Cheap flights from Chicago to San José del Cabo

Flights overview

Useful information for finding cheap flights from Chicago to San José del Cabo and booking your next trip
Cheapest round-trip flights $324
Viva 1 stop 8 hr Mon, Jan 26 — Mon, Feb 2
The cheapest round-trip flight from Chicago to San José del Cabo is currently $324
Cheapest one-way flight $78
Viva 1 stop 8 hr Thu, Jan 29
The cheapest one-way flight from Chicago to San José del Cabo is currently $78
Cheapest nonstop flights $366
United Nonstop 5 hr Thu, Dec 11 — Wed, Dec 17
The cheapest nonstop round-trip flight from Chicago to San José del Cabo is currently $366
Last-minute weekend getaway $400
American Nonstop 5 hr Thu, Nov 20 — Sun, Nov 23
The cheapest last-minute weekend getaway from Chicago to San José del Cabo is currently $400
Cheapest business class flights $1,060
United 1 stop 15 hr Sat, Dec 20 — Fri, Dec 26
The cheapest business class round-trip flight from Chicago to San José del Cabo is currently $1,060
Fastest flight 4 hr 37 min The fastest nonstop flight from Chicago to San José del Cabo takes 4 hr 37 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 Chicago to San José del Cabo is typically January. The most expensive month to fly is typically July.
January
Cheapest
Typical prices: $255–465
July
Most expensive
Typical prices: $380–470

Popular airlines from Chicago to San José del Cabo

  • Southwest
    from $370
    Typical price: $490–830
    1230 weekly connecting flights
    MDW, ORD - SJD Every day
  • American
    Nonstop
    from $366
    Typical price: $430–710
    12 weekly nonstop flights
    ORD - SJD Every day
    403 weekly connecting flights
    ORD - SJD Every day
  • United
    Nonstop
    from $366
    Typical price: $430–730
    7 weekly nonstop flights
    ORD - SJD Every day
    184 weekly connecting flights
    ORD - SJD Every day
  • Delta
    from $370
    Typical price: $475–850
    94 weekly connecting flights
    MDW, ORD - SJD Every day
  • Volaris
    Typical price: $340–510
    44 weekly connecting flights
    MDW, ORD - SJD Every day
  • Aeromexico
    from $377
    Typical price: $510–960
    32 weekly connecting flights
    ORD - SJD Every day

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 31 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 26 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 28 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Popular airports near San José del Cabo

  • Los Cabos International Airport (SJD)
    San José del Cabo Mexico 24 min 6 mi
  • La Paz International Airport (LAP)
    La Paz Mexico 2 hr 13 min 81 mi
  • Cabo San Lucas Internacional (CSW)
    Cabo San Lucas Mexico 47 min 17 mi

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

When are the cheapest days to fly from Chicago to San José del Cabo?
The cheapest flights from Chicago to San José del Cabo are usually in January. Typical ticket prices in January range from $255 to $465.
Which airlines provide the cheapest flights from Chicago to San José del Cabo?
The cheapest round-trip flight from Chicago to San José del Cabo recently found on Google Flights was with Viva from $324. The cheapest one-way flight was with Viva from $78.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San José del Cabo is $370, flying from Dec 12 to Dec 20.
  • The cheapest American flight from Chicago to San José del Cabo is $366, flying from Dec 12 to Dec 18.
  • The cheapest United flight from Chicago to San José del Cabo is $366, flying from Dec 11 to Dec 17.
  • The cheapest Delta flight from Chicago to San José del Cabo is $370, flying from Dec 15 to Dec 24.
  • The cheapest Aeromexico flight from Chicago to San José del Cabo is $377, flying from Feb 1 to Feb 9.
What are the cheapest flights from Chicago to San José del Cabo?
The cheapest round-trip flight from Chicago to San José del Cabo starts at $324 from Mon, Jan 26 to Mon, Feb 2. The cheapest one-way flight starts at $78 and departs on Thu, Jan 29.
How long does it take to fly from Chicago to San José del Cabo?
4 hr 37 min is the shortest flight time from Chicago to San José del Cabo.
When should you fly to San José del Cabo, Mexico?
San José del Cabo is warm and dry year-round, with hot summers (Jun–Sep) and a late-summer hurricane season (Aug–Sep). Major annual events include the Fiesta de San José (Mar), celebrating the city’s patron saint, and Easter (Mar/Apr).
How do I find cheap dates to fly from Chicago to San José del Cabo?
It's easy to use Google Flights to find the cheapest days to fly from Chicago to San José del Cabo.
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 is the best airline to fly from Chicago to San José del Cabo?
What counts as the best airline for your flights from Chicago to San José del Cabo 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 Chicago to San José del Cabo.

In terms of nonstop flights, American is the most popular. American offers 12 nonstop flights and 403 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .

In terms of flights, Southwest is the most popular. Southwest offers 1,230 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .

Other popular airlines flying from Chicago to San José del Cabo are:
  • United offers 7 nonstop flights and 184 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .
  • Delta offers 94 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .
  • Volaris offers 44 connecting flights per week. Volaris flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .
  • Aeromexico offers 32 connecting flights per week. Aeromexico flies from Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .
The number of connecting flights refers to distinct flights with at least one stop between Chicago and San José del Cabo.
Which airlines provide the cheapest flights from Chicago to San José del Cabo?
The cheapest round-trip flight from Chicago to San José del Cabo recently found on Google Flights was with Viva from $324. The cheapest one-way flight was with Viva from $78.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San José del Cabo is $370, flying from Dec 12 to Dec 20.
  • The cheapest American flight from Chicago to San José del Cabo is $366, flying from Dec 12 to Dec 18.
  • The cheapest United flight from Chicago to San José del Cabo is $366, flying from Dec 11 to Dec 17.
  • The cheapest Delta flight from Chicago to San José del Cabo is $370, flying from Dec 15 to Dec 24.
  • The cheapest Aeromexico flight from Chicago to San José del Cabo is $377, flying from Feb 1 to Feb 9.
Which airlines have direct flights from Chicago to San José del Cabo?
Southwest, American and United fly direct from Chicago to San José del Cabo.
  • There are 12 American direct flights from Chicago to San José del Cabo per week. Flights are available every day.
  • There are 7 United direct flights from Chicago to San José del Cabo per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
Which airline provides the cheapest last-minute getaway flight from Chicago to San José del Cabo?
The cheapest last-minute deal between Chicago and San José del Cabo at price $400 is offered by American from Thu, Nov 20 to Sun, Nov 23.
Which airlines have direct flights from Chicago to San José del Cabo?
Southwest, American and United fly direct from Chicago to San José del Cabo.
  • There are 12 American direct flights from Chicago to San José del Cabo per week. Flights are available every day.
  • There are 7 United direct flights from Chicago to San José del Cabo per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
When are direct flights from Chicago to San José del Cabo available?
There are direct flights from Chicago to San José del Cabo on a daily basis.
What are the cheapest direct flights from Chicago to San José del Cabo?
The cheapest direct (nonstop) round-trip flights between Chicago and San José del Cabo start at $366 from Thu, Dec 11 to Wed, Dec 17 with United.
How can I find nonstop flights from Chicago to San José del Cabo?
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to San José del Cabo, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
What are the cheapest business class flights from Chicago to San José del Cabo?
The cheapest business class round-trip flights between Chicago and San José del Cabo start at $1,060 from Sat, Dec 20 to Fri, Dec 26 with United.
What are the cheapest economy class flights from Chicago to San José del Cabo?
The cheapest economy class round-trip flights between Chicago and San José del Cabo start at $324 from Mon, Jan 26 to Mon, Feb 2.
How can I book business class trips from Chicago to San José del Cabo?
To book business class trips from Chicago to San José del Cabo, 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.
Are there any last-minute deals from Chicago to San José del Cabo next weekend?
The best last-minute getaway deal for the next weekend between Chicago and San José del Cabo starts at $400 from Thu, Nov 20 to Sun, Nov 23 with American.
Which airline provides the cheapest last-minute getaway flight from Chicago to San José del Cabo?
The cheapest last-minute deal between Chicago and San José del Cabo at price $400 is offered by American from Thu, Nov 20 to Sun, Nov 23.
How can I find last-minute flight deals from Chicago to San José del Cabo?
To find last-minute flight deals from Chicago to San José del Cabo, 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.

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