How to Plan the Best Chicago to Door County Road Trip
Life in Chicago moves fast. Between busy workweeks, packed calendars, and city noise, sometimes all you need is a change of scenery that doesn’t require a flight or a long travel day. That’s where a Chicago to Door County road trip comes in. In just a few hours, you can trade skyscrapers for shoreline, traffic for trees, and routine for relaxation.
If you’re thinking about hitting the road, this guide covers driving routes, timing, worthwhile stops, and what to expect once you arrive in Door County.
For more info, request your free Door County Vacation Guide! Inside, you’ll find local recommendations for the best restaurants, shops, and events. It’s all you need to plan a fantastic trip!
How to Get from Chicago to Door County
Driving from Chicago to Door County is stress-free, even for first-time visitors. Most travelers take I-94 north out of Chicago before connecting to I-43 North toward Green Bay. Near Green Bay, you’ll transition to WI-57 North, which leads directly into Sturgeon Bay and the heart of Door County.
This route is easy to follow and dotted with rest stops, food options, and places to stretch your legs along the way. You’ll be in Door County before you know it!
How Long Does the Chicago to Door County Road Trip Take?
The full drive is roughly 250 miles and usually takes about four to four and a half hours, depending on traffic and how often you stop. Leaving early in the morning or later in the evening can help you avoid heavier congestion around Milwaukee and Green Bay.
If you’re not in a rush, building in a couple of short stops can make the drive feel quicker and more enjoyable.
Must-See Stops Along the Way
Milwaukee, Wisconsin
About 90 minutes from Chicago, Milwaukee makes a great first break. Walk along the Lake Michigan waterfront, grab lunch, or explore one of the city’s well-known breweries or museums.
Green Bay, Wisconsin
Located just before Door County, Green Bay is ideal for a final stop. Visit the Green Bay Botanical Garden, stroll through Bay Beach Wildlife Sanctuary, or refuel with a casual meal before the last stretch of your drive.
Small Town Detours
Along I-43 and WI-57, you’ll pass smaller towns with local cafés, bakeries, and parks. These quick pull-offs often end up being memorable parts of the trip.
Road Trip Tips for a Smooth Drive
When you travel from Chicago to Door County, we recommend taking I-94 W to I-43 N for the fastest route. Near Green Bay, you’ll hop on WI-57 N to Sturgeon Bay. This 250-mile drive takes about four hours. We suggest stopping along the way to break up the journey, stretch your legs, and see some exciting cities on your trip.
Pack for comfort: Bring snacks, water, and a playlist or podcast downloaded ahead of time.
Plan flexible stops: Even short breaks help keep the drive relaxed and enjoyable.
Watch seasonal traffic: Summer weekends and fall color season can add extra drive time, so plan accordingly.
Arriving in Door County
Whether you crave adventure or prefer a tranquil retreat to nature, Door County, WI, offers endless things to do. Watch a magnificent sunset at Peninsula State Park, indulge in a delicious waterfront meal, or stroll through an eclectic art gallery. For more ideas on how to fill your days in Door County, access our free Vacation Guide.
End Your Journey at The Ashbrooke
You deserve an incredible place to stay after you’ve completed your Chicago to Door County road trip. Experience excellent customer service, top-notch accommodations, and premium amenities as a guest of The Ashbrooke. We’re happy to make your Door County vacation an unforgettable one.
Consider Grande Whirlpool Suite for your next romantic getaway. This luxurious two-room suite features over 600 feet of private space for you and your significant other to enjoy. Relax on your king-size bed, snuggle up by the fireplace, or soak in the two-person whirlpool tub. It’s the ideal place to make your home away from home.
What are you waiting for? Check our availability and book your room today!