10 Best Weekend Road Trips From Chicago Illinois Territory Supply Distance from chicago: 94 miles (approx. 1 hour and 30 minutes) related read: 9 fabulously unique places to stay in illinois. 3. indianapolis, indiana. naptown’s signature event, the indianapolis 500. photo: shutterstock. indianapolis is an excellent weekend road trip from chicago for city dwellers and racing fans. Photo: deer path inn. why you should stay: a sophisticated four star hotel along chicago’s north shore. location: lake forest, illinois. sleeps: 2 4. minimum stay: 1 night. rates from: $349 night. housed in a half timber tudor mansion, deer path inn offers a european escape without traveling far outside the city.
10 Best Weekend Road Trips From Chicago Illinois Territory Supply This list of trips from chicago is broken down into short day trips, long weekend getaways, and extended 7 to 10 day excursions. we’ll start with the shorter drives, as most chicagoans looking for road trips prefer something in the 3 to 5 hour range. 1. st louis, mo. photograph: courtesy shutterstock. driving time from chicago: four and a half hours. while beer, blues and bbq are likely on the top of your st louis bucket list (and rightfuly so. 2. illinois’ great river road. distance: 3.5 hour drive. in a seemingly never ending chain of historical sites and activities, the drive along mississippi river to east dubuque is one of the best road trips from chicago. moline and rock island are two cool detours but you can head straight for east dubuque for its chicago great western. Distance: an hour and 15 minutes by car. best for: a beach and beer or wine combo trip. comprising the eight towns of michiana, grand beach, new buffalo, three oaks, union pier, lakeside, harbert, and sawyer, harbor country is a favored weekend escape from the windy city, thanks to its beach and country offerings.
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