Hipster and Geek Guide to Chicago

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Are you curious about how to explore one of the coolest cities in the USA away from the main sights? Chicago, Illinois is a major tourism destination in the United States, but also has plenty of more hipster, geeky and nerdy attractions for travelers who enjoy getting a bit away from the main tourist sights. 

I hadn’t been back to the U.S. since the dreadful election of November 2016. To be perfectly honest, I wasn’t really sure I ever wanted to go back home, but when the opportunity to travel to Chicago presented itself, I took the chance and fell in love. Seriously, I can’t stop raving about this charming city! Chicago now easily ranks in my top four favorite hipster U.S. cities and it restored a little faith in my home country. 

I felt a welcome sense of community as I wandered the streets full of personality, chatted with the friendly locals, and explored the endless amounts of hipster and geeky things to do in Chicago. If I wasn’t stuffing my face with top-notch farm to table brunch WHILE ordering top-shelf whiskey at 10am (yes, you can do both of those things at the same time!), I was finding nerdy things to do at the planetarium or beating my high score at the local arcade. 

On your next trip to Chicago, get away from downtown and into the peak hipster neighborhoods of Logan Square and Wicker Park with the best hipster and geeky things to do in Chicago. You’ll find amazing brunch, explore local markets and nerdy hot spots, drink craft cocktails and local beer, then lay your head to rest in the coolest digs in the city with this hipster and geek guide to Chicago.

This hipster and geek guide to Chicago also supports local businesses and sustainable travel in Chicago. So you can find the best geeky and hipster things to do in Chicago and feel good while doing them!

Hipster and Alternative Things to Do in Chicago

As with all my hipster and alternative guides, we’re going to explore away from the main tourist attractions. We’ll start with brunch, explore shops, markets, and alternative art galleries. Of course, there’s always time for a nerdy pause to geek out at museums and comic book stores, then do some caffeinating before hitting up some alternative cocktail bars. We’ll then end the day in a chic boutique hotel!

Brunch & Breakfast in Chicago

The Chicago brunch scene is amazing. Some of the best places are only open on the weekends so I had to strategize during my visit, but I was able to get my fill of delicious brunch and it left me eager to come back for more.

Longman & Eagle

You’ll quickly learn the name of this place, Longman & Eagle, as they are the Hipster King in Chicago. This quaint farm to table restaurant, bar and hotel is nestled in the coziest part of Logan Square. It’s basically everything I look for when researching/writing my hipster guides. 

I sat down at a rustic wooden bar for breakfast at 10 am, a little hesitant to order a whiskey flight with my omelet – then I looked around. The guy sitting next to me had gone all out with a glass of top-shelf Four Roses, so I said, “screw it,” and ordered a flight of their best whiskey along with a delicious vegetarian omelet. As soon as I bit into my fluffy omelet it just melted in my mouth. 

The bartender and other patrons rounded out this brunch experience to be one of the best I’ve had in a long time! Their vegetarian options are limited, but just ask your server and they will take care of you.

Pochos

In the heart of Chicago’s Lower West Side, known for its vibrant Latin community culture and arts district, is Pochos. Pochos is the perfect blend of Mexican dishes and flavors blended with your favorite brunch classics. 

You can opt for something classic, like avocado toast, but I recommend ordering something with Mexican flavors. The Vegetarian Rajas has poblano peppers and that delicious Chihuahua cheese, which I just love. Of course, for meat-eaters, their chorizo benedict has an excellent reputation. Pochos really blends the heart and soul of the Pilsen neighborhood, bringing together locals over delicious brunch. 

Lula Cafe

Another great farm to table find, Lula Cafe was recommended by my local friend over at The MVMT Blog. Quite hungover, we entered eager for brunch. We were immediately greeted and seated by a mustache equipped gentleman.

I ordered the special vegetarian breakfast sandwich. It was perfectly crispy on the outside, but soft and warm on the inside. It’s probably because this bread was baked and sourced locally from a Chicago bakery, Publican. It tasted like I was back in Europe. 

You can find the other local companies they source food from on their site. This place is notorious for having a long line, so avoid peak times if you can, but trust me, it’s worth the wait.

Bongo Room

You know that moment when you’re so hungover and in such desperate need of brunch you stumble into the Bongo Room and can’t decide between sweet or savory, so you order both things and demolish them before taking a photo? Yeah, me too. Sorry about the photo. 

I noticed a pattern here, me hungover in Chicago getting all the brunch and taking terrible photos. Thanks for ruining me, Chicago. 

The Bongo Room is the chill option for brunch in Chicago, but they take their food seriously. This was the first time I had a breakfast burrito since I moved to Germany, so my opinion might be skewed, but good god, this burrito was amazing, as were their fluffy and delicious pancakes. Just what I needed after a long night out in Chi-Town.

Native Foods Cafe

This place gets an honorable mention for being a great grab and go vegetarian or vegan cafe. Sometimes for brunch or lunch you need something healthy to feel good about yourself. They have a great variety of vegan bowls, seasoned veggies and lots of yummy juices! It was a total lifesaver.

Markets, Shops, and Art in Chicago

The only souvenirs I buy are traditionally local and handmade, none of those plastic cheap trinkets for me! If you’re the same, you’ll definitely appreciate some of these markets and local shops while visiting Chicago.

Logan Square Farmers Market

This market is regularly named one of the best in Chicago. The market has three principles, to build an alternate food source of fresh local goods, to foster entrepreneurship and to build a better community. Those sound like some pretty great goals to me. 

The market is open year-round – moving indoors in winter – and offers produce, flowers, homemade preserved items along with some live music and festivities.

Squasht Boutique

This local, female-owned shop in the Ukrainian neighborhood of Chicago is filled with handmade fashionable gems that you can take back home to make all your friends jealous! I’m obsessed with their geometric short shorts. 

The owner, Lesley Timpe, was voted best clothing designer in 2013 & 2014 and is making a storm in the Chicago and local fashion industry. If her style isn’t your thing, there’s also plenty of variety from other local designers as well.

Wolfbait & B-girls

I accidentally stumbled into this place on my last day in Chicago. I saw feminist propaganda in the window and had to take a peek and it blew my expectations out of the water. 

Behind the counter, the co-owner was sewing her signature Bruiser jean jumpers at a workstation. The rest of the store was filled with all handcrafted local jewelry, handbags, hats, cards, candles, and soaps. As I shopped in the store I chatted with the co-owner until another woman walked in. She was signing up to be a new vendor with her line of jewelry. The entire set up was empowering and I was proud to be giving my money to this business.

I ended up finding a dress and looked at the tag, “Made in India…” Of course one of the things I wanted to buy was made in India. But wait, no, a local Chicago business has partnered with women in India to make fair priced clothing under healthy living conditions! I settled on this piece, a Bruiser jumper and a jewelry set made out of an old tire. This place is a must to pick up your local Chicago gift for that powerful woman in your life!

First Friday

Head down to the Pilsen neighborhood in Chicago every first Friday of the month for an art walk that puts art first. About 17 local art, music, and design studios host events from between 6pm-9pm at their location.

Hit all of them or just whatever tickles your fancy for a night of art and socializing with like-minded people. If that is not going on then you can find another First Friday event in the city by viewing their local First Friday events.

Geeky and Nerdy Things to Do in Chicago

My favorite part of my hipster guides! Take a step back from the cool edgy culture and let your inner geek out. Chicago is a hot spot for geeks and nerds alike with arcades, planetariums, conventions, comic stores and much, much more.

Adler Planetarium Chicago

One of the more enjoyable planetariums I’ve been to. The staff are part of what makes this one so great. They were very fun to chat and interact with. They were all knowledgeable and made my solo trip there not feel so lonely. 

The planetarium is huge! With three floors of exhibits ranging from the Big Bang, to ancient studies of the stars to the Moon Landing, it really covers just about everything in an interactive and informative way. They have two domed theaters with various shows narrated by a real person and not just a voice over. They even had a real astrophysicist there to answer questions and give a lecture. 

All these things are just scratching the surface of the things to do here. The price ranges based on what you want to do at the planetarium, so it’s accessible to all budgets. Go nerd out at this awesome planetarium and enjoy the amazing view looking back at the Chicago skyline.

Gaming Stores and Events in Chicago

Grab your favorite game and bring it back to the hotel for a night of fun! Or just drop in on a gaming event if you’re traveling and miss your gaming fam back home. 

Chicago has lots of great options for game stores. Stop by Snakes and Lattes for casual pub fare, and a charming library with games you can pull off the shelf and enjoy. Or swing by The Dice Dojo to play all your favorite games for free and as long as you want, in store! Founded by two passionate gamers this true Chicago specialty has a variety of events you don’t want to miss!

Arcade Bars in Chicago

There’s nothing quite like an old school arcade to remind me how truly terrible I am at old school games. Three lives, for a risk taker like me? Please! Nonetheless, I love reminiscing with a good old fashioned arcade bar and Chicago has several to choose from. 

I visited the grungy Logan Square Arcade based on a local’s recommendation where I quickly blew through A LOT of quarters playing Hamburger Time and Ninja Turtles. 

Make sure to also stop by Emporium Arcade, which is slightly more shiny and hipster, but has fewer arcade games and more room for other interactive games like pool and air hockey.

Comic-Con and Conventions in Chicago

Chicago is home to a variety of conventions well worth traveling to the windy city for. From Fan Expo Chicago to Chicago’s Comic & Entertainment Expo (C2E2) you’ll be sure to find a reason to get into cosplay and join one of these lively events. I’m definitely putting the Expo on my bucket list!

Comic Stores in Chicago

I always stop by and support my local comic book store right before I fly out of a city to get some airplane reading material. I picked up a copy of Paper Girls from a local store in Chicago. There are tons to choose from, including Alley Cat Comics, Howling Pages, First Aid Comics, which has amazing reviews and Graham Crackers Comics if you’re staying downtown.

Griffin Museum of Science & Industry Chicago

The largest science museum in the western hemisphere, the Griffin MSI Chicago hosts revolving interactive visits, so every time you come to Chicago they will have something new to inspire you to create. The focus of the museum is to inspire kids to grow their appreciation of STEM fields, so there are tons of interactive and hands-on opportunities. Don’t worry though, it is fun and educational even for adults!

Best Coffee in Chicago

If you’re feeling a bit worn out from exploring all the hipster and geeky things to do in Chicago, make sure to stop by one of these cafes for a quick pick me up. Or kick back and relax to get some work done.

New Wave Coffee

This spacious and vintage coffee shop is a great place to grab a cup to go, sit and relax with your favorite book or get some work done. The furniture is funky and the tiled floor makes you feel like you’ve been transported back to vintage days, but this time the coffee is decent!

Cafe Mustache

I’m not even sure if this place needs more of an explanation than the name. This peak hipster place is more than just a mustache, they have good coffee too. One taste of the vanilla fig latte and you won’t need any more convincing to check it out beyond that. 

If you’re not in the mood for coffee, they also have some local brews and tasty treats. So, swing in to get coffee good enough to grow hair on your face!

Reno Coffee

This place has amazing staff! I’d been in Europe too long and was using unknown terms to order my coffee, but the staff joked right along with me and ended up making it just how I wanted it. 

This relaxed and grungy location is great for morning coffee with a humorous conversation with the staff. It’s right on Logan Square, so you can start your day in the center of the action.

The Wormhole Coffee

Step back into the 80s with decorations like Ghost Busters and Star Wars Posters from everyone’s favorite decade. Sip locally roasted coffee from Halfwit Coffee roaster while you enjoy the relaxing and friendly atmosphere.

Brü Coffee and Co-Working Space

A great place if you’re looking to get any work done while you travel. This co-working space had a lot of room, couches and great WiFi to power your day. I also enjoyed that they had smoothies and juice, though I did not enjoy the plastic they came in. Ask for a for-here cup, before you make the same mistake I did! 

They also have free yoga classes if you need to unwind from working too much. The place could have a better ambiance, but it serves its purpose of fueling you with coffee and space to work.

Craft Cocktail and Local Breweries in Chicago

Billy Sunday

Billy Sunday is a classy and intimate bar with dark woods and a red wine floor, located in the heart of Logan Square. Not only do they mix with top-notch booze, they have a unique arsenal of bitters and ingredients they use. 

Some of my favorites on the list are the fennel pollen, black trumpet mushrooms, and angelica root bitters, which make for exciting new flavors you haven’t tried anywhere else. Order up the classic Old Fashioned or get weird with Box Lunch containing goat milk and oatmeal.

Scofflaw

The first place my local friend and fellow booze connoisseur recommended when I asked for the best cocktail bars. This place feels like home, located in a charming Chicago building, the interior is filled with eclectic furniture and design. Their main poison is gin and they use it well. Try the Victory Lap (pictured).

The Whistler

A more lively and energetic bar, this is a good waterhole to hit the town and let loose. Along with some great cocktails, you’ll find DJs or live music nightly, with no cover! Woo! 

I love that they feature all different types of music from my favorite, electronic, to jazz and country. They even feature different artistic endeavors like film screenings and readings. 

Their cocktail menu changes all the time. Ask your bartender for their seasonal favorite or find their menu posted daily on social media. I felt like a true Chicago local and enjoyed the welcoming scene at The Whistler!

Revolution Brewing

Recommended by another local and beer lover, this place is a friendly and welcoming local brewery. They even had the best vegan burger I’ve had in a while, which was surprising! 

Anyways, their league of hero beers depicts hops as heroes of the day. If you’re an IPA fan, try the Galaxy Hero, brewed specifically for the Chicago Comic and Entertainment Expo! If you’re like me and avoid IPA you’ll love the Bottom Up wheat beer. They have both a brewery and a brewpub to delight all your taste buds.

Forbidden Root

This place is just cool! Chicago’s first botanical brewery opened in 2016 and has made waves ever since. They embrace old botanical brewing techniques and combine your favorite flavors with botanicals like dandelion, wildflower, and ginger. Find something different at this truly unique place that prides themselves on community and great taste.

Boutique Hotels in Chicago

I had the honor to stay at two amazing boutique hotels during my stay in Chicago and would highly recommend both of these based on your needs or budget.

Longman & Eagle

As soon as I read Longman & Eagle allowed you to bunk upstairs I booked it immediately, and it did not disappoint. They only have 6 rooms, but each one has its own unique hipster personality and cool amenities. 

You check in at the bar, so you already know you’re going to have a good time, and after partying the night away you can slip upstairs, play your Fischer Price tape player and fall asleep – only to wake up and head back down for one of the best brunches in the city. 

The staff were welcoming and friendly and the rooms were so quaint. Located in the center of Logan Square on the Blue Line, 10/10 would recommend anyone to stay here, unless of course, you like going to bed early, then you might not like the noise.

The Hollander at The Robey

This place is a combination of a grown-up hostel and boutique hotel. Piggybacking on the famous Robey, this is great for all budgets. 

You can share an adult style bunk dorm with strangers or book one for your whole group. If you like personal space they have private rooms as well. The lobby is always lively with working and social individuals. The exposed ceilings and metal pipes are a stylish way to enjoy your stay. 

The staff were super friendly and the rooms had everything you need for a secure and comfortable night’s sleep. Located in the heart of Wicker Park and right on the Blue Line, it’s a great overall choice.

Book the The Robey

Alternative Neighborhoods

The best hipster neighborhoods in Chicago are the aforementioned Logan Square and Wicker Park. They’re both located on the Blue Line with direct transit to and from the airport and downtown. No matter what hipster or geeky things in Chicago you’re looking for you’ll find them in these areas. 

There are plenty of bars, restaurants, local shops, markets and museums. I stayed in both locations and was able to check out the downtown area and then return to hipsterville for an evening of local fun.

Comment and Share

Thank you, Chicago for making me feel right at home! While initially hesitant, I had a wonderful time exploring all the geeky, nerdy and hipster things to do in the windy city, as well as eating and drinking lots of delicious things.

I hope this guide has shown you all the best geeky, nerdy and hipster things there are to do in the city, so you can check them out when you next visit. Let me know in the comments what you’re most excited about, or if there are any other cool places I should check out next time I’m there.

Make sure you pin and share this so others can find all the best hipster and geeky things to do in Chicago, or you can come back to it when planning your own trip.