Travel Guide | What To Do In Chicago

I am not a city girl by any means. I’m more of a majestic mountain view and sprawling beach kind of gal. But there is something about Chicago that makes me fall in love over and over again. It is the only city that I excitingly try to get back to any chance I can get. Even if it’s in the middle of winter and I have to wear a million layers just to be remotely warm. There’s so much that the city offers. Its public transportation system is perfect for the type of traveler that doesn’t like to rent a car, aka me. It’s affordable compared to some other major cities I’ve visited (here’s looking at you San Francisco and New York City.) It’s full of local pride, good eats, killer art, and some really great people. Which is why it would only make sense to put a post together letting you know what my favorite things to do in my favorite city are. I give to you guys,  a Travel Guide: What to do in Chicago.

Where should I eat in Chicago?

Happy Camper Pizzeria

I know Chicago is all about the deep dish pizza. But I’ll be honest with you after countless people telling me that Lou Malnati’s Pizzeria was THE PLACE to go for the iconic dish I took their word for it. I shouldn’t of because I was GREATLY disappointed. Aside from waiting almost two hours for a small personal pizza, it really wasn’t anything to write home about. So in terms of wanting deep dish I suggest researching some other places.

Howeverrrrr, if you’re willing to try FANTASTIC pizza that is not deep dish then PLEASE do so at Happy Camper Pizzeria. This place is SO cool. Even if you want to skip dinner, you should at least pop into this place for a drink. The atmosphere was bumping and the restaurant itself is huge. It has tables built into Airstream trailers and seats at the bar made of tire swings! If the giant neon sign boasting “Pizza is my porno” isn’t going to win you over then I can tell you the food sure will.

The pizza options are COUNTLESS and there are options for vegetarians, vegans and a lot of different dietary restrictions. It was SIGNIFICANTLY better than the halfway decent deep dish I had at Lou’s. This place is totally a place I would go back to and hopefully get the chance to bring a bunch of my friends.

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Pierogi Heaven

I appreciate Chicago for the fact that they have a MASSIVE Polish community. Which means that I can get as many pierogis as I want. Being one of my favorite foods ever, I can never turn down a chance to stuff my face with these delicious delights. Lucky for me I found a super tiny spot right in the middle of downtown. This place is nothing fancy at all but that’s the way I like it. The plates and utensils are plastic and the portions are plentiful and absolutely delightful. They also served my borscht in a styrofoam coffee cup and I loved drinking it like it was a warm hot chocolate. Haha.

I ordered a full plate of the meat pierogis and a half plate of the potato and cheese. I personally always go meat but if you opt for potato and cheese for preference reasons you will not be disappointed.

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Yuzu Sushi

I will absolutely admit that the reason that I heard about this sushi restaurant was from a video created by Food Insider that I was tagged in by a friend on Facebook. The video showcasing a small sushi spot found in Chicago, Yuzu, combined a few of my favorite things. Sushi, art, and sauces. The video was full of sushi masterpieces, each roll accompanied by an intricate piece of art. I added it to my list of “Places to Go” on Google and made sure I made the visit the next time I was in town.

I was NOT disappointed. The sushi rolls were affordable, fresh and absolutely exquisite. The flavor alone made it one of the best sushi rolls I had in my life. The sushi roll I tried was the Chicago Spring roll and boy, did it live up to its name alright. Like I said, the roll itself was divine, but the best part you ask, WELL LET ME TELL YOU.

My extremely sweet waitress dropped off my plate and looking back at me was the Chicago skyline in the colors of their iconic flag. MADE WITH SUSHI SAUCES. I spent the first 5 minutes figuring out how on Earth I was going to mess up something so beautiful. Those sentiments quickly diminished once I snapped a few shots to remember this beauty. Once I got a taste of how beautifully those sauces matched with my sushi it was a MESS.

The roll itself was sweet, savory and spicy. I could have easily gone for two. I really enjoyed my meal though and felt nice and full by the end. The atmosphere is incredible too! The space is intimate, and the hip-hop beats made for a nice contrast against the modern design of the restaurant.

Some practical info, I went on a random Wednesday around 6pm-ish and I luckily was seated right away (perks of being a solo traveler) even though larger parties waited much longer. This place is definitely on the radar of tourists and locals alike so I would suggest placing a reservation if you’re coming with a larger party or anticipate that there may be a bit of a wait.

Podhalanka

If you’re looking for a high-end restaurant where your 5-course meal is a composition of portions that are the size of your thumbnail then this is NOT the place for you.

IF you’re more into a hearty, authentic Polish meal in a restaurant that looks more like you just stepped into your Grandmother’s living room then Podhalanka is 100% the place for you. The first time I walked in I genuinely thought I walked through a portal that took me to my Grandmother’s house, but instead of the Portuguese news on the TV, it was the Polish news. Doilies adorn the tables, family members pictures are hung on the wall and relics brought back from Poland scream pride throughout this must-visit hole in the wall.

I came into the restaurant with an idea of what I wanted to eat when I came in. What I wanted was not what I would be getting thanks to the insistent recommendations of our waiter. He would say things like “Oh my mamma just made this fresh you will have some of this, let’s add some of that, you girls must be hungry let’s make sure you are fed.” All of these recommendations were at no extra charge and you could tell he took pride in what we were about to eat.

His eyes nearly started watering when I told him about my undying love for Poland and being a non-polish person he was so happy to hear that I had visited his country. We exchanged stories about our love for the country while I enjoyed every single thing he recommended.

ChicagoYelp

Image via Yelp

Stan’s Doughnuts

Another staple in Chicago, you can find Stan’s Donuts everywhere. Their colorful façade is matched in beauty with their delectable treats. The pink bakeries can be found all over but I personally enjoy the smaller less frequented shop in Wicker Park.

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Image via Yelp

Broken English Taco Bar

What really sold me on Broken English Taco bar when I was researching potential spots to check out on my last trip to Chitown was their artwork. There were really unique, colorful murals on the outside walls of the building and the décor inside is fun and bright. Two words I would use when describing myself, so I knew this spot was for me.

After checking out the Cultural Center, you could imagine my sheer delight when I wandered in to find that I had stumbled in during Taco Tuesday, meaning there were $1 tacos in the building! WOOP WOOP.

Well let me tell you, they certainly did not disappoint, I plopped my solo self in a seat at the bar, ordered an obscene amount of tacos, a margarita to wash it down and made a whole bunch of new friends. The service is friendly even when they were slammed with people taking up this awesome deal. The tacos were incredible and the margarita was on point. Highly recommend.

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Portillo’s Hot Dogs

Portillo’s is a staple in this area. They are known for their Chicago style hot dogs and rightfully so because they are DELICIOUS. Take it from a girl who is known for her love of hot dogs, Portillo’s is amazing. There are locations scattered throughout the city with one located directly in the heart of downtown if you’re traveling without a car and want a taste of the classic flavor.

The crinkle fries are where it’s at too! Pro tip, order more than you think you want because the second I finished I wished I could make my entire meal instantly re-appear. However, a massive tour group came in right as I wrapped up and ya girl was NOT trying to wait in that big ole’ line.

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Where are some unique spots in Chicago?

Vintage Shopping on North Milwaukee Ave

Wicker Park is probably one of my favorite neighborhoods in Chicago. It’s ideal if you want to spend the day wandering a neighborhood full of good eats, good art, and a super plus: GOOD VINTAGE SHOPPING. There are some great spots all within walking distance on North Milwaukee Ave. Here are some of my favorites:

  • Kokorokoko

    • If 80’s neon and 90’s style is your thang then stopping here is an absolute must! This colorful store is packed with all sorts of clothing and accessories, so show off some Chicago pride and up your Streetwear game.

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  • Crossroads Trading Co.

    • The smallest of these suggestions, Crossroads Trading Co. still houses some great pieces. There was a pair of high top Reeboks that would have been my new favorite sneakers had they not been 2 sizes too small. I DID score a beautiful necklace however and for a great price!
  • Ragstock

    • This place is MASSIVE and surprisingly inexpensive. Not to mention they have a little bit of everything, both new and used. Check out both floors to see if you find a new staple.

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  • Buffalo Exchange

    • Buffalo Exchange is in a couple cities I’ve been too but it’s always nice to pop in and see what they have in their ever-rotating stock. I didn’t find anything for me here but they still had a really eclectic selection to browse through and their staff is super kind, helpful AND hilarious!

Frederick C. Robie House Frank Lloyd Wright House

I’ve always loved Frank Lloyd Wright and his use of symmetry and art deco in his architecture style. A true king of midcentury design, I was pleasantly surprised to find out that there is quite a bit of Frank Lloyd Wright architecture throughout the city.

The Frederick C. Robie is an entire home designed by the famous architect. They do a guided tour at the top of each hour. The tour itself is informative and insightful. I learned a whole lot about Wright’s style, his commitment to functionality and the history of Chicago that has passed through this home.

At the time there was construction happening. This meant that a decent chunk of the house was blocked off. However, I still saw enough to make up for my ticket. I would recommend contacting the Frederick C. Robie House and see if construction is still occurring and decide if it’s worth your money. Find out more information on admission prices, hours, etc. here.

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Where should I get a cocktail in Chicago?

Mahalo

I accidentally stumbled upon this gem while I was vintage shopping and art hunting in Wicker Park. For some reason whenever I travel solo I end up having more mid-day cocktails than when I’m traveling with my girlfriend or a group. LOL Don’t ask me why I’m really not sure. Well, being in the mood for one of those mid-day cocktails I popped in and was so pleasantly surprised. The decor is bright and colorful and the cocktails are picturesque and delightfully handcrafted.

I didn’t try any of the food but the menu did look enticing. However, the cocktails are to die for.

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Hello….or if you're visiting @mahalochicago ALOHA!! I noticed that I've gathered some new followers on my IG journey so today I want to re-introduce myself. My name is Chantel and I'm a joke-cracking Leo whose love for @marty.neauble is only equally matched by my love of mozzarella sticks and the perfect margarita (not necessarily together). My nose is often buried in a book and my speakers are bumping latin or gangsta jams….or the Moana soundtrack. #noshame . . . . My two immigrant parents (WADDUP PORTUGAL🇵🇹🇵🇹) made sure I was bitten by the travel bug at an early age. My feet and the empty pages in my passport have carried me to 29 different countries through 4 different continents with hundreds of new places on my list. Sorry bank account! 💸💸💸💸 . . ..and no I can't tell you my favorite place without a million stipulations (we talking food, we talking views, we talking people….THERE'S A LOT OF THINGS TO CONSIDER). . . . . . I'm always down for a dance battle and my laugh is USUALLY the loudest in the room. I'm also forever handing out smiles, compliments and high 5's like they're Halloween candy. . . . It's nice to meet you. . . . . Introduce yourself because I don't want followers, I want friends. . . . . . #keepingitcornysince1990

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Flamingo Rum Club

You know you’re at the right spot when you see the giant, colorful flamingo mural that adorns the exterior wall of the Flamingo Rum Club. A swank, vintage style cocktail lounge, the perfect place to dress up and grab a handcrafted cocktail or to dance the night away. They even have burlesque nights which I was sad to see wasn’t happening when I was in town but I would LOVE to catch one here.

The club makes for a perfect setting to see burlesque dancers shimmy and shake with their feathers to the best of jazz.

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Where can I find some art in Chicago?

Greetings from Chicago Mural

A ways past Wicker Park and maybe just a couple of stops up on the Blue line, hop off at California and there is a mural dedicated to the spirit of Chicago. Greetings Tour is a team of artists that create stand out murals in cities all over the United States. Chicago’s even got its own and you can find the exact location here. The mural is filled with elements that Chicago is famous for painted onto the wall of a car part store. Things like deep dish pizza, local sports teams, and the famous Chicago flag are just some of the things you’ll spot in this mural.

Seeing as it is a mural in a parking lot there’s a chance there will be cars blocking portions of the mural. I was lucky enough to have gone in the afternoon and found that there weren’t too many cars parked in front.

The neighborhood that this mural calls home is also FULL of really phenomenal street art. I went specifically for the mural and ended up spending a good chunk of time just getting distracted by the plenty of pieces around that caught my eyes.

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Greetings from a city that is just as windy as its title suggests. Two years ago on my first trip @marty.neauble and I came here to see @majorlazer as a belated birthday rendezvous. For someone who does not consider themselves a city girl by any means, I instantly fell in love with this place. . . . There was something about this vibrant, dynamic city that had me looking like the heart eye emoji everywhere I went. On this trip I wanted to dive deeper into all of the street art I got a taste for on my last trip. I wasn't disappointed. I left downtown and made my way to the west side along N Milwaukee Ave through Wicker Park. The murals here are large, the pieces colorful and each one reps Chitown in its own unique way. This piece was my favorite representation of a city that is absolutely making me reconsider city life. . . . Check out more pieces from @greetingstour to see how they perfectly capture each city they leave their mark in. . . . #chicago #chicagoart #mural #greetingsfromchicago #meettheworld #travelwithme #travel #travelblogger #seetheworld #artistsoninstagram #plussizetravelblogger #visitchicago #travelgram #travelblogger

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Wabash Arts Corridor

As you’ve probably gathered by how many times I’ve mentioned it, Chicago has some UNREAL street art. The Wabash Arts Corridor is a worthy contender of checking out if you’re limited to staying downtown. A short walk from Millenium Park, you’ll find countless pieces of art created by artists all over the world.

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Museum of Contemporary Art Chicago

I knew going to Chicago in April could have been a hit or miss weather wise. Which is why I wanted to make sure I had a bunch of indoor options just in case. When I arrived the weather was foggy and drizzling which made for a perfect museum day.

I really enjoyed the collections found at the Contemporary Art Museum. They even have a gigantic cat skeleton. The rooms were really unique and I enjoyed taking shelter there for a few hours.

You can find all of the information you would need for your visit here.

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The Art Institute of Chicago

I LOVE a good art museum and if you’ve been following along on my journeys you know that I often suggest checking them out. The Art Institue of Chicago is certainly not one to be missed. Their collection is unbelievable and home for famous works like, Nighthawks by Edward Hopper, A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat (one of my personal favorites, the detail work in this piece is stunning), American Gothic by Grant Wood and The Old Guitarist by Pablo Picasso are just some of the few pieces you’re going to find while exploring this sprawling building. A must for art lovers!

You can find more information for your visit like hours and admission prices here.

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Ilva Bolotowsky, "Grey Diamond". Oil on canvas

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Are there any free activities in Chicago?

Chicago Cultural Center

The Chicago Cultural Center is a seriously overlooked gem. Directly looking out onto Cloud Gate it’s next to one of the most visited attractions in Chicago but when I went there were few people enjoying all they had to offer.

There are rotating art exhibits and when I went there was a giant Keith Haring mural and pieces done by the super talented artist, Nina Chanel Abney. Her works are thought-provoking, colorful displays of her talent.

The grand ballroom is also worth wandering around if it’s open. The giant dome in the center gleams in this beautifully lit room with giant floor to ceiling windows overlooking Millenium Park.

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Cloud Gate

As tourist infested Cloud Gate is, it wouldn’t be a proper trip to Chicago without stopping by what’s more famously known as, “The Bean.” A highly recognizable landmark, this is what most people think of when thinking Chicago, you’ll also see it in a majority of pictures when looking up the city.

All of this also means that it is constantly swamped with tourist. UNLESS you’re willing to set your alarm a bit early and get there SUPER early before the crowds hit. I did this on my last trip and it certainly worked in my benefit. Although I didn’t leave as earlyyyyy as I intended (thanks to the cocktails at the Flamingo Rum Club the night before) I still went early enough to have just a few people around me.

Which really worked in my favor because as I was wrapping up my pictures and packing up to enjoy breakfast on a bench nearby, I watched as bus after bus just started flooding tourists into Millenium Park. Get there before 8:30AM to be on the safe side and avoid these busses.

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Remember the other day I was talking about symbols of a city? Well here you have it, probably the most iconic symbol of Chicago, commonly know as The Bean but its actual name is Cloudgate. When you think Chicago this is probably what comes to mind. Which means that yes, it is flocking with tourists. Score a less populated shot by setting that alarm early. I may have hit the snooze button more times than I'm willing to admit but I still managed to get there pretty early (in my standards). Which means I snagged this shot right before a bus unloaded 100 high school kids on a city tour. . . . . . . I may have also stumbled upon the fact that it would take 1,415,926,535 bottles of windex to clean it. Wouldn't want that job. 🙅‍♀️🙅‍♀️ . . . . . . #chicagodowntown #chicagoloop #chicagobean #thebean #cloudgate #chicagoriver #millenniumpark #thebeanchicago #meettheworld #cityviews #girlsborntotravel #girllovetravel #fatgirlstraveling #travelwithme #travel #chicago

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Garfield Park Conservatory

This is hands down my favorite place in Chicago. I’m not kidding whatsoever, this is one of the places that I will be sure to visit on every future visit and desperately count down the days until I can go back.

What exactly is the Garfield Park Conservatory you ask? Imagine the greatest display of plants and flowers alike all brought together in a home that is a sensory delight for any crazy plant person like myself. Even if you’re not crazy about plants the building makes for a lovely way to spend an afternoon as you stroll and take in the drastically different scenery that each building provides.

If you’re all about doing it for the ‘gram (hey, I’m not hating, I GET ITTT) then this spot cannot be overlooked. The perfect backdrop for your new post, the greenhouses that make up the conservatory are beautifully designed and stunning.

Oh, and did I mention it’s free? That part is ALSO amazing.

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Let's talk about #solotravel today. 2018 is proving to be the year that I find myself traveling solo most often. I like the independence of walking however slow or quickly I want. Not caring if I just miss the subway or deciding to let the alarm snooze for an extra hour. Going where my heart desires and letting my feet wander until my stomach starts to roar. Perks like never having to wait for a table or getting the entire row on all my flights. . . . . . But sometimes, I miss conversations over dinner and not having to set up my tripod whenever I want to snap a pic. I miss having someone fall asleep on my shoulder during late flights home. I miss watching the wonder of a new place light up in someone's eyes. I know some people are deadset on traveling solo but I find myself a little torn. Independent Chantel is all for it and then social animal Chantel wants to be surrounded by friends after 12 hours. . . . Am I the only one who can't decide which they like more? Let me know in the comments! . . . . . #chicago #visitchicago #girlsborntotravel #girlswhotravel #travel #fatgirlstraveling #solotraveler #garfieldparkconservatory #greenhouse #tourism #travelgram #passionpassport

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Where should book lovers go in Chicago?

Myopic books

Myopic was the first bookstore I ever wandered into during my first jaunt in Chicago back in 2015 and it has imprinted a little home in my heart. A two-story maze of literature both new and used you can spend ages in here. I say that from experience. Their selection is fantastic and you’re bound to curl up in one of the chairs in the upper portion of the shop and find your new favorite.

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The Joe and Rika Mansueto Library The University of Chicago Campus

You know I love a good library. I have traveled all over the world popping in (often times for a free bathroom) and taking in a moment to appreciate how people cherish their books for the community. When I saw the pictures of The Joe and Rika Mansueto Library I KNEW I had to make my way over.

Well, I, 1. Didn’t realize that it was on the University of Chicago campus and 2. I didn’t realize that you needed a student idea to get into the library.

Being the kind, book nerd that I am I made a desperate plea to the woman at the desk to let me check out this beautiful establishment. The woman was HILARIOUS, we were laughing and joking in no time as I made my pure intentions known. Taking pity on me she signed me up for a potential student pass so I could see the rest of the building. She probably had the right idea because as soon as I walked into the computer lab I was ready to start filling out my application for the school.

The bright, modern computer lab is a piece of architecture’s finest in the city of Chicago. A photographer’s dream, this building provides stark lines and deep contrast. It was a really stunning building. I’m glad my homegirl at the desk let me pop in.

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Stony Island Arts Bank

Sooooo, I will admit that I actually never went into the Stony Island Arts Bank. BUT it is VERY HIGH on my list. I tried to go the last time I was in town and was sadly faced with it being closed. I’m still not entirely sure why since it was supposed to be open, I believe it may have been because of construction. Needless to say, I didn’t get to go inside but I REALLY REALLY REALLLLLLY want to.

Another beautiful collection worthy of being admired by any bibliophile this building’s grand display has been making its way around Instagram.

FUNNY STORY THOUGH

When my Lyft dropped me off I went right up to the front doors excited to go in. I was sadly dealt with locked doors so I optimistically thought “Hmm, maybe there’s a door in the back.” Now while there wasn’t a door, there was a nice looking boy who I thought may be able to give me some insight into why the building was closed.

I walked up and kindly asked, “Hey any chance you could tell me if this is where the Stony Island Arts Bank is?”

He was the one that told me that the building was closed for construction. After this, he asks me “Hey, is by any chance your name Chantel?”

Instantly I responded yes and eagerly asked how we knew each other. I then remembered that I’m supposed to be a responsible and aware female traveler so I tried to switch it up and go, “wait, how do you know me?” This was in my failed attempt at being intimidating LOL. It turns out that this boy followed me on Instagram and recognized my jacket from my recent Ireland pictures and is also dating a woman that happened to work with my honey back in Rhode Island.

LITERALLY THE MOST RHODE ISLAND THING TO EVER HAPPEN TO ME. Let me explain a bit more, if you’re from Rhode Island and you talk to anyone who is also from Rhode Island there’s about a 93% chance that the two of you are going to realize that you both have a mutual friend or even relative! Well, I definitely didn’t anticipate this Rhode Island phenomenon to happen to me all the way in Chicago.

It only made sense to invite my new friend to join my plans for the day and together we had a great time. It was some welcomed, pleasant company!

The city of Chicago has so much to offer and worthy of any visitor. There is always something new to do and a new neighborhood waiting to be explored. If you’re a fan of views, a lover of city life, a self-proclaimed foodie, a lover of architecture, a bookworm, an art aficionado or just someone who has never considered a visit to Chicago now is your time. I hope this Travel Guide on What To Do In Chicago is helping you gear up to buy your ticket.

Have you ever been to Chicago? If so, what are your favorite things to do in the city? Let me know in the comments and don’t forget to pin this post so you can take it on your next trip!

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