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Cheap flights from Chicago to San Juan from $55

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 3/4. 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 to San Juan

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to San Juan that have been recently found on momondo from popular airlines, departing in the coming months.
8:44 pm - 2:54 amORD-SJU
28h 10m1 stop
9:30 pm - 9:27 amSJU-ORD
13h 57m1 stop
$118Frontier
Find Deal
Sat, Feb 15 - Tue, Feb 18
5:00 am - 12:27 amORD-SJU
17h 27m1 stop
7:00 am - 10:36 amSJU-ORD
5h 36mnonstop
$122Spirit Airlines
Find Deal
Tue, Mar 4 - Sat, Mar 8
4:58 pm - 2:54 amORD-SJU
7h 56m1 stop
8:55 am - 4:31 pmSJU-ORD
9h 36m1 stop
$125Frontier
Find Deal
Mon, Feb 24 - Tue, Feb 25
2:29 pm - 12:27 amORD-SJU
7h 58m1 stop
6:00 am - 4:38 pmSJU-ORD
11h 38m1 stop
Tue, Mar 4 - Tue, Mar 11
2:29 pm - 12:27 amORD-SJU
7h 58m1 stop
6:45 pm - 11:56 pmSJU-ORD
7h 11m1 stop
$129Spirit Airlines
Find Deal
Tue, Mar 4 - Wed, Mar 5
8:44 pm - 9:35 amORD-SJU
10h 51m1 stop
9:30 pm - 7:09 amSJU-ORD
11h 39m1 stop
$130Frontier
Find Deal
Sat, Feb 15 - Wed, Feb 19
9:45 am - 9:06 pmORD-SJU
9h 21m1 stop
6:17 pm - 11:49 pmSJU-ORD
7h 32m1 stop
$235Delta
Find Deal
Sun, Mar 2 - Wed, Mar 5
6:00 am - 2:36 pmMDW-SJU
6h 36m1 stop
4:15 pm - 10:20 pmSJU-MDW
8h 05m1 stop
$235Delta
Find Deal
Sun, Feb 9 - Wed, Feb 12
1:20 pm - 12:50 amMDW-SJU
9h 30m2 stops
6:05 am - 2:05 pmSJU-MDW
10h 00m1 stop
$355Southwest
Find Deal
Mon, Feb 24 - Thu, Feb 27
11:00 am - 12:30 amMDW-SJU
11h 30m1 stop
6:50 am - 1:55 pmSJU-MDW
8h 05m2 stops
$371Southwest
Find Deal
Thu, Mar 6 - Thu, Mar 13

Delta flights from Chicago to San Juan

Our best Delta deals on Chicago to San Juan flight tickets
Delta
Mar 2
ORD9:45 amChicago O'Hare Intl
9h 21m
1 stop
SJU9:06 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU6:17 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
ORD11:49 pmChicago O'Hare Intl
Delta
Mar 2
ORD9:45 amChicago O'Hare Intl
9h 21m
1 stop
SJU9:06 pmSan Juan Luis Munoz Marin Intl
Mar 11
SJU5:16 pmSan Juan Luis Munoz Marin Intl
7h 40m
1 stop
ORD11:56 pmChicago O'Hare Intl
Delta
Mar 12
MDW12:51 pmChicago Midway
9h 16m
1 stop
SJU11:07 pmSan Juan Luis Munoz Marin Intl
Mar 18
SJU2:42 pmSan Juan Luis Munoz Marin Intl
8h 41m
1 stop
MDW10:23 pmChicago Midway

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets
Frontier
Feb 15
ORD8:44 pmChicago O'Hare Intl
28h 10m
1 stop
SJU2:54 amSan Juan Luis Munoz Marin Intl
Feb 18
SJU9:30 pmSan Juan Luis Munoz Marin Intl
13h 57m
1 stop
ORD9:27 amChicago O'Hare Intl
Frontier
Feb 24
ORD4:58 pmChicago O'Hare Intl
7h 56m
1 stop
SJU2:54 amSan Juan Luis Munoz Marin Intl
Feb 25
SJU8:55 amSan Juan Luis Munoz Marin Intl
9h 36m
1 stop
ORD4:31 pmChicago O'Hare Intl
Frontier
Feb 15
ORD8:44 pmChicago O'Hare Intl
10h 51m
1 stop
SJU9:35 amSan Juan Luis Munoz Marin Intl
Feb 19
SJU9:30 pmSan Juan Luis Munoz Marin Intl
11h 39m
1 stop
ORD7:09 amChicago O'Hare Intl

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 August, then September is your next best option. Flight prices from Chicago to San Juan during September average around $306.

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 Tuesday when prices can be found for as low as $367. The most expensive day to fly to San Juan is Sunday, with ticket prices averaging around $458.

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 at noon when flights can be purchased for as low as $359. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are $517 on average. Flights to San Juan from Chicago in the evening 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 7 weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $367 when searching 7 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 $298 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

Best Price Found

$55

Fastest flight time

4h 31m

Direct flights

Every day

Airports in San Juan

1 airport
The best one-way flight to San Juan from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $118.
The fastest flight from Chicago to San Juan takes 4h 31m
Direct flights go from Chicago to San Juan every day.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)

  • 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 $124Free CancellationRating
6.0
3,427 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $156Free CancellationRating
6.3
8,086 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $260Free CancellationRating
7.4
8,913 reviews
Search United Airlines flights
JetBluePriceFrom $274Free CancellationRating
7.4
3,156 reviews
Search JetBlue flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $324Free CancellationRating
8.0
8,456 reviews
Search Delta flights
SouthwestPriceFrom $332Free CancellationRating
8.1
4,587 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