Chicago Skyline from the Bicycle Illinois Ending Location

Overall Information

Getting to the Start and from the End
Ride Itinerary
Places We Pass Through
Route Profile Data
Starting and Stopping Towns
Prices and Deadlines


Route OptionsRoute DescriptionCentury Options

Our route parallels Lake Michigan through Chicago and the north shore Chicago suburbs and is almost entirely flat, following fully paved and signed bike paths and trails about 75% of the way. When it does not follow paths, the route primarily follows low traveled residential and secondary roads.

Participants from the Chicago area will be able to get a great day of cycling close to home!

  • Click Here for more information about the types of roads and bike paths the route will follow.
  • Click Here for more information about our riding policies and procedures.

Route Options
There are four possible route options that you can ride.

Hammond to Kenosha
This route is the basis for the event. You will start your ride right over the Illinois/Indiana border in Hammond and finish your ride in Kenosha, riding through 3 states in one day.

Hammond to Kenosha Century
In order to complete a century, you will ride a loop out of the ending location in Kenosha to add on enough miles in order to ride over 100 miles. It will not matter which specific route segments or options you ride from Hammond to Kenosha in order to complete the century.

Hammond to Waukegan
For this route, you will start the ride in Hammond but end in Waukegan, IL. After you arrive in Waukegan you can then take the Metra train back with your bike to Chicago or any Metra station in between. This ride is perfect for riders who do not want to ride the full distance from Hammond to Kenosha or for riders who want to depart the ride early.

  • Click Here for more information about taking the Metra train from Waukegan.

Hammond to Waukegan Century
If you want to complete a century ride but do not want to wait at the end in Kenosha for our return transportation service, this route is the one for you! After you arrive at the end in Kenosha, you will turn around and ride the route back to rest stop 4 in Waukegan.

Route Description

From Hammond to Rest Stop 1 in Downtown Chicago
The event will start at Forsythe Park in Hammond. The park is in Indiana on the eastern shore of Wolf Lake, which the Illinois/Indiana border passes directly through.

The route begins by following a brand new bike path out of the starting location. From there, you will ride directly along the Illinois/Indiana state line for about 3/4 of a mile to the Indiana state sign - make sure to stop and get a picture!

After you head west from the Illinois/Indiana state line you will enter the city of Chicago and ride along the Burnham Greenway Trail which is a rails to trails bike path that proceeds up through quite a bit of Chicago's south side. From there you will ride through Calumet Park and onto the bike path along the brand new "New Lake Shore Drive" which goes through 600 acres that are currently being redeveloped that once housed U.S. Steel's South Works plant. Not only will you be amazed riding past the giant ore walls that once held the raw materials processed into steel, you won't be able to help picturing the giant freighters that once stopped there after travelling across the lake all the way from the iron ranges of Michigan and Minnesota.

At 71st Street, Chicago's world famous Lakefront Trail begins and you will bike on the Lakefront Path directly along Lake Michigan. One of the most amazing things you will ever see is when you catch your first view of the Chicago's awe inspiring skyscrapers and beautiful lakefront as you're coming up the path.

Rest Stop 1 in Downtown Chicago to Rest Stop 2 in Skokie
Our first rest stop will be at DuSable Harbor in downtown Chicago located directly off the Lakefront Bike Path. Located in the heart of downtown at the foot of Randolph Street, the harbor is surrounded by Chicago's towering skyline!

From the end of the lakefront path we will travel along very low traveled residential streets through Chicago's north side, riding past many of Chicago's famous "bungalow" style houses. Then you will then bike to our next rest stop in Skokie on the North Shore Channel Trail, which follows the North Shore Channel canal. Running alongside almost the entire length of the trail is the Skokie Northshore Sculpture Park which contains over sixty large scale contemporary sculptures on exhibit.

Rest Stop 2 in Skokie to Rest Stop 3 in Lake Forest
From rest stop 2 in Skokie you will bike to the start of the Green Bay Trail in Wilmette. The Green Bay Trail parallels the current Metra North Line and is directly on the track bed that once used was for the Chicago North Shore and Milwaukee Railroad, a train service that stopped running more than 50 years ago. Make sure to keep your eyes open for the remnants of the concrete bases of the old stations, especially in Winnetka , Hubbard Woods, and Glencoe!

From the Green Bay Trail, you will bike to the start of the Robert McClory Path in Glencoe which you will follow is almost a direct route to rest stop 3 in Lake Forest. Along the way you will bike through the famous Ravinia Festival in Highland Park and directly past Fort Sheridan in Highwood, a former major United States Army post officially closed by the Army in 1993.

Metra Train Options into downtown Chicago
In case you are unable to finish the ride, you can easily take a Metra Train back into downtown Chicago from rest stops 3 and 4. Bicycles are allowed on the train, subject to restrictions.

  • Click Here for more information about Return Metra Train Service.

Rest Stop 3 in Lake Forest to Rest Stop 4 in Waukegan
Out of rest stop 3, you will continue following the Robert McClory Path immediately past the Great Lakes Naval Station, home of the United States Navy's only boot camp and the largest training station in the Navy.

Rest stop 4 is directly at Waukegan Harbor. Going into and coming out of rest stop 4 there are some very steep hills so get ready for a good challenge climbing them! Our rest stop is in a perfect scenic location and we know the cool breeze off the lake will feel great! In addition, there is also an ice cream stand, hot dog stand, and deli directly at the rest stop so make sure to bring some cash with you and enjoy an ice cold ice cream cone on a hot summer day!

The Waukegan Metra station is only two blocks from rest stop 4 and you can either choose to end your ride there and take the Metra train back into Chicago or ride up to Kenosha and back to rest stop 4 if you don't want to take our return transportation service. Fully assembled bicycles are allowed on the train, subject to restrictions.

  • Click Here for more information about taking the Metra train from Waukegan.

Rest Stop 4 in Waukegan to the Ending Location in Kenosha
About three miles after rest stop 4, the Robert McClory Trail continues with a crushed limestone surface through the remainder of Illinois. You will have the option of either following this path for over eight straight miles across the state line into Wisconsin or continuing on a fully paved on road option primarily following residential streets.

At the Illinois/Wisconsin state line the path becomes paved and all participants cyclists will follow it again. After you cross into Wisconsin the route will turn east for about two miles then turn back north. Here you will be able to ride directly along the shores of Lake Michigan as the route makes its way to our ending location through downtown Kenosha.

Our ending location in Kenosha is at the Lakeside Deck at the Wyndham Garden Kenosha Harborside right in the heart of downtown Kenosha overlooking the Kenosha harbor on Lake Michigan! Free showers and a swimming pool and hot tub are available so you won't have any problem relaxing and getting refreshed after the ride. You'll also be able to get some food and a drink at the bar and restaurant there while waiting for our return transportation service!

Century Options

Both century options will begin at the ending location in Kenosha. After you arrive at the ending location, you can replenish yourself with snacks and sports drinks from our rest stop there before departing to ride either century option.

Kenosha Century Loop Option
If you want to get in a century ride and will ultimately be departing from Kenosha, our century loop will begin and end directly at the ending location. You will head north for just over two miles directly along the Lake Michigan shoreline through Simmons Island Park, then bike north to Racine following the north part of the Kenosha County Bike Trail. You will then turn around and follow the Kenosha County Bike Trail south back into town. Before heading back to the ending location again the route passes right past the Kenosha Velodrome, the oldest operating velodrome in the country. Take a lap or two and see how fast you can go!

Kenosha to Waukegan Century Option
If you want to get in a century ride and will be departing from Waukegan, you will turn around from the ending location and ride the exact same route back to rest stop 4 in order to catch the Metra train back from Waukegan.

P.O. Box 8454 • Chicago, IL 60680 • (877) TOUR-ILL [868-7455]
Copyright© Bicycle Illinois

E-Mail UsJoin Our Mailing List