CHI - SJU

$130 Find Cheap Flights from Chicago to San Juan Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$255
Typical prices: $304-$542
Frontier
Tue 11/27Fri 11/30
ORD - SJU • 1 stop
Cheapest non-stop
$256
Typical prices: $324-$573
Frontier
Fri 1/5Mon 1/15
ORD - SJU • Non-stop
Nonstop flights
Every day
You can fly direct with United Airlines, American Airlines and others. Average duration is 4h 45m.
Direct flights
+1
Direct flights
+1
Top routes
MDW - SJU
Cheapest • 12% average savings
ORD - SJU
Most popular
Insights
Insights
Avoid delays
Frontier
Most punctual • 86% on-time
Night
Best time • Fewest delays
Insights
Insights
When to book
12 weeks
in advance
Our data shows that travelers who book at least 12 weeks in advance save around 6% compared to booking last minute.
Insights
Insights
When to travel
August
Cheapest • 18% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
New York John F Kennedy Intl (JFK)
Cheapest • Avg $283 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 6h 55m (one-way)
Insights
Insights
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We hope you love your trip to San Juan Luis Munoz Marin Intl Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to San Juan (CHI-SJU)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to San Juan

Mon, Mar 1 - Sat, Mar 6
Frontier Logo
3:24 pm - 4:35 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
23h 11m1 stop Philadelphia
Frontier Logo
6:00 am - 10:19 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
18h 19m1 stop Fort Lauderdale
$255Frontier
Fri, Nov 27 - Mon, Nov 30
Frontier Logo
2:52 pm - 3:00 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
22h 08m1 stop Baltimore/Washington
Frontier Logo
3:43 am - 12:59 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
23h 16m1 stop Orlando
$255Frontier
Tue, Dec 15 - Mon, Dec 21
Multiple Airlines Logo
7:00 am - 10:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
13h 44m1 stop Fort Lauderdale
Multiple Airlines Logo
6:00 am - 4:52 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
12h 52m1 stop Fort Lauderdale
$262Multiple Airlines
Sat, Jan 30 - Thu, Feb 4
Multiple Airlines Logo
7:00 am - 11:47 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
14h 47m1 stop Fort Lauderdale
Multiple Airlines Logo
3:16 am - 2:19 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
13h 03m1 stop Philadelphia
$264Multiple Airlines
Mon, Jan 18 - Thu, Jan 21
United Airlines Logo
8:52 am - 3:40 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 48mnonstop
United Airlines Logo
8:25 am - 11:49 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mnonstop
$267United Airlines
Sat, Jan 30 - Fri, Feb 5
United Airlines Logo
2:16 pm - 9:00 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mnonstop
United Airlines Logo
8:25 am - 11:49 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mnonstop
$267United Airlines
Mon, Jan 18 - Thu, Jan 21
American Airlines Logo
5:01 pm - 11:39 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 38mnonstop
American Airlines Logo
7:03 am - 10:35 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
$267American Airlines
Mon, Jan 18 - Thu, Jan 21
American Airlines Logo
5:01 pm - 11:39 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 38mnonstop
American Airlines Logo
7:03 am - 10:35 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
$267American Airlines
Tue, Jan 26 - Tue, Feb 2
JetBlue Logo
7:00 am - 4:23 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 23m1 stop Fort Lauderdale
JetBlue Logo
6:08 pm - 11:47 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 39m1 stop Fort Lauderdale
$275JetBlue
Sun, Jan 24 - Sat, Jan 30
JetBlue Logo
7:00 am - 4:23 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 23m1 stop Fort Lauderdale
JetBlue Logo
6:08 pm - 11:47 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 39m1 stop Fort Lauderdale
$287JetBlue
Booking Insights

Price, demand and travel trends for Chicago to San Juan Luis Munoz Marin Intl Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago to San Juan Luis Munoz Marin Intl Airport?

Round-trip flights from Chicago to San Juan Luis Munoz Marin Intl Airport typically range from $304 to $542. The lowest price found in the past 5 days was $255, on Frontier.

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

Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU) is the cheapest Chicago to San Juan Luis Munoz Marin Intl Airport route, averaging $384 round-trip. Other Chicago to San Juan Luis Munoz Marin Intl Airport routes average $463, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Chicago to San Juan Luis Munoz Marin Intl Airport?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Chicago to San Juan Luis Munoz Marin Intl Airport. It’s 8% cheaper than the average day, while Thursday is the most expensive, with prices 9% higher.

What’s the cheapest month to fly from Chicago to San Juan Luis Munoz Marin Intl Airport?

•August is the cheapest month to fly from Chicago to San Juan Luis Munoz Marin Intl Airport at $334 round-trip.
•December ($528) and November ($505) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 58% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago to San Juan Luis Munoz Marin Intl Airport the cheapest?

Flights from Chicago to San Juan Luis Munoz Marin Intl Airport are cheapest 12 weeks before departure. Booking in this window typically costs about 6% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals
Expert advice

Expert advice for your flight from Chicago to San Juan

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on SJU

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more

Key details for Chicago to San Juan Luis Munoz Marin Intl Airport flights

Low season

October

Cheapest flight

$130
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 41% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport

When to book flights from Chicago to San Juan

Are your dates flexible? Find out the best times to travel from Chicago to San Juan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to San Juan Luis Munoz Marin Intl Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

    These are the earliest and latest flight times currently scheduled from Chicago to San Juan Luis Munoz Marin Intl Airport:

    • Earliest: departs at 12:26 am and lands at 5:11 am
    • Latest: departs at 11:53 pm and lands at 4:38 am.

    The flight takes about 4h 45m.

  • What cabin classes can I book on flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Four cabin classes are available on flights from Chicago to San Juan Luis Munoz Marin Intl Airport:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How long is a flight from Chicago to San Juan Luis Munoz Marin Intl Airport?

    A nonstop flight from Chicago to San Juan Luis Munoz Marin Intl Airport takes about 4h 45m, covering 2,057 miles.

  • Do I need a passport to fly from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago to San Juan Luis Munoz Marin Intl Airport flight?

    Round-trip flights from Chicago to San Juan Luis Munoz Marin Intl Airport range from $304 to $542, with an average of $406 over the past 12 months. Anything below $304 counts as a good deal.

  • How expensive are last-minute Chicago to San Juan Luis Munoz Marin Intl Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) are 0% below the route average of $406. Booking late can sometimes save you money, but inventory is limited.

  • How much can I save by taking a layover when flying from Chicago to San Juan Luis Munoz Marin Intl Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $283 round-trip via New York John F Kennedy Intl (JFK), compared to $435 for nonstop.

  • How does on-time performance compare across airlines flying from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Frontier is slightly above the route average for timely arrivals, while United Airlines has a lower on-time arrival rate. On-time arrival rates on Chicago to San Juan Luis Munoz Marin Intl Airport flights are:

    • Frontier: 86% on time
    • United Airlines: 83% on time
    • American Airlines: 75% on time

    Overall, flights on this route are punctual 80% of the time on average.

  • What is the standard checked-bag allowance on flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Chicago to San Juan Luis Munoz Marin Intl Airport spread across the day?

    Morning is most often the busiest departure period on Chicago to San Juan Luis Munoz Marin Intl Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 25%, and night flights for 25%.

  • Which airlines offer Wi-Fi on Chicago to San Juan Luis Munoz Marin Intl Airport flights?

    Two airlines typically offer in-flight Wi-Fi on Chicago to San Juan Luis Munoz Marin Intl Airport flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Chicago to San Juan Luis Munoz Marin Intl Airport looking right now?

    One-way fares from Chicago to San Juan Luis Munoz Marin Intl Airport are currently lower than usual. Average one-way flight prices are about $136, which is 33% below the typical average for this route.

  • What car rental options are available at San Juan Luis Munoz Marin Intl Airport (SJU)?

    San Juan Luis Munoz Marin Intl Airport (SJU) hosts 5 major car rental companies, with daily rates averaging $41 for economy cars. Top options include:

    • Routes Car & Truck Rentals
    • U-Save
    • Hertz
    • Payless
    • Europcar

  • Which airports can I use when flying from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Flights from Chicago to San Juan Luis Munoz Marin Intl Airport may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at San Juan Luis Munoz Marin Intl (SJU).

  • What time of day has the fewest delays on flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Night flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Chicago to San Juan Luis Munoz Marin Intl Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to San Juan Luis Munoz Marin Intl Airport route, 22% of flights were delayed in the past 3 months, with delays averaging 2h 31m.

  • Which airports do connecting flights from Chicago to San Juan Luis Munoz Marin Intl Airport pass through?

    One-stop flights from Chicago to San Juan Luis Munoz Marin Intl Airport most commonly connect through:

    • New York John F Kennedy Intl (JFK) - 39% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 18% of one-stop connections
    • Orlando (MCO) - 12% of one-stop connections
    • Fort Lauderdale (FLL) - 11% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Yes. Flexible dates can save you up to 16% on flights from Chicago to San Juan Luis Munoz Marin Intl Airport. Tuesday is the cheapest departure day at $375 round-trip on average, while Thursday is the most expensive at $445, a difference of $70.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago to San Juan Luis Munoz Marin Intl Airport?

    4 airlines currently operate flights between Chicago and San Juan Luis Munoz Marin Intl Airport, you can choose from:

    • United Airlines
    • American Airlines
    • Frontier
    • Southwest

  • How much time can I save by choosing a different layover airport from Chicago to San Juan Luis Munoz Marin Intl Airport?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 6h 55m, compared with 7h 13m via Baltimore/Washington (BWI) and 7h 25m via Lambert-St Louis (STL).

  • What is the time difference between Chicago and San Juan Luis Munoz Marin Intl Airport?

    San Juan Luis Munoz Marin Intl Airport is 2 hours ahead of Chicago (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in San Juan Luis Munoz Marin Intl Airport?

    Some of the most popular sights in San Juan Luis Munoz Marin Intl Airport are Viejo San Juan, Puerto Rico Convention Center and Condado Beach. These are among the most viewed places in San Juan Luis Munoz Marin Intl Airport on KAYAK.

  • Which airlines offer free seat selection on Chicago to San Juan Luis Munoz Marin Intl Airport flights?

    The following airlines offer free seat selection on this route:

    • United Airlines
    • American Airlines
    • Frontier
    • Southwest

    Availability depends on fare class.

  • Which airlines offer extra legroom on Chicago to San Juan Luis Munoz Marin Intl Airport flights?

    United Airlines and American Airlines offer extra legroom on this route. Availability can vary by aircraft type and fare class.

  • Which airlines include bags at no extra cost on Chicago to San Juan Luis Munoz Marin Intl Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Frontier: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago to San Juan Luis Munoz Marin Intl Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Thursday. On this route, Tuesday flights average $375, about $70 less than Thursday fares (16% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 12 weeks before you fly. On this route, that window historically saves about 6% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to San Juan Luis Munoz Marin Intl Airport trip for August. Fares historically average $334 round-trip in that month - typically $194 less than the most expensive month, which is December (based on the last 12 months).
  • For the best chance of arriving on time, fly with Frontier. Over the past three months, 86% of Frontier flights from Chicago to San Juan Luis Munoz Marin Intl Airport arrived on time, slightly above the route average of 78%. When flights on this route arrive late, they're delayed by an average of 2h 31m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through New York John F Kennedy Intl Airport (JFK) can be cheaper than flying direct. The cheapest layover option averages $283 round-trip on this route - about $152 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to San Juan Luis Munoz Marin Intl Airport.

    • Coral by The Sea Hotel
    • San Juan Airport Hotel
    • Hampton Inn & Suites by Hilton San Juan

Prefer to fly direct from Chicago to San Juan Airport?

 
Find which airlines fly direct from Chicago to San Juan Luis Munoz Marin Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to San Juan Luis Munoz Marin Intl

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

See more direct flights

More options for your flight from Chicago to San Juan

Complete your trip to San Juan with a hotel stay or car rental

Car rentals in San Juan
Hotels in San Juan
Vacations in San Juan