Day 1: Spend the first day of your trip getting your bearings in the downtown and Magnificent Mile areas. Your first stop is the Museum of Contemporary Art, where you will receive free admission on Tuesdays. Annual exhibitions include mobiles and drawings by Alexander Calder, and some of the sculptures outside the building’s entrance are interesting, to say the least (check out Short Cut). Enjoy a lunch at Café Spiaggia, and be sure to request a table by the window, so you can enjoy views overlooking Lake Michigan at the top of the Magnificent Mile. This restaurant shares its kitchen with Spiaggia, a popular four star Italian restaurant. The pizzas are worth trying. Make your way down the Magnificent Mile, with your first stop at the John Hancock Center, where you will enjoy views from the Observation Deck 94 floors above ground. On a clear day, you can see up to 80 miles and four states. If it’s not too windy, take a walk on the SkyDeck- it feels a bit different than walking on the ground. Continue walking south along the Magnificent Mile, cross the Chicago River, and eventually end up at Millennium Park, where you can’t miss Cloud Gate, the Pritzker Pavilion, and Crown Fountain. We’re pretty proud of this park in the middle of downtown Chicago; hopefully you’ll like it too. Stop by the Chicago Architecture Foundation, and if you’re up for it, take a walking tour of notable buildings in the Loop. Most of the stops are different from buildings pointed out on the architectural river tour that you will take later this week. Enjoy Latin cuisine (and salsa dancing afterward, if you like) at Nacional 27 in River North. Tuesday nights feature tapas tastings for $9.95 per person, with live Latin jazz. For a schedule of nightly events, check out www.nacional27.net. Cap off your evening with a late show at Second City, where you are likely to see at least one of the next-big-things in comedy.

Day 2: Start your second day right with breakfast at Atwood Café, then head over to the Art Institute, where you should not miss the Impressionist and American Collections. Lunch at Russian Tea Time is a bit removed from the usual tourist experience. Here, you can choose cucumber sandwiches to accompany your tea, or you can go for something more substantial like crepes. Full tea service, which includes an individual pot of tea, appetizer, main dish, and dessert, is available for $22.95 per person. You’ve spent the morning in a high-brow environment, so prepare for a bit of a drop in refinement with a stop at Navy Pier, which is sort of like Chicago’s equivalent to DisneyWorld. Not to worry; if crowds of uber-tourists aren’t your thing, hop on an Odyssey cruise for a relaxing escape from land-dwellers. The views of the city are great- take your sunscreen if you plan to stay on the outside deck. The seafood at Fulton’s is always fresh, and the views aren’t bad either. Dine in the shadows of many of the buildings that you’ll learn about in your river cruise tomorrow. This evening, take in a show at the famous Chicago Theatre on State Street.

Day 3: Spend your morning on a neighborhood tour given by the Chicago Office of Tourism, starting at the Chicago Cultural Center (directly across from Millennium Park). One option for today is a tour of three different neighborhoods: Greektown, Chinatown, and Little Italy. If you’d rather focus on one neighborhood, several options are available, just call ahead or check out the website at www.chicagoneighborhoodtours.com. If you don’t grab lunch on your tour, Sopraffina has several different options (pizza, sandwiches, salads, soups), which makes it a popular destination for a quick work lunch. Relax this afternoon on an Architectural River Cruise (wear a hat and wear sunscreen, since you’ll be in the sun for at least 90 minutes) and learn about the history of Chicago’s skyscrapers and how they influenced other American skylines. As they’ll probably tell you on the tour, Chicago’s nickname “The Second City” actually comes from the fact that the city had to be built a second time, following the Great Fire of 1871. Spend the rest of the day on the North Side, where you will find an independent movie theater at the Landmark Century Centre at Clark and Diversey in Lakeview. In the area surrounding the theater, there are several boutiques and shops on Clark (to the north and south) and Broadway to the north. There are a Bed Bath & Beyond and Borders, but most of the stores are individually owned and have a local flavor, in contrast to the national chains in the Magnificent Mile. Broadway and Halsted streets between Belmont and Grace provide the borders of Boystown, the nation’s first officially recognized gay village. It is easily recognized by the rainbow pylons on Halsted. Further to the north, in Andersonville, you will find Hop Leaf Tavern. Here you can choose from literally hundreds of beers, mostly Belgian, to pair with your mussels and frites. It’s a nice escape for locals from the hundreds of generic sports bars in Wrigleyville, and a destination for beer connoisseurs. After dinner, pay a visit to the Green Mill, Chicago’s most famous jazz club (and former speakeasy).