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Flight Deals from San Jose Del Cabo to Chicago O Hare Airport from $265

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Stops

  • Nonstop
    from $718
  • Up to 1 stop
    $438

Airlines

  • Aeromexico
    $438
  • Alaska Airlines
    $479
  • American Airlines
    $496
  • Delta Air Lines
    $438
  • Hawaiian Airlines
    $563
  • United Airlines
    $438

Cabin Class

  • Economy
    $438

Departure Airports

  • Los Cabos International Airport
    $438

Arrival Airports

  • Chicago O Hare Airport
    $438

Layover Airports

  • Austin Bergstrom International Airport
    $624
  • Charlotte Douglas International Airport
    $868
  • Dallas Fort Worth International Airport
    $496
  • Denver International Airport
    $438
  • George Bush Intercontinental Houston Airport
    $438
  • Hartsfield Jackson Atlanta International Airport
    $438
  • Licenciado Benito Juarez International Airport
    $613
  • Los Angeles International Airport
    $660
  • Phoenix Sky Harbor International Airport
    $496
  • Salt Lake City International Airport
    $438
  • San Diego International Airport
    $706
  • San Francisco International Airport
    $479
  • Seattle Tacoma International Airport
    $479

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United Airlines Logo
United Airlines

05/19/25

SJD
18h 43m
DEN

05/20/25

ORD
United Airlines Logo
United Airlines

06/02/25

ORD
4h 58m
DEN

06/02/25

SJD
$438
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/28/25

SJD
18h 15m
IAH

05/29/25

ORD
United Airlines Logo
United Airlines

06/11/25

ORD
5h 40m
IAH

06/11/25

SJD
$438
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/28/25

SJD
11h 10m
ATL

05/28/25

ORD
Aeromexico Logo
Aeromexico

06/11/25

ORD
5h 55m
ATL

06/11/25

SJD
$438
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/20/25

SJD
11h 10m
ATL

05/20/25

ORD
Aeromexico Logo
Aeromexico

06/03/25

ORD
6h 13m
ATL

06/03/25

SJD
$438
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/20/25

SJD
11h 10m
ATL

05/20/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/03/25

ORD
5h 34m
SLC

06/03/25

SJD
$438
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/29/25

SJD
11h 13m
DEN

05/30/25

ORD
United Airlines Logo
United Airlines

06/12/25

ORD
11h 8m
IAH

06/13/25

SJD
$438
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/19/25

SJD
23h 31m
SFO

05/20/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/02/25

ORD
28h 18m
SEA

06/03/25

SJD
$479
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

SJD
9h 9m
DFW

05/20/25

ORD
American Airlines Logo
American Airlines

06/03/25

ORD
13h 56m
PHX

06/04/25

SJD
$496
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/10/25

SJD
25h 35m
SFO

05/11/25

ORD
Alaska Airlines Logo
Alaska Airlines

05/24/25

ORD
14h 7m
SFO

05/25/25

SJD
$497
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/20/25

SJD
14h 10m
SEA

05/21/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/03/25

ORD
18h 20m
SEA

06/04/25

SJD
$508
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/19/25

SJD
23h 31m
SFO

05/20/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/02/25

ORD
14h 7m
SFO

06/03/25

SJD
$563
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

SJD
13h
PHX

05/26/25

ORD
American Airlines Logo
American Airlines

06/08/25

ORD
6h 9m
PHX

06/08/25

SJD
$590
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/29/25

SJD
14h 10m
SEA

05/30/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

06/12/25

ORD
14h 53m
SFO

06/13/25

SJD
$605
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

06/01/25

SJD
12h 14m
MEX

06/01/25

ORD
Aeromexico Logo
Aeromexico

06/15/25

ORD
5h 55m
ATL

06/15/25

SJD
$613
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/28/25

SJD
6h 20m
Direct

05/28/25

ORD
American Airlines Logo
American Airlines

06/11/25

ORD
6h 40m
DFW

06/11/25

SJD
$614
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

SJD
10h 24m
AUS

05/29/25

ORD
American Airlines Logo
American Airlines

06/12/25

ORD
14h 6m
PHX

06/13/25

SJD
$624
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/28/25

SJD
11h 9m
DFW

05/28/25

ORD
American Airlines Logo
American Airlines

06/11/25

ORD
16h 4m
PHX

06/12/25

SJD
$624
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/10/25

SJD
10h 29m
ATL

05/10/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/24/25

ORD
9h 40m
MEX

05/24/25

SJD
$648
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/10/25

SJD
12h 27m
LAX

05/10/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
11h 40m
DFW

05/25/25

SJD
$660
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/01/25

SJD
17h 38m
LAX

06/02/25

ORD
American Airlines Logo
American Airlines

06/15/25

ORD
8h 9m
LAX

06/15/25

SJD
$680
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/29/25

SJD
11h 10m
ATL

05/29/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/12/25

ORD
5h 55m
ATL

06/12/25

SJD
$704
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/10/25

SJD
16h 25m
SAN

05/11/25

ORD
Alaska Airlines Logo
Alaska Airlines

05/24/25

ORD
14h 7m
SFO

05/25/25

SJD
$706
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

05/25/25

SJD
17h 54m
MEX

05/25/25

ORD
Aeromexico Logo
Aeromexico

06/08/25

ORD
5h 55m
ATL

06/08/25

SJD
$717
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/10/25

SJD
6h 18m
Direct

05/10/25

ORD
United Airlines Logo
United Airlines

05/24/25

ORD
2h 43m
Direct

05/24/25

SJD
$718
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/02/25

SJD
11h 32m
MEX

05/02/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/16/25

ORD
5h 34m
SLC

05/16/25

SJD
$729
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/10/25

SJD
23h 39m
SEA

05/11/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

05/24/25

ORD
14h 7m
SFO

05/25/25

SJD
$737
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/25/25

SJD
22h 33m
SLC

05/26/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/08/25

ORD
5h 55m
ATL

06/08/25

SJD
$828
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/02/25

SJD
6h 15m
Direct

05/02/25

ORD
American Airlines Logo
American Airlines

05/16/25

ORD
2h 40m
Direct

05/16/25

SJD
$850
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/01/25

SJD
6h 20m
Direct

06/01/25

ORD
American Airlines Logo
American Airlines

06/15/25

ORD
14h 50m
CLT

06/16/25

SJD
$868
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/19/25

SJD
6h 20m
Direct

05/19/25

ORD
American Airlines Logo
American Airlines

06/02/25

ORD
2h 40m
Direct

06/02/25

SJD
$1035
Free cancellation within 83 hours of booking

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

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

Aeromexico Logo
Aeromexico

Sep 23

SJD
13h 35m
MEX

Sep 24

ORD

as low as

$265

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

Aeromexico Logo
Aeromexico

Sep 23

SJD
15h 11m
MEX
ATL

Sep 23

ORD

as low as

$275

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

Aeromexico Logo
Aeromexico

Mar 17

SJD
11h 6m
MSP

Mar 17

ORD

as low as

$312

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

American Airlines Logo
American Airlines

Sep 24

SJD
17h 5m
LAX

Sep 25

ORD

as low as

$312

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

United Airlines Logo
United Airlines

Sep 24

SJD
8h 55m
IAH

Sep 24

ORD

as low as

$322

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

United Airlines Logo
United Airlines

Dec 22

SJD
5h 9m
Direct

Dec 22

ORD

as low as

$322

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

Alaska Airlines Logo
Alaska Airlines

Sep 24

SJD
14h 43m
SEA

Sep 25

ORD

as low as

$327

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

Delta Air Lines Logo
Delta Air Lines

Oct 26

SJD
13h 29m
MEX

Oct 27

ORD

as low as

$369

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

 Logo

Sep 22

SJD
14h 43m
SEA

Sep 23

ORD

as low as

$378

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

 Logo

Nov 2

SJD
10h 10m
SAN

Nov 2

ORD

as low as

$436

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

 Logo

Feb 2

SJD
21h 11m
PDX

Feb 3

ORD

as low as

$441

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

 Logo

Mar 4

SJD
25h 19m
SFO
SAN

Mar 5

ORD

as low as

$475

Frequently Asked Questions

What is the typical flight duration from San Jose Del Cabo to Chicago O Hare Airport?
The typical flight duration from San Jose Del Cabo (SJD) to Chicago O Hare Airport (ORD) generally ranges from 4 to 6 hours for direct flights. However, many travelers may experience connecting flights that extend travel time to between 7 to 9 hours, depending on layover durations and airline schedules. It is wise to plan ahead and consider peak travel seasons that might affect flight availability and duration. Checking updated itineraries will empower travelers to select options that best match their schedule and comfort preferences.
Are there any direct flights from San Jose Del Cabo to Chicago O Hare Airport?
Yes, there are occasionally direct flights from San Jose Del Cabo (SJD) to Chicago O Hare Airport (ORD), although availability can vary by season and airline. Typically, direct flights operate during peak periods and may be less frequent during off-peak times, meaning connecting flights are often more common. Travelers should verify current schedules and book in advance to secure a direct option, if available, ensuring a more streamlined travel experience and reducing overall transit time.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
The best transportation options from Chicago O Hare Airport to downtown Chicago include using the CTA Blue Line train, taxis, and ride-sharing services. The Blue Line offers an economical ride costing between $5 to $10, with a travel time ranging from 40 to 50 minutes depending on waiting times. Taxis or ride-shares such as Uber and Lyft offer faster door-to-door service with costs typically ranging from $30 to $50. Each option has its benefits, based on cost, convenience, and time sensitivity.
What are the must-see attractions in Chicago for travelers arriving from San Jose Del Cabo?
Chicago offers a plethora of attractions for travelers from San Jose Del Cabo, including iconic landmarks like Millennium Park, the Art Institute of Chicago, and Willis Tower. Additionally, attractions such as Navy Pier and the scenic Chicago Riverwalk provide immersive urban experiences. The city’s cultural diversity is also reflected in its neighborhoods and museums. Each site offers a mix of art, architecture, and local history, making it essential for visitors to allocate sufficient time to explore and enjoy these enriching experiences.
Which local dishes should travelers from San Jose Del Cabo try when visiting Chicago?
Travelers from San Jose Del Cabo should definitely try Chicago’s famous deep-dish pizza, which is renowned for its hearty, layered construction and robust flavor. In addition, sampling a Chicago-style hot dog—with its signature toppings—and an Italian beef sandwich are must-dos for an authentic taste. Local diners and food trucks offer a range of culinary delights that reflect the city’s vibrant multicultural scene. Exploring a variety of neighborhoods may reveal hidden gems where each dish is prepared with unique local twists.
Are there any family-friendly activities in Chicago for visitors from San Jose Del Cabo?
Yes, Chicago boasts many family-friendly activities for visitors from San Jose Del Cabo. Families can explore interactive exhibits at the Museum of Science and Industry and enjoy the educational displays at the Field Museum or Shedd Aquarium. Millennium Park and Lincoln Park Zoo offer outdoor spaces ideal for youngsters and parents alike. Additionally, the city’s numerous parks and river tours provide fun, engaging experiences. Planning a mix of cultural, educational, and recreational activities ensures that every family member finds something appealing during their visit.
What are the best budget-friendly hotels in Chicago for travelers from San Jose Del Cabo?
There are several budget-friendly hotel options in Chicago that appeal to travelers from San Jose Del Cabo. Areas like the Loop and River North offer affordable accommodations with prices typically ranging from $80 to $150 per night. These hotels often include essential amenities such as free WiFi and complimentary breakfast, making them ideal for cost-conscious travelers. Additionally, hostels and boutique hotels in neighborhoods like Wicker Park or Logan Square provide great alternatives. It is advisable to check recent reviews and book early to secure the best deal near public transportation.
What cultural etiquette should travelers from San Jose Del Cabo be aware of when visiting Chicago?
Travelers from San Jose Del Cabo visiting Chicago should be aware that the culture emphasizes punctuality, polite conversation, and tipping customs. In many service-based establishments, a tip ranging from 15% to 20% is standard. Additionally, it is courteous to maintain personal space and wait in orderly lines, especially in busy tourist areas. When dining or socializing, conversations tend to be direct yet respectful. Understanding these norms can enhance interactions and ensure a smooth and respectful experience while navigating social and professional settings in Chicago.
What are the top shopping areas in Chicago for souvenirs that travelers from San Jose Del Cabo should explore?
Chicago offers shoppers several prime areas to explore for souvenirs and unique finds, particularly appealing to travelers from San Jose Del Cabo. The Magnificent Mile features upscale stores and boutiques, providing a mix of high-quality merchandise and local specialties. Nearby, State Street offers accessible options for unique souvenirs and regional handicrafts. Neighborhood markets and local artisan shops in areas like Wicker Park also cater to those seeking authentic, handcrafted items. Exploring these shopping districts allows visitors to collect memorabilia that capture the cultural essence of Chicago.
Is there a specific time of year when Chicago is best visited by travelers from San Jose Del Cabo?
Yes, the optimal time to visit Chicago for travelers from San Jose Del Cabo is typically during the late spring to early fall months, spanning from May to October. During this period, the weather is generally pleasant with temperatures ranging from 65°F to 85°F, ideal for outdoor activities and sightseeing. These months also feature various local festivals and outdoor events that capture the city’s vibrant energy. However, travelers should be prepared for occasional crowds, especially during peak summer months, and consider booking accommodations in advance.
What are the health and safety precautions travelers from San Jose Del Cabo should consider when visiting Chicago?
Travelers from San Jose Del Cabo should take standard health and safety precautions when visiting Chicago. This includes monitoring weather updates, securing personal belongings in crowded areas, and being aware of local emergency numbers. It is also wise to carry travel insurance and keep updated on any current public health advisories. Additionally, if visiting during peak tourist seasons, be cautious of pickpockets in busy zones. Regularly sanitizing hands, planning routes in advance, and staying in well-reviewed accommodations are practical steps to ensure a secure and comfortable trip.
Are there any seasonal events in Chicago that travelers from San Jose Del Cabo should not miss?
Yes, Chicago hosts several seasonal events that are must-see for travelers from San Jose Del Cabo. During the summer, events such as the Celebrate America fireworks and the Chicago Air and Water Show offer spectacular displays. In the fall, the city’s cultural festivals and food events celebrate local cuisine and art. Winter months bring festive holiday markets and ice-skating at Millennium Park. These events provide unique insights into local traditions and create memorable experiences. Checking an events calendar before your visit will help tailor your itinerary to include seasonal highlights.
What unique airport amenities can travelers expect at Chicago O Hare Airport?
Travelers arriving at Chicago O Hare Airport can enjoy a variety of unique amenities designed to enhance their experience. The airport features an array of dining options, ranging from quick-service eateries to upscale restaurants, with prices generally ranging from $10 to $30 for meals. Complimentary WiFi throughout the terminals, modern lounges, and retail shops are available for shopping enthusiasts. Additionally, the airport offers excellent customer service desks and charging stations, ensuring convenience and comfort for both short layovers and prolonged wait times. These amenities add an extra layer of convenience and enjoyment to your travel experience.
What are the best options for public transportation in Chicago for visitors arriving from San Jose Del Cabo?
The best public transportation options in Chicago for visitors from San Jose Del Cabo include the CTA train and bus systems. The CTA Blue Line, which connects Chicago O Hare Airport to downtown, is highly efficient, with fares ranging from $3 to $5 and travel times of around 40 to 50 minutes. Additionally, local buses offer comprehensive routes throughout the city at similar costs. For those seeking a blend of convenience and economy, purchasing a multi-day pass may be worthwhile. These options provide reliable, affordable mobility to explore the city’s various attractions.
What are the customs requirements for travelers flying from San Jose Del Cabo to Chicago O Hare Airport?
Travelers flying from San Jose Del Cabo to Chicago O Hare Airport must adhere to standard U.S. customs and immigration regulations. This includes presenting a valid passport and, where applicable, a visa or ESTA authorization if the traveler is eligible under the Visa Waiver Program. Upon arrival, you may be required to complete customs declaration forms detailing your items and duration of stay. It is advisable to declare any high-value items and be ready to answer questions about your travel purpose. Keeping your documents organized and reviewing updated customs guidelines before departure ensures a smoother entry process.

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