The Best of Chicago in a Weekend

Chicago Stole My Heart

This past year was Nathan and my fifth anniversary. As I opened the card he got me, two pieces of paper fell out. Two plane tickets to Chicago, two nights at the most fabulous hotel, and a city tour. Let me say, I know I am lucky and this was the sweetest, most thoughtful thing anyone has ever done for me. It also made me feel like a humongous pile of poo because I got him a cactus for his office. (To be fair, we agreed to no gifts because I had just gotten laid off.) I’m dying with guilt just typing this.

We had a very early morning flight to Chicago and arrived around 6 am. Getting off the plane I just wanted to sleep but this early flight was honestly a blessing in disguise. Chicago’s public transportation is incredibly efficient. We hopped on the train at the airport and it took us directly into the city and we got off one block from our hotel. Completely stress-free travel is how I like to go.

The Palmer House ChicagoThe Palmer House Hotel

Our hotel was perfect. The Palmer House has incredible grandeur and it made us feel way fancier than we actually are without making us feel out of place. The staff suggested great restaurants, helped us with directions, even offered to order us a private car upon check-out. (Lol, “that won’t be necessary, we have another means of transportation” as we headed toward the peasant train station.) Very few times in my life have I taken a picture of our hotel, but I couldn’t help it with The Palmer House. I mean, look at it! In addition to being gorgeous, The Palmer House is also located in the heart of the big tourist attractions.

The Bean

The BeanI mentioned that our early flight was a blessing and here is why. The Palmer House checked our bags so we didn’t have to worry about them while we walked around waiting to get checked in. We decided to head to the closest attraction which was the famous Bean. AND IT WAS A GHOST TOWN. There was one other couple at The Bean so we swapped photo sessions with them and got so many pictures before the area was swamped with people. We enjoyed casually walking around the parks without being pushed along by swarms of people. Locals on their morning run were so friendly and frequently stopped to give suggestions or offer to take our photo. Be sure to parade around the peaceful water and park trails to check out the art that is hidden everywhere!

Bus Tour/Transportation

As I said before, I like to do travel stress-free and usually the worst part about travelling is navigating to where you want to go without it costing an outrageous amount. Nathan covered this by reserving tickets on the Hop-on Hop-off Bus Tour. I know these get bad reviews because you don’t get an authentic experience, but they are so convenient, reliable, and inexpensive. So when travelling in America, I’m all about these suckers! Sue me. They stop at all of the major attractions and you get a narrated ride along the way. You can get on and off as many times as you like all day and part of the night. (They also come in multi-day passes.)

The Skyline

According to our tour guide, Chicago’s skyline was rated the second greatest skyline in the world! I can definitely see why–it was beautiful! The best spot to take it all in? The Adler Planetarium. The Planetarium is located a little away from the city, but your hop-on hop-off bus tour stops here! I highly suggest getting off at this stop to hang out on the steps of the planetarium and appreciate the gorgeous skyline.

The Pizza

Deep. Dish. My new love. For starters, I love cheese and carbs. If you don’t like excessive amounts of those two things, deep dish is probably not for you. We stopped at Giordano’s on the Navy Pier to try it. Nathan wasn’t crazy about it, but I loved it! (Also note, it’s VERY filling so wear your stretchy pants!) The Navy Pier also has a lot to do for families besides pizza. Shopping, amusement rides, and ice cream shops are everywhere on this little waterfront.

The ShoppingCoffee Shop

If shopping is your thing, check out The Magnificent Mile. Store after multi-level store fills this entire area. My favorite place to shop in a new city however, isn’t H&M or Macy’s. I love exploring the tiny local shops and finding really unique experiences. The picture on the right is of a coffee shop we found somewhere around The Palmer House. I can’t tell you a street–I can’t even tell you the name of the shop but it did have the best Chai Tea. Chicago also has a lot of really great music stores and old bookstores to check out!


What was your favorite part of Chicago? Let me know in the comments!

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