I may earn income from affiliate links or partnerships in this post. *Only travel when it is safe to do so and you are not putting your destination or home country at risk. Some recommended tours, businesses, hotels, and excursions may be closed at this time. Please do independent research.
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 bit 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 I have 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 10 am, (yes you can do both of those things are 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. We’ll find amazing brunch, explore local markets, nerdy hot spots, drink craft cocktails and local beer and then lay our heads to rest and the coolest digs in the city with this hipster and geek guide to Chicago.
This hipster and geek guide to Chicago 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 doing them. It also contains affiliate links. By purchasing any tours mentioned in this post through my link you are helping support this travel blog at no additional cost to you.
Chicago brunch scene was amazing. Some of the places are only on the weekends so I had to strategize during my visit, but I was able to get my fill of 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 are nestled in the coziest part of Logan Square. It’s basically everything I look for, for 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 goes all out with a glass of top-shelf Four Roses. So, I say, “fuck it,” and order a flight of their best whiskey and order up a delicious vegetarian omelet. A soon as I bit into my fluffy omelet it just melted in my mouth. The bartender and other patrons rounded out this brunch experiences 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.
Mon-Sun 9am-3pm / 5pm-1am
657 N Kedzie Ave, Chicago, IL 60647, USA
Dusek’s Board and Beer
Treat yourself to the ultimate foodie brunch by wandering into this historic building that will be your tastebud’s dream come true. Go all out in true Chicago style and order the board and beer, because I mean, beer is for breakfast, right? Their (pictured) Chilaquile also passed by me several times and looked amazing. If you need the vegetarian option, like me, order the vegetarian omelet with seasonal veggies, it was mouthwatering. If their amazing food wasn’t reason enough to go, they were recently awarded the 2016 Michelin Star Recipient, so what are you waiting for? Start your Sunday Funday on Saturday morning and stay late into the night for the party!
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 sat by a mustache equipped gentleman. I ordered up 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.
2537 N Kedzie Ave, Chicago, IL 60647, USA
Start your Sunday Funday on Saturday morning for a one of a kind brunch. This ultra classy dark wood and leather hot spot look like it could be Ron Swanson’s personal restaurant. This place has more vegetarian options than the others, so it made the top of my list! You can enjoy some delicious crispy brussel sprouts or go all out with some classic chicken and waffles covered in hot sauce and maple syrup. I mean, why not, right?
Brunch Sat-Sun 10am-11pm or 4pm
1140 W Madison St, Chicago, IL 60607, USA
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, so were their fluffy and delicious pancakes. Just what I needed after a long night out in Chi-Town.
Mon-Fri 8am-2:30pm Sat-Sun 9am-2pm
They have 3 locations, this is near Wicker Park 1470 N Milwaukee Ave, Chicago, IL 60622, USA
Cure your hangover, here!
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.
Logan Square Farmers Market
This market was named one of the best in Chicago for 2016. This 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 jarred items along with some live music and festivities.
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.
2556 W Chicago Ave Chicago, IL 60622
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 peak 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 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!
3131 W Logan Blvd, Chicago, IL 60647, USA
Vintage Garage Chicago and Flea Market
This is a Chicago hot spot, happening only once a month in the summer months. So, if you’re lucky enough to be in Chicago during one of these Vintage Garage Markets, you’re in luck! You’ll find some real treasures and not just junk like so many garage sales. Every month there is a new theme from vintage clothing to mid-century modern.
Head down to the Pilsen neighborhood in Chicago every first Friday 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 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 is part of what makes this 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 study 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 and this awesome planetarium and enjoy the amazing view looking back at the Chicago skyline.
1300 S Lake Shore Dr, Chicago, IL 60605, USA
Gaming Stores 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 two great options for gaming stores. Stop by The Gaming Goat for a local Illinois franchise run by passionate gamers, in a family environment. 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. haha. Nonetheless, I love reminiscing with a good old fashion 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 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 Wizard World Comic Con to Chicago’s Comic & Entertainment Expo 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 airplane reading material. I just picked up a copy of Paper Girls from a local store in Chicago. There are tons to choose from, but I stopped by G-Mart Comics in Logan Square, since it was close to where I was staying. It was small, but they have what I was looking for and friendly employees. Other options are First Aid Comics, which has amazing reviews and Grahm Cracker comics if you’re staying downtown.
Museum of Science & Industry Chicago
The largest science museum in the western hemisphere, the 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 it is fun and educational even for adults!
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 the vintage days, but this time the coffee is decent!
3103 W Logan Blvd, Chicago, IL 60647, USA
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!
Mon-Fri 7am-2am Say-Sun 8am-3am
2313 N Milwaukee Ave, Chicago, IL 60647, USA
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 ahumorous conversationn with the staff. It’s right on Logan Square, so you can start your day in the center of the action.
2607 N Milwaukee Ave, Chicago, IL 60647, USA
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.
1462 N Milwaukee Ave, Chicago, IL 60622, USA
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 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 made 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.
Sun-Thu- 8am-8pm Fri-Sat 8am-9pm
1562 N Milwaukee Ave, Chicago, IL 60622, USA
Craft Cocktail and Local Breweries in Chicago
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 list 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 and new flavors you haven’t tried anywhere else. Order up the classic Old Fashion or get weird with Box Lunch containing goat milk and oatmeal.
Usually 5pm-2am, but varies on the weekends
3143 W Logan Blvd, Chicago, IL 60647, USA
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).
Normally 5pm-2am with varying weekend hours
3201 W Armitage Ave, Chicago, IL 60647, USA
Photo courtesy of Daniel Segar for Scofflaw Be an outlaw, here!
Recommended to me by my bartender at Longman & Eagle, this gem specializes in Mezcal and Tequila based drinks. Owned by Kaitlyn, who is seemingly a popular local, this place is down to earth and welcoming. I’ll be the first to admit I am not a huge fan of either Tequila or Mezcal, but the mixing they did here, put a smile on my face. My favorite was the Bridges Not Walls, for the obvious awesome name and great flavors of chili and strawberry.
Most days 5pm-2am, staying open late Friday.
3149 W Logan Blvd, Chicago, IL 60647, USA
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!
Mon-Thur: 6pm-2am Fri-Sun: 5pm-2/3am
2421 N Milwaukee Ave, Chicago, IL 60647, USA
Photo courtesy of The Whistler Let Loose!
This dark and moody bar oozes a gothic chic feel. Nestle into to one of their Victorian age sofas and order one of your favorites. Their core menu focuses on classic drinks like the Side Car and Sazerac, without too much originality, but they execute them well. Their strong classic menu has earned them favoritism in the industry scene and even made Food & Wine Magazine top 100 best bar list.
Mon-Sun: 5pm-2am, staying open late Saturday
701 N Damen Ave, Chicago, IL 60622, USA
Photo courtesy of Bar Deville Order Up the Classics!
Recommend 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.
Locations and hours vary
This place is just cool! Chicago’s first botanical brewery it opened last year and is already making waves. 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.
1746 W Chicago Ave, Chicago, IL 60622, USA
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 in their upstairs I booked it immediately, and it did not disappoint. They only have 6 rooms, but each one has it’s 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 was 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 the grown-up hostel and boutique hotel. Piggybacking on the famous Robey, this is great for all budgets. Share an adult style bunk doom 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 was super friendly and the rooms had everything you need for a secure and comfortable night sleep. Located in the heart of Wicker Park and right on the Blue Line it’s a great overall choice.
2022 W North Ave, Chicago, IL 60647, USA
The best 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’s plenty of bars, restaurants, local shops, and 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.
Thank you, Chicago for making me feel right at home! Make sure you pin and share this so others can find all the best hipster and geeky things to do in Chicago.
Susanna grew up in small-town Alaska where the changing climate was always on her mind. Through traveling, she gained an interest in the power of sustainable and regenerative travel. She now attends a Master's program for environmental sustainability and bridges sustainable travel with environmental science. When she's not outside playing, you'll find her drinking whiskey with her cat and partner while trying to get to level 99 in life.