Go to Chicago for a weekend. Trust me. Eat delicious food, take in the Art Institute, listen to Chicago blues, gawk at statuesque skyscrapers, cheer at historic Wrigley Field, and survey the beautiful buildings of Frank Lloyd Wright. This is a place that deserves a visit!
When deciding on a place to stay look to be in the heart of downtown. The Swissotel on Wacker Drive is a fantastic option. The rooms have great views of Navy Pier and the Chicago skyline. Flying in and out of Midway Airport is a no-brainer. It is much smaller than the ever-insane O'Hare, and for a few bucks you can hop on the train and be right in the thick of things swiftly. Oh, and you'll need a relevant book to take with you. The Devil in the White City is a non-fiction novel about architecture and murder during the 1893 World Fair in Chicago. It is a great read and will give you insight into the history of the city.
Boat tours are very touristy but a great way to admire the gravity-defying architecture.
In such an enormous city there are almost too many food options. If you have your heart set on getting some deep dish pizza then try Pizzeria Uno's on East Ohio (or nearby Due's). Hot Doug's has become quite the destination for Chicago hot dogs, but be prepared to wait for an hour or more to get in. Italian beef with giardiniera is great, Frontera Grill's Mexican food is highly recommended, and being obsessed with barbecue led me to Smoque BBQ. It is hard to go wrong with ribs, brisket, mac and cheese, baked beans, slaw and sweet tea.
Take in a baseball game at the historic Wrigley Field. It is in its 99th season hosting major league baseball, and the 97th season for the Cubs. With so many bars and pubs near the stadium this destination easily becomes a day-to-night event.
Walk around Oak Park where you can see many of Frank Lloyd Wright's creations.
Make sure to experience some of the great neighbourhoods outside of the centre of town as well.
The unique corncob shape of the Marina City complex is one example of the various architectural styles that you will see towering over the city.
The Sears Tower (actually now called the Willis Tower) was the tallest building the world for 25 years after construction was completed in 1973. There is an observation deck on the 103rd floor with glass balconies if you dare.
Canadian beer aficionados will enjoy the selection of beers that are unattainable in our home and native land.
Grab a quick brunch at the Hyatt Regency on East Wacker Drive.