How to experience Chicago like a local?

Hi Jenna!

In my opinion the cool neighborhoods to explore would be Wicker Park/Bucktown and Logan Square. There are tons of great restaurants and neat shops in those 'hoods. 

In Wicker Park, I would definitely pick a nice day to enjoy lunch or dinner on the patio at Big Star-their margaritas and tacos are killer and it's a very popular spot! Go at off hours so you don't have to wait as long.

Next door is Dove's Luncheonette, a great spot for brunch, and nearby are Stan's Donuts....

...and Glazed and Infused for delicious doughnuts. Just a little further down are Piece Pizzeria and Brewery , some of the best pizza in the city, and Brobagel for bagels!

Revolution Brewing and Violet Hour are great places to grab drinks - beer and cocktails respectively, and you can get your juice on at Owen + Alchemy.

In Logan Square there is Longman & Eagle where you can eat & rent a room, Lula Café for brunch, Lost Lake for tiki drinks, Billy Sunday for cocktails, The Boiler Room for pizza, and many others.

The Blue Line stop on Damen in Wicker Park can take you downtown to the more touristy things - even as a local I love strolling around Millennium Park on a nice day, or walking through the The Art Institute of Chicago on a weekday when it's not as busy or if it's raining. On a crappy day a stop at the Garfield Park Conservatory is also cool to see.

I would definitely walk along the Lakefront Trail - it's busy but it's one of the things that keeps people in Chicago after dealing with our cold winters! It will be less busy closer to Belmont Ave, north of the North Ave. and Fullerton beaches. 

Chicago Food Planet Food Tours offers a tour of Chinatown Chicago which I've been wanting to check out, and Lagunitas Brewing Company has a great brewery tour and brewpub worth checking out.

Need more recs for a specific area or activity? Let me know!

I'm a big antiquer and a big drinker so I first would recommend hitting up Andersonville for some of the hidden gems that house all kinds of antiques. My favorite is Brownstone, total dive but they have some really cool stuff!

Second, I would suggest drinks at The Berkshire Room, The Drifter for a little speakeasy action, and a little Fleminco dancing at Bordel. Lastly if you're in town on a Sunday, you can't miss Ramen at Yusho Hyde Park!

Hey Jenna! You will LOVE Chicago - how exciting that you get to be here a week long. If I were you I would try and tackle a new neighborhood of the city each night you're here. The best shopping would be Michigan Avenue (if you are looking for stores you can find anywhere - Nordstrom, Gap, Bloomingdales, Victoria's Secret) but if you are looking to be a "local" my favorite stores are in Lincoln Park (The Green Goddess Boutique and Bluemercury Lincoln Park for makeup). Another great area for shopping AND food is Wicker Park - they have tons of cute cafes and shopping. Make sure you go to Stan's Donuts at Six Corners in Bucktown - they have amazing donuts (which btw is a big thing in Chicago right now) another donut favorite of Chicagoans is Glazed Expressions which has several locations throughout the city. I'll give you a few of my favorite places around the city that I frequent often -

Favorite Burger - Au Cheval (prepare to wait a little bit but TOTALLY WORTH IT)

Favorite Boutique Handle With Care (tell Emma Justine sent you)

Favorite tapas style dinner - La Sirena Clandestina (best empanadas)

Favorite workout studio - The Barre Code (if you're looking to get a good workout in)

Favorite bars - Stout Barrel House & Galley DryHop Brewers Public House and Benchmark

Favorite brunch spot - The Publican and Kanela Breakfast Club

Enjoy!!!!!!!

I suggest spending time dining at the patio at Big Star. Shop in Wicker Park. Go to a Cubs game. Bike on the Lakefront Trail - Divvy Bikes are a great way to get around!

One night, get food at Parson's Chicken & Fish, drinks at Scofflaw and then Weegee's Lounge. Another night, check out Revolution Brewing, Emporium Arcade Bar and Antique Taco. Go to The Art Institute of Chicago on Thursday evenings (free day, though only to Illinois residents — can you fake a zip code?), and while you're down there get dinner at Miller's Pub. Go vintage shopping in Andersonville but don't pay high prices in the vintage shops — score some deals at Brownstone Antiques and The Brown Elephant. Go to Hopleaf and Simon's Tavern while you're in Andersonville. Get coffee at Bowtruss Coffee Roasters in the West Loop and check out Girl & the Goat or Publican Quality Meats. For a cheap sandwich in the West Loop, try J.P. Graziano Grocery. If you want to check out some neighborhoods locals live in but that most tourists never go to, take the Red line to Rogers Park and eat at Heartland Cafe and drink at Red Line Tap. Or go to Albany Park: take the Brown line to Kedzie-Brown and eat at Semiramis.

Got to Park Grill for drinks in the late afternoon.  Make sure to go to Old Town to browse the neighborhood.  Hit the Oh Olive French Market store.  Go to W Randolph St and pick a restaurant.   Walk   the lakefront all the way to the museum campus.  Don't miss the The Art Institute of Chicago, its worth the admission. Depending on when you're there, go to the Jay Pritzker Pavilion in Millennium Park  for a free concert.  You can bring your own picnic  and drinks.   A blanket will do.  There are concerts most nights starting in June.  Go to Pizano's for a great thin crust pizza.

You mean you want to come work at my job, clean my house and feed my cats?  :-)  Didn't think so...

If you come here in the summer, you may want to explore the lakefront.  The locals ride their bikes, run, walk, play volleyball.  The Lakefront Trail runs the length of the city (almost), it's 18 miles long.  In the summer there are also quite a few festivals, both neighborhood and central Chicago.

Locals will also spend time in the neighborhood they live in and there are plenty of safe, interesting neighborhoods to explore.  Lincoln Park, you can go to the free Lincoln Park Zoo, check out the Lincoln Park Conservatory, have a meal at RJ Grunts or Café Ba-Ba-Reeba! or Mon Ami Gabi.  Take the el or a water taxi to Chinatown Chicago,  my favorite places to eat are MingHin Cuisine for dim sum or Lao Sze Chuan. In Old Town, you can eat at Adobo Grill or Salpicon and see a show at Second City.  In Andersonville you can have a delicious Turkish dinner and see a belly dancing show at Turkish Cuisine or go to Hopleaf

If you have some time before you visit, you might want to see if you can sign up for emails from either Dish which is by Chicago Magazine or Time Out Chicago, both of which are written for locals and have lots of dining ideas that are not the ordinary