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 $357
Volaris 1 stop 14 hr Mon, Jun 1 — Tue, Jun 9
The cheapest round-trip flight from Chicago to San José del Cabo is currently $357
Cheapest one-way flight $129
Volaris 1 stop 11 hr Wed, Jul 8
The cheapest one-way flight from Chicago to San José del Cabo is currently $129
Cheapest nonstop flights $628
American Nonstop 5 hr Sun, Jul 5 — Tue, Jul 14
The cheapest nonstop round-trip flight from Chicago to San José del Cabo is currently $628
Last-minute weekend getaway $437
Volaris 1 stop 14 hr Thu, May 7 — Sun, May 10
The cheapest last-minute weekend getaway from Chicago to San José del Cabo is currently $437
Cheapest business class flights $1,293
United 1 stop 9 hr Sun, Jul 5 — Tue, Jul 14
The cheapest business class round-trip flight from Chicago to San José del Cabo is currently $1,293
Fastest flight 4 hr 29 min The fastest nonstop flight from Chicago to San José del Cabo takes 4 hr 29 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 April. The most expensive month to fly is typically July.
April
Cheapest
Typical prices: $335–455
July
Most expensive
Typical prices: $380–470

Popular airlines from Chicago to San José del Cabo

  • Southwest
    from $540
    Typical price: $475–770
    1207 weekly connecting flights
    MDW, ORD - SJD Every day
  • American
    Nonstop
    from $569
    Typical price: $425–700
    7 weekly nonstop flights
    ORD - SJD Every day
    494 weekly connecting flights
    ORD - SJD Every day
  • United
    Nonstop
    from $584
    Typical price: $425–720
    1 weekly nonstop flight
    ORD - SJD Every Sat
    195 weekly connecting flights
    ORD - SJD Every day
  • Delta
    from $569
    Typical price: $450–800
    113 weekly connecting flights
    MDW, ORD - SJD Every day
  • Volaris
    from $357
    Typical price: $350–650
    55 weekly connecting flights
    MDW, ORD - SJD Every day
  • Aeromexico
    from $588
    Typical price: $485–920
    35 weekly connecting flights
    ORD - SJD Every day

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 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 23 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 21 min 2 mi
  • La Paz International Airport (LAP)
    La Paz Mexico 2 hr 23 min 76 mi
  • Cabo San Lucas Internacional (CSW)
    Cabo San Lucas Mexico 55 min 21 mi

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

The cheapest flights from Chicago to San José del Cabo are usually in April. Typical ticket prices in April range from $335 to $455.
The cheapest round-trip flight from Chicago to San José del Cabo recently found on Google Flights was with Volaris from $357. The cheapest one-way flight was with Volaris from $129.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San José del Cabo is $540, flying from Jul 27 to Aug 5.
  • The cheapest American flight from Chicago to San José del Cabo is $569, flying from May 31 to Jun 9.
  • The cheapest United flight from Chicago to San José del Cabo is $584, flying from May 31 to Jun 9.
  • The cheapest Delta flight from Chicago to San José del Cabo is $569, flying from May 31 to Jun 9.
  • The cheapest Volaris flight from Chicago to San José del Cabo is $357, flying from Jun 1 to Jun 9.
  • The cheapest Aeromexico flight from Chicago to San José del Cabo is $588, flying from Jul 5 to Jul 13.
The cheapest round-trip flight from Chicago to San José del Cabo starts at $357 from Mon, Jun 1 to Tue, Jun 9. The cheapest one-way flight starts at $129 and departs on Wed, Jul 8.
4 hr 29 min is the shortest flight time from Chicago to San José del Cabo.
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).
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 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 7 nonstop flights and 494 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 1,207 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 1 nonstop flights and 195 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Los Cabos International Airport (SJD) .
  • Delta offers 113 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 55 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 35 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.
The cheapest round-trip flight from Chicago to San José del Cabo recently found on Google Flights was with Volaris from $357. The cheapest one-way flight was with Volaris from $129.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Chicago to San José del Cabo is $540, flying from Jul 27 to Aug 5.
  • The cheapest American flight from Chicago to San José del Cabo is $569, flying from May 31 to Jun 9.
  • The cheapest United flight from Chicago to San José del Cabo is $584, flying from May 31 to Jun 9.
  • The cheapest Delta flight from Chicago to San José del Cabo is $569, flying from May 31 to Jun 9.
  • The cheapest Volaris flight from Chicago to San José del Cabo is $357, flying from Jun 1 to Jun 9.
  • The cheapest Aeromexico flight from Chicago to San José del Cabo is $588, flying from Jul 5 to Jul 13.
American and United fly direct from Chicago to San José del Cabo.
  • There are 7 American direct flights from Chicago to San José del Cabo per week. Flights are available every day.
  • There are 1 United direct flights from Chicago to San José del Cabo per week. Flights are available on Saturday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Chicago and San José del Cabo at price $437 is offered by Volaris from Thu, May 7 to Sun, May 10.
American and United fly direct from Chicago to San José del Cabo.
  • There are 7 American direct flights from Chicago to San José del Cabo per week. Flights are available every day.
  • There are 1 United direct flights from Chicago to San José del Cabo per week. Flights are available on Saturday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Chicago to San José del Cabo on a daily basis.
The cheapest direct (nonstop) round-trip flights between Chicago and San José del Cabo start at $628 from Sun, Jul 5 to Tue, Jul 14 with American.
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.
The cheapest business class round-trip flights between Chicago and San José del Cabo start at $1,293 from Sun, Jul 5 to Tue, Jul 14 with United.
The cheapest economy class round-trip flights between Chicago and San José del Cabo start at $357 from Mon, Jun 1 to Tue, Jun 9.
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.
The best last-minute getaway deal for the next weekend between Chicago and San José del Cabo starts at $437 from Thu, May 7 to Sun, May 10 with Volaris.
The cheapest last-minute deal between Chicago and San José del Cabo at price $437 is offered by Volaris from Thu, May 7 to Sun, May 10.
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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