A Local's Guide to Chicago // Brittany from Boston

A Local’s Guide to Chicago

Posted on Posted in North America, Travel

I love Chicago, it’s such a beautiful and vibrant city. But I’ve spent limited time there and I really wanted to see what this city is like from a local’s perspective. So I reached out to my friend Chris of Nomad & Camera, a Chicago-native, and asked him to share with us the best of Chicago. Read on for what he has to say in his Local’s Guide to Chicago! (And these photos were taken by him as well. Seriously, is he an amazing photographer or what? I love his photography, see more of it here!)

A Local's Guide to Chicago // Brittany from Boston

A Local’s Guide to Chicago

Go local or go home. When I travel I rarely use a guidebook, rather I ask locals for their advice. As a native Chicagoan, if you want to do the Windy City right, here’s what I’d suggest…


  • Revolution Brewing – Chicago is home to 60 microbreweries and counting. If you’re going to be local, then you need to drink local. Goose Island is another fine choice. A personal favorite is Green Line Pale Ale. It’ll make you hoppy inside!
  • Violet Hour – It’s a speak-easy style cocktail lounge with an entrance door that’s nearly hidden in a mural of graffiti.
  • The Bedford – What once was a fancy bank has now been converted into a vault of alcohol and intimate conversations.


  • Ipsento – Home to the nutella latte, nitro, and sustainably grown coffee grounds. It’s next door to a beautiful park with one of the coolest wall murals in Chicago. No shortage of natural light here.
  • Next Door – If you need to work while you’re in Chicago, this is your spot. It’s a coffee shop – coworking space hybrid. Super fast wifi (especially for uploading files to clients if that sounds like you) and lots of private 1-2-3 person rooms for private conversations, tutoring, and seminars. You can even rent out their conference room for free in advance. An amazing community space.
  • The Coffee Studio – This coffeeshop is off the tourist route but has an awesome chill vibe, cool art, and fantastic chai tea lattes. It’s down the street from Kopi, another hidden gem if you prefer a very bohemian, multicultural, almost hostel-like environment.

A Local's Guide to Chicago // Brittany from Boston


  • Lou Malnati’s – Pizzerias in Chicago is its own blog post, but the city is known for deep dish, and Lou’s makes the best of the big name Chicago pizza chains. But I’d also recommend Chicago Pizza and Over Grinder for a truly unique and delicious pizza that’s off the beaten path. It’s located in the downstairs of a building across the street from the infamous St. Valentine’s Day massacre. If going for dinner, get there early because they don’t take reservations.
  • Superdawg – The epitome of the Chicago style hotdog. They do it right. Located on the far northwest side of the city since 1948, it’s worth the drive. It’s a classic drive-in with car hops. While I will admit it’s more than you’d typically pay for a hotdog outside of a ballpark. If you are a true hotdog fan or foodie, it’s worth it. Celery salt, sport peppers, pickled tomato, poppyseed bun, and most importantly NO KETCHUP.
  • The Chicago Diner – “Meat free since ’83” is their slogan and I’d highly recommend this to vegetarian, vegan, or gluten free travelers. The menu is full of typical diner food but the twist is it’s meatless and dairy-free. It’s incredible how good a meatless reuben sandwich can be. And whether you are vegan or not, their dairy-free shakes are insanely delicious.


  • Blue Chicago – Authentic down-home Chicago blues. No frills. Pure blues. Get there early though if you want a seat.
  • Zanie’s or Second City – Two top notch comedy clubs. See comedians there two years before you see them on TV.
  • The Cubby Bear – Located across the street from Wrigley Field, it’s a sports bar after Cubs games, music venue on the weekends, and home to salsa dancing on Sunday nights. Fun Fact: Dave Grohl of the Foo Fighter’s performed his first concert there.    

A Local's Guide to Chicago // Brittany from Boston

Must see’s…

  • Art Institute of Chicago – There’s a reason it was ranked on Trip Advisor as best museum on the planet in 2015. Modern wing = amazing. Plus, it’s walking distance from “The Bean” and Millennium park which is great strolling around when it’s warm or ice skating in colder weather.
  • Architecture Cruise – Nothing better in the summer than cruising through River North past historic skyscrapers left and right. Worth doing even if it’s colder outside.
  • Glessner House – A hidden fortress in the South Loop. It’s a house museum of one of Chicago’s former richest residents. Free tours on Wednesday. I’d highly recommend it in December. You’ll feel like you’re celebrating a true 1800’s style Christmas!

Hot Neighborhoods…

  • Logan Square & Pilsen – For the true hipsters.
  • Wicker Park & Lincoln Park – Checks all boxes. Trendy shops, restaurants, and cafes. Music venues to sports bars.
  • River North & Fulton Market – Higher end restaurants and clubs. Valet parking. Perfect for those that want to experience chic Chicago!

A Local's Guide to Chicago // Brittany from Boston

Getting around…

  • The El – Iconic and affordable. Locals take pride in the line that goes through their neighborhood. Way cheaper than RideSharing, but purchasing a Ventra card is required for riding the CTA (both El and buses). You can purchase at a Walgreens drug store. Costs $5 but that money goes onto your card to use. Note, the Red and Blue line are the only two that run 24/7.
  • Uber/Lyft – Simple. Convenient. No knowledge of the city required.
  • SpotHero – If you’re driving, it’s an app that allows you to reserve a parking spot in advance at a lower rate than what’s advertised on garages. It’s the brainchild of a couple Chicago natives too!

Working out…

  • The 606 Trail – It’s an abandoned railway converted into a 4 mile walk/run/bike path. What’s really cool is the perspective of the neighborhood that you get. You are running at the same level as the second and third floor of buildings.
  • Lakefront Trail – This was my go-to when I trained for the Chicago Marathon and is a beautiful 18 mile path that runs along Lake Michigan. For serious bikers and runners, this is for you.
  • Maggie Daley Park  – If you’re into rollerblading, ice skating, rock climbing, or playgrounds on steroids (seriously this playground is 10x better than what you probably played on at recess) then this is the park for you.

A Local's Guide to Chicago // Brittany from Boston


  • Navy Pier  – Aside from boarding a cruise ship there or watching fireworks on the 4th of July, I don’t get why so many tourists go there. The only Chicagoans you’ll find there are the ones running the shops.
  • Magnificent Mile – It’s a mile full of restaurants and shops that you can find in any major city in the US.
  • Buckingham Fountain – The fountain itself isn’t overrated, but many tourists see it via segway tour. Save the money! Rather I’d suggest making sandwiches or buying a salad and take it to Grant Park and enjoy a picnic. I think that’s the best way to see the fountain and take in the view of the lake and skyline.

Insider Advice

  • Every Monday during the summer there are free concerts in Millennium Park downtown.
  • Chicago host’s Open House Chicago in mid-October every year which allows you free admission into buildings that are normally closed to the public which can range from vertical farming sites to abandoned theaters to secret mobster entrances during prohibition.
  • Chicago’s restaurant week with affordable prix-fixe menus at top Chicago restaurants typically takes place the last week of January into the first week of February.

A Local's Guide to Chicago // Brittany from Boston

A Local's Guide to Chicago // Brittany from Boston

Author Bio

Chris is a nomadic photographer battling an addiction to maps and menus. He practices free-range photography, specializing in travel, outdoor, and adventure-based themes. After four years working as a creative director in Chicago he booked a one-way ticket to Australia in 2013 and has been traveling the world since. In late 2015 he founded his current business Nomad and Camera which specializes in visual storytelling through graphic design, photography, and videography.

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