Gotham city meets deep dish. Ok ok, I know there’s more to Chicago than its architecture and pizza but those are definitely a couple of my favorite things about the windy city. I met up with a couple of friends from back home for a weekend in Chi Town – read on to see where we stayed, what we ate and sights to see here!
Where to Stay in Chicago
Stay at the brand new Hotel Zachary (just opened this spring), and wake up to amazing views of Wrigley Field! Enjoy a blend of classic & contemporary design with a cozy, distinctive boutique hotel feel. Hotel Zachary offers guests an authentic experience in one of the city’s most iconic neighborhoods – Lakeview, and there are plenty of great restaurants and nightlife nearby in Wrigleyville.
I couldn’t get over the view from our room. I mean how often do you get to fall asleep to & wake up right over a ballpark? I can only imagine how exciting this would be during a game. You could even see a bit of the field itself from our room.
Hotel Zachary was designed by its namesake – Wrigley Field architect Zachary Taylor Davis. It has a much cozier feel than a ballpark though, with subdued neutrals that create a comforting space (especially through Chicago’s long winters)!
The staff made us feel so welcomed from the second we stepped foot on the property – and these delicious bites from the West Town Bakery downstairs didn’t hurt one bit!
Curated pieces in each room include artwork from local Chicago artists and a framed replica of Davis’ original blueprint of Wrigley Field sketched in 1922. It’s inspiring to see the beginning outlines of such a massive project that’s now this massive iconic landmark almost 100 years later. After all, everything starts with just the spark of an idea which can launch into something big.
The lobby of Hotel Zachary is just as impressive as its guest rooms.
The lobby features the delicious West Town Bakery & Tap, as well as the swanky whiskey & grill Mordecai.
Customer service is incredible here as well. Everyone is super friendly and helpful, going above and beyond. From the chic, cozy boutique feel to the amazing views, location and great service, I can’t recommend Hotel Zachary enough!
What to Do: Weekend Chicago Activities
Visit the Bean, Millennium Park
The Bean is a fun art installation & photo opp which reflects the Chicago Skyline. First unveiled in Millennium Park in 2004, the Bean is now widely considered a symbol of Chicago. It’s officially named Cloud Gate, since 80% of its surface reflects the sky and it bends down on both sides into the shape of a gate. People flock here, so it’s best to get here early if you want to avoid the crowds! Shout out to the cleaners who come by up to 7 times a day to wipe away all the fingerprints and keep it looking polished.
Sky Deck at Sears Tower
See Chi Town from 103 stories up at the Sears Tower Sky Deck! You get 60 seconds for your party to take pictures in these glass balconies. I’d recommend going on a clear day, since visibility will be low otherwise. If it’s a nice day on the weekend then be sure to leave plenty of time as the lines can get long!
Take an Architecture Boat Tour
Chicago is known for it’s architecture. Take a boat tour on the Chicago River to learn about the many different phases of buildings this city went through. My favorite are the ones that remind me of Gotham City – older buildings with tons of little detailing, which you don’t see too often anymore.
We learned that the Civic Opera Building was made to look like a throne. Sadly it opened just before the Great Depression, so not as many folks were buying tickets to the opera anymore.
Fun fact: the building on the left was secretly made to look like a Champagne bottle during prohibition and is covered in a thin layer of gold on top.
Visit Wrigley Field
The Cubs fell just short of playoffs this season so we couldn’t see a game, but it’s worth a trip to see Wrigley Field or catch a game if you’re a baseball fan.
Play at a Replay
Replay is by far the best barcade (bar/arcade) I’ve been to. It’s a casual spot in Wrigleyville right near Lou Malnati’s pizza, and just a short Lyft ride from Hotel Zachary. All of the games are free, and there was an amazing DJ there too! We need more fun places like this.
Chicago Athletic Association
The Chicago Athletic Association is actually a luxury hotel near Millennium Park. It’s super luxe and swanky, with fun games like bocce ball, foosball, and shuffleboard. Head to Cindy’s rooftop bar in the hotel for great views of Millennium Park and the Bean.
Where To Eat in Chicago
Lou Malnati’s Deep Dish Pizza
Pizza joints in Chicago can divide friendships and cause massive rivalries. We went to Lou Malnati’s and it was delicious, but some people swear by Giordano’s so I want to try them out next time I’m in town.
Little Goat Diner
Girl and the Goat is one of the top restaurants in Chicago, so there can be a 2 hour wait for brunch. Pro tip: head to Little Goat Diner just next door and grab a seat at the bar. It’s first come, first served with the exact same incredible menu!
Some of the best fried chicken I’ve ever had, not to mention delicious french toast with a poached egg in the middle!
We stepped out of the fog to grab a pumpkin pie drink at Stan’s Donuts. They have a fun selection of drinks and donuts here, and it’s right near Millenium Park and the Bean so it’s super convenient.
Max’s Take Out
We got a “real” Chicago hot dog with all the fixings at Max’s Take Out just off of Millennium Park. It’s a small local joint with authentic delicious hot dogs.
Frontera Grill offers authentic Mexican food and has countless awards in the food world, from a James Beard for outstanding restaurant, to Michelin Bib Gourmand and Most Popular Chicago Restaurant by Zagat. Rick Bayless wanted to create a restaurant that felt just like his travels to Mexico. Apart from incredible ingredients, this translates to colorful Mexican folk art and mariachi music.
By the time we sat down for dinner, we were super tired from a long day walking around Chicago, but we could still appreciate how delicious and fresh the ingredients were. The ceviche was my favorite, definitely try it if you come here.
From the architecture, to the food and plenty of activities, Chicago is great for a fun weekend getaway!
Have you been to Chicago? What’s your favorite thing to do there?
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