Flight Routes from Chicago to Los Cabos

Compare cheap outbound and return flights from Chicago (CHI) to Los Cabos (SJD) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest outbound flight
Fastest inbound flight
non-stop flights
22x / week
Flight distance
2,923 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Chicago (CHI) to Los Cabos (SJD)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Los Cabos (SJD) and compare affordable flight deals.

offers
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Matching outbound flightsCHI–SJD · 3 of 3
fromto
dep.arr.
durationstopovers
  1. September 13 – 19, 2026
  2. September 20 – 26, 2026
  3. Sep 27 – Oct 3, 2026
    1. ORDSJD
      nonstop
      1. United Airlines
    2. ORDSJD
      nonstop
      1. American Airlines
    3. ORDSJD
      nonstop
      1. United Airlines

      Important flight information

      Discover more flights around Chicago and Los Cabos

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Los Cabos (SJD)
      Destination country Flights to Mexico
      Departure airport - Destination country Chicago-IL, all airports - Mexico
      Alternative flights to Los Cabos