Cheap flights from San Juan to Chicago

Flights overview

Useful information for finding cheap flights from San Juan to Chicago and booking your next trip
Cheapest round-trip flights $199
Spirit Nonstop 6 hr Thu, Apr 16 — Wed, Apr 22
The cheapest round-trip flight from San Juan to Chicago is currently $199
Cheapest one-way flight $80
Spirit 1 stop 9 hr Tue, Apr 14
The cheapest one-way flight from San Juan to Chicago is currently $80
Cheapest nonstop flights $199
Spirit Nonstop 6 hr Thu, Apr 9 — Wed, Apr 15
The cheapest nonstop round-trip flight from San Juan to Chicago is currently $199
Last-minute weekend getaway $201
Spirit Nonstop 6 hr Thu, Feb 5 — Mon, Feb 9
The cheapest last-minute weekend getaway from San Juan to Chicago is currently $201
Cheapest business class flights $450
Frontier 1 stop 13 hr Thu, Apr 30 — Wed, May 6
The cheapest business class round-trip flight from San Juan to Chicago is currently $450
Fastest flight 5 hr 10 min The fastest nonstop flight from San Juan to Chicago takes 5 hr 10 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 San Juan to Chicago is typically February. The most expensive month to fly is typically June.
February
Cheapest
Typical prices: $165–270
June
Most expensive
Typical prices: $240–335

Popular airlines from San Juan to Chicago

  • Southwest
    Nonstop
    from $364
    Typical price: $385–580
    1 weekly nonstop flight
    SJU - MDW Every Sat
    1590 weekly connecting flights
    SJU - MDW, ORD Every day
  • American
    Nonstop
    from $237
    Typical price: $365–570
    14 weekly nonstop flights
    SJU - ORD Every day
    433 weekly connecting flights
    SJU - ORD Every day
  • United
    Nonstop
    from $237
    Typical price: $335–560
    13 weekly nonstop flights
    SJU - ORD Every day
    207 weekly connecting flights
    SJU - ORD Every day
  • Delta
    from $364
    Typical price: $420–910
    417 weekly connecting flights
    SJU - MDW, ORD Every day
  • Spirit
    Nonstop
    from $199
    Typical price: $230–410
    7 weekly nonstop flights
    SJU - ORD Every day
    25 weekly connecting flights
    SJU - ORD Every day
  • Frontier
    from $222
    Typical price: $250–495
    67 weekly connecting flights
    SJU - MDW, ORD Every day

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 37 min 42 mi
  • Benjamín Rivera Noriega Airport (CPX)
    Culebra Puerto Rico 3 hr 4 min 50 mi
  • Aeropuerto Eugenio María de Hostos (MAZ)
    Mayagüez Puerto Rico 2 hr 17 min 72 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 27 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 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from San Juan to Chicago

The cheapest flights from San Juan to Chicago are usually in February. Typical ticket prices in February range from $165 to $270.
The cheapest round-trip flight from San Juan to Chicago recently found on Google Flights was with Spirit from $199. The cheapest one-way flight was with Spirit from $80.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Juan to Chicago is $364, flying from Apr 30 to May 6.
  • The cheapest American flight from San Juan to Chicago is $237, flying from Apr 23 to May 2.
  • The cheapest United flight from San Juan to Chicago is $237, flying from Apr 30 to May 6.
  • The cheapest Delta flight from San Juan to Chicago is $364, flying from Apr 30 to May 6.
  • The cheapest Spirit flight from San Juan to Chicago is $199, flying from Apr 9 to Apr 15.
  • The cheapest Frontier flight from San Juan to Chicago is $222, flying from Apr 30 to May 6.
The cheapest round-trip flight from San Juan to Chicago starts at $199 from Thu, Apr 16 to Wed, Apr 22. The cheapest one-way flight starts at $80 and departs on Tue, Apr 14.
5 hr 10 min is the shortest flight time from San Juan to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from San Juan to Chicago.
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 San Juan to Chicago 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 San Juan to Chicago.

In terms of nonstop flights, American is the most popular. American offers 14 nonstop flights and 433 connecting flights per week. American flies from Luis Munoz Marin International Airport (SJU) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 1 nonstop flights and 1,590 connecting flights per week. Southwest flies from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from San Juan to Chicago are:
  • United offers 13 nonstop flights and 207 connecting flights per week. United flies from Luis Munoz Marin International Airport (SJU) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 417 connecting flights per week. Delta flies from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Spirit offers 7 nonstop flights and 25 connecting flights per week. Spirit flies from Luis Munoz Marin International Airport (SJU) to Chicago O'Hare International Airport (ORD) .
  • Frontier offers 67 connecting flights per week. Frontier flies from Luis Munoz Marin International Airport (SJU) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between San Juan and Chicago.
The cheapest round-trip flight from San Juan to Chicago recently found on Google Flights was with Spirit from $199. The cheapest one-way flight was with Spirit from $80.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Juan to Chicago is $364, flying from Apr 30 to May 6.
  • The cheapest American flight from San Juan to Chicago is $237, flying from Apr 23 to May 2.
  • The cheapest United flight from San Juan to Chicago is $237, flying from Apr 30 to May 6.
  • The cheapest Delta flight from San Juan to Chicago is $364, flying from Apr 30 to May 6.
  • The cheapest Spirit flight from San Juan to Chicago is $199, flying from Apr 9 to Apr 15.
  • The cheapest Frontier flight from San Juan to Chicago is $222, flying from Apr 30 to May 6.
Southwest, American, United and Spirit fly direct from San Juan to Chicago.
  • There are 1 Southwest direct flights from San Juan to Chicago per week. Flights are available on Saturday.
  • There are 14 American direct flights from San Juan to Chicago per week. Flights are available every day.
  • There are 13 United direct flights from San Juan to Chicago per week. Flights are available every day.
  • There are 7 Spirit direct flights from San Juan to Chicago 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 San Juan and Chicago at price $201 is offered by Spirit from Thu, Feb 5 to Mon, Feb 9.
Southwest, American, United and Spirit fly direct from San Juan to Chicago.
  • There are 1 Southwest direct flights from San Juan to Chicago per week. Flights are available on Saturday.
  • There are 14 American direct flights from San Juan to Chicago per week. Flights are available every day.
  • There are 13 United direct flights from San Juan to Chicago per week. Flights are available every day.
  • There are 7 Spirit direct flights from San Juan to Chicago 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 San Juan to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between San Juan and Chicago start at $199 from Thu, Apr 9 to Wed, Apr 15 with Spirit.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from San Juan to Chicago, 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 San Juan and Chicago start at $450 from Thu, Apr 30 to Wed, May 6 with Frontier.
The cheapest economy class round-trip flights between San Juan and Chicago start at $199 from Thu, Apr 16 to Wed, Apr 22.
To book business class trips from San Juan to Chicago, 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 San Juan and Chicago starts at $201 from Thu, Feb 5 to Mon, Feb 9 with Spirit.
The cheapest last-minute deal between San Juan and Chicago at price $201 is offered by Spirit from Thu, Feb 5 to Mon, Feb 9.
To find last-minute flight deals from San Juan to Chicago, 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.

Search more flights

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