Best Weekend Summer Trips for Couples and Families

C’mon, admit it—you’re counting the days until summer vacation.

Now you’re staring down the calendar, trying to find time for a trip. No problem—whether it’s a couples getaway or packing the kids into the minivan, Fodor’s Travel Executive Editorial Director Arabella Bowen has several great suggestions for in-town excitement and weekend getaways that don’t involve the whole weekend in the car.

What are your top picks for family getaways within a day’s drive of Chicago?

Louisville, Ky. is a 5 hour, 15 minute drive from Chicago; it has great food and the bourbon trail (including the gorgeous Maker’s Mark distillery, which offers free tours) to explore. The 21C Museum Hotel, a fantastic boutique hotel that doubles as a contemporary art museum, was named one of our Fodor’s 100 best hotels in the world in 2011.

If you’re looking for a really unique adventure, try houseboating in Voyageurs National Park in northern Minnesota along the Canadian border. You can rent a houseboat and sail around to various islands, go fishing and swimming, and then dock at small islands and have campfires and camp (or you can sleep in your houseboat). The nearby Boundary Waters Canoe Area is great for experienced canoers, campers, and fishermen—and it’s the most visited wilderness in the U.S. (who knew!). Motor vehicles and boats are only allowed in a few spots here, so it’s very natural and unspoiled. Ebel’s Houseboats has affordable rentals.

Madeline Island, Wis. (in the Apostle Islands in Lake Superior) is another great summer getaway for families. The island is reached by ferry from Bayfield, about an 8-hour drive from Chicago. It’s great for kayaking, fishing, and biking and there’s a little village with shops and dining, along with plenty of quaint bed and breakfasts to choose from and beautiful lakeside cottages for rent.

Do you have any suggestions that would be good for a couple wanting to escape the kids for a weekend?

Niagara-on-the-Lake, near Niagara Falls on the Canadian side. You can either fly to Buffalo and drive over the border or head there via Toronto; it’s also a 9-hour drive from Chicago. The Shaw Festival takes place through summer, and there are many excellent vineyards nearby to explore. The town itself is a charming Old English-style village with afternoon tea at the historic Prince of Wales hotel. The luxurious Harbour House has weekday rates from $260, including breakfast, $100 off the weekend rate!

Portland and the Willamette Valley is a great combo getaway from Chicago. There’s plenty to explore in downtown Portland, with its great foodie scene and creative vibe, but you may want to head straight for the Willamette Valley—a short drive away. There, The Allison Inn and Spa was also a Fodor’s 100 Award winner. It has one of the largest spas in the Northwest, is situated in the heart of Oregon’s wine country and has rates from $315/night.

Chicagoans take pride in knowing everything there is to know about their town. What do you think are some of the hidden gems even long time residents shouldn’t miss?

I love to take in the art scene wherever I travel, and (while) I’m sure many Chicagoans have visited exhibits at the Art Institute, there is also a proliferation of great galleries in River North—improvise your own gallery walk along Superior and Franklin Streets.

What’s your top pick for a fun family restaurant/entertainment venue in Chicago?

The Peggy Notebaert Nature Museum in Lincoln Park is a great place to take kids—it has a butterfly haven and an animal habitat exhibit with a climbable tree house! 

Need more great ideas? Try:

The 10 All-Time Best Family Vacations

Road Trips: 7 Tips for Having Fun

Trekking West Michigan

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