What's Best Time To Fly Over Chicago? Scenic Routes

Chicago, known for its stunning skyline and picturesque lakefront, offers breathtaking views from the air. Whether you're a seasoned pilot or a passenger on a commercial flight, the timing and route of your flight can significantly impact your scenic experience. The best time to fly over Chicago depends on several factors, including the time of day, weather conditions, and the specific route taken.
Timing Considerations

The timing of your flight plays a crucial role in determining the quality of your scenic experience. Morning flights, just after sunrise, can provide a unique perspective on the city, with the golden light of dawn casting a warm glow over the skyline. However, this time of day can also be prone to fog, which may obscure your view. Afternoon flights, on the other hand, often offer clearer skies, but the sun’s position can create glare, making it challenging to capture good photos. Evening flights, around sunset, can be particularly spectacular, with the city’s lights beginning to twinkle as the sun dips below the horizon.
Weather Conditions
Weather conditions can greatly affect the scenic quality of your flight. Clear skies are ideal for taking in the views of Chicago’s iconic landmarks, such as Willis Tower (formerly Sears Tower) and Navy Pier. However, cloudy conditions can add an interesting layer of depth to your photos, with the clouds reflecting the colors of the city’s skyline. It’s essential to check the weather forecast before your flight to plan accordingly.
Time of Day | Weather Conditions | Scenic Quality |
---|---|---|
Morning | Foggy | Poor |
Afternoon | Clear | Good |
Evening | Cloudy | Excellent |

Scenic Routes

Several scenic routes offer stunning views of Chicago’s landmarks and lakefront. One popular route takes you over Lake Michigan, providing a unique perspective on the city’s shoreline and beaches. Another route flies over the Chicago River, offering a glimpse into the city’s industrial and commercial areas. For a more comprehensive view of the city, consider flying over the Loop, the central business district, where you can see iconic buildings like the Willis Tower and the John Hancock Center.
Flight Planning
When planning your scenic flight, consider the following routes and landmarks:
- Route 1: Lake Michigan shoreline, passing over North Avenue Beach and Oak Street Beach
- Route 2: Chicago River, flying over the Merchandise Mart and the Chicago Riverwalk
- Route 3: The Loop, taking in the views of Willis Tower, the John Hancock Center, and Millennium Park
What's the best way to capture scenic photos during a flight over Chicago?
+To capture stunning photos during a flight over Chicago, consider using a camera with a good zoom lens and a polarizing filter to reduce glare. Additionally, try to sit on the side of the plane that offers the best view of the city, and be prepared to take photos during the golden hour for optimal lighting.
Can I request a specific scenic route during a commercial flight?
+While you can't always request a specific scenic route during a commercial flight, you can try contacting the airline in advance to inquire about the planned route and ask if they can accommodate your request. However, please note that the flight route is ultimately determined by air traffic control and weather conditions.
In conclusion, the best time to fly over Chicago depends on your personal preferences and the scenic experience you’re looking for. By considering the timing, weather conditions, and scenic routes, you can plan an unforgettable flight over this beautiful city. Whether you’re a pilot or a passenger, Chicago’s stunning skyline and picturesque lakefront are sure to leave you with lasting memories.