One of my good friends and I decided to visit Chicago to mark our 40th birthdays this year. It was my first time visiting Chicago, so I made sure to hit some amazing spots to get a great feel of the “Windy City”. The name “Windy City” isn’t because of the weather it is actually from the boastful “windbag” politicians of the late 19th century from Chicago. I put together a snapshot of several places we visited on our short stay in Chicago. This post is full of great eats and interesting sights.
My First Time in Chicago: A Casual Guide to Downtown
Where I Stayed
The hardest part of planning for this trip was deciding where to stay. There were so many options. We wanted to stay somewhere that was affordable for us, but still felt upscale. We also wanted something that was near the Navy Pier. TheWhit had everything we were looking for as far as price and location. There was construction happening right outside our hotel which was good for minimal traffic, but not the best for noise. Our room was on an upper floor, so the construction noise didn’t bother us too much. We knew theWhit had a rooftop bar. However, we didn’t know the rooftop bars held nightly events. This was a very convenient for guests of theWhit and those who just want to party downtown. We didn’t get a chance to enjoy it, but there is also a spa in the hotel. We had an issue with our A/C unit, which took sometime to fix, but the staff was attentive to our needs and took care of it.
Getting Around the City
Downtown Chicago is very walkable. That is definitely a bonus for those who are staying downtown. It also helps that all the tall buildings provide great shade for sunny days. Most places that we wanted to visit were within a few miles of us. This made our stay less stressful.
The “L” train is one of the most known train systems in North America. It is a lifeline to Chicago and transports residents and visitors all around this buzzing midwestern city. The “L” train is easy to experience. You can hop on the train from the airport and it will take you where you want to go. If buying a ticket, or pass, seems like too much work, there is the Ventra app that allows you to access your tickets without worrying about losing them. We did not experience the “L” train while we were in Chicago because we didn’t need to. However, the next time I visit I will make sure to grab a ride.
Downtown Chicago is very two-wheel transportation friendly. The bike lanes were super busy with bikes and scooters zipping by all day and night. If you’re visiting and feel confident in your navigation abilities, renting a scooter or bike is a great way to get around the city.
Iconic Chicago Attractions
Millennium Park and “The Bean”
I think if you’re going to be a tourist, you might as well go all in. The Cloud Gate is also known as “The Bean” and is located in Millennium Park in downtown Chicago. As you can imagine, it is very busy with tourists. Don’t let the idea of it being a tourist trap detour you from seeing this stainless steel sculpture. The area is open and it is easy to navigate around so that you can take photos.
Taking an Architectural River Cruise
Sightseeing in some form or fashion is a must the older I get when visiting a new city. The Chicago Architectural Boat Tour is a great way to see downtown Chicago. We stopped by the river during the day when we first arrived. However, we wanted to have a little more ambiance for our boat tour. So, we booked our tour for the early evening as the sun was setting. You do what works for you, but the city lights added a cool pop of color to the city as we gently floated by. The tour guides were very informative and provided a background on the history of Chicago that I did not know previously.
Where I Ate in Chicago
Founded in 1963, Portillo’s is one of the restaurants that put Chicago on the culinary map. There are several Portillo’s locations in Chicago. We stopped at the one located closest to us in downtown Chicago. As soon as you step in you feel like you made a great decision. The menu has something for everyone. From pasta-to-ribs-to-burgers, there is something tasty for hungry visitors. I had to go with one of their staples, the hot dog. Of course, I had to get it Chicago-style. The hot dog was juicy and flavorful. This was the first time I’ve had a poppy seed hot dog bun. It accompanied the hotdog wiener very nicely. A good serving of fries helped to round out my meal. My friend, Ashley, let me have a bite of her char-broiled burger and I told myself the next time I’m there I will get my own because it was really flavorful.
Chicago-Style. Is it Worth It?
When we were planning this trip, Chicago-style deep dish pizza was on the list. We almost didn’t try Giordano’s Pizza. The line was out the door and the lobby was full. Thankfully, the restaurant runs like a well oiled machine. We put our name on the list, waited about 15 minutes, and were seated promptly as occupancy allowed. Of course, we had to have a deep-dished pizza. Six bountiful slices were more than enough for the two of us. The sauce was zesty and savory. The dough was thick enough to hold up against the mountain of ingredients on each slice. My best advice would be to read the menu ahead of time and be careful when ordering. If you order one of the deep-dish pizza’s it does take awhile to bake. Therefore, if you don’t get the toppings correct when placing your order, you’re probably be stuck with it (speaking from experience, lol).
On our last night, we popped into the rooftop bar at Raised. The bar was cute and chic. We ordered drinks and light food. The Yuzu crush was a sweet drink with a slight tartness. We shared the churros which were a nice portion size and came with two dipping sauces. We also ordered the parmesan and rosemary fries that were accompanied by a spicy ketchup. Of the two, the fries were my least favorite. They just were not at all as good as they sounded. However, the churros were warm and soft with the right amount of cinnamon and sugar coating.
more pictures…but I just have to share!
We spent so much time in downtown Chicago and we still didn’t see everything. There are theatre shows, shopping centers, museums, sporting events, and so many restaurants. Chicago is definitely one of those places that you have to visit again and again to really get the full experience. It is buzzing with energy but still maintains a midwestern feel.
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