$121 Find Cheap Flights from Chicago to San José del Cabo - Compare and Save

Among airlines operating Chicago to San José del Cabo flights:

• American Airlines: offers extra legroom; offers free seat selection
• United Airlines: offers extra legroom; offers free seat selection

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

2 airlines operate flights between Chicago and San José del Cabo. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flights from Chicago to San José del Cabo may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at San José del Cabo Los Cabos (SJD).

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

• American Airlines: a cabin bag and a checked bag in Economy Class
• United Airlines: a cabin bag and a checked bag in Economy Class
• Emirates: a cabin bag and a checked bag in Business Class

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

Four cabin classes are available on flights from Chicago to San José del Cabo:

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $387 round-trip via Monterrey Gen Mariano Escobedo (MTY), compared to $649 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $50–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

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

• Mexico City Benito Juarez (MEX) - 40% of one-stop connections
• Guadalajara Miguel Hidal (GDL) - 20% of one-stop connections
• Denver Intl (DEN) - 9% of one-stop connections
• Dallas/Fort Worth (DFW) - 7% of one-stop connections

Mexico City Benito Juarez (MEX) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 14% on the Chicago to San José del Cabo route. Friday is the cheapest departure day at $585 round-trip on average, while Thursday is the most expensive at $679, a difference of $94. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Chicago to San José del Cabo flights, with 100% of flights leaving in that window. Afternoon departures account for 0%, evening flights for 0%, and night flights for 0%.

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

These are the earliest and latest flight times available from Chicago to San José del Cabo:

• Earliest: departs at 7:45 am and lands at 12:34 pm
• Latest: departs at 9:05 am and lands at 1:54 pm.

The flight takes about 4h 49m.

Last-minute fares on this route - booked within 2 weeks of departure - run 4% above the route average of $627. Book 4 weeks before departure for the lowest fares.

A nonstop flight from Chicago to San José del Cabo takes 4h 49m, covering 1,813 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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $369 to $2,716. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from Chicago to San José del Cabo are currently lower than usual. Average one-way flight prices are about $182, which is 31% below the typical average for this route.

Flying via Dallas/Fort Worth (DFW) gives the shortest average 1-stop total travel time at 7h 11m, compared with 7h 18m via Houston Hobby (HOU) and 7h 28m via Denver Intl (DEN).

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

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
• MEXRENTACAR
• Budget
• Advantage

Round-trip flights from Chicago to San José del Cabo range from $502 to $762, with an average of $627 over the past 12 months. Anything below $502 counts as a good deal.

American Airlines is the only airline on the Chicago to San José del Cabo route offering in-flight Wi-Fi. Pricing depends on fare class.