Cheap flights from San Juan to Chicago

Luis Muñoz Marín
SJU
Chicago FSS
CHI

Flight deals from San Juan to Chicago

Below you can see the best deals on flights San Juan — Chicago 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 3 September, from $70.

Top 10 cheap flights from San Juan to Chicago

F9
$ 70

San Juan — Chicago

19:14—23:27
5 Sep 2026
5 h 13 m
Direct flight
F9
$ 70

San Juan — Chicago

19:14—23:27
3 Sep 2026
5 h 13 m
Direct flight
F9
F9
$ 89

San Juan — Chicago

08:45—14:45
9 Sep 2026
31 h
1 stop
F9
$ 90

San Juan — Chicago

19:14—23:27
27 Aug 2026
5 h 13 m
Direct flight
F9
$ 90

San Juan — Chicago

19:14—23:27
1 Sep 2026
5 h 13 m
Direct flight
F9
$ 92

San Juan — Chicago

19:14—23:27
29 Aug 2026
5 h 13 m
Direct flight
F9
$ 92

San Juan — Chicago

19:14—23:27
2 Sep 2026
5 h 13 m
Direct flight
F9
$ 103

San Juan — Chicago

19:14—23:27
25 Aug 2026
5 h 13 m
Direct flight
F9
F9
$ 112

San Juan — Chicago

03:08—15:20
12 Sep 2026
13 h 12 m
1 stop
F9
F9
$ 113

San Juan — Chicago

03:08—15:20
9 Sep 2026
13 h 12 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the San Juan — Chicago flight

Looking for cheap flights from San Juan to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your San Juan — Chicago ticket online at the best price.

The route has direct flights — around 70 flights per week, flights are operated by United Airlines, Spirit Airlines, American Airlines, Frontier Airlines and 1 more airline, a nonstop flight takes about 5 h 5 min, the distance between the cities is around 3,309 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $70Min. price
SeptemberCheapest
MarchPeak season
YesDirect flights
3,309 kmDistance
5 h 5 minTravel time
5Airlines
70 / wkFlights

Flight schedule from San Juan to Chicago

The table shows direct flights from San Juan to Chicago on the selected date. The flight takes approximately 5 h 5 min. Regular flights are operated by United Airlines, Spirit Airlines, American Airlines and Frontier Airlines. Departures from Luis Muñoz Marín International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 14 Aug 2026

Flight ticket prices by day: San Juan — Chicago

Below is a calendar of the lowest flight ticket prices for San Juan — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $70 in September, and the most expensive are around $231 in March. 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

Average one-way fares from San Juan to Chicago by month. Tickets are usually cheapest in September (around $142) and priciest in December (about $222) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$195highMay$151lowSep$142low
Feb$195highJun$195highOct$147low
Mar$204highJul$204highNov$169medium
Apr$160mediumAug$178mediumDec$222high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in March. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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

  • Book ahead: fares for San Juan — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the San Juan — Chicago route are operated by 5 airlines; United Airlines runs the most flights (around 36% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    8x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight SJU → ORD8x/week
      Duration
      5h 9m
      Days
      MTWTFSS
    35.7%Open →
  • Spirit AirlinesNK
    5x/week
    WebsiteFleet: 20544.1M pax/year
    • Direct flight SJU → ORD5x/week
      Duration
      5h 7m
      Days
      MTWTFSS
    21.4%Open →
  • American AirlinesAA
    5x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight SJU → ORD5x/week
      Duration
      5h 6m
      Days
      MTWTFSS
    20.0%Open →
  • Frontier AirlinesF9
    5x/week
    WebsiteFleet: 15329M pax/year
    • Direct flight SJU → ORD5x/week
      Duration
      5h 13m
      Days
      MTWTFSS
    20.0%Open →
  • Alaska AirlinesAS
    1x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight SJU → ORD1x/week
      Duration
      1h
      Days
      MTWTFSS
    2.9%Open →

Cities and airports on the San Juan — Chicago route

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

Departure

San Juan

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

Chicago

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

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Frequently asked questions about the San Juan — Chicago flight

How long is the flight from San Juan to Chicago?

A nonstop San Juan — Chicago flight takes about 5 h 5 min — the distance between the cities is around 3,309 km.

How far is it from San Juan to Chicago?

The distance from San Juan to Chicago is about 3,309 km, which a nonstop flight covers in around 5 h 5 min.

Are there direct flights from San Juan to Chicago?

Yes, there are nonstop flights San Juan — Chicago — around 70 flights per week.

Which airlines fly from San Juan to Chicago?

Airlines operating San Juan — Chicago include United Airlines, Spirit Airlines, American Airlines, Frontier Airlines, Alaska Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do San Juan — Chicago flights use?

Flights from San Juan depart from Luis Muñoz Marín International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from San Juan to Chicago?

The price of a San Juan — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in March. Tickets typically cost between $70 and $231. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights San Juan — Chicago?

Flights San Juan — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from San Juan to Chicago?

To catch a low fare San Juan — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from San Juan

See all
OrlandoNew York CityFort LauderdalePhiladelphiaMiamiSanto DomingoPunta CanaAtlantaDallasCharlotte AmalieHoustonTampaWashington, D.C.BostonTortolaPanama CityHartfordMadridMedellínGustaviaCharlotteBogotaJacksonvilleSaint CroixViequesMexico CitySan AntonioDetroitRaleighTorontoDominicaClevelandVirgin GordaSan JoséCulebraSantiagoProvidenceMinneapolisMontrealThe Valley

Where else you can fly from Chicago

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

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