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Cheap flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to San Juan departing on 10/4. 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 O'Hare Intl Airport to San Juan

Cheap round-trip flights

Spirit Airlines Logo
11:55 am - 2:59 pmORD-SJU
26h 04m2 stops
Spirit Airlines Logo
9:48 am - 1:56 pmSJU-ORD
5h 08mnonstop
$207Spirit Airlines
Find Deal
sáb., oct. 11 - sáb., oct. 18
Spirit Airlines Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
Spirit Airlines Logo
3:19 pm - 9:33 pmSJU-ORD
7h 14m1 stop
$208Spirit Airlines
Find Deal
vie., oct. 24 - mar., oct. 28
Logo
11:57 am - 9:56 amORD-SJU
20h 59m2 stops
Logo
6:22 am - 5:13 pmSJU-ORD
11h 51m1 stop
$209
Find Deal
sáb., oct. 4 - mar., oct. 7
United Airlines Logo
2:20 pm - 8:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
8:10 am - 11:32 amSJU-ORD
5h 22mnonstop
$218United Airlines
Find Deal
mar., oct. 28 - lun., nov. 3
Logo
9:06 pm - 2:51 amORD-SJU
4h 45mnonstop
Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
$219
Find Deal
lun., oct. 27 - mar., nov. 4
United Airlines Logo
3:07 pm - 12:36 amORD-SJU
7h 29m1 stop
United Airlines Logo
8:30 am - 1:55 pmSJU-ORD
7h 25m1 stop
$222United Airlines
Find Deal
mar., nov. 11 - mié., nov. 12
American Airlines Logo
9:45 am - 11:59 pmORD-SJU
13h 14m1 stop
American Airlines Logo
3:00 pm - 7:20 pmSJU-ORD
5h 20mnonstop
$223American Airlines
Find Deal
mié., oct. 15 - mié., oct. 22
Frontier Logo
6:40 am - 5:54 pmORD-SJU
9h 14m1 stop
Frontier Logo
9:00 am - 12:45 pmSJU-ORD
29h 45m1 stop
$224Frontier
Find Deal
jue., nov. 13 - mar., nov. 18
Frontier Logo
6:40 am - 3:24 pmORD-SJU
7h 44m1 stop
Frontier Logo
1:59 am - 11:29 pmSJU-ORD
22h 30m2 stops
$225Frontier
Find Deal
mié., oct. 15 - vie., oct. 17
American Airlines Logo
9:45 am - 11:59 pmORD-SJU
13h 14m1 stop
American Airlines Logo
1:35 pm - 9:23 pmSJU-ORD
8h 48m1 stop
$227American Airlines
Find Deal
mié., oct. 15 - mié., oct. 22

Spirit Airlines flights from Chicago O'Hare Intl Airport to San Juan

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to San Juan flight tickets
Spirit Airlines
Oct 11
ORD11:55 amChicago O'Hare Intl
26h 04m
2 stops
SJU2:59 pmSan Juan Luis Munoz Marin Intl
Oct 18
SJU9:48 amSan Juan Luis Munoz Marin Intl
5h 08m
ORD1:56 pmChicago O'Hare Intl
$207
Find similar
Spirit Airlines
Oct 24
ORD9:06 pmChicago O'Hare Intl
4h 45m
SJU2:51 amSan Juan Luis Munoz Marin Intl
Oct 28
SJU3:19 pmSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
ORD9:33 pmChicago O'Hare Intl
$208
Find similar
Spirit Airlines
Sep 22
ORD6:30 amChicago O'Hare Intl
6h 41m
1 stop
SJU2:11 pmSan Juan Luis Munoz Marin Intl
Oct 2
SJU11:59 amSan Juan Luis Munoz Marin Intl
6h 40m
1 stop
ORD5:39 pmChicago O'Hare Intl
$210
Find similar

United Airlines flights from Chicago O'Hare Intl Airport to San Juan

Our best United Airlines deals on Chicago O'Hare Intl Airport to San Juan flight tickets
United Airlines
Oct 28
ORD2:20 pmChicago O'Hare Intl
4h 40m
SJU8:00 pmSan Juan Luis Munoz Marin Intl
Nov 3
SJU8:10 amSan Juan Luis Munoz Marin Intl
5h 22m
ORD11:32 amChicago O'Hare Intl
$218
Find similar
United Airlines
Nov 11
ORD3:07 pmChicago O'Hare Intl
7h 29m
1 stop
SJU12:36 amSan Juan Luis Munoz Marin Intl
Nov 12
SJU8:30 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
ORD1:55 pmChicago O'Hare Intl
$222
Find similar
United Airlines
Nov 11
ORD1:00 pmChicago O'Hare Intl
7h 22m
1 stop
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Nov 11
SJU2:05 amSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
ORD9:05 amChicago O'Hare Intl
$256
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl 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 septiembre 15, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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

sáb. 10/11

11:55 am-2:59 pm

2 stops26h 04m

San Juan Luis Munoz Marin Intl

sáb. 10/18

9:48 am-1:56 pm

Nonstop5h 08m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 10/24

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

mar. 10/28

3:19 pm-9:33 pm

1 stop7h 14m

$208

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 10/4

11:57 am-9:56 am

2 stops20h 59m

San Juan Luis Munoz Marin Intl

mar. 10/7

6:22 am-5:13 pm

1 stop11h 51m

$209

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 10/28

2:20 pm-8:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

lun. 11/3

8:10 am-11:32 am

Nonstop5h 22m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 10/27

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

mar. 11/4

9:00 am-12:45 pm

1 stop29h 45m

$219

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 11/11

3:07 pm-12:36 am

1 stop7h 29m

San Juan Luis Munoz Marin Intl

mié. 11/12

8:30 am-1:55 pm

1 stop7h 25m

$222

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 10/15

9:45 am-11:59 pm

1 stop13h 14m

San Juan Luis Munoz Marin Intl

mié. 10/22

3:00 pm-7:20 pm

Nonstop5h 20m

$223

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 11/13

6:40 am-5:54 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

mar. 11/18

9:00 am-12:45 pm

1 stop29h 45m

$224

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 10/15

6:40 am-3:24 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

vie. 10/17

1:59 am-11:29 pm

2 stops22h 30m

$225

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 10/15

9:45 am-11:59 pm

1 stop13h 14m

San Juan Luis Munoz Marin Intl

mié. 10/22

1:35 pm-9:23 pm

1 stop8h 48m

$227

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 O'Hare Intl 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 January, then November is your next best option. Flight prices from Chicago O'Hare Intl Airport to San Juan during November average around $349.

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

The cheapest day to depart from Chicago O'Hare Intl Airport to San Juan is on a Monday when prices can be found for as low as $396. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $447.

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 $305. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $447 on average. Flights to San Juan from Chicago O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago O'Hare Intl to San Juan flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $390 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 O'Hare Intl Airport for as low as $319 on momondo.

What cabin class options are available on Chicago O'Hare Intl to San Juan flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to San Juan

Fastest flight time

4h 35m

Direct flights

Every day

Airports in San Juan

1 airport
The fastest flight from Chicago O'Hare Intl Airport to San Juan takes 4h 35m
Direct flights go from Chicago O'Hare Intl Airport to San Juan every day.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

  • How far is Chicago O'Hare Intl to San Juan by plane?

    There are 2067.2 mi between Chicago O'Hare Intl and San Juan. By plane, this route typically takes 4h 38m.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to San Juan?

    Prices for flights from Chicago O'Hare Intl Airport to San Juan are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to San Juan?

  • How old do you have to be to fly from Chicago O'Hare Intl 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 O'Hare Intl Airport to San Juan.

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

    The travel and health documents you'll need for your trip to San Juan may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Juan. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago O'Hare Intl Airport to San Juan

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to San Juan with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $106Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $139Free CancellationRating
6.3
8,015 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,954 reviews
Search Delta flights
JetBluePriceFrom $271Free CancellationRating
7.2
2,912 reviews
Search JetBlue flights
United AirlinesPriceFrom $277Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
American AirlinesPriceFrom $350Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $389Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

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?

All flight searches from Chicago to San Juan on momondo can be filtered to show those which offer flexible booking policies.

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