a beautiful lady walking on the streets of chicago city with her colourful glasses

When you research a trip to Chicago, the Magnificent Mile and Streeterville neighborhoods may pop up as some of the more tourist-saturated areas in the city. But what you may not know is that it’s chock-full of hidden gem restaurants and bars that locals love. One of the many great things about the City of Chicago is its perfect mix of new and old; in the architecture, the cuisine, and the attitudes and ideals of the locals. This neighborhood is the perfect example of this mix, which means that there truly is a little something for everyone to enjoy here. 

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The Magnificent Mile and Streeterville are at the center of the action in Chicago and are easily accessible by public transport (the red line and numerous buses) and by the Water Taxi that moves along the Chicago River. As the neighborhood technically begins just north of the river, this is a great place to start. The Magnificent Mile itself runs from the river to Oak Street, with Streeterville running east of Michigan Avenue to Lake Michigan.

To get a feel for the neighborhood, and the city for that matter, would be an Architectural Boat Tour. Most boats are parked along the Riverwalk, where you can just buy your tickets and hop on the next departing vessel. Some tours (The Chicago First Lady’s) are even guided by a representative of the Chicago Architecture Foundation, whose passion for the beautiful buildings is 100% contagious. 

Whether or not you choose to partake in a cruise, the Riverwalk is still a great place to take in the skyline and have a drink or a bite to eat. Lined with restaurants and bars with al fresco dining, you can sit, sip and watch the yachts pass through.

An important thing to remember when exploring the Magnificent Mile and Streeterville neighborhood is that, despite evidence to the contrary, Michigan Avenue, is not the place to be. While there are many, many stores and restaurants on the main drag Avenue, you would be hard-pressed to find anything that was not a chain. It is a great place to be if what you were really looking for is a mall, but not for anything unique. The real noteworthy establishments are just beyond Michigan Avenue, in either direction. 

There are of course exceptions, the most important of which would be Purple Pig. This wonderful restaurant is nestled into the back of a building just off the beginning of the Magnificent Mile. They are well known for their charcuterie, cheeses, and creative small plates, not to mention a fantastic wine list. If you head down the stairs and head west from the restaurant, you’ll run right into After-Words, an amazing independent book store with an excellent selection of new and used books. It’s a bibliophiles dream!

Another gem that’s hidden in plain sight on Michigan Avenue is the Lookingglass Theatre, located right across from the iconic old Water Tower. It’s a small theater, but their production is spectacular.  You can catch an original play or an old favorite, depending on what’s on their calendar for the year. Just behind the Lookingglass Theatre is the Museum of Contemporary Art - one of the best museums in Chicago - which is saying a lot for a city with 30 or more museums. It always has an amazing and unique main exhibit which is thoroughly advertised throughout the city.    

If you’re looking for somewhere to enjoy the lakefront, cut further east through Streeterville to Ohio Street Beach. Those who head there from anywhere on Michigan Avenue are bound to pass by a fantastic coffee shop by the name of Dollop. This Chicago-area small chain is renowned for its delicious espresso drinks and has a wonderful selection of pastries to satiate your sweet tooth. 

The area you are now walking through is interesting because it contains lots of apartment buildings. This means that on your way to the beach, you will pass dry cleaners, gyms, small grocery stores and pet shops.  There is an underpass that will take you beneath Lake Shore Drive and directly onto the lakefront path. 

If you felt so inclined, you could walk for miles in either direction, or you could continue forward to the beach. On any given day, boats will be anchored beyond the shores here and there will be a good amount of people laying out. It’s not as popular as say, Oak Street or North Avenue Beach, but this is Chicago and the summer heat is brutal. Dip your toes into the Lake and find an open place on the sand to enjoy the view.

Once it gets later in the day, the crowds surrounding Michigan Avenue dwindle just a little as people file into restaurants and bars in the area.  There are obviously many options here, but some of the best ones are located atop hotels, stores or even hospitals. GreenRiver Chicago is located on the 18th floor of one of the buildings that make up Northwestern Hospital. The view from their cozy patio is spectacular and should be caught just as the sun sets. Their cocktails are delicious and they offer a small bites menu outside and a full dinner menu of American fare inside the restaurant. 

Down the street, atop the Hotel Raffaello is Drum Bar, another fantastic rooftop bar, and possibly the best in this area. The view from the roof is beautiful and the handcrafted cocktails are delightful. Rain or shine, this bar has a sophisticated atmosphere for a romantic date night or a night out with friends. 

For something a little grittier, check out Streeter’s Tavern, which is on the west side of Michigan Avenue, set a couple of blocks inward. This basement bar has a ton activities like beer pong, foosball, and giant Jenga. You can’t beat the prices and the DJ usually plays some great 90’s jams. If you’re looking for a real local experience, have a few Old Styles, a shot of Malort here and then grab a Chicago-style thin crust pizza at Pizano’s around the corner. Its cozy atmosphere and kind staff make ordering a pizza and a beer feel like coming home. Try the Rudy Special pizza - it’ll change your life.

For something entirely different but on the same side of Michigan Avenue, Le Colonial features an amazing Vietnamese menu with a French twist. Their beautiful décor and excellent service are perfect for a fancy night out. That’s one of the amazing things about this area - you can find fine dining across the street from dive bars and hot dog stands.