
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $420 (Volaris) |
One-way from | $98 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $726 |
Good round-trip deal | $538 or less |
Good one-way deal | $309 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 5/3
5:15 am-5:49 pm
2 stops14h 34m
San José del Cabo Los Cabos
Fri 5/8
6:07 am-9:53 pm
2 stops13h 46m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 5/7
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Thu 5/14
12:02 pm-11:47 pm
1 stop9h 45m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/24
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Mon 4/27
3:36 pm-12:55 am
1 stop7h 19m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/1
2:15 am-8:00 am
1 stop7h 45m
San José del Cabo Los Cabos
Sat 5/2
8:00 pm-10:50 am
1 stop12h 50m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 5/5
10:05 am-12:50 pm
Nonstop4h 45m
San José del Cabo Los Cabos
Sat 5/9
11:32 am-5:57 pm
Nonstop4h 25m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 5/7
1:45 pm-9:31 am
2 stops21h 46m
San José del Cabo Los Cabos
Thu 5/14
10:24 am-12:00 pm
2 stops23h 36m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/15
6:24 am-5:48 pm
2 stops13h 24m
San José del Cabo Los Cabos
Wed 5/20
10:24 am-12:10 am
1 stop11h 46m
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 5/3
6:00 am-2:10 pm
1 stop10h 10m
San José del Cabo Los Cabos
Wed 5/6
2:20 pm-5:25 am
2 stops13h 05m
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 5/4
5:25 am-10:45 am
1 stop7h 20m
San José del Cabo Los Cabos
Sat 5/9
12:40 pm-4:35 am
1 stop13h 55m
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/8
6:24 am-5:48 pm
2 stops13h 24m
San José del Cabo Los Cabos
Tue 5/12
6:07 am-10:27 pm
2 stops14h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San José del Cabo. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, March is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $263). Flying from Chicago to San José del Cabo in October is currently the most expensive (average of $397). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San José del Cabo as you normally would.
The most flights from CHI to SJD are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
Houston (IAH) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to San José del Cabo on Cheapflights.
Houston (IAH) is the most affordable 1-stop option, with an average round-trip price of $607.
Flights via Houston (IAH) have the shortest average one-way travel time for 1-stop routes: 6h 30m.
Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 09m.
Food
Comfort
Entertainment
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Entertainment
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Entertainment
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Entertainment
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Entertainment
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Comfort
Entertainment
Crew
Boarding
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$386 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$415 | Average$618 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$612 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$655 | FlexibilityNo cancel fee | On-time63% |