Windy City Weekend: 3 days in Chicago

We enjoyed a long, chilly weekend in Chicago in late March 2022. It was a little longer trip from Southwest Missouri, but still a relatively easy drive for a quick getaway. Here’s what we did on our 3-day trip:

Thursday:

We arrived on a rainy afternoon, and decided our first stop would be a visit to Wild Blossom Meadery & Winery. This urban winery is located about 40 minutes outside Chicago and and offered unique options.

Meads are similar to wine, but are fermented with honey instead of grapes. They can range from dry to sweet, and Wild Blossom seemed to have a good variety for everyone. They are open 7 days a week and it makes for a great place to unwind from the hustle and bustle of the city. On Saturdays, they even hold

their own winemaking classes. As wine enthusiasts, we would have loved to attend if we had the opportunity.

Afterwards, we drove to our hotel in Countryside, IL. This was about a 30 minute drive to most attractions in the city, but suited our budget. The rates were much cheaper, plus we didn't have to pay an additional daily parking fee like we would have with many downtown accommodations. We always prefer driving ourselves when possible too, so we can come and go as we please.

Friday:

We ventured into the city to check out all the touristy sights. We walked from Milennium Park to the end of the Navy Pier, to Michigan Ave Shopping, and ended at SkyDeck. We endured many miles to avoid paying for parking at multiple locations - using the SpotHero app was a lifesaver in trying to find the best parking deal in the most mid-center location. Even though our feet were so tired, it ended up being so much fun taking in all city vibes & cool architecture.

We made SkyDeck reservations closer to evening so we had time to enjoy all the Chicago highlights beforehand. The reservations were a little pricey, but offered beautiful city skyline views. The tour

was self paced and lasted around 45 minutes. It started with a brief walkthrough of Chicago history before heading to the 103rd floor. At the final destination, each group got to spend about 1-2 minutes on "the Ledge." This glass box jets out a couple feet from the building and is about 1,400 feet off the ground. Standing in the box was more terrifying than I expected, but it's incredibly instagrammable.

You can spend the rest of the time peering out the large window panes on the main floor or browsing the small gift shop. Reservations are strongly recommended and weekend spots sell out quickly. Luckily the tours are offered multiple times throughout both day & night.

Saturday:

We ate lunch with one of Hunter’s friends from college at an eccentric cafe called Cabra, and then headed outside the main downtown area for a brewery tour.

Revolution Brewing is Illinois' largest craft brewery and distributes mostly to the surrounding Great Lake states and a few places on the east coast. The 45 minute tour included a guided walkthrough of the facility & insight into their production, a beer to enjoy during the tour & a beer tasting. We also received a souvenir beer glass at the end. Space is limited to small groups and reservations can be made in advance online.

We ended our trip with saving the best for last: trying deep dish pizza at Giordano’s. This fast casual chain has many locations around Chicago and was reasonably priced for deep dish. Chicago-style pizza is super filling, so make sure to accurately follow the portion guidelines (we made that mistake and ordered way too much). We loved our time in the Windy City and feel there is so much to enjoy year round!

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