Cheap flights from San José del Cabo to Chicago

Flights overview

Useful information for finding cheap flights from San José del Cabo to Chicago and booking your next trip
Cheapest round-trip flights $322
Volaris 1 stop 9 hr Fri, May 1 — Thu, May 7
The cheapest round-trip flight from San José del Cabo to Chicago is currently $322
Cheapest one-way flight $202
Volaris 1 stop 12 hr Wed, Mar 4
The cheapest one-way flight from San José del Cabo to Chicago is currently $202
Cheapest nonstop flights $377
American Nonstop 5 hr Fri, May 1 — Sun, May 10
The cheapest nonstop round-trip flight from San José del Cabo to Chicago is currently $377
Last-minute weekend getaway $463
Volaris 1 stop 12 hr Fri, Feb 6 — Sun, Feb 8
The cheapest last-minute weekend getaway from San José del Cabo to Chicago is currently $463
Cheapest business class flights $1,032
Frontier 1 stop 10 hr Sat, Mar 7 — Fri, Mar 13
The cheapest business class round-trip flight from San José del Cabo to Chicago is currently $1,032
Fastest flight 3 hr 55 min The fastest nonstop flight from San José del Cabo to Chicago takes 3 hr 55 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from San José del Cabo to Chicago is typically February. The most expensive month to fly is typically June.
February
Cheapest
Typical prices: $350–490
June
Most expensive
Typical prices: $390–520

Popular airlines from San José del Cabo to Chicago

  • Southwest
    from $387
    Typical price: $480–810
    1022 weekly connecting flights
    SJD - MDW, ORD Every day
  • American
    Nonstop
    from $377
    Typical price: $430–720
    12 weekly nonstop flights
    SJD - ORD Every day
    309 weekly connecting flights
    SJD - ORD Every day
  • United
    Nonstop
    from $379
    Typical price: $430–750
    7 weekly nonstop flights
    SJD - ORD Every day
    188 weekly connecting flights
    SJD - ORD Every day
  • Delta
    from $378
    Typical price: $445–920
    250 weekly connecting flights
    SJD - MDW, ORD Every day
  • Volaris
    from $322
    Typical price: $385–650
    50 weekly connecting flights
    SJD - MDW, ORD Every day
  • Aeromexico
    from $376
    Typical price: $510–1,050
    23 weekly connecting flights
    SJD - ORD Every day

Popular airports near San José del Cabo

  • Los Cabos International Airport (SJD)
    San José del Cabo Mexico 22 min 2 mi
  • La Paz International Airport (LAP)
    La Paz Mexico 2 hr 24 min 76 mi
  • Cabo San Lucas Internacional (CSW)
    Cabo San Lucas Mexico 56 min 21 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 27 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from San José del Cabo to Chicago

The cheapest flights from San José del Cabo to Chicago are usually in February. Typical ticket prices in February range from $350 to $490.
The cheapest round-trip flight from San José del Cabo to Chicago recently found on Google Flights was with Volaris from $322. The cheapest one-way flight was with Volaris from $202.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San José del Cabo to Chicago is $387, flying from May 1 to May 10.
  • The cheapest American flight from San José del Cabo to Chicago is $377, flying from May 1 to May 9.
  • The cheapest United flight from San José del Cabo to Chicago is $379, flying from May 1 to May 10.
  • The cheapest Delta flight from San José del Cabo to Chicago is $378, flying from Feb 19 to Feb 25.
  • The cheapest Volaris flight from San José del Cabo to Chicago is $322, flying from May 1 to May 7.
  • The cheapest Aeromexico flight from San José del Cabo to Chicago is $376, flying from Apr 16 to Apr 22.
The cheapest round-trip flight from San José del Cabo to Chicago starts at $322 from Fri, May 1 to Thu, May 7. The cheapest one-way flight starts at $202 and departs on Wed, Mar 4.
3 hr 55 min is the shortest flight time from San José del Cabo to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from San José del Cabo to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from San José del Cabo to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from San José del Cabo to Chicago.

In terms of nonstop flights, American is the most popular. American offers 12 nonstop flights and 309 connecting flights per week. American flies from Los Cabos International Airport (SJD) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 1,022 connecting flights per week. Southwest flies from Los Cabos International Airport (SJD) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from San José del Cabo to Chicago are:
  • United offers 7 nonstop flights and 188 connecting flights per week. United flies from Los Cabos International Airport (SJD) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 250 connecting flights per week. Delta flies from Los Cabos International Airport (SJD) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Volaris offers 50 connecting flights per week. Volaris flies from Los Cabos International Airport (SJD) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Aeromexico offers 23 connecting flights per week. Aeromexico flies from Los Cabos International Airport (SJD) to Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between San José del Cabo and Chicago.
The cheapest round-trip flight from San José del Cabo to Chicago recently found on Google Flights was with Volaris from $322. The cheapest one-way flight was with Volaris from $202.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San José del Cabo to Chicago is $387, flying from May 1 to May 10.
  • The cheapest American flight from San José del Cabo to Chicago is $377, flying from May 1 to May 9.
  • The cheapest United flight from San José del Cabo to Chicago is $379, flying from May 1 to May 10.
  • The cheapest Delta flight from San José del Cabo to Chicago is $378, flying from Feb 19 to Feb 25.
  • The cheapest Volaris flight from San José del Cabo to Chicago is $322, flying from May 1 to May 7.
  • The cheapest Aeromexico flight from San José del Cabo to Chicago is $376, flying from Apr 16 to Apr 22.
American and United fly direct from San José del Cabo to Chicago.
  • There are 12 American direct flights from San José del Cabo to Chicago per week. Flights are available every day.
  • There are 7 United direct flights from San José del Cabo to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between San José del Cabo and Chicago at price $463 is offered by Volaris from Fri, Feb 6 to Sun, Feb 8.
American and United fly direct from San José del Cabo to Chicago.
  • There are 12 American direct flights from San José del Cabo to Chicago per week. Flights are available every day.
  • There are 7 United direct flights from San José del Cabo to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from San José del Cabo to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between San José del Cabo and Chicago start at $377 from Fri, May 1 to Sun, May 10 with American.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from San José del Cabo to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between San José del Cabo and Chicago start at $1,032 from Sat, Mar 7 to Fri, Mar 13 with Frontier.
The cheapest economy class round-trip flights between San José del Cabo and Chicago start at $322 from Fri, May 1 to Thu, May 7.
To book business class trips from San José del Cabo to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between San José del Cabo and Chicago starts at $463 from Fri, Feb 6 to Sun, Feb 8 with Volaris.
The cheapest last-minute deal between San José del Cabo and Chicago at price $463 is offered by Volaris from Fri, Feb 6 to Sun, Feb 8.
To find last-minute flight deals from San José del Cabo to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

Popular trips from San José del Cabo

  1. Los Angeles
    $245
    Mar 5 — Mar 11
    Nonstop 2 hr 37 min United
  2. Chicago
    $315
    May 9 — May 16
    1 stop 7 hr 3 min Volaris
  3. Paris
    $450
    Mar 6 — Mar 13
    1 stop 20 hr 5 min Condor
  4. Singapore
    Feb 5 — Feb 11

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