1. Holland, Michigan is a Dutch style town only two hours drive from Chicago. You can spend a European style weekend here. Just like Holland, you will find Tulip Gardens, Wind Mills, Water Canals etc here. Read more about two day Itinerary to visit Holland at Travel Ideas:Holland, Michigan.
2. Indiana Duns State Park is about one hour drive from Chicago. It is great for Camping or a day trip. There are beaches in Chicago but nothing compares to beaches in Indian Duns State Park and they are free beaches. There are also many activities like fishing, hiking, nature walk, skiing to choose from. Cabins are available for overnight stay. This state park makes for a great cheap family vacation.
3.Starved Rock State Park is another beautiful side trip from Chicago. Great to spend a relaxing weekend or a day. It is one of the most beautiful places in Illinois. It is also called one of the seven wonders of Illinois. Beautiful waterfalls, hiking trails, boating, fishing, ice fishing are some of activities available here.
4.Harbor Country is road trip of choice for Chicago residents. It is collection of 7 lake front communities. Great for shopping, beach combing, dining or just for relaxing. It is only 90 minutes drive from Chicago towards I-90. This is a place of all seasons. If you are looking for summer activities or winter activities, you will find here things to do.
5. Geneva/St. Charles/Aurora Chicago Premium outlets - If you are looking for upscale shopping or dinning, then take I-88 to Aurora Premium Outlets in Geneva/St. Charles Area. This is area's largest outlet mall.
6. If you are looking for some fun activities to do with kids then head out to Wildlife Prairie State Park or Brookefield Zoo. Prairie state park is one of a kind wildlife habitat. You can stay here overnight in cabins or some unique lodging like stable and view the wildlife. Brookefield Zoo is about 30 minutes from Chicago near Oak Parks. It is must see for kids. It has wonderful collection of animals and great exhibits.
7. Wisconsin Dells is a great place for summer activities. It is created by the currents of the Wisconsin River and is a favorite family vacation destination. Lots of indoor and outdoor Water Parks, Theme Parks, Zip lines etc make this a all season place. It is about 3 hours drive from Chicago.
8. Lake Geneva in Wisconsin is a year-round resort town. It is a very lovely place that offers laid back relaxed environment with lots of activities. You can select from horseback riding to fishing to Skiing. It is located only 75 miles from Chicago.