What started as a sandbar in Lake Michigan more than a century ago, Streeterville has exploded in growth in recent decades to become one of the most special and vibrant neighborhoods in the country. It is nestled in the heart of downtown Chicago, with proximity to plenty of the city’s best offerings. Its boundaries are somewhat disputed, but the most accepted are Michigan Avenue to the west, the Chicago River to the south, and Lake Shore Drive to the north and east.

Streeterville Est. 1926 / Courtesy of Building Chicago

Some of my friends wondered why I would ever want to live downtown. After a few years in Streeterville, I can say that moving here is one of the best decisions I’ve made. I love the character and history of the neighborhood, along with the beautiful design and architecture, delicious food, great nightlife, and friendly neighbors. It’s a great place to live, work, and play. There is always plenty going on here, but amidst the busy nature of downtown and the tall buildings, it feels like a little oasis. When I’m not taking photos, I work full-time in The Loop. Going from Streeterville to The Loop is such an easy commute, whether it’s by bus, a short walk, or an even quicker bike ride.

Enjoy the View

Photo by Michael Kirchner

The Lakefront Trail is just steps away from work or home in Streeterville, consisting of 18 miles of premium paved trail access right along the lake for walking, running, and cycling. The trail is just beginning a massive renovation to include separate lanes for cyclists and pedestrians. I’ve had great rides with friends up to and beyond Evanston at the northern end of the trail, and down to Indiana at the southern end.

Some of the best trips you can make on the trail are with a group of friends to go hang out for the day at nearby Ohio Street Beach, or a little farther for Oak Street Beach or North Avenue Beach. 

Photo by Michael Kirchner

Navy Pier is the most well-known attraction in Streeterville. It’s an incredible place and is one of Chicago’s largest tourist attractions, bringing in people from all over the world. Best recognized by the famous Ferris wheel, there’s plenty of shopping, restaurants, and things to do. However, my favorite thing is just walking down to the end of the pier for one of the best views in the city. 

If you’re looking for a more artistic view, don’t forget to stop at the Museum of Contemporary Art. This is one of the biggest contemporary art museums in the world, boasting a substantial permanent collection, as well as hosting many famous exhibitions. While The Art Institute of Chicago gets most of the attention, this museum is absolutely worth a visit.

Food and Drink

Photo by Michael Kirchner

Dollop is my go-to coffee shop in the neighborhood. It’s a nice little place in the heart of the neighborhood with a great environment to get some work done, chat with friends, or enjoy some Metropolis coffee. Go for the coffee, but don’t forget to give some of their sandwiches a try.

The neighborhood has no shortage of great places to eat and drink. If you’re looking for brunch, my favorites are Beatrix and Kanela Breakfast Club. Hit up Copper Fox when the mood strikes for an upscale gastropub with great food and ambiance. I highly recommend GreenRiver on the top floor of the Northwestern Medicine building for a rooftop dinner overlooking the neighborhood. 

If you’re looking for drinks with an Instagrammable view, it’s hard to beat the rooftop lounges at Streeterville Social in the Loews Hotel or the Signature Lounge at the 96th, located at the top of perhaps the neighborhood’s most famous building, the John Hancock Center.

Surrounding Area

Photo by Michael Kirchner

Streeterville boasts some of the best shopping anywhere in the country. Michigan Avenue is one of the biggest names in retail circles, with a steady stream of thousands of people perusing the shops along the street every day.  

Start on the southern end of Michigan at the river and check out the recently opened Apple Store, modeled as a glass box that looks similar to the one found near Central Park in Manhattan. Even if you’re not shopping for a new phone or computer, it’s a marvel. Head up Michigan Avenue and you will find everything from big flagship stores for brands like Nike, Under Armour, Top Shop, The North Face, and Uniqlo to luxury stores like Burberry, Chanel, Gucci, and Cartier. Finish off your shopping trip by heading inside for a more traditional mall. Water Tower Place is right off of Michigan Avenue and, with over 100 stores, it has anything a serious shopping trip would need.


Michael Kirchner is a quantitative trader at a high-frequency trading firm in Chicago. When not solving problems, he is exploring and taking photos, which you can see here as well as on his Instagram.