My group of 5 blogger gals that travel together, Babes That Wander, recently went on our first trip to Chicago and had the best time in The Second City! I may have packed a ton in my luggage, but we only spent the weekend (Friday night through Monday afternoon) in the downtown area. During our few days there, we had a hell of a lot of good food from Chicago restaurants in a short amount of time. In between city sightseeing, I filled my belly and made lots of want-to-be expert judgments on the local sustenance. I created a FREE downloadable 3-day weekend Chicago Travel Itinerary. Here’s a list of must-try eateries around The Garden City (Chicago) that you won’t want to miss during your next girl’s trip!
Chicago Restaurants: Where to Brunch
Pilsen Yards a Chicago Restaurant
Although Pilsen Yards is open for breakfast, lunch, and dinner, I absolutely adored eating at the music-driven restaurant during brunch! With an outdoor patio and plenty of natural lighting coming in from the large windows, Pilsen Yards is aesthetic AF. They compliment the open-air ambiance with music; often, you’ll find a live DJ mixing music in the back room! The high-end and stylized Mexican food will fill you up and their yummy drinks will loosen you up. I recommend getting the Sweet Corn Tamales and either of the Ceviches with The Last Straw to drink!
Shore Club
Did you know that you can hit up the beach while in Chicago? There are 26 miles of scenic lakefront views near The Windy City and they’ll give you sand and water to keep your heart happy. Along the coast of Lake Michigan, you’ll find quite a few restaurants, including Shore Club! With the ultimate beachside service, tropical decor, and cute cabanas, it’s like being transported to any of the best beaches in the world. While I wouldn’t say that the food or drinks were the best of the places listed in this article, they were still really good and the tropic feel was very Miami meets Vegas meets Chicago. Perfect for a girl’s brunch! I recommend getting the Mykonos Board and the Wahoo Tacos, as well as a group club cocktail, for the table.
Must-Try Dinners at Chicago Restaurants
Lou Malnati’s a Chicago Restaurant
Locals will surely tell you that, “Lou Malnati’s is the best Chicago Deep Dish Pizza!” Trust me, I heard it from many of the Chi-Town natives when looking around for places to eat. Besides serving delicious, and authentic, deep dish-style pizza, their service is phenomenal. The servers never left my water running low, and even distributed the shared entree pizza to each plate. I’d say the ‘za here is more of a lasagna, but the crunch of the crust was perfection and not to be missed. Don’t worry if you miss out on this restaurant, as the deep dish pizzas can be delivered cross-country via Taste of Chicago! I recommend getting any of the deep dish pizzas paired with a Caesar salad to share for a group of 4-7.
Girl and the Goat a Chicago Restaurant
One of my favorite restaurant experiences while traveling to Chicago was at Girl and the Goat. This is best eaten family style, as each shareable entree is brought out as it is made. As we enjoyed the amiable lighting and tight seating, I noticed that every single dish had one unique flavor come through in taste. Every part of the meal was delicious and savory, and I know I’ll be checking out the Los Angeles location in the future! I recommend getting everything, but don’t sleep on the Blueberry Pickled-Pepper Corn Bread with Jam.
Sunda a Chicago Restaurant
Similar to the dining experience above, Sunda is also best appreciated via family style where everyone shares the dishes. This modern space is dark and sexy– perfect for a night out. You’ll leave full and happy from having their Southeast Asian inspired food. After eating at Sunda, I recommend getting the Crispy Brussels, Spicy Edamame, Lobster Waygu Roll, and Pork Adobo Rice for the table to share (3-5 people).
Chicago Restaurants and Bars: Places to Get Drinks
Three Dots and a Dash
If you’re looking for more of a party vibe within a bar, Three Dots and a Dash is the place to head for drinks! When you walk up, there is an alley full of outdoor seating, but you can also find yourself in one of the many dark rooms inside for libations. This place is is 21+ years old, so be sure to bring your ID! We found it hard to get a reservation online, but walked right in when we got to the front desk. You’ll find plenty of island and tropical themed liquid refreshments, and they know how to present! Three Dots and a Dash is great for a night out, but also offers private rooms and party options if you want to celebrate. My favorite drink was the Painkiller, but the Shotstapus was a blast for our group and would be fun for 5-10 people taking shots.
The Alderman
Sometimes, it’s essential to feel in on a secret! The Alderman is a bar within a bar located in Pilsen Yards. The cocktail bar doesn’t quite claim the ‘speakeasy’ title, but you’ll definitely get the same vibes when entering the intimate, 16-seat bar in Pilsen, Chicago. The cocktail menu is rotated every few months by the award-winning mixologist Lance, so you’ll be trying the best, and most trendy, drinks to be served in the Chicago area. Be sure to have your ID ready, as this is a drinks-only concept. Although the warm lighting and personal atmosphere is great for a private event, you can book 2-4 guests at at time to enjoy the mood.
Now that you’ve read all about my favorite eats during our girl’s weekend, which Chicago restaurant or bar will you hit up first?!
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This blogpost was sponsored in part by Choose Chicago. Lauryncakes sometimes receives compensation and/or hosted travel and sample products related to blog posts. This Chicago story may include affiliate links for which I receive a small commission at no extra cost to consumers. Be sure to check with businesses and locations regarding travel restrictions and safety precautions before visiting.
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