Chicago is a vibrant and energetic city with no shortage of things to do, neighborhoods to explore, and beauty to find. But as many Windy City dwellers know, sometimes you need to disconnect from the hustle of the big city and embark on a getaway.
Whether you only have time for a quick day trip or are looking to grab a long weekend, we have curated some trips inside and outside of Illinois to help you find the best weekend getaways from Chicago to leave you recharged.
Quick Answer Guide to Weekend Getaways from Chicago
Best Day Trips from Chicago
- Best for Beach-loving shoppers and foodies - Lake Geneva, Wisconsin
- Best for Art and architecture lovers - Milwaukee, Wisconsin
- Best for Girls' weekend or romantic couple's getaway - Galena, Illinois
Best Road Trips from Chicago
- Best for Art and nature-loving beachgoers - Saugatuck, Michigan
- Best for Outdoor enthusiasts, history buffs and soul-seekers - Door County, Wisconsin
- Best for Midwest explorers and foodies - Bloomington, Indiana
Best Weekend Trips from Chicago
- Best for History-loving city slickers in need of low-key island time - Mackinac Island, Michigan
- Best for Mountain lovers, artsy folk - Asheville, North Carolina
- Best for Midwest explorers in search of Texas heat and hospitality - Austin, Texas
Best Day Trips from Chicago
The best day trips from Chicago are destinations that are close enough to be just a two-hour drive from Chicago. These are a perfect choice if you have limited time but want to discover somewhere new. Each spot has plenty to explore.
1. Lake Geneva, Wisconsin
- Perfect for: Beach-loving shoppers and foodies
- Highlights of Lake Geneva:
- Geneva Lake Shore Path
- Unique shops
- Lakeview dining
How to Get to Lake Geneva
Driving to Lake Geneva from Chicago is an easy hour and a half, whichever way you go. Take the Dan Ryan (I-90W/I-94W) to the Tri-State Tollway (I-294N), then to WI-50/75th Street. You can also take the Eisenhower (I-290) to Route 12 and take that right into Lake Geneva.
Things to Do in Lake Geneva
Geneva Lake is the main attraction of this picturesque midwestern getaway. It’s not one of the largest lakes in Wisconsin, but it is stunning.
The 21-mile shoreline boasts a winding 26-mile walking path, much of it offering close-up views of gorgeous homes and landscaping. Grab a Lake Geneva Shore Path map at the quaint little visitor's center on Wrigley Drive.
Shopping and dining are a huge draw, from quirky gift shops and antique stores to upscale boutiques and wine shops.
Whether you like to golf, hike, bike, zipline or boat, there is plenty of outdoor fun in and around the lake. Big Foot Beach State Park and Riviera Beach are just spots where you can camp or take a dip. Enjoy the lake on a brunch, lunch or dinner cruise on Lake Geneva Cruise Line.
Where to Stay in Lake Geneva
From upscale resorts to cozy campgrounds, Lake Geneva has accommodation options for every kind of traveler.
I love the Eleven Gables Inn and Cottage for its downtown location and dog-friendliness. Its historic charm and relaxing vibe make you feel like you're off the beaten path, but you are steps away from all the downtown action.
If you prefer modern luxury for your getaway, the Grand Geneva is about 7 minutes outside of downtown and has everything from fine dining to aromatherapy massage.
2. Milwaukee, Wisconsin
- Perfect for: Art and architecture lovers
- Highlights of Milwaukee:
- The Milwaukee RiverWalk
- Milwaukee Art Museum
- Historic Third Ward
How to Get to Milwaukee
To get to Milwaukee, you can kick back and take Amtrak aboard the 90-minute Hiawatha service, which runs multiple times daily between Chicago and Milwaukee. To drive, take the Edens Expressway (I-94W) to I-43 N, then take I-794 E toward Lakefront.
Things to Do in Milwaukee
With old-fashioned charm and glittering modernity, Milwaukee is Chicago's baby sister city and Wisconsin’s largest city perched prettily on the shores of Lake Michigan.
The Milwaukee Riverwalk winds through the city, making it an ideal way to explore its notable neighborhoods, including the artsy Historic Third Ward, the downtown theater district and Brewers Hill.
The art scene in Milwaukee is thriving and accessible, from the galleries and shops of the Third Ward to the architecturally gorgeous Milwaukee Art Museum. A pedestrian bridge connects the MAM to the city, so you can stroll right into the action.
Milwaukee has a thriving theater scene, with the world-class Marcus Center, Milwaukee Rep, and numerous smaller stages. Before or after the show, there are plenty of places to eat, all within walking distance. Speaking of culture, don’t miss the 20-acre campus of the Harley-Davidson Museum — the only one of its kind.
Where to Stay in Milwaukee
You can find a short-term rental in any neighborhood of the city, ranging from a condo downtown to a lakefront home in nearby Bayview.
I love a chic, stylish boutique hotel. In Milwaukee, I can't decide which I love more between these two: Saint Kate: The Arts Hotel has an artsy vibe, gorgeous décor, and Neapolitan-style pizza.
The Kimpton Journeyman has a stellar location, is pet-friendly, and has a rooftop restaurant and bar.
3. Galena, Illinois
- Perfect for: Girls' weekend or romantic couple's getaway
- Highlights of Galena:
- Main Street: shop, dining, wine
- Galena Ghost Tours
- Garden walks and river trails
How to Get to Galena
Galena is close to a three-hour drive from Chicago. Take the Dan Ryan (I-90W/I-94W) to I-39/s/I-51S, then to US-20W until you hit Main Street.
Things to Do in Galena
While Galena's small-town charm and rich history may have you feeling like you are stepping back in time, this historic town that once housed Abraham Lincoln and served as a Mississippi River steamboat hub has plenty to keep a modern traveler happy.
Wear your walking shoes! Main Street has more than 125 shops and restaurants, many of them in buildings on the National Register of Historic Places.
At night, you'll find plenty of live music from classic rock and bluesy guitar to local talent. Wine lovers should visit Galena Cellars Vineyard in the countryside or drop into the downtown location for a tasting.
If you haven't been on a hiking trail alongside goats before, now is your chance. For a morning walk or evening hike, Hoof It Goat Treks offers a 45-minute prairie hike with their family of goats. If you’re visiting in the snowy months, you’ll find some of the best cross-country skiing and snowshoeing in Galena.
Where to Stay in Galena
There are so many unique lodging options in Galena that you may find it hard to choose. For its luxurious vibe and fascinating history, I recommend the 135-year-old Jail Hill Inn, a county jail turned bed-and-breakfast tucked away within walking distance of the Main Street action.
If the old jail vibe isn't your thing, try the Victorian-chic Galena Inn (formerly the Victorian Mansion), with English gardens, gorgeous porches, and modern amenities.
Best Road Trips from Chicago
If your playlist is longer than two hours and your wanderlust pulls you toward more than a swift day trip, fill up or charge up and head to one of these spots. Leave around sunrise and be settled in your getaway spot by lunch when you embark on one of these road trips from Chicago.
4. Saugatuck, Michigan
- Perfect for: Art and nature-loving beachgoers
- Highlights of Saugatuck:
- Art galleries and artist's studios
- Farm-to-table and vine-to-glass
- LGBTQ+ events
How to Get to Saugatuck
Saugatuck is about 2 hours and 15 minutes from Chicago via the Dan Ryan (I-94E). Take I-94E to the Indiana Toll Road and then to I-196N, following the signs to Holland/Grand Rapids. Head to the Blue Star Highway and drive into town via Lake Street.
Things to Do in Saugatuck
Saugatuck Douglas, Lake Michigan's "Art Coast," is a thriving artsy beach town with scenic waterways and sandy dunes. Saugatuck flies the rainbow flag year-round and is a welcoming and safe environment for all visitors.
Visit Saugatuck Dunes State Park for 2.5 miles of pristine beach and several hiking trails through the wooded dunes. Or spend the day at the impressively beautiful Oval Beach. First, hit Butler Street to pack a picnic with a bottle of wine from The Butler's Pantry and some beach-worthy snacks from American Spoon.
The agricultural abundance of the Michigan coast plays well for the food scene here. There is no shortage of must-visit restaurants, cafes, farmers markets, breweries, wineries, and bars.
Where to Stay in Saugatuck
There is somewhere to stay for every budget and travel style in Saugatuck, from lakeside condo rentals and historic hotels to art suites on the main drag. I am obsessed with downtown Saugatuck's Hidden Garden Cottages and Suites. Want to leave your car parked all weekend? You are mere steps away from everything in these tiny cottages overlooking picturesque gardens. Scratch-baked goods every morning and fresh berries.
The sweet Oriole cottage is a bright and cozy rental that feels secluded but is just a few blocks outside of town. It has a screened porch, a hot tub and every comfort of home.
5. Door County, Wisconsin
- Perfect for: Outdoor enthusiasts, history buffs and soul-seekers
- Highlights of Door County:
- Natural wonders
- Sunrises and sunsets
- History, culture and community
How to Get to Door Count
Take I-94N to I-294N and head to I-43N. From there, take WI-54E/WI-57N to County Q to head into town. The trip takes about four and a half hours. Cedarburg or Elkhart Lake are nearly the halfway point if you need to stop and stretch your legs in a quaint little town.
Things to Do in Door County
Door County, Wisconsin, has small-town charm and a never-ending supply of natural wonders, like the pristine waters of Cave Point County Park and the breathtaking Niagara Escarpment.
Visit the harbor communities on the peninsula. Virtually all of them have a marina, eateries and shops. Egg Harbor and Fish Creek are two of the liveliest spots, with great restaurants, shops and nightlife. Sister Bay is known for its stunning sunsets, and Sturgeon Bay is the home of the Door County Martine Museum and Potawatomi State Park.
Door County has miles of trails. Grab a ferry to Washington Island or Chambers Island to hike, take a bike tour, hit the beach or visit a historic lighthouse. Take a boat ride to look for shallow-water shipwrecks — the county has over 240 known underwater wreckages in all.
In the winter months, snowshoeing, cross-country skiing and ice skating opportunities abound.
Where to Stay in Door County
Every spot on the peninsula will have short-term rentals, adorable inns, charming B&Bs and upscale resorts. The Chanticleer Guest House in Sturgeon Bay is one of our favorite places to stay. The fully restored orchard farmhouse with lush bedding, beautiful gardens, and breakfast baskets is about as Chicago getaway as it gets.
If you want to be closer to downtown, try the quaint Main Street Motel in the heart of Fish Creek.
6. Bloomington, Indiana
- Perfect for: Midwest explorers and foodies
- Highlights of Bloomington:
- The Square
- Fourth Street's international restaurants
- Monroe Lake and State Forest
How to Get to Bloomington
It's just shy of a four-hour trip to Bloomington, taking I-94E and I-80E to I-65S. Follow the signs to the airport, taking I-465S to I-70. From there, follow the signs for Ameriplex Parkway S and take IN-67S/Kentucky Avenue to IN-39S/Morton Avenue. Exit onto I-60 into town.
Things to Do in Bloomington
The Square is downtown Bloomington's shopping district, surrounding the Monroe County Courthouse with dozens of locally-owned boutiques, restaurants, galleries, bookstores, and cafes.
Fourth Street in Bloomington is known as International Row for its authentic cuisine. From Burmese to Turkish and Cajun to Thai, there is something for everyone here.
Kayak in Monroe Lake or grab some sand at Fairfax State Recreation Area. At Bluespring Caverns Park, just 20 miles out of town in Lawrence County, explore the cave system on the hour-long Myst'ry River Voyage.
Where to Stay in Bloomington
The first time I stayed in Bloomington, I stayed at The Biddle Hotel inside the Indiana Memorial Union on the Indiana University campus, which was stately and beautiful.
But if you want a downtown B&B experience, look no further than the historic and unique Grant Street Inn, with its suites and guest rooms spread across five distinct buildings.
Best Weekend Trips from Chicago
When you find yourself with a few days to spare or need more than a quick day trip, hop on one of these short flights to destinations for the best weekend getaways that make you feel like you're worlds away.
7. Mackinac Island, Michigan
- Perfect for: History-loving city slickers in need of low-key island time
- Highlights of Mackinac Island:
- Legends and lore
- Sunrise or sunset kayaking
- Shoreline eateries
Things to Do in Mackinac Island
OK, first: You are on an island. That's number one. Take it in. There is so much clean air and natural beauty — and no city noise or hustle. Also, no cars are allowed on the island.
Outdoor activities are all around on Mackinac Island. Stop into Great Turtle Kayak Tours to rent a kayak, take a lesson or grab a map and see the majestic views up close. If cycling is more your speed, you will have no trouble finding a place to rent one, like Mackinac Wheels and Mackinac Cycle. You can always hop on a carriage ride when your legs get tired.
Arch Rock is a delicate, 146-foot-tall, 5,000-year-old geologic masterpiece on the island. Native American legend views the arch as a bridge used by spirits to descend upon the earth.
Look over the water and sip a Lilac Lemonade at the famous Pink Pony Bar inside the Chippewa Hotel.
How to Get to Mackinac Island
You can fly into Chippewa County International Airport (CIU) or Pellston Regional Airport (PLN) in just over an hour if you drive or take the train to Milwaukee first. You can find a flight from O'Hare or Midway, but finding a nonstop one can be tricky. You can also drive from Chicago and take a ferry from Milwaukee or Manitowoc, which will add up to about eight hours total.
Where to Stay on Mackinac Island
The Chippewa Hotel Waterfront is a must-stay to dive into the whole Mackinac tourist experience. Its colorful island vibe walks the line of kitschy but is clean and classy.
The island also has full-service properties, like the one on Mission Point Resort, which is on my list for the next visit.
8. Asheville, North Carolina
- Perfect for: Mountain lovers, artsy folk
- Highlights of Asheville:
- River arts district
- Waterfalls and mountains
- Downtown Asheville
Things to Do in Asheville
When you are in Asheville, you are in the midst of immense beauty, from the breathtaking waterfalls of Gorges State Park to the foggy canyons of the Great Smoky Mountains and the half-million-acre Pisgah National Forest.
After a morning of waterfall gazing, spend the day at the Biltmore Estate, a French Renaissance Castle in the Blue Ridge Mountains, for experiences earthy or posh: wine tasting and spa time, hiking and river boating. Make time to visit the Eda Rhyne Distilling Company outside of Biltmore, a unique boutique distillery.
Take a day to immerse yourself in the River Arts District's art museums, galleries, and cultural experiences.
How to Get to Asheville
Getting a two-hour nonstop flight from Chicago to Asheville Airport (AVL) is easy, which lands you 15 miles outside the Asheville Historic District. Grab a cab or rideshare, and you'll be downtown within 20 minutes.
Where to Stay in Asheville
Whether you want a single room or an entire bungalow, Airbnb and VRBO have great options in town or nearby. I personally love the Wrong Way River Lodge and Cabins. They're close to everything, super cute, and the canteen has excellent coffee and delicious locally-sourced food. They also have volun-tourism opportunities that let you help out the local community you're visiting.
If you need some mountain-time, cozy up at AVL Bear Haven, a rental duplex on a mountain ridge just three miles outside of Downtown Asheville and four miles to the Blue Ridge Parkway. Wait until you see those views from the front deck with your morning coffee or nightcap.
9. Austin, Texas
- Perfect for: Midwest explorers in search of Texas heat and hospitality
- Highlights of Austin:
- Lake Travis and Krause Springs
- Rainey Street
- Zilker Botanical Garden
Things to Do in Austin
You don't need my recommendations for finding food, drinks or coffee in Austin (though I hold a special place in my heart for Greater Goods Coffee on 5th Street). You'll find excellent food trucks all over town, especially in specific food truck parks throughout the city, like The Picnic. And you must get a beer or cocktail at Lucille on Rainey Street, where it feels like you're hanging out at a huge backyard party (minus relatives or coworkers).
If you've heard about the Congress Avenue Bridge bats, believe me, they live up to the hype. Austin even holds a late-summer festival in honor of the bats. Whether you join watchers on the bridge or catch the view from a kayak in the water, don't miss the show put on by some 1.5 million nocturnal Austin dwellers.
Lake Travis is a reservoir on the Colorado River about a 20-minute drive northwest of downtown. Hang out at a lakeside park, rent a boat or take a zipline to enjoy its 64-mile-long beauty. Visit the floating waterpark of Lake Travis Waterloo Adventures, then Grab a bite at The Oasis around sunset and prepare for one of the most spectacular views you'll ever see.
How to Get to Austin
Nonstop flights from Chicago to Austin-Bergstrom International Airport are easy to find and take less than three hours. From the airport, downtown Austin is a quick 15-minute drive.
Where to Stay in Austin
I am fortunate enough to stay with friends when I visit Austin, but I asked my amigos where they'd recommend Chicagoans tuck in during an Austin getaway.
Depending on your budget, travel style, and desired level of poshness, here are their suggestions: Adina, an eclectic downtown boutique hotel, is a turn-of-the-century mansion turned into a stylish modern retreat, bursting with décor by local Austin artists.
The Heywood Hotel has great Austin feel and is close to Rainey Street and Lady Bird Lake. It has just seven rooms, so book in advance.
This sunny, dog-welcoming guest house rental in South Austin also includes a private outdoor space and all the comforts of home.
Whichever one of these destinations you choose, you’re bound to have the perfect home base for your weekend trips from Chicago — trips that are laid-back, friendly and memorable.