Weekend Getaways

Weekend Getaways

Sometimes a few days away is all you can swing - or all you need - to recharge and refresh. If you are looking for the best 2, 3, and 4 day getaways, we've got you covered. From the best places to go with family to great romantic escapes the following destinations are great places to get away.

First Things First 

Before planning any trip you need to ask yourself a few questions but these are really important if you only have a few days away: 

Only have 1-2 days?

• Skip the flights even if you leave early in the morning*
• Drive no longer than 3 hours in any direction. You might argue that you could fly somewhere for 3 hours but driving gives you the freedom to leave and return whenever you want without being tied to a flight schedule. And, most importantly, you need to factor in security lines and flight delays. 
• *the exception to this would be if it's a city you've been to before so you don't need to see everything and you can just focus on one thing - like eating or shopping. 

Best options from the Chicago area:

Milwaukee -

• Visit the historic Third Ward - Trendy shops and dining abound in this revitalized warehouse district
• Great craft beer scene
• Boutique hotels
• Summerfest!
• Great for couples, families, and girls' weekends

The Ostoff Resort in Elkhart Lake, Wisconsin -

• Great year-round destination - summer beach/winter hiking, snowshoeing, cross-country skiing
• Close to Kettle Moraine State Park for hiking, mountain biking
• Spa facility with extensive spa menu
• Walking distance to charming town with many restaurants, bars, and shopping
• Great for families and girlfriends' getaways  

Other Nearby Options -

• Indianapolis, Galena, Lake Geneva, Madison

Have 3 days?

• This is the sweet spot for weekend getaways - one more day opens up lots of options
• Pick destinations with direct flights - 3 hours max

Louisville -

• 5-hour drive from Chicago
• Hit the Kentucky Bourbon Trail or at least the Urban Bourbon Trail
• Great for foodies
• Museums - Louisville Slugger, Ali, KMAC museum of Arts and Crafts
• Watch the ponies race at the iconic Churchill Downs or hit the Kentucky Derby
• Great for couples and families (especially teens)

Charleston -

• Kiawah - golf, spa, 
• Sullivan's Island
• Food tours, pub crawls, cooking classes
• Kayaking, SUP, biking, sailing
• World Class Golf 
• Historical tours
• Just for kids: crabbing, bike on the beach, crocodile tours, oyster roasts
• Great for families, couples, and girlfriends' getaways  

Montreal -

• Just 2 hours from Chicago!
• Great walking city - explore the old town, the food scene,  and modern Montreal
• Hundreds of festivals
• Amazing street art tours
• Explore the area of Plateau Mont Royale - a charming, colorful neighborhood jammed with shops and restaurants
• Grab a bike and explore the 400 miles of bike paths in the city
• Great for couples and families

Austin -

• Live musical capital of the world
• Food trucks, coffee, and barbecue!
• Hike and bike in Hill Country
• Festivals!
• Destination Spas! Miraval and Lake Austin 
• Best time to visit - spring, fall and winter. Summer is HOT 
• Great for couples and girlfriends' getaways

Philadelphia -

• Go for the history - stay for the food
• Be in the "room where it happened" at Independence Hall
• Take in the museums - The Barnes, Philadelphia Museum of Art, Rodin Museum
• Eat your way through Reading Terminal and then the rest of the city
• Walk in the steps of Ben Franklin
• Run up the Rocky Steps! (don't be shy - everyone does it)
• Great for families and couples

Jackson Hole, Aspen, Vail (or any other ski resort in the summer) -

• Ski towns make great summer/early fall destinations
• Active adventures - hiking, biking, kayaking, horseback riding, golf, fly fishing, white water rafting
• Float trips down the river to see wildlife and spectacular scenery
• Rodeos!
• Photography and wildlife safaris
• Great family vacation

Bahamas -

• Direct flights from the US
• Swim with pigs and dolphins!
• Island hopping by private boat or ferry
• Water sports, tennis, golf
• Food tours, rum tastings, chocolate tastings
• Hotel Spas - SLS Baha Mar/Rosewood
• Great family vacations and girls' spa getaway

Other Options -

• New Orleans
• New York City, NY
• Nashville
• Boston

And if you can squeeze in one more day...

• Leave on a Wednesday (or late Tuesday night for an overnight), return on Sunday.
• 4 1/2 hour flights, overnight flights or flights with stops (opens up beach destinations, Europe and West Coast destinations)

Portland, Oregon -

• Great for foodies;
• Willamette Valley wine tastings and spa retreats
• Biking, hiking the Colombia Gorge
• Best time to travel - June through October
• Great for couples and a girls' getaway

Watch Hill, Rhode Island -

• Quaint seaside village with 3 properties to suit all of your needs
• Ocean House -  Perched high on the bluffs of Watch Hill, Ocean House is an iconic New England seaside resort, with luxurious spa treatments and farm-to-table cuisine
• Weekapaug Inn - Located on the Rhode Island shoreline overlooking Quonochontaug Pond, and the Atlantic Ocean just beyond, Weekapaug Inn offers an effortless combination of casual comfort and luxurious furnishings
• Watch Hill Inn - Situated in the heart of downtown Watch Hill village, Watch Hill Inn is a perfect combination of contemporary comfort and historic seaside allure. Modern conveniences, chic décor and sublime sunsets come standard. 

San Miguel de Allende, Mexico -

• Something for everyone - adventure, foodie, cultural
• Horseback ride, bike or hike in the surrounding countryside
• Michelin-starred restaurants, tequila tastings, wine-tastings, food tours
• Explore art galleries and art studios or take an art class
• Relax poolside or in the spa at the Rosewood Hotel 
• Great for romantic couple's escape or girlfriends' getaways  

Santa Fe -

• Something for everyone - active, food, art
• Just a one hour drive from Albuquerque 
• Explore the mountains by bike, hike, river raft, or ride a llama!
• In summer - rt markets, farmer's markets, music festivals
• In winter - skiing, snowshoeing, cross-country skiing
• Art - visit Georgia O'Keefe museum, New Mexico Museum of Art, Canyon Road Art District
• Cooking classes, food tours, Wine and Chile Fiesta in September
• Great for couples and getaways with friends

San Juan, Puerto Rico -

• Direct flights from Chicago
• Explore Old San Juan 
• Kayak your way around mangrove channels to the glowing waters of the bioluminescent bay
• Hike past mountain waterfalls and check out Taino petroglyphs in El Yunque Rainforest
• Relax on the beautifully restored beaches
• Great for families and couples

Other Options -

• Paris, Amsterdam, Dublin
• Great for: Couples, Families and Extra-long weekends