Chicago, Chicago!



In early November, Chicago is bound to be cold because you expect the wind off Lake Michigan but don’t expect 24 degrees and snow. Two good friends and I were in town for a girl’s weekend.  Thankfully, we three Southern gals were somewhat prepared with heavy jackets and gloves. The light snow on Friday morning was pretty, as it covered the sidewalks and rooftops.  A quick run to the corner Starbucks gave us our first taste of the cold weather and it was a bit slippery but the rest of the city took it in stride on the Veterans Day weekend.

Chicago at Work

The Blake Hotel was our home base for the weekend. It is an older, comfortable hotel located on Dearborn Ave.  It has good access to both the Blue and Red lines of the L for public transit.  With a 1 bedroom suite and a double room, we were had well looked after.

Hotel Blake

We headed out toward our Hop On/Hop Off City Tour. After a longer than expected delay including getting lost we eventually made it to the Hilton on Michigan Avenue to board the bus. I recommend these tours in an unfamiliar city because they give you a good overview of what and where you want to explore. The double-decker bus was covered on the top and it was still cold inside but at least we were out of the wind.  The tour guides provided excellent information on the city and recommendations for restaurants and fun activities.  Friday traffic posed a problem, but that was to be expected on a holiday weekend.

Big Bus

The skyline of Chicago is striking and its architecture impressive, especially when you remember the city was decimated by Great Chicago fire in October 1871, leaving more than one hundred thousand people homeless. The city rebuilt quickly and by 1890 was a major transportation hub.  Ironically, the Chicago fire training academy is located on the site where the Great Chicago fire began.

360 Chicago

Our first stop was the 94 story John Hancock building and the Chicago 360 where you can view the city and the four surrounding states.  Unfortunately, our visit was a bit cloudy, but the city views were spectacular. The observatory opened in 1969 and has thrilled millions of visitors over the years.  The newest addition to the 360 is “the Tilt,” which tilts you away from the building some 30 degrees over Chicago’s “Magnificent Mile” or Michigan Avenue.  This is the place for some stunning photographs.

Lake Michigan

After we descended from the heights, we hopped back on our bus (they leave the designated spots every 30 minutes) to head towards the Chicago River.  We made it just in time to board the First Lady of Chicago Architectural River Tour.  It was a freezing cold night but many braved the temperature and wind of the upper deck where a docent from the historical society provided a 90-minute overview of the Chicago skyline which was resplendent on the November evening.   This is the way to really see Chicago.

Chicago Skyline

Cold and tired, we hailed a cab for a short ride to The Italian Village for dinner. Family owned since 1927 and the oldest Italian restaurant in Chicago, the three restaurants, Italian Village, Vivere and La Cantina will provide you with whatever style of dining you prefer. You can find fine Italian fare here, from family to fine dining. We opted for Vivere, and it was an excellent decision.  The service, wine, and food were excellent. We enjoyed a mid-priced wine from their ample cellar.  The meal and conversation were a satisfying end to a busy day of touring.


Saturday would prove to be a less busy day. We began with brunch at the Cheesecake Factory in the Hancock Tower. Beginning your day with an omelet and mimosa is starting the day right.  We each took a piece of decadent cheesecake to go.   Next, we walked to “the Bean” in Millennium Park.

The Bean

This unique, impressive sculpture draws you into its mirror-like surface.  At 66 feet wide and 33 feet high and has a 12 foot arch in the center.  You get a whole new perspective of your surroundings beneath the arch.   This is not to be missed in Grant Park!

Beneath the Bean

The afternoon was spent watching football, as we are all SEC gals.  We then began our evening with genuine Chicago-style pizza delivered by Lou Malnati’s’ which gave us the strength for our evening journey on a slow boat to Margaritaville.

Chicago Deep Dish Pizza

Escape to Margaritaville

Escape to Margaritaville is a musical comprised of the island styled songs of singer and songwriter, Jimmy Buffett. It is a fun island romp and well worth your time and money.  This was a pre-Broadway run for the show, which will start its run in New York in February.

Cast of Margaritaville
Jimmy Buffett and Lyn Manual Miranda

After the show, it had warmed up a bit and we walked back to the hotel down State Street enjoying Macy’s picture windows that were already decorated for Christmas. It was a nice ending to our brief weekend in Chi-town. Chicago has much to offer a visitor; you need time to enjoy it.

Related posts

Leave a Comment