Winter Weekend In Chicago
This past weekend, my boyfriend, Jesse, and I took our third trip to Chicago together. Our past two visits were summer road trips, whereas this one was a winter work trip for Jesse. We weren’t exactly sure what to expect going into it this time of year, but we had a great time nonetheless. Our long weekend was filled with food, drinks, shopping, snow, and friends. We quickly realized that most of our trip consisted of trying out new restaurants and cocktail bars rather than outdoor activities thanks to the cold and snowy weather. There is so much to see and do in Chicago and we fit as much as we could into our 3 night trip. Here is a daily itinerary of our fun and food filled weekend.
Day 1
Dinner at Quartino Ristorante
We got to our hotel a little after 5 on our first day thanks to traffic. After a long travel day, we worked up quite the appetite and made reservations at Quartino Ristorante. The atmosphere here was romantic and dark, but a little loud. To start we got a ½ liter of Pinot Grigio and bruschetta. The menu was huge so it wasn’t easy to decide what to get. We decided to split the Bolognese (made in-house) and Tuscan sausage risotto...filling but delicious.
Starbucks Reserve Roastery
This is the largest Starbucks in the world that just opened at the end of last year. It consists of 5 floors with a different bar on the first 4 levels and a rooftop terrace. In the heart of the roastery is a 56 foot cask that you can see from each level transferring coffee beans. This is definitely a must see while in Chicago.
Day 2
Brunch at Wildberry Pancakes
On our last visit to Chicago we tried to go here because we had heard how good it was but couldn’t get seated for brunch because there was a 2 hour wait, (luckily now you can get on the Yelp waitlist). We split strawberry almond French toast and an omelette for the perfect sweet and savory combo! I would definitely recommend this spot for a nice filling brunch.
Shopping along the Magnificent Mile
There are many stores to shop along the Magnificent Mile while also getting some steps in. It was nice to get out of the snow for a bit and dry off by exploring some of the indoor malls along the street. Nordstrom, Under Armour, Zara, and Gap just to name a few.
Experience Eataly
One of my favorite things to do while in Chicago is visit Eataly. Their bags say “Took a quick trip to Italy” which is an accurate way to describe it. There is so much to look at and I could easily spend hours here and still not experience everything. Two restaurants, a pasta bar, a bread counter, a wine bar, a gelato bar, a cannoli counter, a cooking school, and many amazing kitchen gadgets and specialty foods all make up Eataly. I bought a cookbook and sipped a glass of wine while flipping through it. We came back a second time for lunch and split a bottle of Rosè and a charcuterie/cheese board that was deliciously authentic.
Work Party at the Hilton
Since we were here for Jesse’s work, we had a work dinner event at the Hilton with food, drinks, and music. The Hilton Chicago building has been around since 1927 and apparently cost 30 million dollars to build. The interior is very historic and beautiful. I can imagine how nice the rooms were and the view for the rooms facing Grant Park and the Buckingham Fountain.
Drinks and Music at Howl at the Moon
Howl at the Moon is a piano bar with a very loud but fun crowd. There was a $5 cover charge on a Thursday night which wasn't too bad. The popular songs and good band were the reason it was so crowded. This is a good spot for fun nightlife.
Day 3
Breakfast at Goddess and the Baker
Such a cute spot for breakfast! There are three different locations and luckily one was right next door to our hotel so I spent a morning here. The interior was very stylish and upbeat. They only take credit card and will bring your food and drinks right to your table. The coffee, bagel with cream cheese, and lemon poppy seed loaf were all delicious. Sad I didn’t discover this place until the second to last day!
Explore Millenium Park
Millenium Park looks a lot different in the Winter, but still a nice area to walk around. Since this was our first trip to Chicago during the winter we wanted to take advantage of it and do something different. What better touristy winter activity to do than ice skate in front of the bean? Unfortunately, we didn’t have the best weather and it was either raining, snowing, or very foggy each day of our trip so we didn't end up skating but it looked like so much fun. It is free to skate but skate rentals were $15 for adults on the weekends.
Drinks at Point & Feather
Point & Feather was actually our second choice for drinks after being told the wait was over an hour at another cocktail bar but we were very happy it worked out that way. A little loud as expected, but the service was great! We met up with an old friend from high school and it was the perfect ambience for cocktails. The bar was lined with bookshelves and had multiple dart boards that groups were playing.
Dinner at Lou Malnati’s
We will never come to Chicago again without getting Lou Malnati’s pizza! It is by far our favorite deep dish pizza in Illinois, (I would say best pizza ever but it is tied with Regina’s Pizzeria in Boston). They have perfected pizza which is why they have locations all over Illinois.