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Cheap flights from Chicago to San Juan from $76

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 5/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to San Juan

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to San Juan.
Spirit Airlines Logo
11:30 am - 5:16 pmORD-SJU
4h 46mnonstop
Spirit Airlines Logo
6:09 am - 10:25 amSJU-ORD
5h 16mnonstop
$189Spirit Airlines
Find Deal
Fri, May 9 - Sun, May 11
Spirit Airlines Logo
4:35 pm - 12:54 amORD-SJU
7h 19m1 stop
Spirit Airlines Logo
6:09 am - 10:25 amSJU-ORD
5h 16mnonstop
$202Spirit Airlines
Find Deal
Sat, May 10 - Fri, May 16
Spirit Airlines Logo
11:30 am - 5:16 pmORD-SJU
4h 46mnonstop
Spirit Airlines Logo
6:09 am - 10:25 amSJU-ORD
5h 16mnonstop
$203Spirit Airlines
Find Deal
Sun, May 11 - Thu, May 15
Spirit Airlines Logo
4:35 pm - 12:54 amORD-SJU
7h 19m1 stop
Spirit Airlines Logo
6:09 am - 10:25 amSJU-ORD
5h 16mnonstop
$205Spirit Airlines
Find Deal
Sat, May 10 - Thu, May 15
Frontier Logo
8:30 am - 7:44 pmMDW-SJU
10h 14m1 stop
Frontier Logo
3:56 am - 12:24 pmSJU-MDW
9h 28m1 stop
$293Frontier
Find Deal
Thu, May 8 - Thu, May 8
Frontier Logo
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
$294Frontier
Find Deal
Mon, May 5 - Thu, May 8
American Airlines Logo
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
American Airlines Logo
3:05 pm - 7:25 pmSJU-ORD
5h 20mnonstop
$372American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
United Airlines Logo
8:49 am - 2:44 pmORD-SJU
4h 55mnonstop
United Airlines Logo
1:05 am - 8:38 amSJU-ORD
8h 33m1 stop
$377United Airlines
Find Deal
Wed, May 28 - Fri, May 30
Southwest Logo
2:20 pm - 10:10 pmMDW-SJU
6h 50m1 stop
Southwest Logo
5:00 pm - 11:45 pmSJU-MDW
7h 45m1 stop
$381Southwest
Find Deal
Tue, Jun 24 - Wed, Jul 2
Southwest Logo
8:40 am - 2:25 pmMDW-SJU
4h 45mnonstop
Southwest Logo
3:45 pm - 10:20 pmSJU-MDW
7h 35m1 stop
$397Southwest
Find Deal
Sun, Jul 13 - Wed, Jul 16

Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets
Spirit Airlines
May 9
ORD11:30 amChicago O'Hare Intl
4h 46m
SJU5:16 pmSan Juan Luis Munoz Marin Intl
May 11
SJU6:09 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD10:25 amChicago O'Hare Intl
Spirit Airlines
May 10
ORD4:35 pmChicago O'Hare Intl
7h 19m
1 stop
SJU12:54 amSan Juan Luis Munoz Marin Intl
May 16
SJU6:09 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD10:25 amChicago O'Hare Intl
Spirit Airlines
May 11
ORD11:30 amChicago O'Hare Intl
4h 46m
SJU5:16 pmSan Juan Luis Munoz Marin Intl
May 15
SJU6:09 amSan Juan Luis Munoz Marin Intl
5h 16m
ORD10:25 amChicago O'Hare Intl

JetBlue flights from Chicago to San Juan

Our best JetBlue deals on Chicago to San Juan flight tickets
JetBlue
May 28
ORD6:15 amChicago O'Hare Intl
9h 00m
1 stop
SJU4:15 pmSan Juan Luis Munoz Marin Intl
Jun 3
SJU8:00 amSan Juan Luis Munoz Marin Intl
11h 36m
1 stop
ORD6:36 pmChicago O'Hare Intl
JetBlue
Jun 21
ORD11:13 amChicago O'Hare Intl
11h 37m
1 stop
SJU11:50 pmSan Juan Luis Munoz Marin Intl
Jul 12
SJU3:25 amSan Juan Luis Munoz Marin Intl
8h 22m
1 stop
ORD10:47 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 $309.

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 $365. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $421.

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 $298. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $409 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 5 weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $365 when searching 5 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 $291 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

$76

Fastest flight time

4h 40m

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 $76. The best round-trip flight deal from Chicago to San Juan found on momondo in the last 72 hours is $189.
The fastest flight from Chicago to San Juan takes 4h 40m
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 40m 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
5.9
3,283 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $142Free CancellationRating
6.3
7,942 reviews
Search Spirit Airlines flights
DeltaPriceFrom $222Free CancellationRating
8.0
7,920 reviews
Search Delta flights
United AirlinesPriceFrom $274Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
JetBluePriceFrom $293Free CancellationRating
7.3
2,924 reviews
Search JetBlue flights
American AirlinesPriceFrom $331Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $343Free CancellationRating
8.0
4,286 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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1 adult
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Wed 4/30
Wed 5/7

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