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

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Stops

  • Nonstop
    from $221
  • Up to 1 stop
    $269

Airlines

  • American Airlines
    $460
  • Delta Air Lines
    $420
  • Frontier Airlines
    $307
  • JetBlue
    $410
  • Spirit Airlines
    $221
  • United Airlines
    $380

Cabin Class

  • Economy
    $221

Departure Airports

  • Luis Munoz Marin International Airport
    $221

Arrival Airports

  • Chicago O Hare Airport
    $221

Layover Airports

  • Charlotte Douglas International Airport
    $524
  • Dallas Fort Worth International Airport
    $420
  • Fort Lauderdale Hollywood International Airport
    $534
  • George Bush Intercontinental Houston Airport
    $380
  • Hartsfield Jackson Atlanta International Airport
    $317
  • Miami International Airport
    $269
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $475
  • New York John F Kennedy Airport
    $410
  • Newark Liberty Airport
    $476
  • Orlando International Airport
    $307
  • Philadelphia International Airport
    $460
  • Washington Dulles Airport
    $468

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Spirit Airlines Logo
Spirit Airlines

05/16/25

SJU
4h 16m
Direct

05/16/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
5h 46m
Direct

05/19/25

SJU
$221
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/15/25

SJU
4h 16m
Direct

05/15/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
5h 46m
Direct

05/19/25

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

05/16/25

SJU
4h 16m
Direct

05/16/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
8h 55m
MIA

05/19/25

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

05/08/25

SJU
4h 16m
Direct

05/08/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/13/25

ORD
5h 46m
Direct

05/13/25

SJU
$271
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/15/25

SJU
4h 16m
Direct

05/15/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
8h 55m
MIA

05/19/25

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

05/16/25

SJU
6h 53m
MCO

05/16/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/19/25

ORD
10h 36m
MCO

05/20/25

SJU
$307
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/09/25

SJU
8h 58m
MCO

05/09/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/23/25

ORD
10h 5m
ATL

05/23/25

SJU
$317
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/09/25

SJU
4h 16m
Direct

05/09/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/23/25

ORD
8h 55m
MIA

05/23/25

SJU
$324
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/08/25

SJU
9h 20m
IAH

05/09/25

ORD
United Airlines Logo
United Airlines

05/09/25

ORD
5h 51m
Direct

05/09/25

SJU
$380
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/04/25

SJU
9h 18m
MCO

05/04/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/18/25

ORD
10h 36m
MCO

05/19/25

SJU
$387
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/06/25

SJU
4h 10m
Direct

05/06/25

ORD
United Airlines Logo
United Airlines

05/13/25

ORD
15h 23m
IAH

05/13/25

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

05/10/25

SJU
9h 56m
JFK

05/10/25

ORD
JetBlue Logo
JetBlue

05/24/25

ORD
9h 46m
JFK

05/25/25

SJU
$410
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/17/25

SJU
10h 49m
ATL

05/17/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/24/25

ORD
9h 17m
ATL

05/24/25

SJU
$420
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/01/25

SJU
9h 20m
IAH

05/02/25

ORD
United Airlines Logo
United Airlines

05/08/25

ORD
5h 51m
Direct

05/08/25

SJU
$420
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/06/25

SJU
7h 41m
DFW

05/06/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/13/25

ORD
5h 46m
Direct

05/13/25

SJU
$420
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/06/25

SJU
6h 10m
ATL

05/06/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/13/25

ORD
9h 26m
ATL

05/13/25

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

05/08/25

SJU
8h 32m
ATL

05/08/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/13/25

ORD
9h 59m
ATL

05/13/25

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

05/15/25

SJU
9h 55m
MIA

05/15/25

ORD
American Airlines Logo
American Airlines

05/19/25

ORD
14h 8m
PHL

05/19/25

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

05/17/25

SJU
7h 9m
IAD

05/17/25

ORD
United Airlines Logo
United Airlines

05/24/25

ORD
5h 51m
Direct

05/24/25

SJU
$468
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/10/25

SJU
10h 29m
JFK

05/10/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/24/25

ORD
8h 41m
MSP

05/24/25

SJU
$475
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/11/25

SJU
8h 40m
EWR

05/11/25

ORD
United Airlines Logo
United Airlines

05/18/25

ORD
5h 51m
Direct

05/18/25

SJU
$476
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/17/25

SJU
6h 23m
PHL

05/17/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
12h 14m
PHL

05/24/25

SJU
$488
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/18/25

SJU
9h 38m
PHL

05/18/25

ORD
American Airlines Logo
American Airlines

05/21/25

ORD
14h 8m
PHL

05/21/25

SJU
$494
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/06/25

SJU
14h 38m
EWR

05/07/25

ORD
United Airlines Logo
United Airlines

05/13/25

ORD
8h 17m
EWR

05/13/25

SJU
$496
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/08/25

SJU
4h 20m
Direct

05/08/25

ORD
American Airlines Logo
American Airlines

05/15/25

ORD
8h 25m
CLT

05/15/25

SJU
$524
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/06/25

SJU
7h 55m
MIA

05/06/25

ORD
American Airlines Logo
American Airlines

05/13/25

ORD
8h
CLT

05/13/25

SJU
$524
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/17/25

SJU
7h 9m
IAD

05/17/25

ORD
United Airlines Logo
United Airlines

05/24/25

ORD
22h 10m
IAD

05/25/25

SJU
$525
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/12/25

SJU
13h 54m
DFW

05/12/25

ORD
American Airlines Logo
American Airlines

05/19/25

ORD
12h 45m
PHL

05/19/25

SJU
$529
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/08/25

SJU
8h 27m
PHL

05/08/25

ORD
American Airlines Logo
American Airlines

05/15/25

ORD
13h 33m
CLT

05/15/25

SJU
$529
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/05/25

SJU
8h 16m
FLL

05/05/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/12/25

ORD
8h 55m
MIA

05/12/25

SJU
$534
Free cancellation within 83 hours of booking

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

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

Spirit Airlines Logo
Spirit Airlines

Jun 3

SJU
4h 16m
Direct

Jun 3

ORD

as low as

$98

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

Spirit Airlines Logo
Spirit Airlines

May 28

SJU
6h 59m
FLL

May 28

ORD

as low as

$119

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

Spirit Airlines Logo
Spirit Airlines

May 16

SJU
21h 56m
MIA

May 17

ORD

as low as

$121

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

Spirit Airlines Logo
Spirit Airlines

May 24

SJU
10h 49m
MCO

May 24

ORD

as low as

$147

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

Frontier Airlines Logo
Frontier Airlines

Jun 7

SJU
9h 1m
ATL

Jun 8

ORD

as low as

$163

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

Frontier Airlines Logo
Frontier Airlines

May 18

SJU
9h 18m
MCO

May 18

ORD

as low as

$163

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

Frontier Airlines Logo
Frontier Airlines

Jun 2

SJU
8h 15m
RDU

Jun 2

ORD

as low as

$182

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

Delta Air Lines Logo
Delta Air Lines

Jun 4

SJU
6h 15m
ATL

Jun 4

ORD

as low as

$195

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

Delta Air Lines Logo
Delta Air Lines

Jun 12

SJU
10h 46m
JFK

Jun 12

ORD

as low as

$195

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

Spirit Airlines Logo
Spirit Airlines

Jun 13

SJU
10h 44m
DFW

Jun 13

ORD

as low as

$200

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

Frontier Airlines Logo
Frontier Airlines

Jun 12

SJU
7h 46m
CLT

Jun 12

ORD

as low as

$218

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

United Airlines Logo
United Airlines

May 24

SJU
17h 50m
IAH

May 24

ORD

as low as

$219

Frequently Asked Questions

What is the typical flight duration from San Juan to Chicago O Hare Airport?
The flight duration from San Juan (SJU) to Chicago O Hare (ORD) generally ranges between 4 to 6 hours, depending on whether the flight is direct or involves connections. This time frame includes the actual flight time and can vary slightly with boarding and taxi times. Travelers should factor in potential delays such as weather conditions. It is advisable to check with your airline for the most current schedule details to plan accordingly, ensuring a stress-free travel experience between these two cities.
Are there any direct flights from San Juan to Chicago O Hare Airport?
Yes, there are direct flights available from San Juan (SJU) to Chicago O Hare (ORD), although availability can vary seasonally. Direct flights typically shorten the travel duration, maintaining the estimated 4 to 6 hours range. However, schedules might change during off-peak times or due to operational adjustments. It is best to verify directly with the airline or booking platform for the most updated flight options and availability. Booking in advance can help secure these preferred routes during busy travel periods.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
From Chicago O Hare (ORD) to downtown Chicago, travelers have several options. The CTA Blue Line train offers a budget-friendly choice at around $5 to $10 and takes 30 to 45 minutes. Alternatively, taxis and ride-sharing services provide convenience with fares ranging from $30 to $50, depending on traffic conditions. Airport shuttles are also available, offering a balance between cost and comfort. Planning ahead by comparing times and fares can help optimize your transfer experience as you transition from the airport to the heart of the city.
What are the must-see attractions in Chicago for travelers arriving from San Juan?
Travelers arriving from San Juan should not miss touring iconic spots such as Millennium Park, the Art Institute of Chicago, and the Willis Tower Skydeck for breathtaking city views. Additionally, exploring vibrant neighborhoods like the Loop and River North can offer cultural insights and dining delights. Each destination presents unique opportunities to experience local art, architecture, and history. Booking tickets in advance for popular landmarks is a wise strategy to avoid long queues and fully enjoy the diverse attractions available throughout this bustling city.
Which local dishes should travelers from San Juan try when visiting Chicago?
Visitors from San Juan should indulge in Chicago’s signature deep-dish pizza, renowned for its thick, buttery crust and hearty toppings. Equally popular are the Italian beef sandwiches and Chicago-style hot dogs, notable for their distinctive preparation and toppings. Exploring neighborhoods like River North or Little Italy can lead to discovering gourmet fusion dishes and seasonal specialties. These culinary experiences are an excellent way to immerse oneself in local flavors, offering a delightful contrast to traditional tastes from San Juan while highlighting regional culinary creativity.
What are the best family-friendly activities in Chicago for visitors from San Juan?
Families visiting from San Juan can enjoy a variety of engaging activities in Chicago. Highlights include interactive experiences at the Museum of Science and Industry, the Shedd Aquarium’s diverse marine life exhibits, and fun outings at Lincoln Park Zoo. Outdoor spaces such as Millennium Park offer seasonal festivals and public art displays that cater to all ages. Planning a mix of educational and recreational outings, while factoring in potential weather changes, ensures an enjoyable trip that combines cultural enrichment with relaxed family time in this diverse urban environment.
Are there any budget-friendly hotels in Chicago for travelers from San Juan?
Yes, Chicago offers a range of budget-friendly hotels suitable for travelers from San Juan. Options in areas such as the Loop or near public transit hubs typically range from $80 to $150 per night, featuring essential amenities and convenient access to local attractions. It is beneficial to read recent reviews and compare prices on various booking platforms to secure the best deal. Additionally, consider booking during off-peak periods to further lower costs, ensuring both comfort and a strategically located stay while exploring the city’s renowned landmarks.
What are the customs requirements for travelers flying from San Juan to Chicago O Hare Airport?
Travelers flying from San Juan (SJU) to Chicago O Hare (ORD) are subject to standard domestic security protocols as both locations are within U.S. borders. A valid government-issued photo ID such as a passport or driver’s license is required, and it is recommended to arrive at the airport at least 2 hours before departure. While there are no international customs procedures, adhering to TSA guidelines regarding prohibited items is essential. Staying updated on any temporary travel advisories will help ensure a smooth transit experience between these two cities.
What are the top shopping areas in Chicago for souvenirs that travelers from San Juan should explore?
Chicago offers diverse shopping areas perfect for finding unique souvenirs. Notable locations include The Magnificent Mile, which houses upscale boutiques and large retail stores, as well as State Street and select neighborhoods like Wicker Park known for local artisan crafts. These districts provide a wide range of items including vintage collectibles, sports memorabilia, and locally themed gifts. Travelers from San Juan are advised to explore these vibrant areas, comparing prices and options, and ensuring a memorable shopping experience that captures the local flavor and cultural heritage of Chicago.
Is there a specific time of year when Chicago is best visited by travelers from San Juan?
Yes, the optimal times to visit Chicago are in the spring (April to June) and early fall (September to October), when temperatures are mild—typically ranging between 55°F and 75°F—and crowds are less intense. These seasons allow for comfortable exploration of outdoor attractions and festivals. Although summer offers lively street events, it can be crowded and warmer. Travelers from San Juan may find these transitional periods ideal for enjoying local sightseeing, outdoor dining, and cultural events while avoiding the extremes of both the winter chill and summer heat.
What are the health and safety tips for travelers from San Juan visiting Chicago?
For optimal safety, travelers from San Juan should remain aware of their surroundings in busy urban areas and public transit. Secure personal belongings, especially in crowded locations, and consider carrying travel insurance that includes health coverage. Keeping essential medications within easy reach and staying informed about weather conditions can also be beneficial. It is recommended to have local emergency numbers saved and to choose accommodations in well-reviewed, central areas. Additionally, following local health advisories and practicing common-sense safety measures will ensure a worry-free experience while exploring the city.
What unique cultural experiences in Chicago should travelers from San Juan not miss?
Travelers from San Juan are encouraged to explore Chicago’s rich cultural tapestry by attending live jazz sessions, local theater productions, and visiting diverse art galleries. Participating in neighborhood festivals such as the Taste of Chicago offers hands-on culinary and cultural insights. Additionally, museums like the Field Museum and cultural centers in areas like Pilsen provide immersive experiences showcasing the city’s history and multicultural heritage. These distinctive activities not only highlight Chicago’s artistic spirit but also allow visitors to connect with community traditions and contemporary creative expressions.
Are there any seasonal events in Chicago that travelers from San Juan should plan their trip around?
Yes, Chicago hosts a variety of seasonal events that appeal to diverse interests. For example, summer stages numerous music festivals and the Chicago Air and Water Show, while winter features festive holiday markets and ice skating events in iconic parks. Fall brings art festivals and food events that celebrate local cuisines. Travelers from San Juan should plan their visits around these seasonal events—typically scheduled between May and September—to fully experience the city’s vibrant community activities, keeping in mind advanced planning for tickets and accommodations amid peak event periods.
What are the best solo travel activities in Chicago for travelers arriving from San Juan?
Solo travelers from San Juan can enjoy a variety of independent activities in Chicago. Highlights include self-guided walking tours exploring public art in Millennium Park, visits to renowned museums like the Art Institute, and leisurely afternoons at local cafés. Additionally, joining specialized walking or food tours can offer both historical insights and social interaction while retaining personal freedom to explore on your own schedule. These activities provide a balanced itinerary that encourages both introspection and engagement with the diverse cultural and urban fabric of Chicago.
What airport amenities can travelers expect at Chicago O Hare Airport when arriving from San Juan?
Chicago O Hare (ORD) offers a range of amenities designed for traveler convenience. Passengers can expect free Wi-Fi, diverse dining options ranging from quick snacks to full-service restaurants where meals run between $10 and $20, and various retail outlets for last-minute shopping. In addition, there are comfortable lounges, charging stations, and designated rest areas. Clear signage and information desks assist with navigation. These facilities ensure that after arriving from San Juan, travelers can relax, refresh, and prepare for their onward journey with relative ease and comfort.

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