Throughout my adulthood, every time I went to Chicago it was for work. It always seemed to be in the winter, and I never left my hotel, or was whisked away to a suburb of the city (“Chicago”). When a wedding took us to the Windy City, I jumped at the opportunity to stay an extra day, and ensure that my trip included a stop at the bean. Our trip was equal parts spending time with friends, and exploring on our own. I loved it.



We only had one evening to enjoy dinner on our own, so a little digging and I found Roister – a highly acclaimed restaurant with an interesting menu and great waitstaff. I had the beet, endive and bleu cheese salad for my starter and a maple poached salmon on top of creamed spinach, mashed potatoes and topped with homemade curried potato chips. The food was delicious and fresh. James had chicken noodle udon soup and shrimp and grits (which he was unable to finish, meaning I had awesome leftovers for breakfast!). Highly recommend and encourage reservations. We went on a Sunday and the place was packed – and completely out of the way, so this is a gem off the beaten path with a reputation.


I could have spent days in Eataly.  My first trip was before a blow out appointment around the corner, and James and I rushed through the two floors of goodies – picking up gluten free pasta, torrone and polenta crisps. Our second trip (because how could we not go back?!) was for a light snack which turned into a mini meal before we went to Roister. The upstairs of Eataly is made up of many food stations. Some you can simply walk up to, sit at and order off of the various menus. Others you had to put your name in for a table. We sat down at the Il Pesce Le Verdure station and ordered the grilled octopus, a cheese plate and stracciatella – a pulled mozzarella with roasted butternut squash, grilled radicchio, apples and toasted walnuts. This was DIVINE.

Revival Food Hall

In search of a quick, but good lunch, James and I stopped by Revival Food Hall to check out their offerings. We ended up at Union Squared Pizza which produces Detroit style pizza. While not deep dish, this was extremely tasty and they had a gluten free version for me. I had artichokes and tomatoes and James had pepperoni.


Want to go to an overly hip coffee bar? Head to Sawada Coffee in Chicago (near the famous Girl and Goat and Little Goat). The cafe is a great little nook inside of a larger BBQ restaurant (the seating is open during the AM to coffee sippers, which makes for a sprawling crowd). James and I both had matcha green tea lattes (James had espresso in his unknowingly and was definitely wired after that). Great place to spend a morning, and I would definitely be a regular if it was in Boston.


We stayed at the Virgin Hotels in Chicago. This hotel is worth every single penny. The staff took excellent care of us, the bed was a knock out (we are even toying with purchasing the mattress for home it was that good!) and the best part? 24-hour check in and flexible (no fee) late checkout. Highly, highly recommend, and trust me, if you’re going to stay downtown, you’re going to pay a pretty penny, so you might as well spend a little more for a fantastic experience.


Architecture Boat Tour

While a bit on the pricey side, we decide to spring for an architecture tour along the river. For two hours we weaved through the city center, taking in the amazing buildings, learning some history and marveling over how quickly Chicago built up after it’s famed fired. We booked through the Chicago Architecture Foundation. You can find more info here.

Goose Island

Our friends got married at Goose Island – which was entirely fitting – but it also meant we got to go on an abbreviated tour of the brewery! James and I learned about the history, where the company makes its “funky” and “experimental” beers before testing them out on the crowds and got to wear some cool safety goggles. If you’re in town, and like beer (or even if you don’t), worth a visit.

Millennium Park 

Oh the bean! How I was so happy to see her in all her glory. And then never returned after my first visit. Be warned, you will fight crowds for the perfect (or not so perfect) picture, but this iconic landmark isn’t to be missed.

Field Museum

What an absolutely amazing, awe inspiring museum. James and I forgot our MOS card in Boston so had to pay entry – though I talked us down from $30 each to a bare bones of $22 each. With only a few hours, we opted not to do any of the traveling/special exhibitions. My favorite part of the entire museum was walking through a reconstructed Egyptian tomb – but then I am always partial to Egyptian artifacts. We wandered through the hall of evolution (also very cool) and gazed upon extremely old dinosaur fossils and bones. There was even a miniature exhibit about the weird fungus moss that grows on plants, metal, pretty much everything. You could easily spend a day here and wish we could have.

Sky Deck at Willis (formerly Sears) Tower

Want a sprawling massive view of Illinois and the Great Lakes? Head on up to the 103 floor of the Willis Tower. The Sky Deck provides you with 360 degree views of the city, and you will definitely spend most of your time there in line waiting to go up. But it was fun, and worth going if you have the time.