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Cheap flights from Chicago to San Jose Del Cabo

14 nonstop flights a week, 2 of them today. Operated by 3 airlines, about 4h 52m in the air, 1,814 mi (2,919 km). Tickets from $263, nonstop from $368.

Flights from Chicago to San Jose Del Cabo

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

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Best fares from Chicago to San Jose Del Cabo

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $263 11 December 2026, with a connection Cheapest nonstop $368 11 December 2026, American Airlines Cheapest weekend departure $263 Fri, 11 December 2026 Cheapest month December 2026 tickets from $263

Chicago to San Jose Del Cabo at a glance

flight time, from 4h 29m to 5h 1m
4h 52m
straight-line distance
1,814 mi (2,919 km)
flights a week
14
flights today
2
first and last departure
08:51 - 09:03
lowest price, with a connection, 11 December
$263
lowest nonstop price
$368
airlines
3

Chicago to San Jose Del Cabo flight schedule

14 flights a week, 2 today, 16 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
AA 1649
American Airlines
08:51 , terminal 3
12:51 Los Cabos, terminal 2
5h
Mon, Thu, Fri, Sat, Sun
Airbus A321
AA 1649
American Airlines
08:55 , terminal 3
12:44 Los Cabos, terminal 2
4h 49m
Daily
Airbus A321
UA 1879
United Airlines
09:03 , terminal 1
13:03 Los Cabos, terminal 2
5h
Daily
Airbus A320

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 2 December.

FlightDepartsArrivesDurationDaysAircraft
AA 1649
American Airlines
08:44 , terminal 3
12:42 Los Cabos, terminal 2
4h 58m
Seasonal
Airbus A321
UA 494
United Airlines
07:04 , terminal 1
10:58 Los Cabos, terminal 2
4h 54m
Seasonal
Boeing 737-800
AA 1649
American Airlines
08:30 , terminal 3
12:28 Los Cabos, terminal 2
4h 58m
Seasonal
Airbus A321
AA 1060
American Airlines
09:30 , terminal 3
13:25 Los Cabos, terminal 2
4h 55m
Seasonal
Boeing 737-800
AA 1649
American Airlines
09:00 , terminal 3
13:01 Los Cabos, terminal 2
5h 1m
Seasonal
Airbus A321
AA 1649
American Airlines
08:32 , terminal 3
12:24 Los Cabos, terminal 2
4h 52m
Seasonal
Airbus A321
AA 2009
American Airlines
09:52 , terminal 3
13:44 Los Cabos, terminal 2
4h 52m
Seasonal
Airbus A321
UA 494
United Airlines
07:15 , terminal 1
11:08 Los Cabos, terminal 2
4h 53m
Seasonal
Airbus A320
UA 1879
United Airlines
09:05 , terminal 1
13:03 Los Cabos, terminal 2
4h 58m
Seasonal
Airbus A320
WN 3636
Southwest Airlines
10:10 Chicago Midway International
13:55 Los Cabos, terminal 2
4h 45m
Seasonal
WN 3636
Southwest Airlines
08:50 Chicago Midway International
12:30 Los Cabos, terminal 2
4h 40m
Seasonal
Boeing 737
WN 3636
Southwest Airlines
08:55 Chicago Midway International
11:35 Los Cabos, terminal 2
4h 40m
Seasonal
Boeing 737
UA 1879
United Airlines
08:40 , terminal 1
11:25 Los Cabos, terminal 2
4h 45m
Seasonal
Boeing 737-800
AA 1649
American Airlines
10:05 , terminal 3
12:50 Los Cabos, terminal 2
4h 45m
Seasonal
Airbus A321
AA 1649
American Airlines
08:40 , terminal 3
11:13 Los Cabos, terminal 2
4h 33m
Seasonal
Airbus A321
AA 1649
American Airlines
08:35 , terminal 3
11:04 Los Cabos, terminal 2
4h 29m
Seasonal
Airbus A321

Days of the week are taken from the schedule for the next 14 days; schedules change by season. San Jose Del Cabo is 1 hour behind Chicago. The search shows seat availability and the price for your date.

Airlines flying Chicago to San Jose Del Cabo

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

American Airlines7 a week United Airlines7 a week Southwest Airlinesfrom 11 March

Airports

Where flights from Chicago to San Jose Del Cabo depart and land

Departure from Chicago

Chicago Midway International MDW

9 mi (14 km) from the city centre

About the airport

Arrival in San Jose Del Cabo

Los Cabos SJD

14 flights a week, terminal 2, 0 mi (0 km) from the city centre

About the airport

Frequently asked questions

How long is the flight from Chicago to San Jose Del Cabo?
A nonstop flight takes 4 hours 52 minutes on average, from 4h 29m to 5h 1m depending on the flight.
How far is San Jose Del Cabo from Chicago?
1,814 mi (2,919 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to San Jose Del Cabo?
American Airlines (7 a week), United Airlines (7 a week) and Southwest Airlines.
How many flights a day are there from Chicago to San Jose Del Cabo?
2 flights today and 14 a week, about 2 a day on average.
When are the first and last flights from Chicago to San Jose Del Cabo?
The first departure is at 08:51 (AA1649), the last at 09:03 (UA1879). Local time.
What is the cheapest upcoming date to fly from Chicago to San Jose Del Cabo?
11 December 2026 (Friday): from $263 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to San Jose Del Cabo?
American Airlines: nonstop tickets from $368 on 11 December by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and San Jose Del Cabo?
San Jose Del Cabo is 1 hour behind Chicago. Schedule times on this page are local to each airport.
Which Chicago airport do flights to San Jose Del Cabo leave from?
Chicago Midway International.