About a month ago I was rummaging through some old books of mine and found a notebook from 2016. I opened the book to one of the pages and found that I had wrote a travel bucket list, and on that list was Chicago.

Time passes us by so fast that sometimes we forget what our dreams and aspirations are. This is why I think writing is so important because it reminds us about ourselves. Before reading that book I didn’t even remember ever writing Chicago on my travel bucket list, but I did. It felt so amazing to know that in a couple of days I would be living a dream of mine, a trip to Chicago. Fast forward to now and it’s been three weeks since my trip, but I wanted to share more of my experiences with you all and create a Chicago Travel Guide.

What to Pack/Wear

Dom and I arrived in Chicago a few days before the first day of summer, but the temps were in the high 90s most of our trip. It was giving real summertime Chi vibes, which I absolutely loved so I dressed accordingly. Here’s a list of the items I packed for a four night stay:

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One thing that I would highly recommend to pack from my list is some comfortable sneakers. I loved that in Chicago you can literally walk just about anywhere. Dom and I visited with this in mind so that’s why I made sure to pack a great selection of sneakers. So happy I did! We walked a total of 31 miles while vacationing there. Talk about getting in your steps!

Where to Stay

Before booking our stay in Chicago, I knew without a doubt that I wanted a view of the river walk. The pictures that I’d seen of the river on social media sold me! So I went searc hing for a hotel that fit my “must-have water view” and that’s when I found the Kimpton Hotel Monaco. The hotel is located in the West Loop area. If you book here, you have to make sure you select a room with a river view and don’t be afraid to ask for a higher floor. Dom and I walked into the room they first gave to us and were not impressed. We requested a higher floor and ended up being on the highest level and got a great view of the river —- lived out my dreams.

Now if I’m being honest we did have a hiccup in the beginning of our stay where there was no hot water the first night. We were initially upset with this, but IHG/Kimpton has such great customer service that they fixed the issue and compensated us for the inconvenience. We understand that things can go wrong, but how a brand reacts or responds to an issue is a testimony of who they truly are. We appreciated the way they rectified the issue and made us still feel like valued customers.

Oh also a big plus with them is that you can communicate with the hotel staff via text so any concerns I had the ability to easily shoot them a text to express them. Also, the location of this hotel was AWESOME! It was right near the river walk, the ‘L’ (this is what Chicagoans call the train system), restaurants, the Bean and more!

What to Do

Where do I even begin! There’s sooooo much to do in Chicago! So much so that Dom and I already have created a new list for when we want to visit again. Here’s a breakdown of what we did each day during our stay.

Day 1

On our first day in Chicago, we made sure to do things that were closer around our hotel. I recommend doing this since your arrival day is normally your shortest day of the trip.

The Bean

Okay you can’t visit the Chi without checking out the Bean sculpture. Funny thing we found out on our Chicago Architecture Boat Tour is that the creator of the Bean doesn’t even like that Chicagoans call it that *haha*. But back to the sculpture, it’s massive and an amazing piece of art. I honestly thought that visiting this would be underwhelming, but it absolutely wasn’t. It’s worth seeing! If you walk towards the steps from the Bean you’ll also get to capture a cool shot of the city street/buildings as you see below.

The Buckingham Fountain

This is another thing on our list that I didn’t think would be as amazing as it was, but again I was wrong. The fountain is located in Grant Park and I have never seen a fountain so big in my life. It’s so beautiful to see in person and you even get a view of Lake Michigan in the background of it.

Reel

Want to get a visual glimpse of our first day in Chicago? Check out this reel recap 😊

Day 2

Chicago Architecture Boat Tour

This experience was one of my favorites! From the views to the tour guide we had, it was just so awesome! I loved learning more about this beautiful city. Tip: Book your tour at the beginning of your trip. Doing this makes you feel like you already know so much about the city! The tour company we went with was Shoreline Sightseeing. If you can, request Spiro to be your tour guide because he was absolutely the best!

360 Observation Deck

The 360 observation deck is located at the John Hancock Center on the 94th floor. It’s a pretty cool experience and you get to see some really great views of the city. There’s also a new attraction called The Tilt. It’s an extra cost and we didn’t feel that it was worth it

Magnificent Mile

The Magnificent Mile is a strip of shopping stores. We walked in a few like Coach, Nike and Under Armour. If you want to do some shopping you have to walk the Magnificent Mile because there are so many options!

Day 3

Went to a Baseball Game

We were super excited to see a game at Wrigley Field since we’ve been to many baseball games in DC. Unfortunately, we didn’t find the experience to be that exciting and were underwhelmed. But it could have just been us so I would still recommend to see it for yourself. I will say that it was awesome to see Lake Michigan and the city from where we sat. Always here for a great view!

Explored the Navy Pier

The Navy Pier overlooks Lake Michigan and has some rides for kids and a Ferris Wheel. I was mostly excited to get on the Ferris Wheel! It’s a great way to get an amazing view of the city.

Day 4

Sky Deck

If I had to choose which activity was my favorite, it would have to be the Sky Deck. It’s an observation deck that is located at the Willis Tower on the 103rd floor. The views are unmatched and they even have what they call The Ledge which is box that is extended out and overlooks the city. I was a little fearful of the height when I walked out into the box, but content creator mode kicked in and I was good! This is such a bucket list experience!

Art Institute of Chicago

I am always here to see some great art and the Art Institute of Chicago did not disappoint. It is a huge exhibit so prepare to view a lot. We didn’t even get to see everything so I can’t wait until we can visit again.

Garfield Park Conservatory

The Garfield Conservatory was so whimsical and it just filled my heart with joy. I was amazed at everything I saw here. I talk more about my visit here in My Visit to the Garfield Park Conservatory blog post.

Day 5

Shedd Aquarium

The Shedd Aquarium was pretty big and a lot to see. My favorite part was watching a dolphin show and also their Caribbean Sea exhibit. There is also a good amount of touch and feel exhibits, which was cool.

Day 6

This was our last day in the city, but our flight was not scheduled to leave until around 8 pm. So we checked our bags with our hotel and went to explore the city a little bit more.

Field Museum

I’m convinced that the museums in Chicago are just all massive because the Field Museum definitely fit this description too. This museum takes you on a journey through time. We particularly loved the Southeast Asia and the Africa exhibits.

Travel Tip

I highly recommend purchasing activity tickets from CityPass if you plan to do a lot around the city. We purchased the plan where it includes admission into 5 attractions and you get to select two more attractions from four options. This was such a great value! The Sky Deck was included in our pass and it allowed us to get expedited entry.

Transportation

If you’re worrying about how to get around the city, please stop. Chicago is one of the easiest cities to get around. We either walked, caught an Uber or train. An Uber was always a last resort for us and as mentioned earlier we did ALOT of walking, which I enjoyed so much. Using the train here was so easy and inexpensive. Loved that the cost of a train ride is only $2.50 no matter where you travel to.

Places to Eat

I enjoyed everything we ate in Chicago! We tried everything from Chicago pizza, upscale dining, popcorn, donuts and more! The Chi did not disappoint and I truly wish all of these places were in the DMV *inserts sad face*, but here’s a list of all the places.

• Egg Harbor Cafe
• Firecakes Donuts
• Garrett’s Popcorn
• Giordano’s
• Goddess & The Baker
• Maison Marcel
• Miller’s Irish Pub
• Portio’s
• Remington’s
• River Roast
• The Dearborn

Well that is a wrap on my visit to Chicago! Let me know in the comments if there is anything else you would like for me to share. Also, if you want to see more of our trip check out my Instagram highlight and more on my page.

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