• Chicago skyline

Getting to Know Chicago’s Neighborhoods

When I moved to Chicago in August 2012, I heard it everywhere: “Nothing beats a Chicago summer!” It was 85 degrees, and sunshine practically swept people into the streets and parks, and onto the beach. The energy was electrifying. Smiles enveloped every face I biked past.

Then, four months later, when Winter’s cold heart exposed itself, I realized, yes, that claim was true! Nothing beats a Chicago summer…when compared to its winter!

So, in celebration for all that locals consider great about the Windy City, let’s consider a warm-month visit and soak it all up!

Chicago is split into neighborhoods that bleed one into the other. Each has its own feel–it’s undeniable. We’re going to hop around some of the most popular, which includes some of my favorites, and tour the town together.

Where to Stay

There are hundreds of hotels from which to choose in Chicago. And it’s all about personal preference. Some love the glamour of Michigan Avenue, some prefer the neighborhood charm of Old Town. Here are a few suggestions:

  1. Chicago Athletic Hotel — off Michigan Avenue across from Millennium/Grant Park. Boasts a renovated, Titanic-like decor.
  2. Hotel Lincoln — off Clark Street, across from the park, just on the border of Lincoln Park and Old Town. Great rooftop bar overlooking the lake and park.
  3. The Drake Hotel — off the Magnificent Mile, on the edge of the Gold Coast, one block from Lake Shore Drive Bike Path.

How to Get Around

Mapview Chicago

  1. Rent a bike. You can either visit a bike shop to rent by the day or week, or rent a Divvy city bike (Chicago’s rental program). Make sure to dock your bike at various ports around town every 30 minutes or you’ll get charged extra.
  2. Walk, walk, walk!
  3. Drive, though parking is infamously difficult in Chicago.
  4. Uber.
  5. But really, just bike!


Downtown chicago

  • Explore Millennium and Grant Parks, between Lake Shore Drive and Michigan Avenue. This is where the annual music festival Lollapalooza is held. Go for a run; take a stroll; grab a bite to eat at the cafe next to the water exhibit; stand under The Bean and photograph your reflection.
  • Walk up and around the bridges that cross the Chicago River, even consider going on the architectural boat tour.
  • Stop into the Art Institute of Chicago. Don’t forget to look up and marvel at the intricacies of the design and structure.
  • Bike up and down Lake Shore Drive by the marina.
  • Some favorite, healthy downtown restaurants include:
    • Protein Bar, with various locations downtown, is an ideal option for a fast, super healthy meal.
    • Lyfe Kitchen, just north of the river, offers vegetarian, vegan options.
    • Green Zebra, for vegan fare.
  • Some favorite social hangouts downtown include:
    • Hub51, off Hubbard Street, is a hotspot for socializing. Day, evening, nighttime, it’s always busy.

Old Town

Between Lincoln Park and the Gold Coast, this charming neighborhood draws a ton of young professionals and families. Delicious restaurants, popular (but not clubby) bars, hilarious comedy shows, and boutique as well as mainstream shops.

  • For a butt-kicking workout, check out SproigSport or GoCycle.
  • Grab breakfast at Nookie’s in Old Town off Wells Street. Their breakfast foods are traditional and consistent, and it’s a true neighborhood favorite.
  • Walk or bike to North Avenue Beach for some volleyball, people watching, a dip in Lake Michigan. Stop into Castaways (the huge boat-like structure on the beach) for a drink or a snack.
  • Head back to Wells Street to people watch and catch a comedy show at the famous Second City or Zanies (2 drink minimum). (The shows sell out quickly; consider buying tickets earlier in the day.)
  • Dine at Old Town Pour House (gorgeous decor) or Kamehachi.
  • And then cap the evening off with a drink at Old Town Social off North Ave.

Lincoln Park

Lincoln Park Zoo

The hub of DePaul University, Lincoln Park is known for its college-town appeal, the free, walkable zoo, its proximity to the lake, and sports bar. However, even if way past that college stage of life, don’t fret, here’s where and what to do to avoid that:

  • Sweat it out at Yoga Six or any of the other dozen studios in the area.
  • Sit outside at Dunlays on Clark for brunch. Omelettes, salads, sandwiches, perfection!
  • Bike or stroll around the neighborhood streets, especially the street on Fullerton Ave between Clark and Lincoln. Stunning!
  • Burwood Tap off Wrightwood, Gaslight Bar and Grille, and D.O.C Wine Bar are a few local favorites.

Wicker Park/Bucktown

Wicker Park

To the west of Lincoln Park, Wicker Park/Bucktown is a booming neighborhood, drawing hipsters, creatives, and young professionals and families alike.

  • Hop into an OrangeTheory class off North Ave. just west of the highway. You’ll thank me after.
  • Enjoy a taco brunch at Big Star and stay for a drink and/or the people watching.
  • There are a few small parks in the area so, while you walk around and explore, stop into one or two to sunbathe in the grass.
  • You can also bike on the 606 trail that used to be a railroad.
  • Dine at Peace Pizza for a slice and a salad and a beer, or Native Foods Cafe off Milwaukee for a health-filled vegetarian meal.
  • Be a local and hang at Bucktown Pub for a bit that evening.

Lakeview: Wrigleyville/Boystown

Just north of Lincoln Park, Lakeview is filled with serene, quaint streets, as well as craziness from the ballpark and the local gay scene. There’s something for everyone.

Lakeview Athletic Club

  • Stop into the Lakeview Athletic Club for a weight workout or a fitness class, or walk across the street to the UFC fight gym for a challenging, punch-throwing workout.
  • For some delicious, health-conscious food, stop into Chicago Diner, a vegetarian restaurant even the meatest of meat eaters enjoy.
  • Or, visit Cozy Noodles ‘n’ Rice for Asian cuisine or Pick Me Up Cafe for an extensive menu for all taste buds and dietary preferences.
  • Then head north a bit toward Montrose Beach for a run in the sand, some volleyball, or another dip in the lake. From there, start moving inland and a bit south again toward Wrigleyville/Boystown.
  • Head toward the Cubs stadium. Don’t let its partying/drinking/frat-boy reputation deter you from exploring Wrigleyville. Restaurants and bars line the streets, inviting locals and tourists to stay for a game. Scalp a ticket a few minutes after the game has started, or watch a game at the Cubby Bear or any of the other dozen bars up and down Clark and Addison Streets.

Lincoln Square

An area of town filled with families, it’s growing more popular and it’s main drag is adorable.

  • For the CrossFit lover, check out CrossFit Defined off Lawrence.
  • Seattle Sutton’s Healthy Eating is a healthy meal planning service. Visit the location off Damen.
  • Stroll the square, stopping into coffeeshops off Lincoln Avenue, maybe see a movie at the theater, and then at night, though not in Lincoln Square, head a bit southeast toward Uptown to the Green Mill, a Chicago staple for its historic music scene.

What is missing from these lists are the long-awaited neighborhood street festivals that enliven the streets in various parts of town during the summer weekends. Check the schedule here and book it there. Food, music, drinking, socializing–you’ll find it all.

The author and Vitamin World do not have a relationship with the businesses mentioned in this post. 

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