Geneva, Illinois
Distance from Chicago: 44 miles West; 1-hour drive (or train ride)
Why it made our list: An easy 1hr drive or about-the-same Metra ride provides the quickest escape from the city. This cool little town along the Fox River has infinity outdoor restaurants tailor-made for waterfront drinking. We recommend Fiora’s or Gratto, but either way an overnight stay at the Herrington Inn is a must.
Pro tip: Get out into Island Park for some quality nature time or take a trip to nearby St. Charles, where you can sip vodka lemonades on Salerno’s on the Fox’s massive outdoor patio while watching old-timey paddle wheel boats drift past. THE HERRINGTON INN & SPA GENEVA, IL
Grand Beach, Michigan
Distance from Chicago: 70 miles East; 1.25-hour drive
Why it made our list: This little strip of beach between Michigan City and New Buffalo has long attracted Chicagoans looking for a quick escape from the city, including former mayor Richard Daley, who maintains a summer residence here. There’s not a ton to do besides bringing a cooler of beer to the shore and beaching yourself like a beer-drinking whale. And that’s sort of the point.
Pro tip: Climb a 240ft dune at the nearby Warren Dunes State Park, or head into Sawyer and fill up your growler at Greenbush Brewing Company, which you can also take back to the beach. Are you seeing a pattern here?
Lake Geneva/Delavan, Wisconsin
Distance from Chicago: 83 miles Northwest; 1.5-hour drive
Why it made our list: While Lake Geneva may be the best known of Chicago-area retreats, at 90 minutes away you still can’t beat it. Sip cocktails at Downtown spots like the 1885 Victorian mansion Baker House, or the locals dive Fat Cats, before making your way to the relatively undiscovered nearby town of Williams Bay, where you can hike the entire length of the lake shore with hardly anyone getting in your way.
Pro tip: Nearby Lake Delavan offers a quiet lakeside arboretum as well as some of finest dive bars in the state. Hogan’s Goat is a locals-heavy must-visit, as is The Inn Between, where all you need to do to start the party is dock your boat.
How Chicago Sees the Rest of Illinois
Ottawa, Illinois
Distance from Chicago: 90 miles Southwest; 1.5-hour drive
Why it made our list: This historic town, located at the intersection of the Fox and Illinois rivers, is best known as the entryway to Starved Rock State Park, where tall bluffs and canyon waterfalls provide a unique outdoor experience. But the hard-boozing town itself is also worth a visit, especially the lively waterfront hangout Red Dog Grill.
Pro tip: Escape the crowds of Starved Rock with a trip to see the equally cool bluff-side expanse of Buffalo Rock State Park. Oh, and if you’re staying the night, don’t even think of staying anywhere other than the Starved Rock Lodge.
Saugatuck, Michigan
Distance from Chicago: 141 miles Northeast; 2.25-hour drive
Why it made our list: The main attraction here is the pristine Oval Beach (cited by theTribune as the Midwest’s best beach), where you can rent kayaks, sailboats, and even do a little sport fishing. Sand dunes and paddleboat rides also vie for your attention at this Hampton-style retreat, but a laid-back meander through the art gallery-lined Downtown works too.
Pro tip: Art is great and all, but even if you failed art class you’ll have a chance for redemption at Saugatuck Brewing Company… where you can brew your own beer.
New Glarus, Wisconsin
Distance from Chicago: 151 miles Northwest; 3-hour drive
Why it made our list: What if you could take a trip to Switzerland without, you know, taking a trip to Switzerland? Discover the next best thing in New Glarus, “America’s Little Switzerland”. Sure, there may not be mountains. But they’ve got more than enough Swiss chalets and fondue to make up for it. Oh, and did we mention New Glarus Brewing Company? Yeah, we thought you might like that.
Pro tip: New Glarus beer is only available in Wisconsin, so stock up before you hit the state border.
Galena, Illinois
Distance from Chicago: 170 miles West; 3-hour drive
Why it made our list: As one of TripAdvisor’s “Top 10 Charming Small Towns”, Galena has you covered if you’re into strolling cobblestone streets amidst historic mansions and hotels. If you’re feeling more active, they’ve got you covered with rafting trips, a nearby ski resort, and bluff hikes overlooking the Mississippi River. In other words, they’ve got you covered.
Pro tip: Stay off General Grant’s beaten path (he used to live here) at the LeFevre Inn, nestled on 100 acres of land just outside of town, where you can either chill in the outdoor hot tub or paddleboard the private lake.
Door County, Wisconsin
Distance from Chicago: 276 miles North; 4.5-hour drive
Why it made our list: With dozens of great little towns situated on a beautiful peninsula that’s surrounded on both sides by water, there’s a lot to get to here. From ferry trips, to a car-free island campsite (Rock Island State Park), to a secluded beachside getaway (Newport State Park), let’s just say it’s well worth the trip. Even if you have to drive through Green Bay to get here.
Pro tip: There are few things better in life than sitting on patio furniture in the huge yard at Fred & Fuzzy’s Waterfront Bar & Grill and watching the sun set over the water with a drink in your hand.
Traverse City, Michigan
Distance from Chicago: 318 miles Northeast; 5-hour drive
Why it made our list: Across Lake Michigan from Door County in Northern Michigan sits Traverse City, another town equally worthy of the excursion. 35 miles of scenic coastline and massive mounds of sand to roll around in at Sleeping Bear Dunes State Park? Check. Willy Wonka-approved chocolate vodka at Grand Traverse Distillery? Check. Awesome views of the Grand Traverse Bay at every turn? You bet.
Pro tip: Get your mangy mane cut at the in-house Salon Saloon located inside Right Brain Brewery. Barber shop + brewery… what could possibly go wrong?
Mackinac Island, Michigan
Distance from Chicago: 406 miles Northeast; 6.25-hour drive plus 30-minute ferry (or multi-day boat trip)
Why it made our list: Sometimes you really want to get away from it all. And Mackinac Island is about as far away as you can get. Sandwiched between the Northern tip of Michigan and the Upper Peninsula, the only way to get around on the car-free island is by bike or horse-drawn carriage. With rugged, unspoiled beaches and towering white mansions, the only thing harder than getting here is leaving.
Pro tip: If you don’t feel like driving, you can race your sailboat the entire length of the 300 nautical-mile trip during the Chicago Yacht Club’s annual Chicago to Mackinac Race.
