Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline VivaAerobus

The cheapest airline(s) flying from Chicago to San Jose Cabo is VivaAerobus.

  • VivaAerobus VivaAerobus
  • Alaska Airlines Alaska Airlines
  • Aeromexico Aeromexico
  • Volaris Volaris
  • JetBlue Airways JetBlue Airways
  • American Airlines American Airlines
  • United Airlines United Airlines
  • Southwest Airlines Southwest Airlines
  • Air Canada Air Canada
Cheapest Month February

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Chicago to San Jose Cabo is February.

  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
Cheapest Day of the Week Friday

The cheapest day(s) of the week to fly from Chicago to San Jose Cabo is Friday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Duration
    • Shortest
    • Longest
  • Stopover
    All
  • Airline Filter by Airline
    View All Airline
  • Availability
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 08:25 ORD
    12:10 SJD
    4Hrs, 45m Direct
  • ORDChicago O'Hare International Airport 08:25 - SJD 12:10 4h 45m Direct
  • ORDChicago O'Hare International Airport 08:25
  • SJDSan Jose Cabo Airport 12:10
  • 4h 45m
  • Direct
  • American Airlines (AA 1649)Boeing 737 800
  • American Airlines (AA 1649)
    • M
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 08:27 ORD
    12:12 SJD
    4Hrs, 45m Direct
  • ORDChicago O'Hare International Airport 08:27 - SJD 12:12 4h 45m Direct
  • ORDChicago O'Hare International Airport 08:27
  • SJDSan Jose Cabo Airport 12:12
  • 4h 45m
  • Direct
  • American Airlines (AA 1649)Boeing 737 800
  • American Airlines (AA 1649)
    • -
    • -
    • -
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 09:04 ORD
    12:57 SJD
    4Hrs, 53m Direct
  • ORDChicago O'Hare International Airport 09:04 - SJD 12:57 4h 53m Direct
  • ORDChicago O'Hare International Airport 09:04
  • SJDSan Jose Cabo Airport 12:57
  • 4h 53m
  • Direct
  • United Airlines (UA 1879)Boeing 737 800
  • United Airlines (UA 1879)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 09:45 ORD
    13:37 SJD
    4Hrs, 52m Direct
  • ORDChicago O'Hare International Airport 09:45 - SJD 13:37 4h 52m Direct
  • ORDChicago O'Hare International Airport 09:45
  • SJDSan Jose Cabo Airport 13:37
  • 4h 52m
  • Direct
  • American Airlines (AA 2668)Boeing 737 Max 8 Passenger
  • American Airlines (AA 2668)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 Max 8 Passenger
No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
What’s the fastest flight time from Chicago to San Jose Cabo?

The fastest flight time for direct flights from Chicago to San Jose Cabo is 4 hours 45 minutes. Check latest flight schedules & prices on Wego.

How far is San Jose Cabo from Chicago?

The flight distance between Chicago and San Jose Cabo is 2926km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 08:25. The last flight of the day departs at 08:25. See the full list of flight times on Wego.

How many airlines offer direct flights from Chicago to San Jose Cabo?

There are 2 airlines that offer direct flights from Chicago to San Jose Cabo. Find out the list of airlines on Wego.