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Flight Deals from Chicago O Hare Airport to San Juan from $98

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Stops

  • Nonstop
    from $236
  • Up to 1 stop
    $253
  • Up to 2 stops
    $463

Airlines

  • American Airlines
    $452
  • Delta Air Lines
    $440
  • Frontier Airlines
    $317
  • JetBlue
    $355
  • Spirit Airlines
    $236
  • United Airlines
    $462

Cabin Class

  • Economy
    $236

Departure Airports

  • Chicago O Hare Airport
    $236

Arrival Airports

  • Luis Munoz Marin International Airport
    $236

Layover Airports

  • Charlotte Douglas International Airport
    $452
  • Dallas Fort Worth International Airport
    $458
  • Detroit Metropolitan Airport
    $460
  • Fort Lauderdale Hollywood International Airport
    $284
  • General Edward Lawrence Logan International Airport
    $436
  • Hartsfield Jackson Atlanta International Airport
    $317
  • Miami International Airport
    $253
  • New York John F Kennedy Airport
    $355
  • New York LaGuardia Airport
    $465
  • Newark Liberty Airport
    $468
  • Orlando International Airport
    $269
  • Philadelphia International Airport
    $337
  • Reagan Washington National Airport
    $463
  • Washington Dulles Airport
    $468

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Spirit Airlines Logo
Spirit Airlines

05/16/25

ORD
5h 46m
Direct

05/16/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/22/25

SJU
4h 16m
Direct

05/22/25

ORD
$236
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
5h 46m
Direct

05/19/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/23/25

SJU
4h 16m
Direct

05/23/25

ORD
$236
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
8h 55m
MIA

05/19/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/23/25

SJU
4h 16m
Direct

05/23/25

ORD
$253
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/17/25

ORD
8h 19m
MCO

05/18/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/25/25

SJU
4h 16m
Direct

05/25/25

ORD
$269
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/12/25

ORD
8h 55m
MIA

05/12/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/29/25

SJU
4h 16m
Direct

05/29/25

ORD
$269
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/24/25

ORD
8h 19m
MCO

05/25/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/30/25

SJU
4h 16m
Direct

05/30/25

ORD
$278
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/13/25

ORD
5h 46m
Direct

05/13/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/27/25

SJU
6h 59m
FLL

05/27/25

ORD
$284
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/22/25

ORD
9h 12m
FLL

05/22/25

SJU
Spirit Airlines Logo
Spirit Airlines

05/25/25

SJU
4h 16m
Direct

05/25/25

ORD
$284
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/15/25

ORD
7h 50m
MCO

05/16/25

SJU
Frontier Airlines Logo
Frontier Airlines

05/19/25

SJU
8h 28m
MCO

05/19/25

ORD
$317
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/09/25

ORD
7h 50m
MCO

05/10/25

SJU
Frontier Airlines Logo
Frontier Airlines

05/12/25

SJU
8h 28m
MCO

05/12/25

ORD
$317
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/11/25

ORD
10h 36m
MCO

05/12/25

SJU
Frontier Airlines Logo
Frontier Airlines

05/25/25

SJU
7h 46m
ATL

05/26/25

ORD
$317
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/12/25

ORD
10h 36m
MCO

05/13/25

SJU
Frontier Airlines Logo
Frontier Airlines

05/26/25

SJU
7h 46m
ATL

05/27/25

ORD
$317
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/05/25

ORD
12h 52m
PHL

05/06/25

SJU
Frontier Airlines Logo
Frontier Airlines

05/09/25

SJU
8h 58m
MCO

05/09/25

ORD
$337
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/04/25

ORD
9h 40m
JFK

05/04/25

SJU
JetBlue Logo
JetBlue

05/14/25

SJU
8h 3m
JFK

05/14/25

ORD
$355
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/14/25

ORD
10h
JFK

05/14/25

SJU
JetBlue Logo
JetBlue

05/17/25

SJU
9h 56m
JFK

05/17/25

ORD
$400
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/08/25

ORD
19h 34m
JFK

05/09/25

SJU
JetBlue Logo
JetBlue

05/12/25

SJU
26h
BOS

05/13/25

ORD
$436
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/11/25

ORD
9h 53m
ATL

05/11/25

SJU
Delta Air Lines Logo
Delta Air Lines

05/17/25

SJU
9h 34m
ATL

05/17/25

ORD
$440
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/13/25

ORD
11h 1m
ATL

05/13/25

SJU
Delta Air Lines Logo
Delta Air Lines

05/20/25

SJU
10h 32m
ATL

05/20/25

ORD
$450
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/26/25

ORD
13h 33m
CLT

05/26/25

SJU
American Airlines Logo
American Airlines

05/29/25

SJU
4h 20m
Direct

05/29/25

ORD
$452
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/11/25

ORD
9h 20m
BOS

05/11/25

SJU
JetBlue Logo
JetBlue

05/25/25

SJU
8h 3m
JFK

05/25/25

ORD
$456
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/26/25

ORD
13h 33m
CLT

05/26/25

SJU
American Airlines Logo
American Airlines

05/29/25

SJU
11h 1m
CLT

05/30/25

ORD
$457
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/13/25

ORD
5h 40m
Direct

05/13/25

SJU
American Airlines Logo
American Airlines

05/19/25

SJU
11h 54m
DFW

05/19/25

ORD
$458
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/12/25

ORD
9h 17m
ATL

05/12/25

SJU
Delta Air Lines Logo
Delta Air Lines

05/26/25

SJU
6h 26m
DTW

05/26/25

ORD
$460
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/14/25

ORD
8h 25m
MIA

05/14/25

SJU
American Airlines Logo
American Airlines

05/24/25

SJU
12h 4m
PHL

05/24/25

ORD
$460
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/26/25

ORD
5h 55m
Direct

05/26/25

SJU
United Airlines Logo
United Airlines

05/29/25

SJU
4h 19m
Direct

05/29/25

ORD
$462
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/14/25

ORD
12h 43m
DCA
CLT

05/14/25

SJU
American Airlines Logo
American Airlines

05/17/25

SJU
9h 55m
MIA

05/17/25

ORD
$463
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/18/25

ORD
5h 52m
Direct

05/18/25

SJU
United Airlines Logo
United Airlines

05/25/25

SJU
4h 19m
Direct

05/25/25

ORD
$464
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

ORD
13h 14m
LGA
CLT

05/20/25

SJU
American Airlines Logo
American Airlines

05/28/25

SJU
8h 21m
MIA

05/28/25

ORD
$465
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/14/25

ORD
5h 51m
Direct

05/14/25

SJU
United Airlines Logo
United Airlines

05/24/25

SJU
6h 35m
IAD

05/24/25

ORD
$468
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/16/25

ORD
5h 51m
Direct

05/16/25

SJU
United Airlines Logo
United Airlines

05/31/25

SJU
8h 47m
EWR

05/31/25

ORD
$468
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago O Hare Airport to San Juan

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

Jun 3

ORD
5h 46m
Direct

Jun 3

SJU

as low as

$98

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

May 27

ORD
26h 19m
FLL

May 28

SJU

as low as

$132

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

May 25

ORD
12h 20m
BWI

May 25

SJU

as low as

$135

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

May 16

ORD
8h 19m
MCO

May 17

SJU

as low as

$143

Chicago, US (CHI) - San Juan, PR (SJU)

Spirit Airlines Logo
Spirit Airlines

May 29

ORD
11h 45m
MIA

May 29

SJU

as low as

$148

Chicago, US (CHI) - San Juan, PR (SJU)

Frontier Airlines Logo
Frontier Airlines

May 17

ORD
10h 36m
MCO

May 18

SJU

as low as

$153

Chicago, US (CHI) - San Juan, PR (SJU)

Frontier Airlines Logo
Frontier Airlines

Jun 2

ORD
10h 16m
ATL

Jun 2

SJU

as low as

$163

Chicago, US (CHI) - San Juan, PR (SJU)

JetBlue Logo
JetBlue

May 25

ORD
8h 45m
BOS

May 25

SJU

as low as

$190

Chicago, US (CHI) - San Juan, PR (SJU)

JetBlue Logo
JetBlue

May 21

ORD
9h 46m
JFK

May 22

SJU

as low as

$190

Chicago, US (CHI) - San Juan, PR (SJU)

Delta Air Lines Logo
Delta Air Lines

May 25

ORD
8h 41m
MSP

May 25

SJU

as low as

$195

Chicago, US (CHI) - San Juan, PR (SJU)

United Airlines Logo
United Airlines

Jun 11

ORD
13h 28m
IAH

Jun 11

SJU

as low as

$227

Chicago, US (CHI) - San Juan, PR (SJU)

American Airlines Logo
American Airlines

Jun 1

ORD
5h 40m
Direct

Jun 1

SJU

as low as

$229

Frequently Asked Questions

What is the typical flight duration from Chicago O Hare Airport to San Juan?
The typical flight duration from Chicago O Hare Airport to San Juan generally falls between 4 to 5 hours, though factors such as weather conditions and the specific flight path can affect these estimates. Direct flights tend to stick closer to this range, while connecting flights might extend travel time slightly. For travelers, it’s a good idea to plan for potential delays and to check with the airline for the most current schedules. This information helps in planning transfers or activities upon arrival.
Are there any direct flights from Chicago O Hare Airport to San Juan?
Yes, there are direct flights available from Chicago O Hare Airport to San Juan, although availability may vary depending on the season and airline schedules. Direct flights usually offer a smoother travel experience, saving time compared to connecting flights. It is advisable to check current flight schedules and book in advance to secure a direct option. These services often run on a regular schedule, making planning easier for visitors who prefer a straightforward travel itinerary between the two cities.
What are the best transportation options from San Juan airport to downtown or popular tourist attractions?
Transportation options at San Juan airport include taxis, rideshare services, rental cars, and local buses. Taxis generally charge between $20 to $35 to reach downtown areas, while rideshares like Uber or Lyft offer competitive rates starting around $15. Rental cars are available from approximately $40 per day, ideal for extended stays and versatility. Additionally, local buses provide budget-friendly travel, though with longer travel times and potentially less convenience. Choosing the right option depends on your budget, travel preferences, and itinerary in the destination area.
What are the must-see attractions in San Juan for travelers arriving from Chicago O Hare Airport?
Must-see attractions in San Juan include the historic streets of Old San Juan, Castillo San Felipe del Morro, and the Cathedral of San Juan Bautista. Visitors can also enjoy vibrant neighborhoods like Condado and Isla Verde, which offer both scenic beach views and lively cultural experiences. Walking the cobblestone streets reveals colorful colonial architecture, local cafes, and boutique shops. Planning a day to explore these landmarks provides both historical insights and the opportunity to partake in the local gastronomy scene, making the visit enriching and memorable.
Which local dishes should travelers from Chicago O Hare Airport try when visiting San Juan?
Travelers visiting San Juan are encouraged to try local culinary delights such as mofongo, a mashed plantain dish with savory fillings, and lechón asado, a slow-roasted pork dish. Other must-try items include tostones (fried plantains), arroz con gandules (rice with pigeon peas), and local seafood specialties. Many local eateries and street vendors offer authentic and affordable versions of these dishes, usually ranging from $10 to $20 per meal. Sampling these options provides a taste of the vibrant local food culture, making your culinary journey both delightful and immersive.
Are there any family-friendly activities in San Juan for visitors from Chicago O Hare Airport?
Yes, San Juan offers many family-friendly activities that cater to all ages. Families can explore interactive museums, enjoy the beaches such as Condado Beach, or take guided historical tours through Old San Juan’s cobblestone streets. Numerous parks and public spaces host cultural events and seasonal festivals, often free or with minimal entrance fees ranging from $5 to $15 per person. These activities provide an immersive experience in local history and culture while ensuring a safe, engaging environment for children and adults alike.
What are the best accommodations in San Juan for travelers from Chicago O Hare Airport?
There are various accommodation options in San Juan tailored to different budgets and preferences. Luxury resorts and boutique hotels in areas like Condado or Old San Juan typically range from $250 to $400 per night, offering amenities such as beachfront access and spa services. More budget-friendly hotels and guesthouses can be found starting at $100 to $150 per night, while vacation rentals provide additional space and home comforts. It is advisable to book in advance during peak travel seasons and to consider location convenience in relation to key attractions or beach access.
What are the customs requirements for travelers flying from Chicago O Hare Airport to San Juan?
Since San Juan is part of a U.S. territory, travelers departing from Chicago O Hare Airport do not go through the standard international customs process if they are U.S. citizens. However, non-U.S. citizens must carry valid passports and any relevant travel documents. It is also important to note that certain security checks are still in place at both departure and arrival points. Always verify the latest travel advisories and documentation requirements before traveling, as regulations can change and may differ for individual circumstances.
What are the top cultural experiences in San Juan for visitors from Chicago O Hare Airport?
Top cultural experiences in San Juan include exploring the historic streets of Old San Juan, with its well-preserved colonial architecture and vibrant local art scene. Visitors can tour landmarks like Castillo San Felipe del Morro and immerse themselves in local music and dance at traditional festivals. Additionally, art galleries, museums, and artisan markets add depth to the cultural experience. Attend local culinary events to sample traditional dishes and participate in community festivities. These activities provide an authentic insight into the local heritage and lifestyle.
Is there a specific time of year when San Juan is best visited by travelers from Chicago O Hare Airport?
The best times to visit San Juan are typically during the spring months (April to June) and early fall (September to November), when the weather is pleasantly warm and humidity is moderate. These periods often have fewer crowds compared to the peak winter season, offering a more relaxed atmosphere for exploring historical sites and enjoying outdoor activities. Travelers should also consider local festival calendars, as events can enhance the cultural experience. Additionally, these shoulder seasons generally offer more competitive prices on accommodations and activities.
What are the most affordable dining options in San Juan for travelers from Chicago O Hare Airport?
Affordable dining in San Juan can be found in local eateries, food trucks, and casual cafes, where meals typically cost between $10 to $20. Street vendors and local markets offer authentic dishes like tostones and empanadas at lower prices. Neighborhoods away from major tourist spots may have budget-friendly family-run restaurants that serve hearty local fare. Researching recommendations online or asking locals for hidden gems can reveal options that not only preserve authenticity but also provide a taste of everyday life at a fraction of the cost associated with more tourist-oriented establishments.
What are the best places to shop for souvenirs in San Juan for travelers from Chicago O Hare Airport?
Souvenir shopping in San Juan is best experienced in areas like Old San Juan, where artisan boutiques and local craft markets offer a range of items from handcrafted jewelry and local art to traditional textiles and culinary spices. Prices vary, typically ranging from $10 to $50 depending on the item’s complexity and uniqueness. Additionally, shopping centers and dedicated souvenir stalls near major attractions provide convenience, while local bazaars often feature one-of-a-kind finds that capture the cultural heritage of the region. It’s worthwhile to compare options to secure the best quality at reasonable prices.
Are there any seasonal events in San Juan that travelers from Chicago O Hare Airport should not miss?
Yes, seasonal events are a major attraction in San Juan. The annual San Sebastián Street Festival in January is a vibrant celebration of music, art, and local culture that draws visitors from all over. Additionally, summer events, art fairs, and local food festivals provide opportunities to experience the region’s traditions and lively community spirit. These events usually feature live performances and local culinary specialties, with admission fees typically ranging from free to about $10-$20. Timing your visit to coincide with one of these events can offer an unforgettable, immersive cultural experience.
What are the health and safety precautions travelers from Chicago O Hare Airport should be aware of when visiting San Juan?
Travelers should take common health and safety precautions when visiting San Juan. Stay updated with local advisories and weather conditions, especially during hurricane season from June to November. It’s advisable to use sunscreen, stay hydrated, and avoid prolonged sun exposure. Keep personal belongings secure in crowded tourist areas and be aware of your surroundings. In terms of health, consider travel insurance and carry any necessary medications, while also checking if any vaccinations or extra health precautions are recommended. Visiting reputable medical facilities if needed and adhering to local safety regulations can ensure a worry-free experience.
What unique airport amenities can travelers expect at San Juan airport when arriving from Chicago O Hare Airport?
Travelers arriving at San Juan airport can enjoy a variety of unique amenities designed for a comfortable transit. Modern facilities include duty-free shopping areas with a selection of local and international products, a range of dining options from quick bites to sit-down meals, and comfortable lounges for a relaxed wait. Free Wi-Fi is available throughout the terminal, and information kiosks offer tourist tips and local maps. Additionally, the airport boasts efficient security and check-in services, making for a streamlined process upon arrival. These conveniences help set the tone for a pleasant start to your stay.

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