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Flight Deals from Chicago O Hare Airport to San Jose Del Cabo from $192

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Stops

  • Nonstop
    from $567
  • Up to 1 stop
    $414
  • Up to 2 stops
    $419

Airlines

  • Aeromexico
    $414
  • Alaska Airlines
    $435
  • American Airlines
    $429
  • Delta Air Lines
    $414
  • Frontier Airlines
    $471
  • Hawaiian Airlines
    $463
  • United Airlines
    $503

Cabin Class

  • Economy
    $414

Departure Airports

  • Chicago O Hare Airport
    $414

Arrival Airports

  • Los Cabos International Airport
    $414

Layover Airports

  • Austin Bergstrom International Airport
    $429
  • Dallas Fort Worth International Airport
    $485
  • Denver International Airport
    $471
  • George Bush Intercontinental Houston Airport
    $503
  • Hartsfield Jackson Atlanta International Airport
    $419
  • Licenciado Benito Juarez International Airport
    $414
  • Los Angeles International Airport
    $485
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $575
  • Norman Y. Mineta San Jose International Airport
    $601
  • Phoenix Sky Harbor International Airport
    $475
  • Portland International Airport
    $773
  • Salt Lake City International Airport
    $424
  • San Diego International Airport
    $658
  • San Francisco International Airport
    $435
  • Seattle Tacoma International Airport
    $435

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Aeromexico Logo
Aeromexico

05/29/25

ORD
9h 29m
MEX

05/29/25

SJD
Aeromexico Logo
Aeromexico

06/25/25

SJD
11h 30m
MEX

06/25/25

ORD
$414
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/31/25

ORD
9h 40m
MEX

05/31/25

SJD
Delta Air Lines Logo
Delta Air Lines

06/14/25

SJD
11h 30m
MEX

06/14/25

ORD
$414
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/31/25

ORD
9h 40m
MEX

05/31/25

SJD
Aeromexico Logo
Aeromexico

06/25/25

SJD
11h 30m
MEX

06/25/25

ORD
$414
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

06/10/25

ORD
10h 32m
ATL
MEX

06/10/25

SJD
Aeromexico Logo
Aeromexico

06/14/25

SJD
11h 30m
MEX

06/14/25

ORD
$419
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/29/25

ORD
9h 29m
MEX

05/29/25

SJD
Delta Air Lines Logo
Delta Air Lines

06/12/25

SJD
9h 27m
SLC

06/12/25

ORD
$424
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/13/25

ORD
5h 55m
ATL

06/13/25

SJD
Delta Air Lines Logo
Delta Air Lines

06/20/25

SJD
9h 27m
SLC

06/20/25

ORD
$429
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/12/25

ORD
11h 24m
AUS

06/13/25

SJD
American Airlines Logo
American Airlines

06/16/25

SJD
11h 50m
AUS

06/16/25

ORD
$429
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

06/04/25

ORD
12h 13m
ATL
MEX

06/04/25

SJD
Aeromexico Logo
Aeromexico

06/10/25

SJD
11h 22m
ATL

06/10/25

ORD
$429
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/29/25

ORD
14h 7m
SFO

05/30/25

SJD
Alaska Airlines Logo
Alaska Airlines

06/12/25

SJD
14h 3m
SEA

06/13/25

ORD
$435
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/09/25

ORD
30h 18m
SEA

06/10/25

SJD
Alaska Airlines Logo
Alaska Airlines

06/13/25

SJD
14h 3m
SEA

06/14/25

ORD
$451
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/06/25

ORD
14h 7m
SFO

06/07/25

SJD
Alaska Airlines Logo
Alaska Airlines

06/10/25

SJD
14h 10m
SEA

06/11/25

ORD
$455
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/29/25

ORD
14h 7m
SFO

05/30/25

SJD
Hawaiian Airlines Logo
Hawaiian Airlines

06/12/25

SJD
14h 3m
SEA

06/13/25

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

05/31/25

ORD
5h 9m
DEN

05/31/25

SJD
Frontier Airlines Logo
Frontier Airlines

06/14/25

SJD
11h 53m
DEN

06/14/25

ORD
$471
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

ORD
13h 56m
PHX

05/30/25

SJD
American Airlines Logo
American Airlines

06/12/25

SJD
6h 30m
Direct

06/12/25

ORD
$475
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/15/25

ORD
4h 25m
DFW

06/15/25

SJD
American Airlines Logo
American Airlines

06/19/25

SJD
10h 22m
PHX

06/19/25

ORD
$485
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/13/25

ORD
6h 9m
PHX

06/13/25

SJD
American Airlines Logo
American Airlines

06/17/25

SJD
9h 23m
DFW

06/17/25

ORD
$485
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/30/25

ORD
15h 47m
PHX

05/31/25

SJD
American Airlines Logo
American Airlines

06/13/25

SJD
10h 55m
LAX

06/13/25

ORD
$485
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/12/25

ORD
11h 8m
IAH

06/13/25

SJD
United Airlines Logo
United Airlines

06/16/25

SJD
20h 41m
DEN

06/17/25

ORD
$503
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/10/25

ORD
12h 18m
SEA
LAX

06/10/25

SJD
Alaska Airlines Logo
Alaska Airlines

06/17/25

SJD
20h 30m
SEA

06/18/25

ORD
$513
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/31/25

ORD
2h 43m
Direct

05/31/25

SJD
United Airlines Logo
United Airlines

06/14/25

SJD
9h 35m
DEN

06/15/25

ORD
$514
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/27/25

ORD
18h 20m
SEA

05/28/25

SJD
Hawaiian Airlines Logo
Hawaiian Airlines

06/10/25

SJD
14h 10m
SEA

06/11/25

ORD
$518
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/06/25

ORD
11h 8m
IAH

06/07/25

SJD
United Airlines Logo
United Airlines

06/10/25

SJD
11h 30m
IAH

06/10/25

ORD
$519
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/31/25

ORD
2h 43m
Direct

05/31/25

SJD
United Airlines Logo
United Airlines

06/14/25

SJD
6h 18m
Direct

06/14/25

ORD
$567
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/12/25

ORD
12h 13m
MSP
MEX

06/12/25

SJD
Delta Air Lines Logo
Delta Air Lines

06/16/25

SJD
11h 25m
MEX

06/16/25

ORD
$575
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/04/25

ORD
12h 27m
SEA
SJC

06/04/25

SJD
Alaska Airlines Logo
Alaska Airlines

07/02/25

SJD
18h 19m
LAX
SEA

07/03/25

ORD
$601
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/04/25

ORD
12h 27m
SEA
SJC

06/04/25

SJD
Alaska Airlines Logo
Alaska Airlines

07/02/25

SJD
22h 56m
SFO

07/03/25

ORD
$622
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/01/25

ORD
16h 13m
SFO
SAN

06/02/25

SJD
Alaska Airlines Logo
Alaska Airlines

06/25/25

SJD
14h 3m
SEA

06/26/25

ORD
$658
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/14/25

ORD
2h 43m
Direct

06/14/25

SJD
United Airlines Logo
United Airlines

06/21/25

SJD
6h 18m
Direct

06/21/25

ORD
$677
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/31/25

ORD
7h 52m
PDX

05/31/25

SJD
Hawaiian Airlines Logo
Hawaiian Airlines

06/14/25

SJD
11h 22m
PDX

06/14/25

ORD
$773
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/01/25

ORD
16h 13m
SAN

06/02/25

SJD
Alaska Airlines Logo
Alaska Airlines

06/25/25

SJD
14h 3m
SEA

06/26/25

ORD
$780
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago O Hare Airport to San Jose Del Cabo

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

American Airlines Logo
American Airlines

Jun 12

ORD
11h 15m
DFW

Jun 13

SJD

as low as

$192

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Alaska Airlines Logo
Alaska Airlines

Jul 29

ORD
15h 35m
SEA

Jul 30

SJD

as low as

$192

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Alaska Airlines Logo
Alaska Airlines

May 30

ORD
14h 7m
SFO

May 31

SJD

as low as

$192

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Frontier Airlines Logo
Frontier Airlines

May 31

ORD
5h 9m
DEN

May 31

SJD

as low as

$198

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Hawaiian Airlines Logo
Hawaiian Airlines

Jun 3

ORD
18h 20m
SEA

Jun 4

SJD

as low as

$212

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Aeromexico Logo
Aeromexico

Aug 20

ORD
9h 58m
MEX

Aug 20

SJD

as low as

$215

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

American Airlines Logo
American Airlines

Jul 18

ORD
2h 40m
Direct

Jul 18

SJD

as low as

$215

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Aeromexico Logo
Aeromexico

Jul 1

ORD
12h 11m
ATL
MEX

Jul 1

SJD

as low as

$220

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

American Airlines Logo
American Airlines

Jun 15

ORD
13h 30m
AUS

Jun 16

SJD

as low as

$220

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

Delta Air Lines Logo
Delta Air Lines

May 25

ORD
5h 34m
SLC

May 25

SJD

as low as

$220

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

American Airlines Logo
American Airlines

Jul 15

ORD
14h 24m
CLT

Jul 16

SJD

as low as

$220

Chicago, US (CHI) - San Jose del Cabo, MX (SJD)

American Airlines Logo
American Airlines

Jun 4

ORD
5h 8m
PHX

Jun 4

SJD

as low as

$220

Frequently Asked Questions

What is the typical flight duration from Chicago O Hare Airport to San Jose Del Cabo?
The typical flight duration from Chicago O Hare (ORD) to San Jose Del Cabo (SJD) generally ranges between 4 to 6 hours. Direct flights, when available, can be close to 4 hours, but most itineraries include layovers which extend the total travel time nearer to 6 hours. Be sure to consider seasonal variations and weather conditions, as these factors may affect the flight duration. Planning ahead by checking with carriers for the latest schedule details will help ensure a smooth experience during your journey.
Are there any direct flights from Chicago O Hare Airport to San Jose Del Cabo?
Direct flights between Chicago O Hare and San Jose Del Cabo are not consistently available throughout the year. At times, seasonal or special service routes offer non-stop options, but most itineraries include a layover in a connecting hub such as Dallas, Los Angeles, or Phoenix. Availability tends to fluctuate based on demand and seasonal scheduling. It is advisable to check current airline schedules to see if any direct flights are being offered during your planned travel dates.
What are the best transportation options from San Jose Del Cabo airport to downtown or popular tourist attractions?
Upon arrival, viable transportation options include shared shuttles, private taxis, and rental cars. Shared shuttles generally cost between $20 to $35 per person, while taxis typically range from $30 to $50 depending on distance and time of day. Rental cars may cost anywhere from $25 to $60 per day, offering maximum flexibility for exploring local attractions. Additionally, some hotels provide complimentary transfers, so it’s worthwhile to inquire at the time of booking. These options help ensure convenient ground travel to downtown areas and nearby points of interest.
What are the must-see attractions in San Jose Del Cabo for travelers arriving from Chicago O Hare Airport?
Key attractions include the historic downtown district with its vibrant art galleries, local boutiques, and the charming Mission of San José del Cabo Church. Visitors should also explore Plaza Mijares, where local markets and cultural displays occur regularly. Nearby scenic beaches offering water sports and relaxation add to the appeal. To enrich your visit further, sample authentic local cuisine at recommended eateries. These experiences collectively offer a blend of cultural, historical, and natural attractions that enhance the journey after departing from Chicago O Hare.
What are the most affordable dining options in San Jose Del Cabo for travelers from Chicago O Hare Airport?
Affordable dining options abound in local taquerias, street food stalls, and casual family-run restaurants where meals typically cost between $5 to $15. These establishments serve traditional dishes, including tacos, quesadillas, and fresh seafood. Neighborhood cafés and market food courts offer a mix of quick bites and sit-down meals, which are both economical and flavorful. Exploring local food stands can provide an authentic culinary experience without straining your budget, ensuring you enjoy an immersive taste of local flavors shortly after arriving from Chicago O Hare.
What cultural customs should travelers from Chicago O Hare Airport be aware of when visiting San Jose Del Cabo?
When visiting, it’s important to greet locals with a friendly 'hola' and engage in polite, relaxed conversation. Punctuality tends to be more flexible compared to U.S. standards, especially during social gatherings. Modest dress is recommended when visiting sacred sites or churches, and a customary tip ranging from 10% to 15% is appreciated at eateries and service spots. Embracing these local norms helps bridge cultural differences and enriches your travel experience, ensuring a respectful and enjoyable visit to San Jose Del Cabo.
Are there any family-friendly activities in San Jose Del Cabo for travelers from Chicago O Hare Airport?
Yes, the destination offers numerous family-friendly activities that cater to all ages. Gentle beaches allow kids to safely enjoy the waves, while resorts often provide dedicated children’s programs, including pool games and interactive workshops. Engaging activities such as guided eco-tours in nearby natural parks, local art exhibits, and cultural festivals add educational and fun elements. These varied options ensure families can partake in both relaxation and adventure, making the transition from Chicago O Hare to this vibrant locale smooth and enjoyable for every member.
What are the best shopping areas for souvenirs in San Jose Del Cabo for visitors from Chicago O Hare Airport?
The best shopping experiences are found in the local downtown area, where artisan boutiques and craft markets offer unique souvenirs. Small galleries and local vendor stalls present hand-made items, ranging from traditional crafts to modern art pieces, with prices typically between $5 to $50. This setting provides a wonderful opportunity to purchase authentic mementos while engaging with local culture. Whether you’re seeking unique jewelry, handcrafted décor, or local art, exploring these shopping areas can make for both a practical and enriching stop after your flight from Chicago O Hare.
What health precautions should travelers from Chicago O Hare Airport consider before visiting San Jose Del Cabo?
Travelers should ensure routine vaccinations are up-to-date and consider additional shots like hepatitis A or typhoid based on regional advice. It is wise to purchase travel insurance—typically ranging from $50 to $150—to cover medical emergencies. Drinking bottled or filtered water and practicing good hygiene will help avoid gastrointestinal issues common in new environments. Additionally, bring along insect repellent during warmer months to prevent mosquito bites. Keeping abreast of any local health advisories or COVID-19 guidelines will help ensure a safe and healthy journey.
What are the best seasonal travel tips for visiting San Jose Del Cabo from Chicago O Hare Airport?
Travel during the shoulder seasons—late spring, early summer, or early fall—to benefit from milder weather, fewer crowds, and lower airfares and hotel rates, often reduced by 10% to 30% compared to peak periods. These times also feature local festivals and culinary events that enhance the cultural experience. Packing layers and sun protection is advisable as temperatures can fluctuate. Research seasonal events and weather forecasts ahead of time to plan your activities, ensuring you make the most out of your visit after departing from Chicago O Hare.
Is there a specific time of year when San Jose Del Cabo is best visited by travelers from Chicago O Hare Airport?
Yes, the optimal travel period typically extends from October through April. During these months, cooler and more comfortable temperatures make sightseeing and outdoor activities very pleasant. While hotel and airfare prices may vary, many travelers find that the weather and local events significantly enhance their overall experience. This period features fewer extreme weather conditions and offers cultural events and festivals that enrich the visit. Planning your trip during these months allows for a balanced itinerary that suits various interests after leaving Chicago O Hare.
What are the top outdoor activities in San Jose Del Cabo for travelers arriving from Chicago O Hare Airport?
Outdoor enthusiasts can enjoy a wide spectrum of activities including beach outings, snorkeling, and diving among the vibrant coral reefs. Kayaking and paddleboarding offer additional water sports experiences, while guided eco-tours or hiking in nearby nature reserves provide scenic views and adventure. Many of these activities range in price from $20 to $100 depending on duration and rental fees. These varied options ensure visitors who have flown from Chicago O Hare can indulge in both relaxing leisure and energizing outdoor pursuits during their stay.
What airport amenities are available at San Jose Del Cabo for travelers arriving from Chicago O Hare Airport?
The airport features several modern amenities designed for convenience, such as a variety of dining options from fast food to full-service restaurants and a duty-free shopping area offering local souvenirs. Free Wi-Fi, ATMs, and reliable currency exchange services ensure operational ease. Additional services include rental car counters and information desks to assist with ground transportation arrangements. These well-maintained facilities guarantee that travelers from Chicago O Hare enjoy a comfortable and efficient transition from the plane to local transportation and accommodation.
What are the customs requirements for travelers flying from Chicago O Hare Airport to San Jose Del Cabo?
Travelers are required to present a valid passport and, if applicable, a tourist visa upon entry. Customs regulations allow duty-free purchases, but items exceeding the designated value—typically between $200 and $500—must be declared. It is important to be familiar with both U.S. exit and Mexican entry procedures to avoid delays. Maintaining organized documentation of your travel documents and any high-value purchases is recommended. Following these guidelines will help ensure a smoother transition and compliance with customs requirements on your journey.
Are there any unique cultural festivals in San Jose Del Cabo that travelers from Chicago O Hare Airport should not miss?
Yes, the region hosts distinct cultural festivals that celebrate local art, music, and cuisine. Notable events include the monthly Art Walk, which transforms the town’s historic district with exhibitions and live performances, and seasonal food festivals featuring traditional culinary delights. These festivals provide immersive experiences that showcase regional heritage and foster community interaction. Planning your visit around these events not only enhances your cultural insight but also adds memorable, hands-on experiences. Checking local event calendars before your trip will ensure you enjoy these unique attractions after departing from Chicago O Hare.

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