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Direct flights from Cleveland to Chicago

Did you mean Flights from Chicago to Cleveland?

Flightmap/Flights from CLE/CLE to MDW

Cleveland

United States

CLE

Cleveland Hopkins International Airport

Chicago

United States

MDW

Chicago Midway International Airport

Route
Nonstop service available
Distance
306 miles
Marketing airlines
1 airline
Aircraft
4 aircraft types
Dates
Oct 19, 2026 – Aug 2, 2027

Observed award fares

A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.

Departure window: 2026-10-23 – 2026-11-21.

No recent fares appear in this limited preview. This does not mean the route is sold out. Use the search controls to check other dates and routes.

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Explore these airports and cities

  • Flights from CLE
  • Flights to MDW
  • Award flights to Chicago

Cleveland to Chicago route overview

Cleveland Hopkins International Airport (CLE) serves Cleveland; Chicago Midway International Airport (MDW) serves Chicago.

The airports are 306 miles apart by great-circle distance.

Roame's current schedule feed shows nonstop service from CLE to MDW.

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Published schedule dates span Oct 19, 2026 – Aug 2, 2027.

Marketing airlines on the Cleveland to Chicago route

These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.

Aircraft flying from CLE to MDW

Frequently asked questions

Which airports serve the Cleveland to Chicago route?

Cleveland Hopkins International Airport (CLE) is the origin airport and Chicago Midway International Airport (MDW) is the destination airport.

How far is Chicago from Cleveland?

CLE and MDW are approximately 306 miles apart by great-circle distance.

Are there direct flights from CLE to MDW?

Yes. Roame's current schedule feed shows nonstop service from CLE to MDW.

Which airlines market flights from CLE to MDW?

Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.

Which aircraft fly from CLE to MDW?

Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H), Boeing 737 MAX 8 (7M8), 7S7 and JET.

More routes from Cleveland

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  • MSPMinneapolisUnited States
  • LGANew YorkUnited States
  • PHLPhiladelphiaUnited States
  • IAHHoustonUnited States
  • DCAWashingtonUnited States
  • DFWDallas-Fort WorthUnited States
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