Running the Chicago Lakefront Trail in the Fall

Now that we are getting some crisp fall days, I want to finally start running on the Lakefront Trail instead of just my usual loop around Portage Park. I'm a bit intimidated since I always drive to my destinations and have no idea what I'm doing over there. I'd be coming from near Irving and Central, probably super early on a weekend, like 7 AM. Where is the best place to park my car without paying $30? Is the stretch near Montrose Harbor decent for a beginner, or is it a madhouse? My biggest concern is safety as a woman running alone that early, and also, are there actual bathrooms or am I relying on a Dunkin'?

The Montrose stretch is perfect for what you're describing. I run there all the time. At 7 AM on a weekend, you can usually find free street parking on Montrose Ave just west of Lake Shore Drive, or on Simonds Dr right by the harbor. It gets way worse after 8:30 AM when the soccer games start. The path is wide there and you'll see tons of other runners, so you won't feel isolated. The bathrooms at the beach house are usually open until mid-October, but a heads up, they shut off the outdoor water fountains for the winter any day now, so bring your own water bottle.

I'm going to push back a little on the Montrose suggestion. It's nice, but it gets chaotic with cyclists, strollers, and big running groups. I think the northernmost part of the trail is better. Try parking near Ardmore Ave and running north from there. It's much quieter, more of a neighborhood feel, and the path up to the end of the trail at Hollywood Beach is beautiful in the morning. You feel less like you are dodging traffic. It's also completely free to park in that area if you find a spot on the side streets.

As another West Sider, my trick is to avoid driving altogether. The traffic and parking hunt just stresses me out before the run even starts. I usually take the Blue Line to Logan Square, then bike over to the Fullerton entrance. The stretch from Fullerton south to North Ave is a total circus, but if you go north from there it thins out a bit. If you must drive, I have a friend who swears by parking way south near 31st street and running north toward the Shedd. He says the lots are cheaper and always have space early in the day.

Driving is the only way for me coming from the south suburbs. I always run the Museum Campus loop. Parking at the Adler lot is not cheap, but on a non-Bears game morning it is predictable and I am right on the path in two minutes. The view of the skyline running north from the planetarium can't be beat. It's worth the parking fee just for that. It's a very open area though, so when that wind whips off the lake it can be brutal, even on a sunny day.

This is all so helpful, thank you everyone. I think for my first time I'll take the advice from BuenaParkBeth and try the Montrose Harbor area since it is a straight shot for me down Irving Park Rd. Knowing I can probably find free parking before 8 AM makes it feel much more doable. Great tip about the water fountains being shut off, I would have been caught without water for sure. I feel a lot more confident about not getting lost or feeling unsafe now. I'll report back!

Glad you're going to try Montrose! One more thing on the bathroom situation - if the beach house ones are locked for the season, the Montrose Harbor building (the one with the bait shop) has public restrooms on the north side of the building. They're usually open year-round during daylight hours. Have a great run!