While takeoff scenery is minimal on both sides due to Midway's flat surroundings, the left side wins overall because of the dramatic Rocky Mountain views during the Denver approach and descent, which are the standout visual feature of this route.
Flown MDW to DEN? Did we get it right?
Flight Path
Chicago to Denver is 893 miles (1,437 km), a flight of about 2 hours 15 minutes.
Great Plains of Iowa and Nebraska, Missouri River, gradual rise in elevation toward the High Plains before the Rockies come into view near Denver
Great circle distance and headings ›Phase by phase

Takeoff from MDW
RIGHTDepartures from Midway heading southwest give right-side passengers a view over Chicago's southern suburbs and Lake Michigan's shoreline briefly recedes behind, while the left side mostly sees flat industrial landscape. The distinction is minor since this is a short, flat-terrain departure phase.

Landing at DEN
LEFTArrivals into Denver from the east typically approach with the Rocky Mountains and Front Range visible on the left side as the plane descends, offering dramatic elevation change and peaks like the Rockies foothills. This is the most scenic moment of the flight given Denver's iconic mountain backdrop.
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About This Route
Which side of the plane should I sit on flying from Chicago Midway International (MDW) to Denver International (DEN)?
Sit on the Left side of the plane for the best views on flights from Chicago to Denver. While takeoff scenery is minimal on both sides due to Midway's flat surroundings, the left side wins overall because of the dramatic Rocky Mountain views during the Denver approach and descent, which are the standout visual feature of this route.
What can I see during takeoff from Chicago Midway International in Chicago?
During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Departures from Midway heading southwest give right-side passengers a view over Chicago's southern suburbs and Lake Michigan's shoreline briefly recedes behind, while the left side mostly sees flat industrial landscape. The distinction is minor since this is a short, flat-terrain departure phase. Notable sights include: Chicago southern suburbs, Midway airport grid, flat Illinois farmland.
What can I see when landing at Denver International in Denver?
When landing at Denver International (DEN), sit on the Left side for the best views. Arrivals into Denver from the east typically approach with the Rocky Mountains and Front Range visible on the left side as the plane descends, offering dramatic elevation change and peaks like the Rockies foothills. This is the most scenic moment of the flight given Denver's iconic mountain backdrop. Notable sights include: Front Range of the Rocky Mountains, Denver skyline, high plains transition zone.
How long is the flight from Chicago to Denver?
The flight from Chicago Midway International (MDW) to Denver International (DEN) takes about 2 hours 15 minutes. The shortest flight path between them is 893 miles (1,437 km); winds and air traffic control usually add a few percent.
What does the Chicago to Denver flight path pass over?
Great Plains of Iowa and Nebraska, Missouri River, gradual rise in elevation toward the High Plains before the Rockies come into view near Denver