This post is made possible in part by my Patreon supporters, and for Rasmussen Travels for setting up the trip. Thank you.

I love Chicago. I love everything about it. There is always so much to do, so much to see, and a two day weekend does not even begin to scratch the surface of what the Windy City has to offer.

I stayed at Hotel Allegro, a Kimpton hotel right in the Loop.1 I arrived late Friday night, and they were completely attentive to everything I needed. Parking was expensive, but that is how it goes in cities. They also provided a complimentary coffee bar in the mornings and a complimentary wine social in the evening. I definitely recommend staying there.

This was a white chocolate cocoa with cinnamon and peppermint.

Unfortunately, it was a very foggy weekend, so the beauty of the skyline was not visible. However, with this being an El Niño winter, it was still warm enough to go outside and do a bit of urban exploring. During the holiday season, the windows at Macy’s (pronounced “mɑrʃəl fildz” like “Marshall Field’s”)2 on State Street are all decorated. I will not spoil the surprise of what the theme is this year, but after most recent years being very weird, this year was pleasantly nice. Only a couple blocks west on the Daley Plaza is the outdoor Christkindlmarket, where they sell Old World Christmas decorations, and have a large Nativity Scene on the eastern side. As I walked past, the crowd was too great to go up to any of the vendors. It is easier to navigate the market during evening hours, when the crowds have passed on.

Chicago is also full of museums ranging from zoos, art institutes, and cultural museums. Within walking distance of the Loop is the Chicago Art Institute (right next to Millennium Park), and the Museum Campus (just south of Grant Park, which itself is right next to the Art Institute). The campus contains three museums: the Adler Planetarium, the Field Museum, and the Shedd Aquarium. While I recommend all three, I recommend the Shedd Aquarium the most. For roughly $40.00, you can get a sample of many freshwater fish all over the world, a glimpse of the world’s various reefs, an entertaining water show, and a special rotating exhibit (which was a world amphibian exhibit at the time of this post). Or get a $75 single, $150 couple, or $195 family membership, and in two visits, it is paid off, plus discounts on the in-house movie, food court, and gift shop. I go any chance I get, and always get something new out of it.

I mentioned earlier Millennium Park. It is definitely a modern masterpiece of the city. It is a part of northern Grant Park, and offers a lot to see and do in the small area it contains. The first thing many people see is the Cloudgate (pronounced “bin” like “Bean”, see below), and all the “selfie-sticks” that come with it. Just to the immediate east of the Bean is the open-air amphitheater, which is a modern art piece in and of itself. There is also a garden to walk through, with a number of different plant species, most of which are indigenous to Illinois. During the holidays, there is an open air skating rink with free admissions and a $12 rental fee for skates. South of Millennium Park is the rest of Grant Park. The shinning jewel of Grant Park is Buckingham Fountain (see below), the traditional start of Route 663. During the summer, there is a water show at the top of every hour. However, it is turned off and drained during the winter. But, its architecture is still a sight to behold, as it is modeled after the fountain in Versailles. My recommendation, grab a coffee to go at Intelligentsia (my personal favorite coffee shop) from across Michigan Avenue, and take a leisurely stroll for most of the afternoon around all of Grant Park, maybe even making a stop inside the Art Institute. After the afternoon of enjoying the outdoors, head back across Michigan Avenue and enjoy a tea and a vodka from Russian Tea Time.
So many selfies.
This will be in its watery beauty come mid-April.
The nightlife of the Loop and surrounding area is quite fun and enjoyable. Just north of Millennium Park on Michigan Avenue is Sweetwater Tavern. With the hearty burgers and well priced drinks, it is a great start to a evening. Straight north on Clark Street, across the Chicago River from the Loop, is a tiki bar called Three Dots and a Dash. This is one of those bars that is found by going into the alleyway off of the street. Once inside, you are greeted with Polynesian décor and rum all around. They even sell drinks to share among 3-4 people. A little closer to the river, off of Kinzie Street and LaSalle Street, is a country bar called Old Crow Smokehouse. I, for one, and not a big country music fan, but they have live music and good priced drinks. I cannot think of a better way to end a weekend night.

Overall, I barely touched what Chicago has to offer. I barely touched what the Loop has to offer. Chicago is one of those cities that I can go back for more, and cannot wait to go back.

1. The Loop in Chicago is a location in downtown. It is the commercial centre of the city. The name comes from the elevated train rail system (the “L”) making a full loop around in roughly a 2 mile perimeter, before branching off to their terminals.
2. Marshall Field’s was bought out by Macy’s in 2005. Most Chicagoans do not accept the name change and still call it by it’s Chicago name rather than the New York name.
3. I say traditional start, as it is not the actual start of Route 66. In actuality, Route 66 started on Lake Shore Drive and Jackson St just north of the fountain. But, I am willing to still call it the start of Route 66 given its beauty.

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