Girls Trip to Chicago: a Complete Weekend Guide 

This girls trip to Chicago is in collaboration with Choose Chicago.

A few weeks ago, I got to take my first Babes That Wander trip to the Windy City, Chicago! Babes That Wander is a travel group a group of bloggers and I formed before the pandemic. As you have probably noticed, there has been a constant conversation about the lack of diversity in influencer trips and travel groups. It has been something that has been discussed by various bloggers/influencers and brands alike. Our group, Babes That Wander, is a group that has been founded to fill that void – aiming to show audiences that diversity is important and, through diversity, brands can reach a larger audience. 

After a year of being a group, we finally met up in Chicago for a girl’s trip. Y’all we had the best time! We did a lot of walking, saw so much and ate some amazing food. I’m excited to share all we did in Chicago below!

Girls Trip to Chicago: a Complete Weekend Guide 

Where to Stay

21c Museum Hotel

A hotel AND a museum?! That’s exactly what you get at 21c! 21c Museum Hotel is one of the newest hotels in River North and a must-visit destination if you’re visiting the Windy City. This hotel was so close to the Magnificent Mile (where all the good shopping is) and was the coolest hotel. The first two floors are a contemporary art museum that is free to the public. Who doesn’t want to sleep in a contemporary art museum? It’s such a unique concept and unlike any hotel, I’ve ever stayed at. 21c just announced some new hotel packages that are perfect for your next getaway! They include the Unlock Chicago Package, Art Lovers Package, Pet Package, Girls Getaway Package, and Love is Love Package. There’s something for everyone!

What to Do

See the Chicago Theatre Sign at Night

We did this on our first night in town and the sign was an easy 15-minute walk from our hotel. We split up duties among the group. One person watched the purses and equipment, another kept an eye on traffic, one did video b-roll and the other two were shooting/posing. We all got amazing shots here and as soon as we were done the lights shut off. Talk about perfect timing!

The Bean at Millennium Park

No matter how many times you go to Chicago, you have to visit the bean. It’s right next to Lurie Gardens and the Art Institute but we made a special trip there at 7:30 a.m. If you want an epic shot with as few people as possible, get there as early as you can! Luckily, I roomed with Iesha who is a morning person so she motivated me to get up most mornings for a good shot. Once 8 a.m. hits, it starts getting crazy crowded!

Chicago Greeter Tour

Have you ever heard of Pilsen in Chicago? I hadn’t either until this trip! Pilsen is a neighborhood in the Lower West Side of Chicago. This neighborhood is rich in Latino culture and is full of art, music, nightlife, and culinary tradition! In Pilsen, bold murals have blossomed all over the community and in the front of homes, railway overpasses, and train platforms. You can also find colorful collections at the National Museum of Mexican Art.

For over 150 years, Pilsen has been a port of entry for immigrants. Now blended in the close-knit Mexican-American community are creative types and students. You’ll also find vintage shops, coffee houses, and quaint cafes. We also found some amazing authentic Mexican food! You can’t help but feel inspired when you’re walking around Pilsen.

The FREE Chicago Greeter tour was led by expert local, Sherry Wolf, who guided us through Pilsen. These tours can also guide you through other areas of Chicago. Sherry shared all about Pilsen’s history, diverse cultural traditions, iconic landmarks, and off-the-beaten-path gems.

Tours can range from two to four hours and are conducted in over a dozen languages. Your guide can even customize your tour to focus on architecture, foodie culture, LGBTQ+, family fun, and more.

Chicago’s Architecture Foundation Center River Cruise Aboard Chicago’s First Lady

One of my absolute FAVORITE things to do in Chicago is an architecture cruise. We almost got rained out of our First Lady Cruise, but the babes weren’t going to let a little rain stop our fun! A boat cruise is the best way to experience Chicago. Whether you’re alone, with family, or on a date, anyone will take new knowledge out of the cruise.

Trip Advisor’s user reviews rated this as the #1 tour in the city and is the only cruise partnered with the Chicago Architecture Foundation. The docents are highly trained and provide a detailed narrative of Chicago’s architectural styles and the stories of the people who built and designed Chicago. The cruise is 90-minutes and has indoor/outdoor seating, a full-service bar, and is loads of fun!

Art Institute

You can’t visit Chicago and not go to the Art Institute. It’s one of the top-rated museums in the world and home to the greatest collection of Impressionist paintings outside of Paris. We saw works by Monet, Renoir, Seurat, and Van Gogh. But what we were most excited to see were the Obama Portraits. They had a whole exhibit on Kehinde Wiley’s painting of President Barack Obama and Amy Sherald’s portrait of former First Lady Michelle Obama. It was so incredible seeing these in person and loved how different they are from other Presidential portraits.

Another exhibit I loved was Bisa Butler’s textile portraits. The artist uses textiles to interrogate the historical marginalization of her subjects while using scale and subtle detail to convey her subjects’ complex individuality. Her pieces were so powerful and I loved learning about the artist herself!

Lurie Garden

Right next to Millennium Park is an urban oasis, Lurie Garden. The garden’s design pays homage to Chicago’s transformation from flat marshland to an innovative green city. It’s such a fun and unexpected surprise and it feels like a secret little spot in the city. It’s pretty magical and a must-see in person!

Sky Deck

After completing an extensive redevelopment, Skydeck Chicago reopened to the public in April 2021. The revamped Skydeck Chicago provides a can’t-miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The complete transformation encompasses the attraction’s lower level, delivering an interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago. The lower-level museum is further complemented by a visit to the internationally recognized observation deck to take in the city from 103 floors up and step out on The Ledge; the four thrilling glass floor balconies extending from the Tower.

Once you get to the tower, we split into two groups to get our photos out on the ledge. You have about 30 seconds to get the perfect photo (they time you) so if you want an epic shot for Instagram, research poses beforehand and have your camera settings ready!

Also, make sure you book your tickets in advance!

Where to Eat

Three Dots and a Dash

Who doesn’t want to go to a fun tiki bar on a girl’s trip?! When Iesha and I landed, we were researching fun places to go and see. We saw this on Instagram and were dying to go and see it for ourselves! So we grabbed Lauryn and headed over for a quick drink. This was the cutest tiki bar with indoor and outdoor seating and the cutest cocktails. Definitely make a reservation beforehand, but we loved every second we spent at Three Dots and a Dash!

Lou Malnati’s

You can’t go to Chicago and not get some deep-dish pizza! Considered the oldest family name in Chicago pizza, Lou Malnati’s is as rich in history as its pizza is in flavor. Every Lou Malnati’s pizza is handmade from scratch using the finest and freshest ingredients. Every year, the Malnati team hand selects California vine-ripened tomatoes for the perfect sweet and tangy taste. The fresh mozzarella cheese comes from the same small dairy that has supplied Lou Malnati’s for over 40 years. And their family’s secret recipe for flaky, buttery crust has been passed down from generation to generation. You’ll know with every bite that each pizza was made with care and special attention.

We split a pizza and did a half and half. It was divine. We inhaled every crumb and loved every minute of it!

Also, the service we got there was top tier, we were so spoiled by our waitress!

Venteux

As I said earlier, we went to Millennium Park early to get some good shots at the bean. Well, this girl needs coffee to function so we hit up Venteux when we were done. They were packed out but we managed to snag a table outside. The interior was so chic and modern with palm print wallpaper and high ceilings. I also loved the latte art that came with my caffeine fix. Definitely stop by for some coffee and good conversation.

Pilsen Yards

I talked earlier about our walking tour of Pilsen and how cool the neighborhood was. While you’re there stop at Pilsen Yards. Pilsen Yards is a bar-centric and music-driven hangout in the heart of Pilsen with an open-air vibe and plenty of room to spread out safely and comfortably. Executive Chef Armando Gonzalez’s has created a menu of inspired Latin street food, from tacos to ceviches, and hummus to carne asada, Each dish is plated up next to mezcal, tequila, and whiskey charged bar program from beverage director Lance Bowman, and it’s all on the cheap.

We had the best meal there and they were also kind enough to show us their speakeasy bar, The Alderman. The Alderman is a small bar inside Pilsen Yards with some very classy and sophisticated cocktails. It’s the perfect spot for a first date, special occasion or girl’s night out. Make sure you make a reservation! Also, if you see Paul one of the owners, tell him the babes say hi!

Girl & the Goat

One of the meals we were most excited about was the Girl & the Goat. As one of the first restaurants on Chicago’s famed Restaurant Row in the West Loop, Stephanie Izard’s Girl The Goat began in 2010 with a goal of serving bold, global flavors to the local community and guests. Since then, their desire is to treat guests like family and has remained the same. The plates are all family styled and I think we ordered 8 different dishes to share! Definitely recommend putting this at the top of your Chicago dining list. Try the sourdough bread, green beans and chicken thighs.

Shore Club Chicago

Want to get out of the city and just be at the beach? Well, Shore Club does just that while still being in the city! Shore Club Chicago offers an experience rivaling those on the best beaches around the world. World-class food, great service, and entertainment. Shore Club is an extension of the community in Lincoln Park and The Gold Coast offering an upscale dining experience with unparalleled views of Lake Michigan.

We started with some Frosé, worked up to a cheese board, and then enjoyed our meal. The vibe was so fun and playful. I felt like I was in Miami and about to hit the beach! Sit inside for a break from the heat or rent an outside cabana with friends and go jump in the lake when you need to cool down. It’s fun all around!

Sunda

Our last meal of the trip was at Sunda! By seamlessly melding most of the cooking techniques and flavors found throughout Asia, Sunda creates a menu that allows customers to choose the dining experience they desire. This was another restaurant that was family style and we dined on dishes like sushi, edamame, chicken and yummy cocktails. Again, another great spot for a date night with a special someone!

All in all, we had an AMAZING first Babes That Wander Trip. I can’t wait to see where we’re headed next. Have you ever done a girls trip to Chicago? Tell us where we should go for our next trip below!

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