Favorite thing: If you are walking and shopping on State Street in Chicago during the holidays (November and December), be sure to stop by the Macy's on State Street (111 N. State St.) to check out their beautiful holiday window displays. Also be sure to visit inside the store itself to see Christmas decorations as well as a giant Christmas tree.
My favorite walk, though, is strolling across the Michigan Avenue Wacker Drive bridge, over the Chicago River.
Fondest memory: Views of the city, from many different vantage points. My favorite, though, is the one from the Wacker Drive Bridge.
Attending the free events at Grant Park (outdoor movie every Tuesday in summer, Grant Park Orchestra every Wed-Sun in summer).
People watching at the Taste of Chicago (the week during, before and after Independence Day).
Watching a Steppenwolf/Goodman play.
Walk over the Michigan Ave bridge in the early evening, just north of Lake Street. It's hard to describe the experience but you get a feeling that you're in the greatest city in the world. It's something about the skyline lit up and the water below the bridge rushing by. Just make sure it's a warm night because the wind whistles over that bridge at considerable speed. Enjoy.
Fondest memory: Eating an early dinner on Taylor Street and then heading up to the Signature Room bar and watching the sunset while having a few drinks. The Signature Room is on the 95th floor of the John Hancock Building.
Walk up and down Michigan Avenue (primarily between the Wrigley Building [by the bridge over the Chicago River] and Lake Shore Drive [just past the Hancock Building]). This is what's called the Magnificent Mile, which is just a line of shops, many high-end, and places to eat (but mainly shops). The best time to be here is Christmas, though, with the holiday rush!
Fondest memory: Being in Chicago at Christmastime, the day after Thanksgiving. Everything on Michigan Ave. is lit up, there are people everywhere, shopping for their Christmas gifts. Marshall Field's has the traditional Christmas window displays, and if you're lucky enough to be there on a cold, snowy December (or November) day, it just completes the whole Christmasy feeling. Ah, but I can't stop there... get a hot espresso drink or some hot chocolate, and mmmmmmm.... good times. But, there's more... an outdoor ice-skating rink if it's cold enough, musicians on the street, and the German Christmas market - Christkindlmarket (pictured here).
Walk by the lakefront and go to North Pier. North Pier is always a party like atmosphere. A ferris wheel is there to give a great view. It includes restaurants and shops, an Imax theater, and a Shakespear company.
Fondest memory: I love watching the old movies on the weekend at the Music Box theatre.
walk along the beach while looking at the city. Feel the wind. Buy a hot dog and tell jokes. You can stay away from Michigan Avenue and walk around the city neighborhoods. That's where the most interesting people, shops and sites can be found (not on the tourist walk).
Fondest memory: I miss cabs and the train when I'm not here. It's never hard to get home. I also miss all the people walking around the streets, no matter how cold it is. You can always count on not feeling alone.
Walk the Loop and look at every single building. The buildings in Chicago are magnificent! With a book (preferrably Lonely Planet's Chicago guide) on hand, it's like having an architectural history class.
Fondest memory: Chicago was pretty nice. The roads were wide and straight (compared to Boston) and easy to navigate. The people were very friendly (again, compared to Boston!!).
Favorite thing: Take a walk along Michigan Avenue, lots of people, lots of shopping (but I only window shopped), and feel the energy of the city.
walking through the city, along the lake side, shopping, I had a great time here!
And the weather was perfect!
Favorite thing: Take a walk down Michegan Avenue. There is a lot of neat shops and buildings. Below is a picture of Michegan Avenue taken from the Art Museum