Bike Route from Chicago to Milwaukee

Bicycle Route from Chicago to Milwaukee

This will be my detailed breakdown of the bicycle route I took to get from Chicago to Milwaukee. I’m definitely not saying that this is the route that every one should take, and in my opinion this is definitely not the best route.

Before we get started, I’ll tell you three things about this route:

  1. This IS NOT a good route for road bikes. It can be done (I did it on a road bike), but the route is made up of streets, nicely paved trails, crappy old paved trails, and crushed limestone trails.
  2. This IS a good route for people that want to spend the least amount of time on roads and streets… except for the beginning when there is quite a bit of street riding. That can be changed though if you really wanted to avoid streets.
  3. I chose this route because it was one of the only routes that made the trip over 100 miles (101.5 to be exact). It can be done in less than 100 miles… I saw a few different routes that were around 90 miles.

The Route

The best way to show you this route is through this great site called Map My Ride where you can map your own rides and share them with other people. I’ve already mapped my route from Chicago to Milwaukee on Map My Ride, so you can easily open this map and follow along with the notes I have outlined below. Let’s get started!


  • I start my ride at the corner of Halsted Street and North Avenue in Chicago. You don’t have to start here, but take a look at the streets I take north to get to the North Branch Trail. You can also take a look at my post on the Best Bike Route from Downtown Chicago to the North Branch Trail.
  • The entrance to the park and the place where you pick up the North Branch Trail is at the corner of Milwaukee and Damon. When you reach Damon, look over to the right across the street and you’ll see a small parking lot. That’s where you enter and pick up the North Branch Trail (one of the best trails around Chicago!).


  • North Branch Trail (miles 10-25) – Pretty simple to just follow the main trail for this entire section. The only tricky part is when you get to Dempster Street (mile 15). You have to cross Dempster, then cross over Lehigh Ave and the train tracks and follow the sidewalk until you pick up the trail again (turning left into the park).
  • At mile 23, when you reach Tower Road, you’ll have a choice to follow the trail to the left (across Tower Road) or keep going straight and cross Tower Road a little later. It doesn’t matter which one of these you do, because they both meet up at the same place just south of Dundee Road.


  • If you took my route around the forest preserve, you run right into Dundee Road where you can take a right and head east for about 400 yards and take a left onto Hohlfelder Road (just a little side street to keep us off main roads).
  • Head north on Hohlfelder (take a look at all the nice big houses…) and once you reach the end of the street take a right on Westley Road. This street end and you sit in front of Green Bay Rd. Depending on when you’re riding, this road can be pretty busy, but a lot of bikes ride this road, so cars tend to be used to it. Take a left and head north!
  • You’re only on Green Bay Road for about .5 miles and then you take a right on Lake Cook Road (first light you come to). You’ll cross over some more train tracks and then on your left there will be a street called St. Johns Ave.
  • St. Johns Ave will actually end up being a dead end (I believe), but before it ends there is a left turn into what looks like a parking lot. This is where you pick up the Robert McClory Bike Path that you will be riding for the majority of your time in Illinois.


  • This trail or path (whatever you want to call it) goes right by the entrance to Ravinia and then after that actually turns into the bike trail.
  • The trail is a little bumpy, but it’s not that bad. A lot of riders will actually ride on the road that runs parallel to the trail, which is St Johns Road (it starts back up again after Ravinia).


  • This section is sort of a choose your own adventure… I like to get on St Johns Ave and take that until I get to Walker Ave. I take Walker west to Wuakegan and then head north on Waukegan for another couple miles until I cross over the street and pick up the Robert McClory Bike Path again (at Old Elm Road).
  • It is possible to follow the bike path, but it sort of twists and turns all over the place so I like to take a more direct route. You can see on the map where the bike path goes if you’re interested in following the path and staying off of the streets.


  • Mile 34 is Lake Forest, where there are some little shops across the train tracks (food and such) and a train station which can be a great place for a bathroom break or just a rest.
  • Follow the trail here… nothing special!


  • Right here is where people get tricked (me included) and they lose the trail. Look at the map and you’ll see that the outlined path does a little loop. You actually have to cross over Sheridan and then loop around under a bridge and come out on a street that doesn’t even seem like a bike trail anymore. It is… or at least it will be!
  • Well, the trail isn’t that great anymore and neither is the scenery. Take this trail with the crushed limestone all the way into Wisconsin though!


  • As you enter into Wisconsin the trail will turn into the Kenosha County Bike Trail and you’ll lucky enough to switch back over to a nicely paved trail, and this will go on for about 3 1/2 miles. Enjoy it while you can!


  • Here you’ll reach the end of the bike trail and cross over 89th street and get in the bike lane on 30th Avenue.
  • Stay on this street for a few miles and it will eventually turn into Wood Road. If I remember correctly, the bike lane doesn’t last forever, but it’s not a bad street to ride on.
  • Just before you reach mile 60, you’ll take a right onto 35th street. Then, shortly after you pass 28th Avenue there will be another bike trail to pick up on your left. On the map it’s named the County Bike Trail.


  • 7 1/2 miles of paved bike trail! You’ll cross over streets from time to time, but this is a pretty decent bike trail.


  • The County Bike Trail ends as you reach 16th Street and here you can take a right (crossing over West Blvd) and heading east on 16th Street for just a couple blocks until you reach Quincy Street.
  • Take a left on Quincy Street and head north until you get to Washington Avenue, which crosses diagonally just before mile 68.
  • Cross over Washington Avenue and get on the sidewalk for a couple minutes until you veer off to the right on the Root River Pathway.


  • I got a little confused during this section of the route, but if you’re ready for it, it’s not bad at all. Once you get on the bike path you do a little turn and start heading east and riding parallel with 12th Street for about 1/4 of a mile.
  • Pay attention here because the bike path will stop, turn left and cross over 12th Street. Wave hello to any golfers that are teeing off!
  • At mile 69, it seems like the bike path ends, but you just need to get on Horlick Park Drive for a couple minutes and then pick up the path again on your left after you cross over a small bridge.
  • Stay on the bike path, go over another small bridge and stay right on the path. Cross over Spring Street, then another small bridge.
  • After the bridge you’ll have to cross over Domanik Drive and stay on the path for a couple minutes longer, or you could just take a left and stay on Domanik Drive because you’ll have to get on it in a couple minutes anyway.
  • We leave the Root River Pathway here (just before mile 70) because the path only stays paved a little while longer and then turns into crushed gravel.


  • You’re on Domanik Street now and headed up a steep but short hill, and as the road turns right it changes into Jefferson Street.
  • Stay on Jefferson Street for about 1/4 mile and once you reach Westwood Drive you’ll take a right. You’re not on Westwood Drive long until you run into Northwestern Avenue.
  • Cross over Northwestern Avenue and pick up the Root River Pathway again.
  • You’re not on the bike path long until you reach High Street. If you look at the map, you could basically take Mt Pleasant Street north from here until you reach Layard Avenue and take a right, but for some reason (possibly less traffic) I took a right on High Street, then a left on Summit Avenue and then met up with Layard Avenue.
  • You can do whatever is easiest for you, but once you reach Layard Avenue take a right and go until you cross over the train tracks. There will be another bike trail on the left right after the train tracks.


  • Ah, wonderful crushed limestone again! This starts out as the County Road Trail and turns into the MRK Trail.
  • When I took this trail in early August 2013, part of the trail was closed after we crossed over 3 Mile Road. I ignored the sign and kept going, but I did end up having to walk up to the train tracks, cross a small bridge and then walk back over to pick up the trail again.
  • If you’re not up for walking near train tracks, then find another way around if you see that this trail is still closed.
  • The MRK Trail continued after that, but it does end once you reach 6 Mile Road, where you’ll need to take a left and travel streets for a little while again.

MILES 76.5-80.5: STREET

  • Head west on 6 Mile Road until you meet up with Douglas Avenue where you’ll take a right and head north.
  • This road does not really have a bike lane, but it has a good size shoulder so it’s not too bad of a road to ride on.
  • You’ll only be on Douglas Avenue for a couple miles and then shortly after mile 79 you’ll take a left onto County Line Road.
  • Travel west on County Line Road for about a mile and keep looking for a bike trail on the right. It almost looks like a drive way, but there is a little sign there for the Oak Leaf Trail, and a small space for a few cars to park.


  • The Oak Leaf Trail is a pretty good trail, except for the annoying gates that they have up at every cross street, where they leave just a small space for you to get through with your bike.
  • Unfortunately this section of the trail only lasts a couple miles and then you’ll reach Ryan Road where you’ll need to take a left.
  • Ryan Road will have signs pointing out that it is dead end, but keep heading west! The road will end, but you’ll pick up the Oak Leaf Trail again right after mile 83.
  • The bike trail then takes a sharp right at Shepard Avenue (although I believe there are no street signs to tell you what street it is)… It’s the first street you come to!
  • Shortly after you take the right and start heading north, the trail will break off twice. When it breaks off left you’ll want to stay straight, and then when it breaks off to the right, take the trail to the right.
  • You’ll stay on this bike trail for a couple miles, crossing over a few different streets until you come to Drexel Avenue (around mile 85.5).
  • The bike trail will keep going right, but take a right on Drexel Avenue and ride east on this street for about 3/4 of a mile.
  • You’ll cross over some train tracks and you’ll see the Oak Leaf Trail again on your left. Drexel Avenue is a pretty busy street, so be careful riding on it and then be careful crossing over it to get on the bike trail again.
  • Stay on the Oak Leaf Trail until you reach Milwaukee Avenue (just before mile 88). The bike trail will keep going, but you’ll need to take a right on Milwaukee Avenue and head east towards the lake!


  • Ride Milwaukee Avenue for about a mile until it looks like the street is making a big turn right. Before it does that, take a left onto 6th Avenue/Mill Road and head down the hill!
  • Cross over a small bridge and take you’re first right onto Oak Creek Parkway (although I don’t think there’s a street sign telling you what road it is).
  • This road winds around through the woods and then comes around up a hill and turns into Grant Park Drive (not that you really need to know that).
  • Shortly you get to the top of the hill you’ll see the trail starting up on the right side again.


  • According to the map this bike trail may look like a lakefront trail, but it’s not. You’ll be riding through the woods on a very bumpy and winding trail. It wouldn’t have been so bad if it wasn’t for the rough trail.
  • The first chance I got, I got back on Grant Park Drive and took that until I met up with S Lake Drive.
  • I stayed on South Lake Drive (which wasn’t a bad street to ride on) for about 4 miles and shortly after I passed E Howard Avenue (on the left) I saw the bike trail again and got back on.
  • It wasn’t as bad this time and it actually went along the lakefront which was nice.


  • Right after South Shore Park I came to a parking lot and it seemed like the lakefront trail was ending.
  • Once you get to this point, it’s up to you exactly how you want to get into the city and where exactly you want to go. There were quite a few streets that had construction which caused me to take alternate streets and then cut back to the street I planned on taking.
  • From the lakefront, I just wanted to find a good street to get me over to Kinnickinnic Avenue, which is a good street with bike lanes.
  • From there I had to get over to 2nd Street and head north so that I could get over the bridge where 2nd Street turns into Plankinton Avenue.
  • I took Plankinton Avenue right to the Riverwalk in downtown Milwaukee where my friend and I were meeting up with my girlfriend for lunch.

Wrap Up!

Well, what did I learn?

  1. There’s no easy route from Chicago to Milwaukee… maybe there’s an easier route, but I won’t know until I try it again.
  2. When you see a sign that says “Trail Closed” there’s a pretty good chance that the trail is actually closed!
  3. Always take a break and buy some Cheetos and a Snickers bar if it starts raining.

I hope this will help some people find their own route to/from Milwaukee! If you have any comments or suggestions, please feel free to leave them below!

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