The Lady Boss' Guide to Chicago

Chicago is one of the best cities for self-employed individuals and entrepreneurs. Going off on my own almost four years ago now, I’ve had the chance to get to know the city in a different way. It became my office playground like many other people who are in similar career paths and work environments. I’ve explored different neighborhoods and found a few favorite spots to return to and a few spots that are better for casual coffees with friends. For a productive day “out of the office,” I learned quick that cafes and coffee shops with a strong internet connection are vital. It’s also a perk if they offer real food and not just snacks or pastries as well as plenty of outlets. To meet with colleagues or clients, it’s important to find spots with a lower noise level or at least moderate so you can have a conversation without screaming. Some of the best spots are tucked away in the neighborhoods of Chicago and others are right in the heart of downtown. All it takes is a little exploration to find the right ones!

Where to Work Remote
DOWNTOWN: Two Zero Three at the Virgin Hotel. This particular coffee shop has made an appearance around these parts quite a few times. It seems surprising that one of the best spots to get work done would actually be within a hotel but hear me out. For starters, Two Zero Three is located on Lake and Wabash, primo location in the Loop near Michigan Avenue, State Street, commuter trains and public transportation. Second, they serve up a mean espresso and coffee. The environment is super chill with an eclectic mix of seating and tables, all comfortable might I add. There’s ample space to find a spot but it’s popular so don’t be surprised if it’s packed. They have a bunch of records on vinyl that they’ll play and there are snacks along with real food in case you get hungry. Two Zero Three is one of, if not my favorite coffee shop in the downtown area.

Cappuccino at Two Zero Three

View of the Patio at Colectivo

NEIGHBORHOOD: One of my newly discovered gems, Colectivo Coffee in Lincoln Park is one of the most unique coffee shops I’ve discovered. Located on Clark and Deming, Coletivo is a simple bus ride away or a brief walk from the red and brown lines. Here’s why I love it. This particular location is 90% outdoors all year round. The seating area is made out of an outdoor patio that is sheltered by a roof so you can work rain or shine. Once the weather gets too cold, about half of the patio is enclosed and heated while the other half is warmed by fire pits. It’s the perfect spot to get work done when you’re feeling low on inspiration because Colectivo makes you feel like you’re on vacation. A downside...the outlets are kind of spread out and not the best as far as accessibility goes. It’s also a local favorite so don’t be surprised if gets full up.

Where to Meet Clients + Colleagues
DOWNTOWN: Le Pain Quotidien Magnificent Mile. I’m not typically one for chains but Le Pain Quotidien won a special place in my heart when I couldn’t find a decent internet connection anywhere in Washington DC. Besides a trusty wifi signal, Le Pain Quotidien has feel-good European bistro-style food without the guilt. The location on Michigan Avenue has plenty of space that extends towards the back making it perfect if you need a little extra privacy. It doesn’t get busier during peak times but the staff is accommodating, patient, and efficient. For more intimate meetings, grab a table for two in a sunny corner. For work sessions, ask for a spot at one of the long tables. Make sure you grab an omelet or one of their delightful tartines. I can never visit Le Pain Quotidien without having their bread!

NEIGHBORHOOD: The Allis at Soho House is another one of my favorite places in the city. Sophisticated, casual, elegant, and welcoming, The Allis is a million things all in one. Located in the West Loop on Green St. and Randolph, it’s not a bad location by any means but more accessible to anyone coming from downtown or the west. I like The Allis for meetings because it doesn’t get very noisy during the day and there’s plenty of space to choose from for privacy. The service is top notch and polite and the menu has something for everyone. It’s part restaurant, part coffee shop so get some work done before or after your meeting and impress your colleague or client for lunch or breakfast.

Latte at the Allis

Grilled Cheese & Tomato Soup at the Allis

Where to Grab a Quick Lunch
DOWNTOWN: Goddess & the Baker is one of the best local sandwich chains. An extension of Goddess & the Grocer which began in Wicker Park, Goddess & the Baker on Wabash between Monroe and Madison has the best sandwiches, salads and breakfast that can be enjoyed at the restaurant or on-the-go. It’s great quality food for not a terrible price. They also serve up a full coffee and espresso menu as well as tea and other drinks. I love seeing what they have in-season. Their specialty menu tends to change on a monthly basis it seems. For example, you can try a Maple Sage Latte at the moment! I’ve had quite a few of the items on their menu but I’m partial to the Santa Monica Turkey and Chicken Club. Avocado is my weakness!

NEIGHBORHOOD: Located in Union Station just outside of downtown in the West Loop is the Chicago French Market. This market has everything you could possibly want for a grab-and-go lunch from sushi to barbecue to poke bowls and crepes. It can get a little crowded during peak hours but is completely worth at least one visit in your lifetime. From soups to sandwiches, lobster rolls to pierogi, the Chicago French Market celebrates a variety of different cultures. Everyone can find something to eat here, even the pickiest of eaters. I love to grab something that won’t leave me feeling overly stuffed to save room for gelato or macarons. When in a French market, always save room for macarons!

The Chicken Club at Goddess & the Baker

Where to Have Lunch Unrushed
DOWNTOWN: Atwood at The Alise Chicago. With a prime location at Washington and State, Atwood has floor to ceiling windows on the State and Washington sides of the restaurant and an upscale yet casual dining experience. The restaurant serves seasonal American fare with a twist. For example, you won’t get grilled cheese. You’ll get grilled cheese made with smoked gouda, cheddar, and tomato jam. They have an exceptional cocktail and drink menu as well in case you want to enhance your lunch with an afternoon libation. Atwood is a place where you feel comfortable with a group or by yourself. And since it’s located within The Alise Chicago, you’ll be dining solo among others who are visiting on their own as well.

NEIGHBORHOOD: One of Chicago’s favorite chicken spots, Honey Butter Fried Chicken has become a local favorite and for good reason too. The counter-service restaurant serves its famous fried chicken with a side of homemade honey butter, only the best thing you will ever taste...EVER. Get a classic basket of fried chicken with a side of corn muffins or the Honey Butter Fried Chicken Sandwich. This chicken and that honey butter haunts my dreams! Honey Butter Fried Chicken is located on Elston in the Avondale neighborhood (way north) so it can be a hike for some...myself included. But it is 100% worth it. There are alot of wonderful things to say about their menu and I can sit here all day but you don’t have hours to read what I have to say. And let’s be honest, you’d rather try the chicken then listen to me talk about it. So next time you’re in the Avondale area, stop by and grab yourself what’s sure to be some of the best chicken you’ll ever eat.

Where to Unwind (aka, Happy Hour)
DOWNTOWN: Pinstripes in River North is one of the more unique, versatile experiences I’ve had downtown. Located on Illinois closer towards Navy Pier, Pinstripes is a unique concept featuring a full restaurant, bar and patio as well as bowling and bocce ball. The River North location has a gorgeous, expansive patio along the river where you can take advantage of happy hour specials Monday through Friday and good ones too! They offer $5 house wine and tap beer or $6 well drinks. Their menu includes a variety of pizzas and flatbreads, sliders and more. What’s better is that they offer gluten-free options which is one of the reasons a friend and I chose this restaurant before seeing A Simple Favor a few weeks ago. We ordered the Pepperoni Pizza with a gluten-free crust (there is a surcharge for gluten-free), and I couldn’t resist the Hummus and Avocado platter. Everything was very tasty.

The Hummus & Avocado Platter at Pinstripes

The Gluten-Free Pepperoni Pizza at Pinstripes

NEIGHBORHOOD: This one is a tie between two fantastic Lincoln Park restaurants: Cafe Ba Ba Reeba and Stella Barra. Both exceptional for their own reasons, I couldn’t choose because each restaurant has amazing food and drinks plus unbeatable happy hour specials. Cafe Ba Ba Reeba has bite-size tapas starting at just $1 and Stella Barra serves pizza by the slice for $2.95. With happy hour menus that could easily turn into a light dinner, you can't go wrong with either of these spots. Both of their happy hours are Monday through Friday from 4-6PM. If you ask me, hit them both up. Head to one for the 4PM hour and the other for the 5PM hour and get the best of both worlds. They’re literally less than a block apart on Halsted Street. You only live once, right?