Chicago, Illinois: The Hidden Gems and the Gluten-Free Vegan Eats You Won’t Forget

Fair warning, this article is going to be a long one! I explored as much of this city as my blister-laden feet would let me. (That is not a joke, please for the love of feet, DON’T forget your shoe inserts for your boots–those boots everyone sings are for walking–will destroy your feet without them.)

If I had to say, Chicago, IL is probably the most anticipated place I’ve ever wanted to travel. There are so many friends I’ve had that lived here at one point and they all raved about it, so I’ve always wanted to know what all the hoo-ha over this place is about.

Moving here was never an idea, so there were a few specific reasons Chicago made the #1 spot on my travel list. First of all, Arizona doesn’t have the awe-inspiring, expansive downtown that this city has. It’s huge, the buildings are sky high, and there is literally an endless list of things to do. Patio bars, lake activities, shops, restaurants, bars, comedy, art, museums, parks…the list goes on and on!

Of course, as I mentioned, I was also interested in the midwest gluten-free vegan cuisine. There was plenty of that, and let’s just say, Taco Tuesday will never be the same after the tacos I had downtown. (More on that later.) Finally, I was thrilled to explore the Graphic Design scene as Chicago is one of the top design hubs in the US. I got the opportunity to meet with two amazingly talented designers during my trip.

Touristy Landmarks & Things To Do

The shiny bean: (FREE)

This ranked top of my list for landmarks to see. Don’t even try to tell me you wouldn’t want to take a selfie in the most giant fish eye “mirror” you’ve ever seen. What’s the point of a giant shiny bean you may ask? Who knows. You mustn’t question giant, shiny art. That’s all I have to say.

Buckingham Fountain: (FREE)

A giant, multilevel fountain with beautiful changing lights at night. I saw it both day and night, and must say that the nighttime aesthetic appeal is far greater than with the daylight. The pictures really didn’t do it justice. You’ll find couples walking hand in hand, little kids laughing and playing…it’s storybook. Plus, I happened to be a part of a (most likely illegal) “bucket list” item of two young adults. They needed a photographer for their split second dunk in the fountain.

Sears Tower (Willis Tower) Sky Deck: ($20)

Are you up for a thrill? If so, you’ll want to set aside some cash to sail 103 stories up in an elevator, under a minute. Watch for those popping ears, that’s a lot of altitude to gain in such a short amount of time. The 360 view of the city is absolutely phenomenal. You can walk around as long as you’d like, too, so take it all in! The day I went was stormy/cloudy so visibility was low. Make sure to go on a sunny day for the best experience. Although, nothing beats being “in” a cloud; that part was stellar! I’d be lying if I told you the view was my favorite part, though. The best part of this experience is the clear glass “Sky Decks” that extend a few feet out from the building. Pose 103 floors above nothing but air if you dare! The gymnast in me never dies, so I frightened the whole crowd by doing a handstand. Boy was that horrifying. -_- And I’d do it again in a heartbeat!

Navy Pier: (FREE)

Make sure to head out to Navy Pier for some more amazing views. You’ll feel the “awe” factor as you realize that all that rippling water is indeed a lake; Lake Michigan to be exact. I definitely found myself asking how that could actually be a lake when you can’t see the other side. On Navy Pier, there are shops, arcade games, and of course, the giant Ferris wheel. Also, a variety of boat tours dock here (for cost.)

Lincoln Park Conservatory: (FREE)

This (incredibly humid) greenhouse was filled with more varieties of plants than I’ve ever seen in my life. A few of my favorites included the Alligator Fern, Spiral Ginger, and Croton (pictured.) Most importantly, did you know that there are hundreds of types of Orchids?? This native Arizonian didn’t. There are so many, in fact, that there was an entire room devoted to JUST orchids. WOWZA.

Pilsen Neighborhood: (FREE)

I absolutely loved this neighborhood for all the street art. The artist in me rejoices to see “graffiti” that brightens a neighborhood instead of defacing it. The artists that decorated the walls and buildings here spent obvious time and thought into the colors, design, and placement of each of these inspiring pieces.

Michigan Avenue/”Magnificent Mile”: (FREE)

Shops, huge department/retail stores, sights, people. There’s just about everything you’d ever want on the Mag Mile. It’s hard to make this mile long stretch of pure enjoyment a single part of your day, so plan on leaving a day just to walk in and out of shops, grab lunch and/or drinks, and people watch. Best of all, the shiny bean, Buckingham Fountain, and Navy Pier are very close by, so it’s easy to hit all these stops in the same day. I absolutely loved feeling like a little part of the buzzing city with ominous buildings on either side. It was hard to resist blowing my life savings in all the great stores, too. Not to mention, your pick of cafes and 5-star restaurants on every corner.

The “L” train: ($varies)

Also known (to me) as the most complicated and confusing rail system ever, the L is a network of trains that expand across the city in all directions. Locals will be happy to admit it took them months or years to get used to these trains and how they work. I’ll be happy to admit that I was always lost when getting on or off a train. I asked people for help constantly. All that confusion aside, you’ll test your sense of direction and enjoy more of the city by using the L. It’s a fast and convenient way to get to all corners of Chicago. The more I got lost, the more of this awesome city I got to explore.

Bobby’s Bike Hike: ($32-65; varies)

Great way to get around the city. You can rent a bike for a few hours, half a day, or the full day. Make sure to reserve a bike online ahead of time for a discount and so you’re guaranteed a bike the day you want it! I rented a month in advance, but it helped that I wanted one on a Tuesday, not the weekend. Personally, I wanted to do my own exploring, but there are also guided bike tours if you’re not feeling so bold. When it comes to downtown biking, I was almost always scared for my life. Unlike Arizona, bike lanes are not common, and it is illegal to ride on the sidewalk. You must be with traffic, and they WILL drive within inches of you at all times at high speeds.

It was a thrill, and a terror at the same time. I tried giving cars their own extra room at all times, which prompted a “Well aren’t you cute. Screw that guy” from a friendly biker who passed me as I was giving up my right of way (read: trying not to die) to an apparently undeserving cab.

Anyway, this trusty bike (named Stumpy) took me all over downtown from restaurants to the shiny bean, Lincoln conservatory, Magnificent Mile, Michigan Beach Path, and everywhere in between. My legs were gluten-free noodles by the end of the day. I’d give Bobby’s Bike Hike 5 stars for the quality of the bike and customizable experience. (They also have plenty of options for kids!)

Gluten-free Vegan Food

Chicago Diner: ($9-15+)

3411 N Halsted St, Chicago, IL 60657


Located in the Wrigleyville neighborhood, this quaint little diner will take you back to the 60s. Red table tops, big clock above the food window, neon signs, and a juke box. Best part? It’s 100% vegan with tons of gluten-free options as well. I chowed down on a Portobello Truffle Melt with GF bread. It was loaded with marinated mushrooms, arugula, tomato, onions, Teese® Vegan Mozzarella, and a nice spread of white truffle aioli.

You get your choice of a side and I went with my favorite, sweet potato fries. I’d like to report a happy experience with this sandwich, but it can best be described as less than “blah.” I loaded the thing with salt in an attempt to bring out any flavors at all, with no success.

Plus, the vegan cheese did an extreme disservice to the poor sammich. Even the sweet potato fries would have benefited from some type of seasoning. I would love to give this adorable diner another shot, but this first experience was enough to keep me from returning.

Karyn’s on Green: ($8-16+)

130 S Green St, Chicago, IL 60607


This is where I found the best tacos of my entire life. Five stars, right away for this sensational dish alone. Past that, the whole menu is vegan, there are gluten-free options (plus soy free, nut free, and raw options), the ambiance was pleasant, and service was delightful.

A big, two-story window expands the length of the street-facing wall giving a great view outside. (It happened to be pouring when I was there, so that was the only way I’d be excited to experience that type of rain. It would have been a different story if I was outside riding Stumpy still.) Distilled water is poured from glass jars and you have the option to drink from a selection of wine and spirits, too.

So back to the tacos. These heavenly, heavenly tacos. “Chicken” Fajita Tacos to be exact. Delightfully seasoned soy “chicken” with peppers, onions, fresh pico de gallo, guacamole wrapped up in corn tortillas. Natural cut french fries accompanied these tacos and there was even homemade ketchup for dipping. I also took advantage of my first vegan ranch in almost a year. FREAKING YUM. Even if you’re not vegan, go here. You won’t be sorry.

Karyn’s Cooked: ($10-15+)

738 N Wells St, Chicago, IL 60654


It is probably obvious by the name, but Karyn’s Cooked is a sister restaurant to Karyn’s on Green. (There is also Karyn’s Raw, but I didn’t have time to enjoy that one.) For whatever reason, the Mexican food options were really striking my fancy on this trip, so I ended up getting the Flautas here.

A tofu and carrot mix were stuffed inside a corn tortilla and fried for a crispy, palette pleasing entree. They were also topped with a soy sour cream and a scoop of homemade guacamole. Mix and match the greens, pico de gallo, and black beans on the side however you’d like. Five stars to Karyn for another hit restaurant, also downtown.

The Grand Lux Cafe: ($10-18+)

600 N Michigan Ave, Chicago, IL 60611


First of all, I’ll note that this was more of an experience rather than a gluten-free vegan restaurant. If you call ahead for a reservation, you won’t have to wait over an hour to get a seat next to the window, which overlooks Magnificent Mile. Either way, it is worth it to sit by the window so you can people watch and take in more of the delight that is Chicago downtown.

After a mildly intense back-and-forth with my waiter about what was okay for me to eat with my allergies, I went with the Chili-Lime (Chicken; substitute grilled tofu) and Mango Salad. All the aforementioned “option sorting” this was such an unexpected treat to my taste buds. The chef did a corn meal crusted grilled tofu with mango, avocado, jicama, corn, onions, cilantro, mixed lettuce, and a citrus vinaigrette on the side. For whatever reason, their chili-lime vinaigrette wasn’t gluten-free or vegan (not sure which.)

Don’t come here expecting extensive knowledge from the staff about food allergies. It was like pulling teeth to get definitive answers. That being said, the salad was exquisite and overall atmosphere of this restaurant very appealing. It is also worth noting that a piece of bleu cheese ended up in my salad, which caused a painful migraine later, so beware when dining here if your allergies are extreme.

Native Foods Cafe: ($8-11+)

218 S Clark St, Chicago, IL 60604


It’s always a good start when the staff is just as excited as you are to try out their restaurant for the first time. (And I’m not talking about the owner, either.) My cashier was happy to help me find a delicious entree, and stayed patient with me too, even though they were closing very soon. For my first time visit, I even got a complimentary fresh watermelon mint juice.

I decided on the Sesame Kale Macro Bowl. It had grilled tempeh on a bowl of steamed kale, brown rice, ginger sesame sauce, sauerkraut, and toasted sesame seeds. Plus, a small side of cucumber seaweed salad. At first, they forgot the ginger sesame sauce, which I can admit is what pulled this otherwise bland bowl together. I am super partial to tahini and ginger, though.

All in all, it is very reasonably priced, and the portions are nice and big. I ended up taking some back to the hotel with me.

So there you have it! Chicago in a nutshell! This is my longest article yet, so if I forgot something important, please leave me a comment below. Or better yet, shoot me an email.

Share this: