$220 Find Cheap Flights from Chicago Midway Airport to San José del Cabo - Compare and Save

Only Economy Class is available on flights from Chicago Midway Airport to San José del Cabo.

A nonstop flight from Chicago Midway Airport to San José del Cabo takes 00m, covering 1,804 miles.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Round-trip flights from Chicago Midway Airport to San José del Cabo range from $578 to $759, with an average of $644 over the past 12 months. Anything below $578 counts as a good deal.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $321 round-trip via Denver Intl (DEN), compared to $633 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737-800 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Airbus A320-100/200 variants.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $519 to $3,336. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Chicago Midway Airport to San José del Cabo are currently lower than usual. Average one-way flight prices are about $248, which is 15% below the typical average for this route.

San José del Cabo Los Cabos Airport (SJD) hosts 5 major car rental companies, with daily rates starting from around $1 for economy cars. Top options include:

• Hertz
• America Car Rental
• Budget
• MEXRENTACAR
• Advantage

Flights from Chicago Midway Airport to San José del Cabo usually depart from Chicago Midway (MDW) and arrive at San José del Cabo Los Cabos (SJD).

One-stop flights from Chicago Midway Airport to San José del Cabo most commonly connect through:

• Houston Hobby (HOU) - 73% of one-stop connections
• Phoenix Sky Harbor Intl (PHX) - 14% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 9% of one-stop connections
• Denver Intl (DEN) - 5% of one-stop connections

Yes. Flexible dates can save you up to 24% on flights from Chicago Midway Airport to San José del Cabo. Saturday is the cheapest departure day at $580 round-trip on average, while Tuesday is the most expensive at $759, a difference of $179.

Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Flying via Houston Hobby (HOU) gives the shortest average 1-stop total travel time at 7h 15m, compared with 7h 24m via Denver Intl (DEN) and 7h 41m via Phoenix Sky Harbor Intl (PHX).

San José del Cabo is 2 hours behind Chicago Midway Airport (Mexican Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Old Town Gallery is one of the most viewed places in San José del Cabo on KAYAK.

Among airlines operating Chicago Midway Airport to San José del Cabo flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.