I was asking myself the same question when one my friend was about to come to visit me. With all great places that we have around Chicagoland, there should be no problem. And here is where I took her:
1. CHICAGO DOWNTOWN: This should be definitely first on your list. This is why they want to come to Chicago. I would even suggest to take the train to downtown and walk. Since there should be lots of walking it is better that you wear very comfortable gym shoes. Walk along Michigan Avenue that shows lots of prestigious buildings (one of them is Chicago Tribune Building that has inset of stones from famous buildings all over the world) and is great for shopping. When you come to Chicago Water Tower and Pumping Station be sure to mention that these two building were the only public buildings who survived the fire of 1871. I would suggest that you take your guest to John Hancock Center . The restaurant on the top ("Signature Room" ) is actually higher than observatory both on Hancock and Sears Tower ( highest building in America). For almost the same amount as your ticket for observatory would be you can get a drink there. Go east toward Michigan Lake and walk to Navy Pier, where you can make lots of pictures of downtown and sit and have dinner.
2. BROOKFIELD ZOO OR LINCOLN PARK ZOO: If you live in Chicago, it is closer for you to take your guest to Lincoln Zoo. For Brookfield Zoo, which is bigger and located in near west suburb Brookfield, you will need at least half day to see everything. Lincoln Zoo you can see in about 2-3 hours. Close to Lincoln Zoo is also Michigan Lake, so you can take a walk along the lake too.
3. CHICAGO BOTANIC GARDEN: It is located in northern Chicago suburb Glencoe and if you like flowers you will spend really nice day. Since there are 23 gardens that sit on 385 acres, plan to stay here all day.
4. NAPERVILLE: This is a very nice town located in west suburb. Has European feel, with little stores, narrow streets and beautiful river walk. If you have not been in Europe, this town with give you some idea how it is there. You can take your guest to Naper Settlement, 19th century historic museum village with costumed villagers, too.
5. LONG GROVE VILLAGE: Stroll cobblestone sidewalks in this charming historic village, full of stores and galleries. Lots of festivities are organized throughout the year.
6. MORTON ARBORETUM: If you enjoy nature, you can follow walking paths through forests and along the lakes and have your child play in Children's Garden and climb up the tree house. Since you can drive through the park, you can chose in which parking you want to park the car and start your hike from there. It is located in Lisle, west Chicago suburb.
7. CHICAGO MUSEUMS: There are many museums in Chicago, but I prefer to take my guests to Field Museum or Aquarium. In the evening I take them to Rush street for dinner, which is always full of people and nice restaurants.
8. RAVINIA: Located in Highland Park. During summer you can come here and enjoy this unique picnicking. Bring a blanket and look for your favorite spot on the lawn and listen symphony, pop and jazz concerts. As the night comes you will enjoy great concert at candlelight as you gaze at the stars above. Your guest will love this unique experience.
9. ERNEST HEMINGWAY BIRTH HOUSE AND MUSEUM AND FRANK LLOYD WRIGHT HOME AND STUDIO: You can view houses of famous American novelist and architect at the same time, because they are all located in Oak Park.
10. GRAUE MILL AND MUSEUM: Located in Fullersburg Woods Forest Preserve in Oak Brook and it was once a family home used also to hide runaway slaves on their journey to freedom in Canada. President Abraham Lincoln reportedly visited Graue Mill. I like to take my guests there because there is a beautiful river walk too.
I hope you will enjoy this Chicagoland tour the same as your guest. I know I did.
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