Chicago (April 2016)
This little 5-day trip to the Windy City was the “unofficial” start of our traveling adventures. It was also the trip where I discovered the need for detailed itineraries. I had researched places we wanted to see and things we wanted to do, but I armed myself with only a small list and two dinner reservations.
Day 1 began with a very early flight into Midway, and our first stop was Union Station to store our luggage in lockers. I’ll be honest, this part was a bit stressful, having never really been here before, but it worked out fine. Our next destination was Millennium Park to see the Bean. After taking a few pictures and what seems like the required selfie, we grabbed lunch and beers at Tavern at the Park.
Our Airbnb was ready after lunch, so we made a quick trip to get our luggage and then headed to the Old Town neighborhood. My husband researched where to stay and could not have picked a more perfect area for us. Old Town is very similar to our neighborhood in Nashville, and this instantly put us at ease. We settled into our studio apartment and, exhausted at this point, elected to walk around and explore the neighborhood a bit and grab dinner. We ate at Old Town Pour House – an excellent choice for two casual, drained tourists.
Day 2 started early with a run along the lakefront (you can’t beat those views!), and then we found Nookie’s, an adorable restaurant serving yummy comfort food. After a quick breakfast, we hopped on a train to Winnetka, IL, so that we could see the Home Alone house in person. I won’t disclose the address of the house because it is a private residence, but I can tell you that it wasn’t hard to find through Google and Pinterest.
I am a bit Christmas obsessed, so this became my favorite excursion of the trip. The train was charming (my first train ride!), and Winnetka was beautiful. The house was a very short walk from the train station, and the hubs and I were trying to be covert, although I’m guessing we were the exact opposite. We took a couple of quick pictures and hightailed it back to the station. My only regret is that the outing was a bit rushed, as we were trying to make the next train. We have already decided that, on the next trip, we will go back to Winnetka and spend some more time there. We noticed a lot of cute shops and restaurants on our way to the train station.
We grabbed lunch at Lou Malnati’s (our first Chicago deep dish experience!), and it definitely lived up the hype. After New York (of course!), it has been the best pizza I’ve ever had. We decided to walk back to our apartment rental with a slight detour for the Magnificent Mile. I have to admit that we did not stay long – it was just too crowded to enjoy it. Our dinner spot was a restaurant that I found while researching Chicago through Pinterest.
I absolutely loved RM Champagne Salon! The décor was amazing, and it was incredibly romantic. The drinks and food were fantastic. I will mention that the serving sizes are bit small. I was fine, but the hubs had to have a “second” dinner on the way home. The restaurant is nestled in a really cool area that we would have loved to explore more. The beer garden next door looked really fun!
Day 3 began with coffee and breakfast at Eva’s Café, a local coffee shop in the neighborhood. I love finding local spots on our travels! Up next was the Architectural Boat Tour. I had heard from several people that, if we don’t do anything else, we must do this boat tour. We were able to see all of the famous skyscrapers and architectural gems, and it was interesting to get the perspective from the Chicago River. I also found our tour guide to be extremely knowledgeable.
We strolled along the River Walk and grabbed some hot dogs for lunch (we had to get an authentic Chicago hot dog while we were here!) The afternoon was spent at the Field Museum and a walk through Lincoln Park (it was a beautiful, sunny day). We ate dinner at the Signature Room on the 95th floor of the John Hancock Tower. It was absolutely lovely, from the atmosphere to the drinks and the food. You can’t beat that view! My one regret is that I did not request a table by the window when we arrived. They warned me when I made the reservation that you have to ask when you get there, but I got nervous and didn’t. I will definitely remember this if we decide to eat there again.
Day 4 commenced with breakfast at Flo Restaurant, which became my favorite meal of the whole trip. Another great find through Pinterest research, I ordered the fruity pebble french toast and devoured it (so good)! Wrigleyville was next for an early afternoon baseball game between the Cubs and the White Sox. We grabbed beers at Casey Morans before the game. We got there just in time, too, as it quickly filled up.
I was so pumped to get to watch at game at Wrigley Field – it’s so historic. After the game ended, we watched kids go down to the field and run the bases. It was precious! When we got back to Old Town, we were exhausted, so we took it easy for our last dinner and went back to Lou Malnati’s. Yep, that’s right, one last deep dish pizza.
I completely fell in the love with Chicago on this trip – a perfect long weekend getaway!
-xoxo CD