1 stop
$194Spirit Airlines
Sun, Jan 18 - Thu, Jan 22
Multiple Airlines Logo
9:18 am - 6:58 pm
ORD
-
SJU
7h 40m1 stop
Multiple Airlines Logo
3:53 am - 3:52 pm
SJU
-
ORD
13h 59m1 stop
$195Multiple Airlines
Sat, Feb 28 - Tue, Mar 3
Frontier Logo
8:00 am - 2:53 am
MDW
-
SJU
16h 53m1 stop
Frontier Logo
6:30 am - 6:13 pm
SJU
-
MDW
12h 43m1 stop
$196Frontier
Sat, Feb 28 - Wed, Mar 11
JetBlue Logo
7:45 am - 6:07 pm
ORD
-
SJU
8h 22m1 stop
JetBlue Logo
10:25 am - 7:36 pm
SJU
-
ORD
11h 11m1 stop
$196JetBlue
Tue, Jan 20 - Sat, Jan 24
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
$197Spirit Airlines
Tue, Feb 17 - Thu, Feb 26
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
3:53 am - 3:52 pm
SJU
-
ORD
13h 59m1 stop
$198Multiple Airlines
Tue, Feb 17 - Mon, Feb 23
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m1 stop
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
$199Frontier
Mon, Mar 2 - Mon, Mar 9
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
$199Spirit Airlines
Sun, Jan 25 - Wed, Feb 4

JetBlue flights from Chicago to San Juan

Our best JetBlue deals on Chicago to San Juan flight tickets
JetBlue
Jan 20
ORD7:45 amChicago O'Hare Intl
8h 22m
1 stop
SJU6:07 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU1:20 pmSan Juan Luis Munoz Marin Intl
8h 16m
1 stop
ORD7:36 pmChicago O'Hare Intl
$196
Find similar
JetBlue
Jan 6
ORD10:55 amChicago O'Hare Intl
11h 19m
1 stop
SJU12:14 amSan Juan Luis Munoz Marin Intl
Jan 13
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
$202
Find similar
JetBlue
Jan 23
ORD7:45 amChicago O'Hare Intl
8h 20m
1 stop
SJU6:05 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU1:20 pmSan Juan Luis Munoz Marin Intl
8h 16m
1 stop
ORD7:36 pmChicago O'Hare Intl
$205
Find similar

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Mar 2
MDW9:22 pmChicago Midway
10h 32m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
Mar 9
SJU3:22 pmSan Juan Luis Munoz Marin Intl
7h 57m
1 stop
MDW10:19 pmChicago Midway
$199
Find similar
Frontier
Jan 8
MDW6:10 amChicago Midway
7h 09m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
Jan 14
SJU4:35 pmSan Juan Luis Munoz Marin Intl
7h 44m
1 stop
MDW10:19 pmChicago Midway
$200
Find similar
Frontier
Feb 19
ORD1:54 pmChicago O'Hare Intl
10h 31m
1 stop
SJU2:25 amSan Juan Luis Munoz Marin Intl
Feb 22
SJU2:54 amSan Juan Luis Munoz Marin Intl
8h 17m
1 stop
ORD9:11 amChicago O'Hare Intl
$201
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 December 28, 2025.
Use the filters below to find and compare flights from Chicago to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/10

5:50 am-4:21 pm

1 stop8h 31m

San Juan Luis Munoz Marin Intl

Tue 1/13

1:22 pm-4:37 pm

Nonstop5h 15m

$192

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/8

6:57 pm-3:06 pm

1 stop18h 09m

San Juan Luis Munoz Marin Intl

Sat 2/21

8:53 pm-9:39 am

1 stop14h 46m

$193

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

9:23 am-6:58 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Thu 1/22

11:52 am-6:16 pm

1 stop8h 24m

$194

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/28

9:18 am-6:58 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 3/3

3:53 am-3:52 pm

1 stop13h 59m

$195

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

8:00 am-2:53 am

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:30 am-6:13 pm

1 stop12h 43m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/20

7:45 am-6:07 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:25 am-7:36 pm

1 stop11h 11m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/17

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Thu 2/26

12:32 pm-3:48 pm

Nonstop5h 16m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 2/17

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Mon 2/23

3:53 am-3:52 pm

1 stop13h 59m

$198

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

Mon 3/9

3:22 pm-10:19 pm

1 stop7h 57m

$199

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/25

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:22 pm-4:37 pm

Nonstop5h 15m

$199

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 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 and San Juan?

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in April, then January is your next best option. Flight prices from Chicago to San Juan during January average around $343.

What is the cheapest day to depart on your flight to San Juan?

The cheapest day to depart from Chicago to San Juan is on a Monday when prices can be found for as low as $386. The most expensive day to fly to San Juan is Friday, 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 $324. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $442 on average. Flights to San Juan from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to San Juan flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $394 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 for as low as $336 on momondo.

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

There are 4 cabin classes available to choose from on Chicago 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 to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan

Fastest flight time

4h 31m

Direct flights

Every day

Airports in San Juan

2 airports
The fastest flight from Chicago to San Juan takes 4h 31m
Direct flights go from Chicago to San Juan every day.
There are 2 airports in San Juan. From Chicago there are direct flights to San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

  • How far is Chicago to San Juan by plane?

    San Juan is 2052.1 mi away from Chicago. 4h 31m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to San Juan?

    Prices for flights from Chicago to San Juan refresh daily.

  • How many operators does momondo search for flights from Chicago to San Juan?

  • How old do you have to be to fly from Chicago 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 to San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The travel and health documents required for your trip to San Juan 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. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago to San Juan

Compare and see reviews for airlines that fly from Chicago to San Juan with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $115Free CancellationRating
5.7
3,064 reviews
Search Frontier flights
JetBluePriceFrom $136Free CancellationRating
7.2
2,901 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,212 reviews
Search Spirit Airlines flights
DeltaPriceFrom $190Free CancellationRating
7.9
8,016 reviews
Search Delta flights
United AirlinesPriceFrom $282Free CancellationRating
7.4
9,114 reviews
Search United Airlines flights
American AirlinesPriceFrom $362Free CancellationRating
7.2
11,071 reviews
Search American Airlines flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,250 reviews
Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Juan from Chicago.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

Yes. All flights to San Juan from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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?

Yes momondo offers price alerts on flights to San Juan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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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