Chicago is a city that I called home for three years in my young adult life as a college student.  I loved the city a lot, back then, which is why I am perplexed that it took me so many years to return after graduation.  But I am glad I did!

While the motivation to return was spurred by my desire to attend homecoming to see my Northwestern Wildcats play live, I also had the challenge of creating a fun itinerary for my travel partner who had never been to Chicago, as well as one that would introduce me to parts of Chicago I had never explored or remind me of the parts of Chicago that I enjoyed the most.  As is the case with all my trips, it seems, the long weekend was jam packed with things to do and see!

On my arrival into O'Hare Airport, I opted for the convenience and the nostalgia of the "L" public train (subway and elevated) transportation to get into town.  It's only a 45 minute ride to reach the "loop" where my hotel was located, and you can not BEAT the fare - $2.25 single ride!  Compare that to maybe $30-40 for a cab and the same timeframe (with traffic).  When I was in college, I remember there was a flat $20 taxi rate for students to Evanston, but since I was usually not in a hurry, I would just take the L and pocket the difference (thanks mom and dad!).

For this trip, I chose a hotel that was convenient to the meeting points for our scheduled tours, to the central part of tourist Chicago, and to the L lines we needed, located on Wacker Drive a block from Michigan Ave.  When I walked into the room, I was greeted with this amazing view!!!

Since my friend wasn't arriving until the evening, and I had to pick up my tailgate and football tickets, I hopped on the red and purple lines to head north to Evanston and explore my old stomping grounds/campus.  For such a mish-mosh of architectural styles, Northwestern is surprisingly pretty -- ok well, it grows on you.  But really, you can't beat certain views on campus:

View of North Campus and Student Center from "Lake Fill"

South Campus Fall Foliage

University Hall on South Campus

Arch I passed through every day on my way to class

View of Chicago from the Lake Fill

OK, that's enough reminiscing...back to Chi-TOWN!

Back downtown, my friend safely arrived just in time to grab a quick bite to eat then head to the late show at Second City!  Home to some of the best improvisational comedians in the past 50+ years, Second City is one of Chicago's best attractions.  John Belushi, John Candy, Dan Aykroyd, Eugene Levy, Bill Murray, Shelley Long, Gilda Radner, Mike Myers, Chris Farley, Steve Carell,  Steven Colbert, Amy Sedaris, Tina Fey, Jane Lynch, and more all got their comedy starts at this theater.  

The next day, it was time to explore downtown Chicago.  What better way to do that than on a bicycle.  We joined Bobby's Bike Hike to take the morning lakefront neighborhood tour that started out in Streeterville, between Michigan Ave. and Lake Shore Drive on the north side of the Chicago River.  Streeterville is the first section of the city built on a filled in area of Lake Michigan, expanding the city boundary line east onto the growing amount of silt at the mouth of the river and the landfill material created to make Lake Shore Drive.  There is a very interesting story of George Streeter, who tried to claim this land as his own by creating the "District of Lake Michigan" through fraud and deceit, but all he got was the lasting honor of being the neighborhood namesake, in the end.  It is now home to some of Chicago's most famous landmarks - the John Hancock building and the Water Tower shopping and residential building.

Next, we traveled north on Rush Street to view some of the mansions of the North Side - more commonly referred to as the Gold Coast -- that initiated the move of the wealthy from the South Side and includes one of the most famous pieces of real estate in Chicago:  1340 North State Parkway.  This address was given to a 70 room mansion that had a notorious swimming pool in the basement called The Grotto.  While it was built in 1899 for Dr. George Swift Isham, its most famous owner was Hugh Hefner from 1959 to 1974 and was the original Playboy Mansion.  After Hefner moved to LA permanently, the mansion was first leased then sold to the Art Institute of Chicago for $1, and it was turned into dormitories.  Now, the property has been turned into condos that sell for more than $6 million each.   

Continuing north to Lincoln Park, we wandered through the old German neighborhood and took a short break at the Lincoln Park Zoo before heading back south along the Lake Michigan beach towards Navy Pier to finish out the tour.

View from Lincoln Park Zoo

The afternoon was spent back up in Evanston to enjoy a special Second City production that was Northwestern themed, then go to Ryan Field for some tailgating and football against Penn State with fellow alums, including SNL's Seth Meyers (this year's grand marshall) and NBC News/Today Show (and my former dorm mate) reporter, Peter Alexander.

Our final day of a packed three day weekend was spent learning more about the vast array of architectural contributions along the Chicago Riverfront.  There are several architectural boat tours offered, but the original and best is the First Lady tour offered by the Chicago Architecture Foundation and presented by a very knowledgeable docent from CAF.

Chicago is a great city for architecture because its history of rebuilding afforded the opportunity for innovation through creative modern design to solve problems and meet the needs of the society at that particular time, whereas a place like New York, already dense with buildings,  had to grow and adapt through renovation or planned destruction.  Chicago is where some of the world's first skysrapers were built, and where a river was reversed to solve the city's sewage disposal and associated health epidemic issue.  It also has the highest number of renowned architects represented by one or more buildings and structures, including Frank Lloyd Wright.

Boarding the boat beneath Michigan Avenue off of the Wacker Drive side of the river, we began heading west on the Chicago River.  First building of the day was the newest addition to the Chicago skyline:  Trump International Hotel and Tower - the tallest (90 stories) structurally all-concrete building in the world.

Trump Tower

Bending on the river after State Street, we were treated to several art deco masterpieces and armchair style buildings on the south side of the river and two structures built in the 1960s on the north side: Marina City and 330 N. Wabash.

 As we approached the end of the Main Branch of the Chicago River, we saw a neat brick building and the famous Merchandise Mart.  Designed by Graham, Anderson, Probst & White, the "Mart" was originally used as a distribution center for Marshall Field & Company.  It spans two city blocks and has 4 million square feet of floor space, the largest floor space area in the US at the time in 1930, until the Pentagon was built in the early 1940s with its 6.6 million square feet.  The Mart's design included several art deco features: pyramidal towers, set backs, and bands of chevrons.  The pedestals along the riverfront facade hold busts of famous merchants.

Merchandise Mart

 The highlight of the South Branch part of the cruise was, of course, the iconic Willis Tower (formerly known as the Sears Tower).  This 108 story building was completed in 1973 and held the title of the world's tallest building for 24 years, until it was surpassed by the Petronas Twin Towers in Kuala Lumpur in 1998.  It still is the tallest freestanding structure in the US and the 2nd tallest in North America.  Designed by Skidmore, Owings, and Merrill, it was the first building to use a concept called bundled tube construction.  More on Willis Tower later...

The tour made its way back to its dock, passing by the beautiful Wrigley Building, the NBC building and, finally, turning around at the mouth of the river next to the famous Navy Pier.  I was very familiar with this particular part of the river during my college years for another reason.  It was the location for the Northwestern Crew boathouse.  Many early mornings were spent on this part of the river!

Navy Pier
Mouth of the Chicago River

After we disembarked from the First Lady, we walked a few short blocks to Millennium Park.  Opened in 2004 to celebrate the new millennium, this public park is the home for many large modern art sculpture installations.  The most popular one, for obvious reasons, is the Cloud Gate sculpture.

The final destination on this whirlwind Chicago adventure was the architecture tour highlight: the Willis Tower.  While it's breathtaking to look at from the outside, the Willis Tower also provides an opportunity to let your inner daredevil out and literally have your breath taken away.  The SkyDeck attraction is on the 103rd story of the building.  It offers spectacular 360 degree views of the Chicagoland region, especially on a clear, haze-free day.  But the long lines are for one of four skyboxes.  These thick glass boxes extend out approximately 4 feet from the side of the western facade of the building to give you an unforgettable view - 1,353 ft above Wacker Drive.  I am not a fan of heights, but I pushed myself over that mental block to step out there.  Look at the photo below for a taste of the experience.  It was a lot easier to take the photo when I was sitting on the floor of the box, looking UP at the cameraman!!!

While this was a challenging itinerary for less than three days in Chicago, I think we accomplished a ton and experienced even more.  The bike tour, as well as the boat tour, made it very easy to cover a lot of ground.  And Second City is a must do for any trip to the Windy City!  But, I feel like we probably needed another 2-3 days to really get through all of the major spots, including the museums, shopping on the Magnificent Mile (Michigan Avenue), additional historical and architectural highlights, and the growing theater district.  And timing a trip around baseball season to see Wrigley Field in action is always a good idea!  Maybe next time....