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Cheap flights from Chicago to San Juan

Chicago
CHI
San Juan
SJU

Flight deals from Chicago to San Juan

Below you can see the best deals on flights Chicago — San Juan for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 24 August, from $88.

Top 10 cheap flights from Chicago to San Juan

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F9
$ 116

Chicago — San Juan

00:44—06:44
16 Aug 2026
5 h
Direct flight
F9
$ 116

Chicago — San Juan

00:44—06:44
15 Aug 2026
5 h
Direct flight
F9
$ 118

Chicago — San Juan

00:44—06:44
22 Aug 2026
5 h
Direct flight
F9
$ 118

Chicago — San Juan

00:44—06:44
24 Aug 2026
5 h
Direct flight
F9
$ 118

Chicago — San Juan

00:44—06:44
23 Aug 2026
5 h
Direct flight
F9
$ 123

Chicago — San Juan

00:44—06:44
19 Aug 2026
5 h
Direct flight
F9
$ 125

Chicago — San Juan

00:44—06:44
18 Aug 2026
5 h
Direct flight
F9
$ 125

Chicago — San Juan

00:44—06:44
17 Aug 2026
5 h
Direct flight
F9
$ 137

Chicago — San Juan

00:44—06:44
3 Aug 2026
5 h
Direct flight
F9
$ 137

Chicago — Fort Lauderdale

08:05—12:28
19 Aug 2026
3 h 23 m
Direct flight
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Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — San Juan flight

On this page, you can find and buy flight tickets for the route from Chicago to San Juan. The distance between the cities is 3,309 km, and the flight frequency reaches 22 flights per week, providing flexibility when choosing your departure time.

Flights are operated by United Airlines, American Airlines, and Frontier. Please note that ticket prices change constantly, so we recommend using the price dynamics chart and checking information on how to get to the airport of departure and transportation from the airport of arrival.

Flight ticket prices by day: Chicago — San Juan

Below is a calendar of the lowest flight ticket prices for Chicago — San Juan by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $88 in ,, and the most expensive are around $299 in r. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → San Juan, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$264highMay$218mediumSep$172low
Feb$259highJun$236highOct$179low
Mar$271highJul$230mediumNov$253high
Apr$241mediumAug$190lowDec$282high

Some values are estimated based on seasonality.

When to fly

The climate in San Juan remains warm year-round: the highest temperatures are recorded in August (up to 30.3°C), while September is considered the rainiest month. The lowest precipitation occurs during the winter-spring period, making it a comfortable time for a trip.

According to price statistics, the most budget-friendly month for flying is August, with ticket prices starting $85. Peak pricing is recorded in June, when offers start $310, as well as in December and January due to high demand during the holiday season.

November is a great time to book, with prices starting $113 and moderate rainfall. It is recommended to avoid flying in September and October if you want to minimize the risk of getting caught in the season of prolonged tropical rains.

Temperature · San Juan

Dry and wet days · San Juan

Wind speed and direction · San Juan

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How to get the best deal on a Chicago — San Juan ticket

  • Compare offers from low-cost carriers Frontier and Spirit with those from legacy airlines, keeping in mind that the former often charge extra for checked bags and carry-on luggage.
  • Use the low price calendar on this page to see the difference in cost for nearby dates, which can be quite significant for this route.
  • For flights over 3,000 km, it's often more cost-effective to book tickets for Tuesday or Wednesday, as weekend departures are traditionally more expensive due to high demand.
  • Monitor the price dynamics chart: if you see an offer starting $89, it's considered an excellent price for this route and a good reason to book.

Airlines

There are 5 airlines operating on the Chicago to San Juan route, with United Airlines and American Airlines being the primary carriers. A total of about 22 flights per week are operated, including both direct flights and options with convenient connections. You can view the detailed schedule and select a suitable flight from the list below by clicking on the carrier's card.

  • United AirlinesUA
    9x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → SJU9x/week
      Duration
      4h 55m
      Days
      MTWTFSS
    41.5%Open →
  • American AirlinesAA
    5x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → SJU5x/week
    21.5%Open →
  • Frontier AirlinesF9
    5x/week
    WebsiteFleet: 15329M pax/year
    • Direct flight ORD → SJU5x/week
      Duration
      4h 57m
      Days
      MTWTFSS
    21.5%Open →
  • Spirit AirlinesNK
    2x/week
    WebsiteFleet: 20544.1M pax/year
    • Direct flight ORD → SJU2x/week
    9.2%Open →
  • Alaska AirlinesAS
    1x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight ORD → SJU1x/week
    6.2%Open →

Cities and airports on the Chicago — San Juan route

Flights Chicago — San Juan depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Luis Muñoz Marín International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

San Juan

SJU
Puerto Rico
About the cityHow to get thereWeatherAll about the country Puerto Rico
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — San Juan flight

How long is the flight from Chicago to San Juan?

The estimated travel time for a direct flight is about 4 hours 15 minutes, given the distance of 3,309 km between the cities.

Which airlines serve this route?

Regular flights are operated by airlines such as United Airlines, American Airlines, Frontier, Spirit, and Alaska Airlines.

Are there direct flights between the cities?

Yes, direct non-stop flights are regularly operated from Chicago to San Juan, allowing you to reach your destination as quickly as possible.

Which airport does the flight arrive at?

Flights from Chicago arrive at the island's main international airport — Luis Muñoz Marín (SJU), located near downtown San Juan.

How much does the cheapest ticket cost?

Airfare is dynamic and depends on the departure date; current minimum fares for your dates are always displayed in the low price calendar on this page.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from San Juan

See all
OrlandoNew York CityFort LauderdalePhiladelphiaMiamiSanto DomingoPunta CanaAtlantaDallasCharlotte AmalieHoustonTampaWashington, D.C.BostonTortolaPanama CityHartfordMadridMedellínGustaviaCharlotteBogotaJacksonvilleSaint CroixMexico CityViequesDetroitSan AntonioRaleighDominicaTorontoClevelandVirgin GordaCulebraSan JoséSantiagoProvidenceMinneapolisThe ValleyMontreal

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