Cheap flights from Chicago to San Juan

Flights overview

Useful information for finding cheap flights from Chicago to San Juan and booking your next trip
Cheapest round-trip flights $162
Frontier 1 stop 8 hr Fri, May 15 — Sat, May 23
The cheapest round-trip flight from Chicago to San Juan is currently $162
Cheapest one-way flight $88
Frontier 1 stop 9 hr Fri, May 8
The cheapest one-way flight from Chicago to San Juan is currently $88
Cheapest nonstop flights $174
Spirit Nonstop 5 hr Thu, May 14 — Sat, May 23
The cheapest nonstop round-trip flight from Chicago to San Juan is currently $174
Last-minute weekend getaway $256
Frontier 1 stop 17 hr Fri, Apr 24 — Sun, Apr 26
The cheapest last-minute weekend getaway from Chicago to San Juan is currently $256
Cheapest business class flights $424
Frontier 1 stop 9 hr Mon, May 4 — Wed, May 13
The cheapest business class round-trip flight from Chicago to San Juan is currently $424
Fastest flight 4 hr 35 min The fastest nonstop flight from Chicago to San Juan takes 4 hr 35 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to San Juan is typically January. The most expensive month to fly is typically August.
January
Cheapest
Typical prices: $165–260
August
Most expensive
Typical prices: $245–345

Popular airlines from Chicago to San Juan

  • Southwest
    Nonstop
    from $261
    Typical price: $360–570
    1 weekly nonstop flight
    MDW - SJU Every Sat
    1822 weekly connecting flights
    MDW, ORD - SJU Every day
  • United
    Nonstop
    from $232
    Typical price: $335–630
    14 weekly nonstop flights
    ORD - SJU Every day
    164 weekly connecting flights
    ORD - SJU Every day
  • American
    Nonstop
    from $257
    Typical price: $340–590
    7 weekly nonstop flights
    ORD - SJU Every day
    412 weekly connecting flights
    ORD - SJU Every day
  • Delta
    from $256
    Typical price: $420–1,050
    416 weekly connecting flights
    MDW, ORD - SJU Every day
  • Spirit
    Nonstop
    from $199
    Typical price: $235–450
    7 weekly nonstop flights
    ORD - SJU Every day
    25 weekly connecting flights
    ORD - SJU Every day
  • Frontier
    from $162
    Typical price: $235–475
    122 weekly connecting flights
    MDW, ORD - SJU Every day

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Popular airports near San Juan

  • Luis Munoz Marin International Airport (SJU)
    San Juan Puerto Rico 15 min 4 mi
  • Antonio Rivera Rodríguez Airport (VQS)
    Vieques Puerto Rico 2 hr 35 min 42 mi
  • Benjamín Rivera Noriega Airport (CPX)
    Culebra Puerto Rico 3 hr 3 min 50 mi
  • Aeropuerto Internacional Rafael Hernández (BQN)
    Aguadilla Puerto Rico 1 hr 50 min 70 mi

Frequently asked questions about flying from Chicago to San Juan

The cheapest flights from Chicago to San Juan are usually in January. Typical ticket prices in January range from $165 to $260.
The cheapest round-trip flight from Chicago to San Juan recently found on Google Flights was with Frontier from $162. The cheapest one-way flight was with Frontier from $88.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San Juan is $261, flying from Apr 27 to May 6.
  • The cheapest United flight from Chicago to San Juan is $232, flying from May 2 to May 8.
  • The cheapest American flight from Chicago to San Juan is $257, flying from Apr 26 to May 5.
  • The cheapest Delta flight from Chicago to San Juan is $256, flying from May 2 to May 8.
  • The cheapest Spirit flight from Chicago to San Juan is $199, flying from May 14 to May 20.
  • The cheapest Frontier flight from Chicago to San Juan is $162, flying from May 15 to May 23.
The cheapest round-trip flight from Chicago to San Juan starts at $162 from Fri, May 15 to Sat, May 23. The cheapest one-way flight starts at $88 and departs on Fri, May 8.
4 hr 35 min is the shortest flight time from Chicago to San Juan.
Peak travel is Dec–Jul. A tropical climate ensures warm temperatures and frequent rainfall year-round. The San Sebastián Street Festival (Jan) is a huge open-air party, with music, food and rum cocktails, plus local artists displaying their paintings around Old San Juan. Festival Casals (varies Feb/Mar) is a classical music festival staged in honor of cellist Pablo Casals, who founded the Puerto Rico Symphony Orchestra. Hurricane season is Jun–Nov.
It's easy to use Google Flights to find the cheapest days to fly from Chicago to San Juan.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Chicago to San Juan really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to San Juan.

In terms of nonstop flights, United is the most popular. United offers 14 nonstop flights and 164 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) .

In terms of flights, Southwest is the most popular. Southwest offers 1 nonstop flights and 1,822 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) .

Other popular airlines flying from Chicago to San Juan are:
  • American offers 7 nonstop flights and 412 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) .
  • Delta offers 416 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) .
  • Spirit offers 7 nonstop flights and 25 connecting flights per week. Spirit flies from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) .
  • Frontier offers 122 connecting flights per week. Frontier flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) .
The number of connecting flights refers to distinct flights with at least one stop between Chicago and San Juan.
The cheapest round-trip flight from Chicago to San Juan recently found on Google Flights was with Frontier from $162. The cheapest one-way flight was with Frontier from $88.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San Juan is $261, flying from Apr 27 to May 6.
  • The cheapest United flight from Chicago to San Juan is $232, flying from May 2 to May 8.
  • The cheapest American flight from Chicago to San Juan is $257, flying from Apr 26 to May 5.
  • The cheapest Delta flight from Chicago to San Juan is $256, flying from May 2 to May 8.
  • The cheapest Spirit flight from Chicago to San Juan is $199, flying from May 14 to May 20.
  • The cheapest Frontier flight from Chicago to San Juan is $162, flying from May 15 to May 23.
Southwest, United, American and Spirit fly direct from Chicago to San Juan.
  • There are 1 Southwest direct flights from Chicago to San Juan per week. Flights are available on Saturday.
  • There are 14 United direct flights from Chicago to San Juan per week. Flights are available every day.
  • There are 7 American direct flights from Chicago to San Juan per week. Flights are available every day.
  • There are 7 Spirit direct flights from Chicago to San Juan per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Chicago and San Juan at price $256 is offered by Frontier from Fri, Apr 24 to Sun, Apr 26.
Southwest, United, American and Spirit fly direct from Chicago to San Juan.
  • There are 1 Southwest direct flights from Chicago to San Juan per week. Flights are available on Saturday.
  • There are 14 United direct flights from Chicago to San Juan per week. Flights are available every day.
  • There are 7 American direct flights from Chicago to San Juan per week. Flights are available every day.
  • There are 7 Spirit direct flights from Chicago to San Juan per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Chicago to San Juan on a daily basis.
The cheapest direct (nonstop) round-trip flights between Chicago and San Juan start at $174 from Thu, May 14 to Sat, May 23 with Spirit.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to San Juan, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and San Juan start at $424 from Mon, May 4 to Wed, May 13 with Frontier.
The cheapest economy class round-trip flights between Chicago and San Juan start at $162 from Fri, May 15 to Sat, May 23.
To book business class trips from Chicago to San Juan, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and San Juan starts at $256 from Fri, Apr 24 to Sun, Apr 26 with Frontier.
The cheapest last-minute deal between Chicago and San Juan at price $256 is offered by Frontier from Fri, Apr 24 to Sun, Apr 26.
To find last-minute flight deals from Chicago to San Juan, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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