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Flight Deals from Chicago to San Jose from $124

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Stops

  • Nonstop
    from $558
  • Up to 1 stop
    $374
  • Up to 2 stops
    $617

Airlines

  • Aeromexico
    $914
  • Air Canada
    $769
  • American Airlines
    $502
  • AVIANCA
    $374
  • COPA Airlines
    $441
  • Delta Air Lines
    $483
  • JetBlue
    $638
  • Spirit Airlines
    $526
  • United Airlines
    $535

Cabin Class

  • Economy
    $374

Departure Airports

  • Chicago O Hare Airport
    $374

Arrival Airports

  • Juan Santamaria International Airport
    $374

Layover Airports

  • Charlotte Douglas International Airport
    $502
  • Dallas Fort Worth International Airport
    $502
  • Don Miguel Hidalgo Y Costilla International Airport
    $914
  • El Dorado International Airport
    $638
  • Fort Lauderdale Hollywood International Airport
    $526
  • General Edward Lawrence Logan International Airport
    $617
  • George Bush Intercontinental Houston Airport
    $535
  • Hartsfield Jackson Atlanta International Airport
    $483
  • La Aurora Airport
    $374
  • Licenciado Benito Juarez International Airport
    $914
  • Miami International Airport
    $521
  • Monseñor Óscar Arnulfo Romero International Airport
    $385
  • Montreal Trudeau Airport
    $787
  • New York John F Kennedy Airport
    $637
  • Orlando International Airport
    $617
  • Philadelphia International Airport
    $796
  • Reagan Washington National Airport
    $667
  • Tocumen International Airport
    $441
  • Toronto Pearson Airport
    $769

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AVIANCA Logo
AVIANCA

07/06/25

ORD
6h 5m
Direct

07/06/25

SJO
AVIANCA Logo
AVIANCA

07/08/25

SJO
22h 5m
GUA

07/09/25

ORD
$374
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/05/25

ORD
6h 10m
SAL

07/05/25

SJO
AVIANCA Logo
AVIANCA

07/08/25

SJO
22h 5m
GUA

07/09/25

ORD
$385
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/04/25

ORD
7h 30m
GUA

07/04/25

SJO
AVIANCA Logo
AVIANCA

07/10/25

SJO
11h
SAL

07/10/25

ORD
$408
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

07/09/25

ORD
16h 28m
PTY

07/10/25

SJO
COPA Airlines Logo
COPA Airlines

07/16/25

SJO
9h 27m
PTY

07/17/25

ORD
$441
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/08/25

ORD
6h 21m
ATL

07/08/25

SJO
Delta Air Lines Logo
Delta Air Lines

07/22/25

SJO
10h 48m
ATL

07/23/25

ORD
$483
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/06/25

ORD
13h 40m
DFW

07/06/25

SJO
American Airlines Logo
American Airlines

07/10/25

SJO
9h 37m
CLT

07/10/25

ORD
$502
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/06/25

ORD
17h 5m
DFW

07/06/25

SJO
American Airlines Logo
American Airlines

07/12/25

SJO
11h 37m
MIA

07/13/25

ORD
$521
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/30/25

ORD
11h 48m
MIA

06/30/25

SJO
American Airlines Logo
American Airlines

07/14/25

SJO
14h 55m
MIA

07/14/25

ORD
$521
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/22/25

ORD
6h 14m
FLL

06/22/25

SJO
Spirit Airlines Logo
Spirit Airlines

07/06/25

SJO
11h 17m
FLL

07/06/25

ORD
$526
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/29/25

ORD
12h 21m
IAH

06/30/25

SJO
United Airlines Logo
United Airlines

07/13/25

SJO
16h 20m
IAH

07/14/25

ORD
$535
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/04/25

ORD
15h 46m
IAH

07/05/25

SJO
United Airlines Logo
United Airlines

07/18/25

SJO
16h 20m
IAH

07/19/25

ORD
$535
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

06/26/25

ORD
6h 14m
FLL

06/26/25

SJO
Spirit Airlines Logo
Spirit Airlines

07/02/25

SJO
11h 17m
FLL

07/02/25

ORD
$538
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

07/05/25

ORD
4h 14m
Direct

07/05/25

SJO
United Airlines Logo
United Airlines

07/19/25

SJO
6h 34m
Direct

07/19/25

ORD
$558
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/16/25

ORD
6h 5m
Direct

07/16/25

SJO
AVIANCA Logo
AVIANCA

07/20/25

SJO
8h 40m
Direct

07/20/25

ORD
$595
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/08/25

ORD
6h 15m
CLT

07/08/25

SJO
American Airlines Logo
American Airlines

07/15/25

SJO
9h 37m
CLT

07/15/25

ORD
$609
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/01/25

ORD
6h 10m
SAL

07/01/25

SJO
AVIANCA Logo
AVIANCA

07/08/25

SJO
19h 15m
MCO
BOS

07/09/25

ORD
$617
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/08/25

ORD
20h 5m
SAL

07/09/25

SJO
AVIANCA Logo
AVIANCA

07/22/25

SJO
19h 15m
MCO
BOS

07/23/25

ORD
$634
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/07/25

ORD
10h 10m
JFK

07/07/25

SJO
AVIANCA Logo
AVIANCA

07/13/25

SJO
8h 40m
Direct

07/13/25

ORD
$637
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/20/25

ORD
7h 30m
GUA

07/20/25

SJO
AVIANCA Logo
AVIANCA

07/27/25

SJO
22h 15m
BOG

07/28/25

ORD
$638
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/03/25

ORD
18h 49m
BOS
MCO

07/04/25

SJO
JetBlue Logo
JetBlue

07/09/25

SJO
19h 15m
MCO
BOS

07/10/25

ORD
$638
Free cancellation within 83 hours of booking
COPA Airlines Logo
COPA Airlines

06/22/25

ORD
11h 5m
PTY

06/22/25

SJO
COPA Airlines Logo
COPA Airlines

07/06/25

SJO
22h 49m
PTY

07/07/25

ORD
$649
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/20/25

ORD
14h 55m
DCA
MIA

07/21/25

SJO
American Airlines Logo
American Airlines

07/27/25

SJO
16h 26m
MIA

07/27/25

ORD
$667
Free cancellation within 83 hours of booking
AVIANCA Logo
AVIANCA

07/16/25

ORD
17h 35m
GUA

07/17/25

SJO
AVIANCA Logo
AVIANCA

07/20/25

SJO
22h 15m
BOG

07/21/25

ORD
$676
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

07/11/25

ORD
6h 21m
ATL

07/11/25

SJO
Delta Air Lines Logo
Delta Air Lines

07/25/25

SJO
10h 48m
ATL

07/26/25

ORD
$700
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

07/15/25

ORD
25h 25m
JFK

07/16/25

SJO
JetBlue Logo
JetBlue

07/20/25

SJO
19h 15m
MCO
BOS

07/21/25

ORD
$703
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/21/25

ORD
8h 50m
YYZ

06/21/25

SJO
Air Canada Logo
Air Canada

07/16/25

SJO
25h 9m
YYZ

07/17/25

ORD
$769
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/20/25

ORD
14h 55m
DCA
MIA

07/21/25

SJO
American Airlines Logo
American Airlines

07/27/25

SJO
15h 13m
MIA
CLT

07/27/25

ORD
$780
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/16/25

ORD
28h 50m
YUL

07/17/25

SJO
Air Canada Logo
Air Canada

07/21/25

SJO
12h 21m
YUL

07/21/25

ORD
$787
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/01/25

ORD
15h 39m
PHL
CLT

07/02/25

SJO
American Airlines Logo
American Airlines

07/06/25

SJO
9h 51m
DFW

07/07/25

ORD
$796
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

07/08/25

ORD
10h 7m
MEX

07/08/25

SJO
Aeromexico Logo
Aeromexico

07/15/25

SJO
22h 47m
MEX
GDL

07/16/25

ORD
$914
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago to San Jose

Chicago, US (CHI) - San Jose, CR (SJO)

Spirit Airlines Logo
Spirit Airlines

Jun 4

ORD
26h 50m
MCO

Jun 5

SJO

as low as

$124

Chicago, US (CHI) - San Jose, CR (SJO)

Spirit Airlines Logo
Spirit Airlines

May 27

ORD
6h 28m
FLL

May 27

SJO

as low as

$152

Chicago, US (CHI) - San Jose, CR (SJO)

 Logo

Jun 7

ORD
7h 30m
ATL

Jun 7

SJO

as low as

$174

Chicago, US (CHI) - San Jose, CR (SJO)

JetBlue Logo
JetBlue

May 27

ORD
20h 46m
JFK

May 28

SJO

as low as

$221

Chicago, US (CHI) - San Jose, CR (SJO)

COPA Airlines Logo
COPA Airlines

May 14

ORD
13h 59m
PTY

May 14

SJO

as low as

$225

Chicago, US (CHI) - San Jose, CR (SJO)

American Airlines Logo
American Airlines

May 14

ORD
10h 8m
DFW

May 14

SJO

as low as

$233

Chicago, US (CHI) - San Jose, CR (SJO)

American Airlines Logo
American Airlines

May 15

ORD
6h 51m
MIA

May 15

SJO

as low as

$233

Chicago, US (CHI) - San Jose, CR (SJO)

United Airlines Logo
United Airlines

May 25

ORD
4h 14m
Direct

May 25

SJO

as low as

$245

Chicago, US (CHI) - San Jose, CR (SJO)

United Airlines Logo
United Airlines

May 17

ORD
16h 10m
DEN

May 17

SJO

as low as

$249

Chicago, US (CHI) - San Jose, CR (SJO)

United Airlines Logo
United Airlines

May 24

ORD
13h 51m
IAH

May 25

SJO

as low as

$249

Chicago, US (CHI) - San Jose, CR (SJO)

AVIANCA Logo
AVIANCA

Jun 4

ORD
6h 5m
Direct

Jun 4

SJO

as low as

$251

Chicago, US (CHI) - San Jose, CR (SJO)

Air Canada Logo
Air Canada

May 27

ORD
13h 15m
YYZ

May 27

SJO

as low as

$253

Frequently Asked Questions

What is the typical flight duration from Chicago to San Jose?
The typical flight duration from Chicago to San Jose usually ranges between 4 to 5 hours, although it may vary slightly based on the airline and weather conditions. Direct flights often run quicker, while itineraries with a layover could extend the total travel time. It is advisable to check the schedule when booking since the travel time can fluctuate. This information is particularly useful for visitors from Chicago who want to plan their arrival and departure times accurately and make the most of their time exploring San Jose.
Are there any direct flights from Chicago to San Jose?
Yes, there are direct flights from Chicago to San Jose available on select airlines. Direct options typically reduce overall travel time by eliminating layovers, which can be beneficial for travelers managing tight schedules. However, availability depends on the season and specific airline offerings, so it is wise to confirm the schedule when booking. This clear route allows visitors from Chicago to plan a more streamlined journey and quickly start enjoying the cultural and recreational activities awaiting them in San Jose.
What are the best transportation options from San Jose airport to downtown?
For a smooth transfer from San Jose’s airport to downtown, several reliable transportation options are available. Rideshare services like Uber and Lyft offer door-to-door convenience with fares typically ranging between $15 to $30, while taxis are also an option, generally costing between $25 to $50. Shared airport shuttles provide a cost-effective alternative with prices around $12 to $20. Additionally, public transit can be considered if you are looking to save more on travel expenses. These options are especially practical for visitors coming from Chicago who seek predictability and comfort.
What are the must-see attractions in San Jose for travelers arriving from Chicago?
In San Jose, visitors from Chicago will find a range of must-see attractions that blend history, art, and local flavor. The Tech Interactive offers engaging exhibits on technology and innovation, while the Rosicrucian Egyptian Museum provides a unique glimpse into ancient cultures. Additionally, San Pedro Square Market and local neighborhoods with vibrant street art provide authentic experiences. Each attraction is designed to cater to diverse interests, ensuring that travelers can explore cultural landmarks, interactive museums, and local markets during their stay in San Jose.
Which local dishes should travelers from Chicago try when visiting San Jose?
Travelers from Chicago should sample the rich local cuisine in San Jose, which features an array of flavorful Costa Rican dishes. Be sure to try the traditional casado, a plate that typically includes rice, beans, salad, plantains, and your choice of meat. Gallo pinto, a beloved breakfast dish made with rice and beans, is another local staple. Additionally, fresh ceviche and local tropical fruits provide refreshing options. These dishes give visitors an authentic taste of regional flavors while offering a culinary adventure that mirrors San Jose’s vibrant cultural diversity.
What are the best family-friendly activities in San Jose for visitors from Chicago?
Families traveling from Chicago will enjoy a host of family-friendly activities in San Jose that cater to various age groups. The Children’s Museum offers interactive exhibits that are both educational and entertaining. Parks such as La Sabana provide ample space for picnics and outdoor play, while local zoos and botanical gardens serve as engaging learning environments. Additionally, cultural centers and interactive art installations give families a chance to explore regional heritage together. These activities ensure that all family members have a memorable, enjoyable, and educational experience during their San Jose visit.
Are there any budget-friendly hotels in San Jose for travelers from Chicago?
Yes, San Jose offers several budget-friendly hotel options for travelers from Chicago. Budget accommodations generally range from $50 to $100 per night, depending on factors such as location and season. Many of these hotels offer convenient access to public transportation and are situated near key attractions. It is recommended to check recent reviews and booking platforms to secure competitive rates. These affordable lodging choices allow visitors to balance their travel budget while still enjoying comfortable amenities and proximity to local cultural and culinary experiences.
What are the top outdoor activities in San Jose for visitors from Chicago?
Outdoor enthusiasts from Chicago will appreciate the variety of outdoor activities available in San Jose. Options range from exploring local parks like La Sabana and experiencing leisurely bike rides to venturing out on guided hikes in nearby natural reserves. Additionally, day trips to locations like Poás Volcano and La Paz Waterfall Gardens offer breathtaking natural landscapes and wildlife sightings. These activities typically vary in duration from a few hours to full day excursions, providing adventurous travelers with numerous ways to immerse themselves in the region’s natural beauty while enjoying a refreshing escape from urban life.
What are the customs requirements for travelers flying from Chicago to San Jose?
Travelers flying from Chicago to San Jose should be aware of the customs requirements applicable when entering Costa Rica. Typically, visitors need a valid passport with at least six months of validity from the date of entry. U.S. citizens generally do not require a visa for stays of up to 90 days but must complete the necessary arrival forms and adhere to local customs regulations regarding declarations of goods. It is advisable to verify current entry requirements prior to departure as policies may change, ensuring a smooth process upon arrival in San Jose.
What are the best seasonal travel tips for visiting San Jose from Chicago?
For visitors from Chicago planning a trip to San Jose, seasonal travel tips can enhance the experience. During the dry season, typically from mid-December to April, the weather is ideal for outdoor sightseeing and exploring cultural landmarks. In contrast, the rainy season from May to November requires carrying rain gear and planning for potential delays in outdoor activities. Additionally, booking accommodations and tours in advance during peak season can secure better rates and availability. These practical tips enable travelers to adapt their plans according to seasonal changes, ensuring a more comfortable journey.
Is there a specific time of year when San Jose is best visited by travelers from Chicago?
Yes, many visitors from Chicago find that San Jose is best visited during the dry season, which typically spans from mid-December through April. During this period, favorable weather conditions allow for comfortable exploration of outdoor attractions and local landmarks. However, the cooler and less crowded rainy season might also appeal to those seeking off-peak travel deals, even though outdoor activities may be affected. Each season offers a unique travel experience, so consider your activity preferences and seasonal pricing when planning your itinerary for an optimal visit.
What are the unique cultural attractions in San Jose for travelers from Chicago?
San Jose boasts several unique cultural attractions that offer visitors from Chicago an immersive insight into local heritage. Explore vibrant art districts, such as Barrio Escalante, which is home to eclectic galleries and artisan cafes. Cultural institutions like the National Museum and the historic Teatro Nacional reflect the city’s rich history and performing arts tradition. Additionally, local markets and community events provide a taste of everyday life and traditions, ensuring that travelers enjoy a multi-dimensional cultural experience that showcases both historical significance and modern artistic expression.
Are there any local events in San Jose that travelers from Chicago should not miss?
Travelers from Chicago should look out for local events in San Jose that highlight the region’s dynamic cultural scene. Annual festivals such as art fairs, music concerts, and traditional food expos provide an engaging look into local traditions and community life. Events like the International Arts Festival and local culinary celebrations allow visitors to experience regional creativity firsthand. It is advisable to check event calendars ahead of time, as dates and timings might vary seasonally. These lively events serve as a practical way to immerse yourself in San Jose’s vibrant cultural atmosphere during your visit.
What are the best rideshare options from San Jose airport to downtown?
Ridesharing options from San Jose’s airport include popular services such as Uber and Lyft, which consistently offer safe and efficient rides to downtown areas. These platforms generally charge between $15 to $30 and provide real-time fare estimates, making budgeting easier for travelers from Chicago. The convenience of door-to-door transport ensures a smooth transition after a long flight. Additionally, some local rideshare providers may offer competitive pricing and promotions. Always review user ratings and confirm the estimated travel time before booking to ensure the most reliable service during your transfer.
What are the health and safety tips for travelers from Chicago visiting San Jose?
When traveling from Chicago to San Jose, prioritizing health and safety is essential. Ensure that your passport and relevant travel documents are up-to-date and that you have travel insurance covering health emergencies. It is recommended to check for any required vaccinations or health advisories before departure. While San Jose is generally safe, stay aware of your surroundings, especially in crowded areas, and use reputable transportation services. Additionally, keep copies of important documents and local emergency contacts handy. These practical steps help in reducing unexpected issues, ensuring a secure and enjoyable stay in San Jose.
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