Quick Guide: Chicago

Sports, great architecture, museums, excellent shopping, dining and outdoor activites; there's something for just about every personality in Chicago, Illinois.  I like to think of Chicago as a cleaner, smaller version of Manhattan.  (At least parts of it)  Chicago sits in northeast Illinois on the shores of Lake Michigan.  As someone who's been visiting Chicago for nearly 30 years, and grew up just down the road in St. Louis, I'm going to give you a quick guide to the city.

Getting Here

Chicago is the third largest city in the US by population, behind New York City and Los Angeles.  It's home to Chicago O'Hare International Airport, one of the world's busiest gateways.  Flying to Chicago from either the East or west coasts is easy and flights are frequent.  If you're a fan of Southwest, check out Midway Airport.  You can also hop on Amtrak, which has several trains that connect or pass through the city.


Chicago's nickname is the Windy City.  If you've ever been to Chicago in the winter you know why.  The city's tall skyscrapers funnel the wind and cold air coming off the lake and can make walking around brutal.  Thankfully Chicago also experiences warmer weather.  

Late Spring and Early Fall

During these seasons enjoy warm days and cool nights.  This is the perfect time of year to visit.  You can often times get away with shorts and a light jacket, but keep jeans or pants handy for evenings.


Chicago can get hot during the summer.  Highs can soar into the 90's and even hit the triple digits.  The best way to cool off is hit the beach on Lake Michigan.


In winter make sure you pack warm.  Temperatures can dip well into the single digits or below.  Factor in the windchill and Chicago can be frigid during the winter months.

Where to Stay

Michigan Avenue, also referred to as the Magnificent Mile, is always my pick neighborhood when staying in Chicago.  You can find a wide range of hotels within one to two blocks of Michigan Avenue, from the height of luxury such as the Four Seasons, Ritz-Carlton and The Peninsula, to more budget friendly options such as the Red Roof Inn in Downtown.  Staying on or near Michigan Avenue will put you within walking distance of shopping, great restaurants, and various tourist attractions.


Chicago has some of the tallest skyscrapers in the world.  In fact, until the construction of One World Trade Center in New York City, Willis Tower (formerly the Sears Tower) was the tallest building in the US.  Built in the 1970s, Willis Tower held the record for tallest building in the world for more than 20 years.  There's an observation level near the top that offers amazing panoramic views of the city.  In my opinion this is a must see attraction.  

Willis Tower is on the southern end of downtown and on the North end is the iconic John Hancock Center.  This skyscraper on Michigan Avenue is also one of the tallest buildings in the world.  It also has an observation level as well as restaurant and bar.  Here's a tip, visit the restaurant for dinner for amazing views of the city lights after dark.  A more recent addition to the Chicago skyline is the Trump International Hotel and Tower.

If you can bring your gaze from the sky back towards the ground you'll also see some interesting architecture at the Chicago Water Works.  This stone building sits on N. Michigan Avenue and is one of the few buildings in the city to have survived the great Chicago fire.  Now used as art gallery space, the water works used to house water pumping equipment for city residents.


This is far from an all inclusive list, but here are some great things to do and see while in Chicago:


Chicago is a major metropolitan city with a variety of food to fit just about any type of food you may be looking for.  With that said, Chicago is often known for a few things deep dish pizza, hot dogs and steak houses.  While I often like to share my opinions on food, I'm not going to make any specific recommendations.  Mainly because I don't eat pizza!  Ask the locals and they'll tell you the best places to go.  By the way, a Chicago-style hot dog is mustard only.  If you ask for ketchup they may look at you funny.