The 606 Trail in Chicago at Sunrise

My wife and I are thinking about moving out of the south suburbs, and I keep telling her how great city life can be. To prove it, I want to take her for a sunrise walk on the 606 this weekend. I feel like the view of the skyline with the sun coming up has to be amazing. The problem is, I have never actually done it. We would be driving up from Oak Lawn around 5 AM. Is there any decent street parking near one of the access points that early, say near the Western or Damen ramps? And is it actually safe before the sun is fully up, or is it going to be empty and creepy? Trying to make a good impression here, not get our car towed or spook my wife into staying in Palos forever.

It is a great idea. The trail is definitely used that early, mostly by serious runners, so you will not be totally alone. I live right off the Damen ramp. For parking, do not even try on Damen or Milwaukee. Your best bet is to look for a spot on a side street like Churchill or Cortland just west of Western. It's all residential and you should find something easily at that hour. The best skyline view is on the stretch between Western and Damen, so you are looking at the right area. It is worth the early wakeup.

I am going to disagree, I think sunset is way better on the 606. The light hitting the buildings from the west is just as nice and the trail has a much better energy in the evening. Plus when you are done you can just hop off at Damen and walk to a dozen places for a drink or dinner. In the super early morning it can feel a little isolated between the access ramps and not much is open right when you get off. Just something to consider if you are trying to sell the 'city life' vibe.

If you want a quieter experience, try the west end of the trail. The Ridgeway and Lawndale ramps are way less crowded and you can usually park right on Cortland or Bloomingdale Ave itself. It has more of a neighborhood feel and less of the intense runner scene. You do not get the same direct skyline view but the green space around Julia de Burgos Park at the start is really nice at dawn. Afterward you can drive down Division for some great coffee or breakfast burritos.

We took our kids on their bikes for a sunrise ride there last summer and it felt perfectly safe. Everyone out that early was just focused on their workout. We parked near the Kimball entrance with no issue at all.

Thanks for all the input, this is exactly what I needed. That tip about parking on a side street west of Western is perfect, Bucktown_Rob. WickerParkJen, your point about sunset is fair, but I am committed to the sunrise mission. I think since we will be together it will feel fine. We will try the Western ramp this Saturday and walk east for the view. Wish me luck on convincing the wife.