Best Day Trips From Chicago to Take on Your Bike
Itchin’ to take a bike tour but can’t ditch Chicago for too long?
These cycling adventures can be done over a weekend or even in just an afternoon!
With a sprawling bike path network in and around Chicago, there’s lots of adventures you can take, whatever your riding skill may be. Combine these trails with a robust commuter rail network, then you have the option of taking it easy on the way back into town by hopping on a train. Keep reading for a couple trips you can take to get you started.
Nature lovers looking for a scenic afternoon trip will love checking out the Botanic Gardens.
40mi round trip or 20 miles out & UN-N Metra back from Braeside Station
The Chicago Botanic Gardens up north in Glencoe are a great way to surround yourself with natural beauty without having going too far. The North Branch Trail keeps you separated from cars & takes you through a paved, shaded, tree-lined path, which is a great break if you’re used to riding with all the cars in the city streets.
The north trailhead of the North Branch Trail rests right at the southern end of the Chicago Botanic Gardens, which means you can get there if you just hop on the trail at any point & ride north. A good spot to start is either at Milwakee & Devon, or by Gompers Park just off of Foster. The whole trail is about 20 miles so you can go out there, stop for lunch, enjoy the gardens & head home all in a day. You can learn more about the Botanic Gardens and all you can explore around there by clicking below.
For the beer sommelier who wants to ride some light gravel, try riding out to Two Brothers Roundhouse.
100 round trip or 50mi out & BNSF Metra back from Aurora Station
The Illinois Prairie Path takes you through mies and miles of some of the best prairieland the prairie state has to offer. This trail is a highlight of the western suburbs and, best of all, it ends with an amazing restaurant. Two Brothers Roundhouse has an expansive beer garden, they are host to great live music, and their menu boasts food that everyone will enjoy; no better way to end a ride than a tasty dinner & a cool beer!
There’s a couple ways to get to the east trailhead of the Illinois Prairie Path. Depending on where in Chicago you start, you can take either Augusta Boulevard or Lake Street west for about 10miles before turning south to get to the start of the path. When the Prairie Path branches in two directions in Wheaton, make sure to take it south. It’s worth noting that some of the trail is made up of crushed limestone, so you might not want to take out your roadie with super skinny tires. At the very end of the trail, Two Brothers Roundhouse will be waiting for you with great food & drinks.
If you like sleeping under the stars, you should go on an overnight camping adventure to Illinois Beach State Park.
84mi round trip or 42mi out & UP-N Metra Back from Zion station
Bikepacking is just like backpacking, but (as the name suggests) you throw all your gear onto your bike instead of your back. Imo, this makes camping a lot easier since the bike becomes your pack mule instead of yourself. Heading up to Illinois Beach Sate Park is a great way to dip your toe into this kind of adventure since it’s not crazy far outside of the city & you can even take the train home if your legs get too worn out on the way out. The campground itself is right along the beach so you can also enjoy some time out in the sun & water.
Illinois State Beach rests at the north end of a series of three trails that lead right out to the campground. You can start by taking the North Shore Channel Trail north to the Green Bay Trail before hopping onto the Robert McClory Bike Path almost into Wisconsin before taking a right onto Lebanon Ave and ride northeast onto 27th Street, where you turn right before cutting north to Shiloh Blvd which you can ride all the way east into the park.
Beach Bums seeking an out-of-state getaway: Seek out the Indiana Dunes.
134 round trip or 67 one way & South Shore Line back from Dune Park Station
With Indiana Dunes State Campground less than a mile away from the beach, a ton of cute B&Bs scattered throughout the area & plenty of hotels to choose from in Michigan City (ironically still in Indiana), there’s lots of ways to turn this long ride into an extended vacation. There’s tons to do here too beyond just a lazy day at the beach or exploring the dunes that line the south shore of Lake Michigan. The ride itself is mostly flat and takes you past some real gems on the south side of Chicago like Jackson & Calumet Parks as well as skirting around the edges of Gary by old steel mills. Just like the dunes themselves, this ride will showcase all the rich history of this region. Click below to learn about everything the dunes have to offer!
To get to the dunes you can hop onto the Lakefront Path and take that south through Calumet Park. Then there are three rails-to-trails that you can take which will take you around Gary on a flat, paved surface. The trails are the Erie Lackawanna Trail, Oak Savannah Trail & Prairie Duneland Trail, in that order. After the trails, you can take a series of calm, county roads to get you to the entrance of the state park. The last trail will take you onto North Calumet Road which you take north before making a right onto Indian Boundary Road, then left onto Brummett road. Next, you turn right on County Road 450 which turns into East 1400 Road before finally turning left onto North 500 East. To get back, you can take the South Shore Line from Dune Park Station all the way to Millennium Station. Just make sure to check which trains will allow bikes; you can click below to plan your trip.