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Chitown – How to Have a Great Weekend in Chicago

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Written by Jamie Shannon.

Chicago has always been one of my very favorite places to visit. The great architecture, the food, shopping; the windy city has something truly amazing around every corner. When my grandma decided to take my brother, Joe, to Chicago for his graduation present because he had never been, my mother and I begged to be able to tag along.

We left on a Friday afternoon and took the train from East Lansing to Chicago which takes about 4 and half hours. In my opinion, the train is the easiest way to get to the city. Driving downtown can be a hassle and the parking fees are a little on the outrageous side.

When we arrived at Union Station, we took a cab to our hotel to get settled in. Our hotel that we stayed at is called the Inn of Chicago and is right in the heart of the city on Ohio Street and the famous Magnificent Mile. It was the absolute perfect location. The hotel itself has been updated recently so it is very nice on the inside. The rooms are pretty small, but we were not going to spend much time in the room anyway. The Inn also had a rooftop terrace to look out over the city which wasamazing at night. Once we got checked in, my brother and I headed to U.S. Cellular Stadium while my grandma and mom went to have dinner. My friend, James, from my study abroad trip is originally from Chicago and happened to have two extra White Sox tickets. The stadium was amazing and the crowd noticeably anxious for the game to begin as Chicago was playing the Boston Red Sox; it was certainly going to be an exciting nine innings. Luckily, the White Sox won and stayed to watch the fireworks over the stadium after the game!

The next day we woke up and decided to walk to the Navy Pier. For as many times as I had been to Chicago, I had never been to the pier and it definitely lived up to the hype. It has wonderful views of the Chicago skyline as well as numerous little shops. I did not get to ride the giant Ferris Wheel because the rest of my party are afraid of heights but definitely next time!

After the navy pier we were getting hungry so we decided to go to the famous diner called Ed DeBivic’s. It was a neat little place that had great old style burgers with a sassy staff that perform dance numbers on the countertops. I would definitely suggest going there for lunch to get the full experience.

We spent the rest of the day on the hop-on hop-off bus tour around the city which I believe is the very best way for newcomers to see all of Chicago. It is a three day pass for $35 per person with tours of downtown and three other neighborhoods which include the Lincoln Park Zoo, Wrigley Field, Chinatown, and Little Italy. You can get off at all of the must see stops such as Millennium Park, Willis Tower (formerly Sears Tour), John Hancock Building, Chicago Theatre, Magnificent Mile, and Navy Pier.

For dinner we were strongly advised to go to either Pizzeria Uno or Pizzeria Due for some famous Chicago style pizza. Both are owned by the same owner and are not to be confused by the restaurant chain of Uno’s. These particular pizza places are the real deal! We chose to try Pizzeria Due since it was right around the corner from our hotel and didn’t seem to have as long of a line as Pizzeria Uno. Now I am not a lover of deep-dish pizza, but wow, this pizza was amazing! I highly suggest trying one of these two restaurants while in Chicago.

The heat index was over 100 the following day so we took some of the local’s advice and went to one Chicago’s twenty beaches. When I think of Chicago, beaches are the furthest thing from my mind, but they are actually very nice and well kept. There were hundreds of boats out on Lake Michigan enjoying their Sunday afternoon as well. That evening we ate dinner at Weber Grill which was a fabulous steak house, I highly recommend it!

Monday morning we got up early to get the Willis Tower (formerly the Sears Tower) and experience the Sky Deck. Our tour guide said that lines can be up to three hours long! We figured that by going early and on a Monday, it would not be nearly as bad. It was probably about a half an hour by the time we got our tickets and got up to the Sky Deck. Definitely worth the wait! The price is a little on the expensive side at $17 per adult ticket, but if you have never experienced the SkyDeck, I highly recommend it; it is definitely a unique experience. The 360 degree view of the city is absolutely extraordinary! The Sky Deck is quite an experience in itself. There are four glass boxes that extend out over the ledge so it is almost as if you are walking on air. Admittedly we were all a little shaky at first, but when we finally got out there it was simply breathtaking.

Once down from the SkyDeck, we headed over to Millennium Park to see the now famous art piece called Cloud Gate or mostly commonly referred to as “The Bean.” The piece looks exactly like a giant bean and has a mirrored surface that reflects the magnificent Chicago skyline.  It is quickly becoming one of the most popular sites to visit in the city. After taking part in a quick photo shoot, we decided to spend the rest of the time roaming around the park before we had to go back, collect our luggage and head to the train station. If you have time in this wonderful city, I suggest spending some time in one if not more than one of their fabulous parks. They are well kept and the green scenery adds balance to the already beautiful city.

If you’re looking for a quick weekend trip, Chicago is just a short train ride away, but I guarantee that you’ll wish you stayed a little while longer! Call Classic Travel and we can help make the most out of your time spent in the Windy City!