Less than 24 Hours in the the Windy City: Chicago

John Hancock Center

After spending just a few hours in Chicago we started to suspect the Chicago Department of Tourism of planting actors throughout the city to keep up airs of Midwest charm and friendliness. Right off the bat, on the way from the airport we ran into a lady working the toll booth who was what Serena called, “ the nicest person she has ever seen working a toll booth”.  Now, Serena was raised in New York City where the words “nice” and “toll booth” are normally not spoken in the same sentence but I had to agree!  She seemed genuinely happy to see us and I think she would have continued a conversation if not for the cars stacking up behind us. We continued on to the Hotel where we immediately dropped our things off and loaded up the baby stroller to head out in search of something to eat.

Chicago Bikers

Where to Stay:

The Whitehall/ 105 East Delaware Place

Excellent hotel with a great location in reach of most of Chicago’s major attractions. Sitting in the shadow of the John Hancock Center, there are plenty of places to eat within walking distance and only a few blocks from the lake/beach. We were only in the hotel long enough to arrive, sleep and wake up but the room was huge and the bed was past comfortable. The elevator was the size of a high school locker and took maneuvering with a stroller but not a big deal.

I had been to Chicago once before in my early twenties but I would be hard pressed to recall much about it except a couple of night clubs, late night strangeness at the Wiener Circle and a terrible hangover.  Outside landing and departing the airport, I am not sure I even went outside while the sun was up during my weekend stay in Chicago. With that said, I looked forward to seeing the city in the slowed pace that only pushing a baby stroller will allow.

Where to Eat :

Ditka’s Steakhouse / 100 E. Chestnut

Can you feels this kid's excitement about Ditka's?

This is pretty much the face I made when my steak came to the table.

When figuring what to eat it was a no-brainer that it would either be steak or pizza. Once I found out that Ditka’s Steakhouse was right around the corner from our hotel the decision was easy.

The weather was nice so we decided to take a seat outside on the sidewalk. Sitting outside with a baby is usually the easiest choice, the people walking by keep him entertained and if he starts tossing a fit you can quickly push the stroller into Chicago rush hour traffic. That was a joke so no need to call Child Protection Services, if anything we need protection from him most of the time.

I can’t say where Ditka’s ranks in a city with such a reputation of great steakhouses because it’s the only one I have been to, but everything we had was excellent.  I can say that between the three of us we loved and devoured everything that came to the table :

RIbye Ditka's

“Kick Ass” Paddle Steak $42.95 – bone in premium gold angus ribeye, 20oz

The Prime “Fridge” Burger $11.95 – cheddar, mustard, mayo, onions, pickles, lettuce, tomato, hand cut fries

Black Jack Smashed Sweet Potatoes $6.50 – sweet, creamy with bacon on top, perfect

Jalapeno Hash Browns $6.50 – a little bit of crunch with a jalapeño kick

Black Jack Smashed Sweet Potatoes and Jalapeño Hash Browns

Black Jack Smashed Sweet Potatoes and Jalapeño Hash Browns

I didn’t say it was cheap but it was more than good. My only regret is that I never went inside to peep the memorabilia, see what the inside of the place looked like and make sure the “coach” wasn’t inside.  I think I was too busy chatting with strangers who stopped to talk in what might be the most talkative city in the United States (not a complaint, just an observation).
Mike Ditka's Restaurant on Urbanspoon

What to do:

Walk along or jump in Lake Michigan

A man and his best friend enjoy Lake Michigan at the Ohio Street Beach

A man and his best friend enjoy Lake Michigan

After that meal the only thing we could do to avoid exploding was to walk. High buildings, happy people and a cool waterfront make Chicago a great city to stretch your legs. We walked east from Ditka’s down Chesnut towards Lake Michigan. One we reached Lake Shore Drive we headed south and found an underpass and kept walking south along the lake. There were paved running and bike lanes along the lake that had no shortage of runners, walkers and bikers. There were droves of people swimming in the lake and lounging by at the Ohio Street Beach. The Ohio street beach is smaller than the North Street and Oak street beaches but tends to be less crowded. Its a great urban beach that offers excellent views of the city’s skyscrapers, shallow water and of course full of happy people. We saw the lights of a big Ferris Wheel in the distance and continued walking south towards it.

Be a Tourist and Visit:

The Navy Pier

After walking about a mile we came to the Navy Pier. The Navy Pier is a tourist entertainment complex that juts out 3,300ft into Lake Michigan (the largest pier in the world at its time of completion). Built in 1916, the facility has seen various uses, housing for personnel during war (WWI and WWII), commercial ship traffic, Navy training center, college classrooms, public gathering place and in 1990 reborn as a multi-use entertainment park.

The ferris wheel at the Navy Pier

The ferris wheel at the Navy Pier

Yes if you looked in the dictionary for tourist trap you would find  a picture of the Navy Pier.  It has all the symptoms of a tourist trap, restaurants with overpriced food, and high priced sugary cocktails, too many people and little shops with overpriced “I Love Chicago” t-shirts. With that said, we walked the pier sipping our +$10.00 margaritas, paid to have a caricature drawn of the boy and took him for his first Ferris Wheel ride where we had an unmatched view of the city. When we are a tourist, we don’t mind sticking our foot in the trap at least once.

We grabbed another high dollar sugar bomb and started our walk back to the hotel. After a long day of travel, Devin was knocked out before we reached the hotel. We were equally tired with sore feet to match from a day of traveling and walking the city.

Chicago skyline

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Categories: Reviews, Travel


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