Because virtually everything but the Water Tower burned down in Great Chicago Fire, what you see is the vibrant rebuilding and re-rebuilding of America’s most American of cities. Let’s say you have a limited time to see Chicago, what do you want to be sure to see so that you can say you haven’t missed the highlights?
Best Chicago Attractions
The Skydeck at The Willis Tower
By Mike Gonzalez (TheCoffee) via Wikimedia Commons
From here you can see it all, get your bearings, point out the landmarks, and observe the city’s grid system of streets and the wonderful shoreline where it kisses Lake Michigan. Up at an altitude of 1,353 feet the horizon stretches to most of the rest of Illinois the west, all the way to Wisconsin to the north and over to Indiana to the southeast. We could say on a clear day you can see New York City but that would be stretching it. Feeling extra brave, try The Ledge, extending four feet outside the 103rd floor.
Chicago Line Cruises Architectural Tour
This Chicago River boat tour is the best way to see most of Chicago’s Loop while enjoying a cruise along the river that they turn green on St Patrick’s Day. From your place on board, you can see why Chicago is the most noted city in the world for skyscrapers. They were born here (after your boat tour, see the Reliant Building and the Monadonk Building, and peep into the Rookery to see the airy lobby by Frank Lloyd Wright). You will have a brief look at Lake Michigan and the Navy Pier as well. A nice treat: complimentary cookies, lemonade and coffee on board.
Art Institute
Go for the amazing, priceless and inspiring collection of jaw dropping art. Iconic favorites with art lovers everywhere are these jaw dropping treasures from the museum’s permanent collection: Grant Wood’s “American Gothic”, Edward Hopper’s “Nighthawks”, Monet’s “Haystacks” and “Waterlilies”, Van Gogh’s “Self Portrait” and “Bedroom”, Picasso’s The Red Armchair”, George Seurat’s pointillist masterpiece, “ A Sunday on Le Grand Jatte” and the mesmerizing blue leaded glass of the Chagall Chapel. Museum store lovers will love this museum store.
Field Museum
Yes you could spend the whole day here, and so be selective in your viewing choices, unless you have oodles of time to be in Chicago. Go for Sue the T Rex and all of the other amazing the dinosaur bones, the exotic Egyptian exhibit, the evolving planet area, and the Native American people area.
Money Museum at the Federal Reserve Bank
Have your photo taken with a million dollars and go home with a lovely parting gift bag filled with shredded money. The museum is in the Federal Reserve of Chicago and even though money doesn’t grow on trees, the museum entry is free. 
Favorite Chicago Restaurants
Berghoff
After being closed and re-organized for about a year, the Berghoff re-opened as its former three-part restaurant/cafe/bar in 2007 with a new menu. It’s now considered German cuisine fused with Contemporary American, tagged as “tradition with a twist.” Their brown bread and their own brewed beer or root beer is de rigueur, as you enjoy them in the mellow murals dining rooms. If you are going for lunch be sure to get there about a quarter to 12 or a tad earlier as the place fills up with in the know Chicagoans who work in the surrounding skyscrapers.
Gene and Georgetti Steakhouse
Since 1941, in what looks like an old house just under the L you get the best steaks in a city famous for steak. Yes there are a lot of fine steakhouses to choose from, but for the real taste of Chicago you simply do not want to miss G and G’s. “The stakes are so big they don’t fit on the plates!” is what we exclaimed the first time we dined here.
The Parthenon Greek Restaurant
This Chicago institution is often voted the best Greek restaurant in Chicago; it is justly famous for its “Best Saganaki” (flaming cheese) and the joyful sounds of “Opa!” as it is delivered to your table. The restaurant is a festive place to have a memorable meal. The wait staff is delightful and the food is scrumptious. Need we remind you to save room for the baklava?
The Signature Room at the 95th
Up on the top of the John Hancock Tower, this is an over-the-top splurge dining adventure in every way, as you perch on the skyscraper’s 95th floor, high above the city with sweeping views of the Lake Michigan and the Loop.
The Walnut Room
The Walnut Room at Macy’s on State Street (formerly Marshall Field’s) is a Chicago tradition. Shippers and diners converge here to look out the huge “Chicago windows” and enjoy dining elegance that suggests a bygone era. Sample the chicken pot pie, for which they are famous.
By the way, yes many of the places in this Quick Guide to Chicago are also in your favorite Chicago movie, “Ferris Bueller’s Day Off”. However, you will not find the restaurant where the “sausage king” had lunch—that is actually a private home that was transformed into a restaurant for the movie.
