Flight Routes from Cleveland to Chicago Midway

Compare cheap outbound and return flights from Cleveland (CLE) to Chicago Midway (MDW) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€271
Fastest flight
non-stop flights
31x / week
Flight distance
493 km
Time difference

Flight schedule from Cleveland (CLE) to Chicago Midway (MDW)

Select a travel date in the flight schedule for the route from Cleveland (CLE) to Chicago Midway (MDW) and compare affordable flight deals.

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Matching outbound flightsCLE–MDW · 11 of 11
fromto
dep.arr.
durationstopovers
  1. October 18 – 24, 2026
  2. October 25 – 31, 2026
  3. November 1 – 7, 2026
    1. CLEMDW
      nonstop
      1. Southwest Airlines
    2. CLEMDW
      nonstop
      1. Southwest Airlines
    3. CLEMDW
      nonstop
      1. Southwest Airlines
    4. CLEMDW
      nonstop
      1. Southwest Airlines
    5. CLEMDW
      nonstop
      1. Southwest Airlines
    6. CLEMDW
      nonstop
      1. Southwest Airlines
    7. CLEMDW
      nonstop
      1. Southwest Airlines
    8. CLEMDW
      nonstop
      1. Southwest Airlines
    9. CLEMDW
      nonstop
      1. Southwest Airlines
    10. CLEMDW
      nonstop
      1. Southwest Airlines
    11. CLEMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Cleveland and Chicago Midway

      Departure airport Airport Cleveland - Hopkins International Airport, OH (CLE)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      Departure airport - Destination country Cleveland - Hopkins International Airport, OH - United States
      Departure airport - City-Code Cleveland - Hopkins International Airport, OH - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway
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