Travel Insights: Top Travel Destinations for Chicagoans


RelayRides blogger Sydney Jarod shares his latest travel insights on where are the best places for Chicagoans to travel. 

Chicago is a fine city with a sophisticated yet unpretentious urban culture, great music festivals like the annual Pitchfork Music Festival and strong sports traditions with its 2013 Stanley Cup winning Blackhawks and its love-able but perennially underperforming 3-and-2 Bears and the 66-and-96 Cubs. It’s also a food city with the best pierogis, brats and steaks in the country. Sometimes though, even Chicagoans need a break from Chicago. Real estate data service Trulia has shown us where Chicagoans love to escape, so we’ve listed them here along with some of our top recommendations for how to get there.

Grand Beach and Union Pier in Berrien County, MI

Distance from Chicago: 70 miles

Long before Berrien County became a popular destination for Chicagoans in search of a get-away, the village of Union Pier was a favored haven for Chicago’s artists and writers. Nearby, Grand Beach was decidedly more well-to-do and now hosts several homes designed by Frank Lloyd Wright. Celebrate your own design sensibilities during your next trip to the shore by renting Erinn’s 2007 MINI Cooper or Marcus’ 2013 Fiat 500.

Lake Geneva, WI

Distance from Chicago: 80 miles

In the Roaring 20s, many of the wealthy “robber barons” of the era built fine mansions in Lake Geneva before it became a haven for mobsters during the Depression and much later the home of Hugh Hefner’s first Playboy club. Now, Lake Geneva is the site of second homes for Chicagoans—gangsters and players alike. Show off your own danger and flash during your next visit by renting David’ 2007 Ford Mustang or Leila’s 2008 Jaguar X-Type.

Galena, IL

Distance from Chicago: 160 miles

A charming small town known for its 1800s architecture and love-hate relationship with its flood-prone river of the same name, Galena was home to many Civil War era celebrities like former general and US president Ulysses S Grant and is now the location of many second homes of the proud people of Chicago. (Galena made our great President’s Day weekend trips list too.) For your next trip to this national treasure, consider renting your own presidential car like Joel’s 2011 Ford or William’s 2012 Lincoln.

Wisconsin Dells

Distance from Chicago: 200 miles

Boasting some of the largest water parks in the US (check out our favorite water parks here), the city of Wisconsin Dells is a summer destination that got its start with tourists who wanted to see the striking sandstone formations that line the nearby gorge along the Wisconsin River. When you’re ready to cool off, rent Huzaifa’s 2010 Toyota Prius or Megan’s 2007 Pontiac Vibe for the drive up north.

The Door Peninsula

Distance from Chicago: 240 miles

Chicagoans have fallen in love with the Door Peninsula for its rural charm and for the rock outcroppings and sand dunes that edge that shores of this beautiful lakefront. For your next trip to the shore, we recommend Katelynn’s 2012 Volkswagen Jetta or Wayne’s 2013 Audi A5.

The Lake Country of Wisconsin’s Northern Highlands

Distance from Chicago: 330 miles

Home to over 1,100 lakes, Chicagoans love to escape to the Northern Highlands for the great boating, hiking, fishing and cross-country skiing. Summer or winter you’ll find yourself returning here too and when you do, make sure to take a rugged vehicle like David’s 2008 Nissan Xterra or Megan’s 2003 Mercury Mountaineer for your next outdoor adventure.

Rent now and start your vacation today

When the city starts to feel a little too crowded, you know its’ time to get out to your favorite little small town. However, when you do get out of town on vacation, you don’t have to leave the convenience and variety of the city behind, and you don’t have to settle for a plain old vehicle from a traditional car rental company. Sign up today!.