Several months ago I hit the jackpot and won the ticket lottery for the Mumford & Sons show in Chicago. The concert was a few days before my birthday so my partner & I decided to turn it into a mini-birthday celebration weekend!

He decided that he would be in charge of accommodations while I was in charge of activities. These words lit a fire under me because if there’s one thing I know I’m good at, it is planning trips (unfortunately, I don’t take 70% of the trips I plan haha). His only request being that I don’t plan dinner for Saturday night because he wanted to take me out for a nice dinner at a special restaurant.

We decided we’d leave later on a Thursday then take Friday off from work so we could explore before the concert. And so my planning began…


My partner booked us into The Blackstone; this gorgeous hotel, completed in 1910, is located right off of Michigan Ave and despite its renovations it manages to maintain the classic charm of a time gone by. The minute you walk in you’re greeted by plush furniture and luxe appliances, every surface gilded in glam and history. There’s even a decent sized hutch filled with KOVAL liquor (made locally) and small postcard-sized photos of historical moments at The Blackstone. Everyone from Martin Luther King Jr. to President Kennedy, even The Beatles walked the hallowed halls of The Blackstone.

We crashed onto one of the most comfortable mattresses I have ever slept on and woke to a great view of the city. The rooms are complete with all the necessary amenities and I’m also now convinced that on top of needing an all marble bathroom in my future house.


One thing I loved about staying at The Blackstone is that it is so centrally located! We took a Lyft from the airport to the hotel initially but almost all of downtown is within walking distance or a quick trip by train.

If you pull it up on Google, you’ll see the hotel is located right around the corner from a metro station (blue “M” boxes). This is  the Red Line, keep walking two more blocks and you’ll have access to the Blue Line, and not much further from that you’ll have the Pink/Brown/Orange/Purple Lines, so you’ve pretty much got the whole city covered within a 10 block radius.

The train system is pretty straight forward – you can buy a single ride pass but it’s a much better deal to just grab a day pass so you can shuffle back & forth. I don’t know if we got lucky or if it’s always this way, but we didn’t run into any train delays and the station attendants we talked to were more than happy to answer our questions. While we used the train for big distance jumps (or when my feet and hips needed a break), most of the city is insanely walkable. A large part of our day Saturday was spent just meandering around downtown, south of the river, taking in a lot of the architecture and charm Chicago has to offer!


I think the better question would be, “what don’t you want to do?” We knew we only had 2 1/2 full days in the city so I started my planning process by doing a ton of research on what Chicago has to offer…which was overwhelming haha. I’m a sucker for a great outline and a nerd for a good looking list, so the first thing I did was make a rough outline of the different things I thought we would enjoy as well as recommendations from friends who live there.

I then broke that list down by location, starting from closest to our hotel and out. The further away things were the lower the likelihood we would get to them. As the list started to get smaller I put them down by category (food, drink, activity, etc) and then by priority within those categories. I gave the list to my partner for him to whittle down further.

There were a few things I really wanted to do like a River Architecture Tour or a Ghosts and Gangsters Tour but I had a feeling the cold Chicago weather would be less than cooperative. Next time we end up here, especially if it’s in the summer, these will be at the top of my list!

We decided to primarily stay south of the river, so with what was left on the list the first thing I did was buy a CityPass and I cannot recommend it enough! We were able to see some great attractions, under one low price, and most of them had line jumping queues where CityPass holders could go right to the front. Once we finalized a plan of attack, we were left with the following activities:

The Adler Planetarium When I found out that my partner had never been to a planetarium I knew it was the first place I wanted to take him. The Adler Planetarium is a gorgeous building, friendly to both adults and children, and has some of the most passionate museum workers I’ve ever come across! It’s a relatively simple museum, full of great information and brilliant short films about different parts of the universe. It only took us a couple of hours to get through the museum but by the end of it, my darling was blown away by the majesty that surrounds us! #GoalAccomplished

 Millenium Park You’ll find a few Chicago tourist traps in this park, the biggest one being “The Bean”. However, if you walk the park from top to bottom it bleeds into Grant Park, so you’ll come across some other lovelies like The Buckingham Fountain, and The Millenium Founders Monument. We came at the wrong time of year but apparently, during the Spring and Summer, the gardens are dreamy, there are several concert series in the Jay Pritzker Pavilion, countless art installations, and even an outdoor rock wall for climbing.

The Chicago Cultural Center This wasn’t something I had originally put on our list but when we walked past the gorgeous public library I knew we had to go in. A relatively quick walkthrough, they’ve got a great hallway filled with some of the musical greats that came from Chicago, a few smaller art exhibits from local artists, and a bit about the city’s history.

The United Center We were here for Mumford & Sons but when this stadium isn’t hosting amazing bands, it’s also home to The Chicago Bulls and The Chicago Blackhawks. It’s a small to medium sized stadium that gave our concert a great intimate feel while also allowing the people in the “nosebleeds” to have an awesome view of the show. I’ve seen Mumford play several times and I think this might have been my favorite show so far!

360 Chicago The Chicago CityPass allows you entrance into both the Skydeck at The Willis Tower (sorry Kerri, I know it’s Sears Tower forever) and into 360 Chicago. After reading the reviews for both, we decided that we’d rather see all of Chicago instead of a small piece of a picturesque view. Since the weather was scheduled to be mainly overcast, we decided that we’d rather have a nighttime view so we went after dinner on Saturday night. According to Google, 9 pm is relatively slow because they close at 10 pm, and sure enough, it is indeed the perfect time! The views were breathtaking so once we’d made a lap we went to the bar, relaxed for an hour and enjoyed our front row seats to the windy city.

The Field Museum We assumed this museum would be quick like The Adler Planetarium, we were definitely wrong. Leaving it to our last morning was a mistake but we still got through 3 exhibits before having to check out of the hotel. They had two visiting exhibits, “Mummies” (Egyptology is another obsession of mine) and “The National Geographic Wildlife Photographer of the Year” exhibit, both of which were beyond amazing and I would highly recommend if they come to your city. Most importantly, I FINALLY GOT TO MEET SUE! If you don’t know me personally then you likely weren’t aware that I’m slightly obsessed with dinosaurs. I find them absolutely beautiful creatures and I’m constantly in awe of their existence as well as their evolution that gave us some of the creatures still on the earth today! I have goodness knows how many tiny dinosaur toys and figurines on my desk at work, not to mention a killer dino onesie. Okay, so obsessed might be a bit of an understatement…


The Bongo Room– Since our flight was delayed we didn’t end up getting into our hotel until 3 am. We took liberties with the fact that we were on vacation and decided to sleep in but woke up starving. We eased into the morning by walking a couple of blocks from our hotel to this simple restaurant that you would probably pass if you weren’t looking for it. Their menu was basic but their food was divine! I forgot how big midwest portions are but it was completely worth it because their breakfast burrito is going on my top 5 list!

 Stan’s Donuts & Coffee This adorable little donut shop is not only full of delicious treats but it is complete with delectable decor. They make a killer espresso and I’m convinced that whatever batter they make their donuts with is infused with witchcraft.

Wildberry Pancakes & Cafe hands down some of the best, if not the best, pancakes I’ve ever had! They have HUGE portions, and most of their menu items will potentially leave you in a sugar coma, but oh goodness is it worth it. Be forewarned, because they are so delicious there is usually an insane wait time! If you use the Yelp app, you can see what the average wait time is and get in line online so that you can check in a little later once you get to the restaurant.

R&M Champagne- This is the restaurant that my partner chose for our special date night. It took us a hot minute to find because it’s tucked away in a cobblestone alley but the path is marked by a slightly faded logo on the main street sidewalk and lit by twinkling lights. The interior feels like a step into old Paris, with candles everywhere and soft lighting for the perfect element of romance. While the food and wine were amazing, the only issue we had was the general volume of the restaurant. It’s definitely not their fault or within their control, but we came in expecting something a little more intimate. Between the music and customers, we pretty much had to yell in order to hear each other.

Portillo’s– We finished up our food tour by hitting a Chicago staple before we headed to the airport. Portillo’s started as a quaint little hot dog stand in the 1960s and grew to over 50 locations (generally in the midwest). They’ve got a little bit of everything, from pasta to hamburgers, but you can always keep it simple with their classic Chicago style hotdog.


The KerrymanAfter the Mumford concert we met up with a friend for a quick drink at The Kerryman. Known as “Chicago’s liveliest Irish bar”, you feel the authenticity from the minute you walk in. The doorman (John) along with the 3 owners, all hail from Co. Kerry while their Head Chef is from Co. Limerick, so no matter what you’re there for, you’ll leave with a little slice of Ireland.

Broken ShakerThis awesome cocktail bar will have you feeling like you’re on vacation when you sit inside. With a very “island life” vibe, this bar focuses on specialized mixology. Utilizing fresh local ingredients and global flavors, the bartenders strive to shake up the perfect blend of flavor to fit your palate. They have a rotating menu that changes roughly every 3 months but if you’re wanting to take the gamble, feel free to tell the bartender a few other drinks you like and then see what surprise he shakes up! Our bartender was awesome, randomly gave us tasters of different liquors he thought we would like. I got a drink that tasted like delicious alcoholic lemonade and could easily get me into some summer trouble.


Since we were limited on time and energy, there were quite a few things that we didn’t get to see or do in our 2.5 days. Both of us loved our time in the city so we’ve made a list of things to hit when we come back, feel free to leave a comment with anything we missed!

  • The rest of The Field Museum
  • Wrigley Field
  • The Harold Washington Library
  • Myopic Books
  • Giordano’s Pizza
  • The Art Institue of Chicago

I am so happy that we blew into town for this trip, not only was it relaxing but there were tons of activities for any interest we had! This city, rich in history and culture, is definitely one that we’ll be adventuring back to.

Be sure to follow along and read up on on all my travel adventures here.

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