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Flight Deals from Chicago 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
  • Southwest Airlines
    $537
  • United Airlines
    $503

Cabin Class

  • Economy
    $414

Departure Airports

  • Chicago Midway Airport
    $419
  • 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
  • Kansas City International Airport
    $551
  • Licenciado Benito Juarez International Airport
    $414
  • Los Angeles International Airport
    $485
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $575
  • Nashville International Airport
    $579
  • Norman Y. Mineta San Jose International Airport
    $601
  • Phoenix Sky Harbor International Airport
    $475
  • Salt Lake City International Airport
    $424
  • San Francisco International Airport
    $435
  • Seattle Tacoma International Airport
    $435
  • William P Hobby Airport
    $537

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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

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
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
Aeromexico Logo
Aeromexico

06/10/25

MDW
5h 30m
ATL

06/10/25

SJD
Aeromexico Logo
Aeromexico

06/14/25

SJD
11h 30m
MEX

06/14/25

MDW
$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
Aeromexico Logo
Aeromexico

06/04/25

ORD
12h 13m
ATL
MEX

06/04/25

SJD
Aeromexico Logo
Aeromexico

06/12/25

SJD
11h 23m
ATL

06/12/25

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
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

06/13/25

SJD
14h 3m
SEA

06/14/25

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

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
American Airlines Logo
American Airlines

06/08/25

ORD
11h 20m
DFW

06/09/25

SJD
American Airlines Logo
American Airlines

06/21/25

SJD
11h 50m
AUS

06/21/25

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

06/14/25

ORD
12h 51m
PHX

06/15/25

SJD
American Airlines Logo
American Airlines

06/21/25

SJD
11h 50m
AUS

06/21/25

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

05/31/25

ORD
12h 50m
IAH

06/01/25

SJD
United Airlines Logo
United Airlines

06/14/25

SJD
9h 35m
DEN

06/15/25

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

06/12/25

MDW
14h 20m
AUS

06/13/25

SJD
Southwest Airlines Logo
Southwest Airlines

06/16/25

SJD
12h
HOU

06/17/25

MDW
$537
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

06/12/25

MDW
11h 5m
MCI
AUS

06/13/25

SJD
Southwest Airlines Logo
Southwest Airlines

06/16/25

SJD
12h
HOU

06/17/25

MDW
$551
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
Southwest Airlines Logo
Southwest Airlines

06/12/25

MDW
11h 5m
MCI
AUS

06/13/25

SJD
Southwest Airlines Logo
Southwest Airlines

06/16/25

SJD
12h 35m
PHX
BNA

06/17/25

MDW
$579
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

Top Deals on flights from Chicago to San Jose Del Cabo

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

American Airlines Logo
American Airlines

Jun 12

ORD
15h
DFW

Jun 13

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)

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)

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
16h 27m
SEA

Jun 4

SJD

as low as

$212

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

Aeromexico Logo
Aeromexico

Aug 14

ORD
9h 17m
MEX

Aug 14

SJD

as low as

$215

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

American Airlines Logo
American Airlines

Jul 15

ORD
2h 40m
Direct

Jul 15

SJD

as low as

$215

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

Aeromexico Logo
Aeromexico

Jun 7

ORD
12h 43m
ATL
MEX

Jun 7

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)

Aeromexico Logo
Aeromexico

Jun 15

ORD
5h 55m
ATL

Jun 15

SJD

as low as

$220

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

Aeromexico Logo
Aeromexico

May 5

ORD
11h 55m
MSP
MEX

May 5

SJD

as low as

$220

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

American Airlines Logo
American Airlines

Jul 24

ORD
13h 11m
AUS

Jul 25

SJD

as low as

$220

Frequently Asked Questions

What is the typical flight duration from Chicago to San Jose Del Cabo?
The typical flight duration from Chicago to San Jose Del Cabo generally ranges from 4 to 6 hours. Direct flights, when available, often take closer to 4 to 5 hours, while flights with layovers may extend the journey to about 6 hours. Variations depend on the route, weather conditions, and the airline. For a smooth travel experience, consider checking real-time flight durations and booking with flexible schedules to accommodate any delays.
Are there any direct flights from Chicago to San Jose Del Cabo?
Yes, there are direct flights available from Chicago to San Jose Del Cabo, particularly during peak travel seasons. However, availability can vary based on the time of year and seasonal demand. Direct flights tend to offer a more streamlined journey, typically saving time compared to connecting flights. It is advisable to compare schedules and prices as direct flight options can range in frequency and cost, ensuring you find a service that fits your travel plans.
What are the best transportation options from San Jose Del Cabo airport to downtown or popular tourist attractions?
At San Jose Del Cabo airport, several transportation options balance comfort and cost. Taxis and rideshare services like Uber typically offer door-to-door service with fares ranging from $25 to $50, depending on the destination. Shared shuttles and pre-arranged hotel transfers are also available, often saving money when traveling with a group. Additionally, some travelers opt for rental cars to freely explore surrounding areas. It is beneficial to compare rates and pre-book services for convenience once arriving from Chicago.
What are the must-see attractions in San Jose Del Cabo for travelers arriving from Chicago?
Must-see attractions in San Jose Del Cabo include its vibrant art district, historic mission, and quaint town center with colonial architecture. In addition, visitors can explore scenic beaches, local markets, and cultural galleries that showcase regional art and handicrafts. A stroll along the marina offers dining and shopping opportunities, while nearby natural reserves provide opportunities for outdoor activities. This blend of culture, art, and nature appeals to those traveling from Chicago seeking both relaxation and enrichment during their visit.
What are the top dining options in San Jose Del Cabo that travelers from Chicago should try?
Top dining options in San Jose Del Cabo offer a mix of authentic regional cuisine and refined international dishes. Travelers from Chicago should explore local establishments serving fresh seafood, traditional Mexican fare, and fusion dishes. Upscale restaurants near the waterfront, such as those offering open-air dining with ocean views, provide a unique experience, while casual taquerias and family-run eateries offer budget-friendly choices. Meals typically range from $15 to $50 per person, allowing visitors to enjoy diverse culinary adventures regardless of taste or budget.
Is there a specific time of year when San Jose Del Cabo is best visited by travelers from Chicago?
Yes, the best time to visit San Jose Del Cabo is generally between November and April when the weather is pleasantly warm and the humidity is lower. This season offers comfortable conditions for beach activities and cultural exploration, making it an attractive alternative for those escaping colder weather in Chicago. Peak tourist season may bring slightly higher prices, so planning early or traveling during the shoulder months can provide a balanced experience of pleasant weather, manageable crowds, and cost-effective options for accommodations and activities.
What are the customs requirements for travelers flying from Chicago to San Jose Del Cabo?
Travelers from Chicago flying to San Jose Del Cabo must ensure a valid passport and may require a tourist visa depending on their nationality and trip duration. Customs guidelines typically necessitate declaration of any goods purchased abroad that exceed duty-free allowances, and travelers should be aware of restrictions on certain items like alcohol and electronics. It is recommended to review both U.S. exit and Mexican entry requirements before departure. Staying informed about changing regulations via official government websites will help avoid any last-minute surprises at customs.
What are the best family-friendly activities in San Jose Del Cabo for visitors from Chicago?
Family-friendly activities in San Jose Del Cabo cater to all ages with a range of engaging options. Enjoy relaxing beach days, gentle water sports, and interactive cultural tours that explore local art and history. Families can also explore eco-parks and wildlife sanctuaries offering educational experiences. Additionally, organized excursions such as boat trips or guided village tours provide insights into the local heritage. With diverse options that balance adventure and relaxation, visitors from Chicago can tailor their itinerary to keep all family members entertained in a safe, vibrant environment.
Are there any local festivals in San Jose Del Cabo that travelers from Chicago should not miss?
Yes, local festivals in San Jose Del Cabo offer vibrant experiences that should not be missed. Annual events such as art festivals, culinary fairs, and music celebrations capture the cultural essence of the region. Events like the San Jose Del Cabo Cultural Festival typically feature live music, local crafts, and traditional dance performances. For travelers from Chicago, participating in these festivities provides an immersive way to experience the local culture while enjoying seasonal festivities. Check local tourism websites ahead of time for event dates and detailed programs.
What are the most affordable dining options in San Jose Del Cabo for travelers from Chicago?
Affordable dining options in San Jose Del Cabo include vibrant local taquerias, small family-run eateries, and local street food stalls offering authentic meals at economical prices. Meals in these venues generally range from $8 to $20. These establishments often serve traditional Mexican dishes such as tacos, burritos, and fresh ceviche. Travelers from Chicago can enjoy an authentic taste of regional cuisine without breaking the bank. It is recommended to ask locals for recommendations as these hidden gems often provide genuine culinary experiences and great value.
What are the best car rental options in San Jose Del Cabo for travelers from Chicago?
Car rental options in San Jose Del Cabo include both international chains and reputable local agencies, offering a range of vehicles from compact cars to SUVs. Daily rental rates typically range from $40 to $70, depending on the vehicle class and rental duration. Rental services are available at the airport, making pick-up and drop-off convenient upon arrival from Chicago. It is advisable to compare prices, read reviews, and confirm insurance coverage details in advance to ensure a hassle-free travel experience while exploring the broader region at your own pace.
What are the unique cultural experiences in San Jose Del Cabo for travelers arriving from Chicago?
Unique cultural experiences in San Jose Del Cabo include exploring its historic district with art galleries, local artisan workshops, and traditional cooking classes. Visitors can immerse themselves in indigenous crafts and music performances that bring the region’s heritage to life. Interactive tours, such as visits to local artisans’ studios and historical landmarks, offer deeper insights into the local traditions. This rich cultural tapestry is an excellent complement to a relaxing beach vacation, providing a varied and engaging itinerary that appeals to travelers from Chicago seeking authenticity and immersive local experiences.
What are the best places to shop for souvenirs in San Jose Del Cabo for travelers from Chicago?
Shopping for souvenirs in San Jose Del Cabo is a delight, with a variety of markets and boutique shops offering unique handcrafted items and local art. Visit the central market and artisan shops where you can find traditional Mexican textiles, ceramics, and locally made jewelry. These purchases typically range from $10 to $50, depending on the item. The vibrant shopping areas provide an opportunity to interact with local artisans and discover authentic keepsakes. Travelers from Chicago should reserve time to explore these areas, as they offer memorable insights into regional culture and craftsmanship.
Are there any health precautions travelers from Chicago should be aware of before visiting San Jose Del Cabo?
Yes, health precautions for visitors from Chicago include ensuring that routine immunizations are up-to-date and considering additional vaccines such as Hepatitis A or Typhoid based on individual risk. Given the warm climate, it is important to stay hydrated, use sun protection, and be cautious with street food by choosing vendors with high hygiene standards. Travelers should also check for any local advisories or regional outbreaks and consider travel insurance that covers medical emergencies. Consulting with a healthcare provider before departure can help tailor specific precautions for a safe visit.
What are the best seasonal travel tips for visiting San Jose Del Cabo from Chicago?
Seasonal travel tips for visiting San Jose Del Cabo include planning for varying weather conditions. Winter months, from November to April, offer mild temperatures ideal for outdoor activities, while summer may be hotter and more humid, suggesting a focus on early morning excursions and indoor activities during midday. Packing lightweight clothing, sun protection, and comfortable footwear is essential. Travelers from Chicago should also consider booking accommodations and activities well in advance during peak season, and explore local events or festivals that add cultural insights to the vacation.

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