Why I went here? The first time was to just to visit the city. It just happened to be that my family also had a function to attend so I tagged along. Last year, I went to meet up with a friend who was in town for business. Chicago has plenty to offer. It is one of the country’s financial capitals (home to The Chicago Mercantile Exchange which is the largest derivative trader in the world), a venerable sports town (Chicago Bulls anyone), and has one of the most unique cultures. It is also one of the most eye catching big cities in the United States.
Best time to visit? The best time is summer, between the months of June and August. Summer brings up the best weather and the biggest events in town. You have the Taste of Chicago anywhere from end of June to mid July (this year it’s July 11-15th) and of course Lollapalooza in August (Aug 3-5th in 2012).
Best way to get there? From Dallas, fly to either Chicago O’Hare (ORD) or Midway Airport (MDW). Both airports are connected to the trains that service downtown Chicago. O’Hare with blue and Midway with orange. The travel time ranges from 35-50 mins and 25-40 minutes respectively. One way fares range from $4-$8.
What to see/do? Chicago’s city architecture is unique and fascinating to view. Most of the buildings that currently stand came from the restructuring of the city after The Great Chicago Fire of 1871. To appreciate Chicago’s best views, take a boat tour on the Chicago River. Several operators run 60-90 minute long cruises at the North Pier dock (along Wacker Dr in between Columbus and Michigan Aves). The Art Institute is also a must see for architecture lovers. The museum location itself is worth the trip (with its location near Grant Park), and it houses a whopping 300,000 works of art. Adjacent to the Art Institute is Millennium Park where some of the best American architects display their work. A bit further south on Michigan is the Field Museum. If traveling with tykes, this is a good place to take them. There are lots of interactive rooms and this natural history museum is home to Sue, the most complete skeleton of the once mighty Tyrannosaurus Rex. For a peek of Chicago from the top, visit the observation deck at John Hancock Center. This is one of Chicago’s tallest buildings and the view is unmatchable (except perhaps from the lake itself.) The building has a restaurant on the 95th floor that’s open for brunch, lunch and dinner. Lastly, a trip to Chicago isn’t complete without riding the ever popular “L” train. It is aptly named so because it is short for “elevated”, which is in reference to location of the majority of the tracks. Ride it around the Loop and you will get a close up view of the buildings that make up the Chicago skyline.
Where to sleep? The majority of big name hotels are either on Wacker Dr or on Michigan Ave so my suggestion will be to book around these areas. They are convenient to most of the sites around town and have plenty of food and drink options to choose from. It is also close to the theater district and the waterfront. The Hyatt Regency (where I stayed) and the towering Hotel Renaissance are a couple of places to look into south of the river. Along Michigan Ave, check out The Four Seasons or The Peninsula (if your pocketbooks can afford it), or gear a couple of blocks west to the likes of Homewood Suites (a Hilton Hotel) and the Hampton Inn in Downtown.
Food and drinks: Chicago is famous, notably for a couple of gastronomy items: its pizza, and its hotdog. The original deep dish was said to have originated from Pizzeria Uno. If you do decide to dine here, get the original “Numero Uno.” Come early for dinner or be prepared to wait at least 45 minutes for a table. Lou Malnati’s is another Chicago staple. With several locations around the city, this is a more viable option if craving for pizza. The pie is what made this place legendary more than the ingredients itself. The Malnati Chicago Classic is my recommendation. Chicago style hotdog includes an all beef frankfurter, simmered, and garnished with mustard, onions, relish, tomatoes, and a cucumber spear. Chicago is full of hotdog stands but for some of the best ones, pay Hot Dougs or Superdawg a visit.
Why I would go back? Chicago is a fun town. It just has the right mixture of indoor and outdoor activities (with its parks, theater and beaches.) The people here are also a draw. They have that relaxed Midwestern attitude despite being in one of the biggest metropolis in the country. Additionally, it is one of the more attractive places for me to cool off during the intense summer heat down here in TX. Lastly, I plan to explore the enormously grand Art Institute even further and perhaps pop around one of the bars, sit back and listen to some old school jazz.