DIY Chicago Food Tour

Chicago Skyline

I don’t eat to live, I live to eat….and I can’t think of a better place to do that than in Chicago.  If you google Chicago food tours, you will be amazed at all the different food tours out there.  But why pay someone to take you around Chicago to eat when you can DIY and save some money?  In addition to spending money for a food tour guide I always wonder, is that really the best thing to eat, or is that what the tour company is being paid to promote?  All of the food items that have become a part of this tour are honest-to-goodness what I feel to be THE BEST things to eat in Chicago based on the innumerable goodies that have ended up in my belly, not from any money that has ended up in my wallet.

So, you might be wondering what my credentials are and why you should be listening to me right now. All I can say is, if universities gave out degrees in food consumption, I would have several Ph.D.’s under my belt. You can call me doctor, Dr. Bolin. So how did I earn these degrees? Well, while I live in Arizona, I have been fortunate enough to spend the last 3 summers in my most favorite city in the world, Chicago. And during that time I have eaten at over 150 different food establishments.

So, where do I start? Well I guess that depends on how many days you have here. I could fill up your entire calendar with yummy deliciousness, but I’ll just focus on a single day. Because for one, maybe you have a very short stay, or two, and probably more likely, you’re not as crazy as me where you plan your entire trip around eating.

So what’s the key to being able to spend your entire day eating without gaining a bajillion pounds? That would be….no cabs, no Uber and no Lyft to get from place to place. You must use your own two feet; you can walk or take a bike. Didn’t pack your bike you say? No problem, take a Divvy bike.  And another bonus to using your own two feet? When you spend your day walking or biking from place to place, you get to see much more of this beautiful city.

Warning: the food you are about to consume is super yummy and not part of a healthy diet.

Breakfast (budget-friendly @~$3)

Doughnut Vault
Doughnut Vault – Photo by Kari Skaflen

Donuts! Once you’ve tasted a donut from one of Chicago’s artisanal donut shops, you’ll be saying Dunkin who?   As far as I am concerned there are 4 big players in the downtown area. Doughnut Vault, Stan’s Donuts, Firecakes and Do-rite Donuts. Depending on what “best donut” list you are reading, you will find each one of these will take a turn in the #1 ranked spot.

My personal favorite is Doughnut Vault, specifically the Franklin location. It literally looks like a vault on the inside, and is the size of one too. When you go, I hope you don’t want to sit down inside to eat your donut, because it’s standing room only at this joint. About 8 people fit inside at any one time and like a trendy nightclub, people can only get in as other people come out. And get there early! Like at least 15 minutes before they open because there will already be a line forming and unlike other donut shops which bake and stay open all day, this place closes up shop as soon as they sell out of their freshly prepared batches, which is usually well before noon! They have roughly six “standard” donut flavors and then a rotating special each day. If you can only get one, I recommend the vanilla glazed. It’s a simple, raised donut, but done to perfection.

Breakfast (spend a little more @~$13)

Have a little more money to spend, or simply want a larger, more nutritious breakfast? Then look no further than Wildberry Pancakes and Café.   It is THE BEST breakfast joint in Chicago. Not only is the food superb and you get a lot of it but it’s also inexpensive. You know that saying, all good things come to those who wait? Well get there early, or you will certainly be waiting (up to an hour or more) for that good thing called Wildberrys. Your best bet is to go on a weekday if you can (slightly shorter lines than the weekend), but even on a weekday (especially in the summer) I still recommend getting there no later than 8:30 am. At that point you will likely have only a 15-30 minute wait.   In a hurry? Download the Nowait app to see the current wait times and get your name on their list before you even leave your hotel.

Signature Berry Bliss Pancakes
Signature Berry Bliss Pancakes

OK, so you have made it inside, now what to eat?   My biggest dilemma when I go to breakfast is always, do I want pancakes or eggs? Eggs or pancakes? Well guess what, here you can have your eggs and eat pancakes too!  The egg dishes come with your choice of toast or pancakes. Whaaaat??? Yeah, you heard that right, free pancakes included with your meal! And not only that, but for a mere $1.50 extra you can upgrade to their specialty pancakes. My absolute favorite are their Signature Berry Bliss pancakes. These fluffy buttermilk pancakes are topped with fresh berries, vanilla anglaise, blackberry coulis and berry mascarpone cream.   My mouth is watering just thinking about them. And if for some crazy reason that doesn’t sound absolutely delicious to you, I also highly recommend the banana cream pie or cinnamon roll pancakes. As far as egg dishes go, my two favorite are the homemade corned beef hash for $10.50 and the Napa Valley fig omelet for $12.00. If you like coffee, you’ll love theirs. They serve intelligentsia coffee, soooo much better than Starbucks. Sorry Starbucks lovers.

Lunch (budget-friendly @~$5)

Chicago Style Hot Dog
Chicago Style Hot Dog

It’s hard to say what Chicago is better known for, its hot dogs or its pizza. Either way, you really need to try both while you are here. So hopefully you are visiting for more than 1 day or you have an extra-large belly. As far as hot dogs go, you’ll definitely want to hit up Kim and Carlo’s hot dog stand at Museum Campus, just east of the Field Museum. Not only do they have delicious dogs, but you can’t beat the views of the skyline from the campus, nor the bike ride up the lake to get there.

When you go, get the Chicago style dog ($4). That’s right, the Chicago style dog, with good ole fashioned Vienna beef. I don’t want to see a turkey dog in your hand or any other shenanigans like that.

What’s on a Chicago dog you ask? It’s topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices, sport peppers and a dash of celery salt all on a poppy seed bun. But the more important question might be: what’s NOT on a Chicago style hot dog? That would be ketchup. Don’t ask for it. Just. Don’t.

Kim and Carlo’s can be a hefty walk if you’re staying in the loop or anywhere north of the loop, so a Divvy bike is the best way to get there.   Not only do you get some much needed exercise, but you get to ride along Lake Michigan the entire way there. It doesn’t get any more beautiful than that folks.

Blaze Pizza Assembly Line
Photo by Blaze Pizza

Now on to pizza. The big question here is: deep dish or thin crust? Well, for the budget-friendly option, you don’t have to think much because deep dish is not an option at Blaze Pizza. But that’s not a bad thing.   Their thin crust pizzas are cooked to perfection at the Blazing fast speed of 180 seconds. A die-hard Chicago pizza fan, I was very skeptical of this “fast food” pizza joint which had a similar feel to subway – walk down the line, pick out your ingredients and watch them be added to your pizza as it’s passed down towards the oven.  But it came highly recommended from an acquaintance, and at a price of $5 for their simple pie (mozzarella, parmesan, red sauce, sea salt & oregano) it wasn’t going to be a huge loss if I didn’t like. So I decided to give it a try and to my surprise, not only did I like it, I loved it! When I’m in the mood for pizza and don’t want to wait 30-45 minutes for one to arrive at my table, I head over to Blaze Pizza. Fast, cheap and super tasty…you can’t beat that combo. Oh yeah, and if you download their app before you get to the cashier, you get a free drink that you can use on your current visit.

Lunch (spend a little more @~$20)

deep dish pizza art
Deep dish pizza OR work of art? You decide.

Now, if you want to experience one of Chicago’s more famous pizza joints with a Chicago deep dish pizza, there are several to choose from. Just like the donut shops, there are some big players whom, depending on which “best pizza” list you read, will all appear in a #1 ranked spot.  Pull over a few Chicagoans while you’re walking down the street and ask them their favorite pizza place and you’ll likely get 3 or more different answers. There are tons of really good pizza places in Chicago but most people would probably agree that the big players are: Giordano’s, Lou Malnatti’s, Pizzeria Uno, Pizano’s and Gino’s East. Now, my personal favorite is Giordano’s and truth-be-told, I’m actually more of a thin crust lover than a deep dish one, regardless of the pizza joint. But, the primary reason I like Giordano’s better than the others is because of the crust. Lou Malnati’s, Pizzeria Uno and Pizano’s all have a buttery crust. In my opinion, the pizza tastes too rich when you combine a buttery crust with all that cheese. But a lot of people love their buttery crusts, so if that’s your jam, go for it.  Of those three, I would recommend Pizzeria Uno’s deep dish, either the Chicago Classic (sausage) or the Prima Pepperoni. But beware, if you really want a thin crust pizza, you can’t get it at Pizzeria Uno, they only serve deep dish.   All the other pizzeria’s I’ve listed serve both thin and deep dish.  And if you’re looking for something to read while you wait 45 minutes for your deep dish pizza to bake, check out the history of the Chicago Deep Dish pizza.

Afternoon Snack (budget-friendly @~$5)

Garrett Mix
Garrett Mix

When you’re walking down the street and suddenly the smell of sweet, buttery caramel corn flows over your entire body and you think the doorway to heaven has opened before you, take a closer look and you’ll see the sign on the door actually reads Garrett Popcorn Shops.  They have several different flavors and you can sample them all, but I recommend the Garrett Mix (a small bag will be plenty) – it’s a combination of their sweet caramel crisp and savory cheese corn.  The mix is great because after you bite into the sweet caramel corn and your taste buds are saying, “Mmmm, now let’s taste salty”, you can switch to the cheese corn and then when they say, “Mmmm, let’s taste sweet again”, you can switch back to the caramel.  And then you can switch back to the cheese and then back to the caramel and then back to the cheese and then back to the caramel and then….oh wait, the bag is empty.  Good things come in small packages.

Oberweis ice cream - scoops of apple pie and chocolate peanut butter in a waffle bowl
Oberweis ice cream – apple pie and chocolate peanut butter

Ice cream.  Hopefully you’re here in the summer so you can enjoy these frosty treats.  If you’re feeling ambitious, head out to Oberweis Ice Cream and Dairy Store at 3055 N. Sheffield Ave.  It’s the one place I’m going to let you take public transportation to (one way that is).  Hop on the Red Line towards Howard and get off at Belmont.  You’ll have a 3 minute walk from there.  Oberweis has been around since 1915.  They serve farm fresh milk out of glass bottles and the freshest, creamiest ice cream you will ever lay your tongue on.  My favorite flavors are chocolate peanut butter and apple pie (a seasonal flavor).

Rainbow cone from Navy Pier in Chicago
Rainbow cone from Navy Pier

Take a Divvy back – because you need to make room for dinner.  You’ll have some side streets to ride on as you head east towards the lake, but once you hit the lake, enjoy your 25 minute bike ride south, with the cool blue lake to your left and the sparkling Chicago skyline right in front of you.

If you’re not quite up for trek out to Oberweis, you’re in luck because Rainbow Cone just opened a location at Navy Pier.  While they can’t compare to the Oberweis quality (no one can), the rainbow cone is not to be missed.  Five, yes count ‘em, five flavors of ice cream are found on the rainbow cone – chocolate, strawberry, palmer house (New York vanilla with cherries and walnuts), pistachio and orange sherbet.  Try one; your mouth will thank you.

Afternoon snack (spend a little more @~$24)Remington's Menu

If you’re looking for a snack that is a little more savory because you don’t have a sweet tooth, or five like me, then head over to Remington’s on Michigan ave.  It’s a great place to sit outside, enjoy the weather and people watch.   Their Moscow mule is especially refreshing on a warm summer afternoon, as theirs is made with ketel one orange vodka, which gives it a nice citrus flair.  And the best thing to pair with a mule? A lobster of course, lobster deviled eggs that is.  I don’t like lobster (yes that’s right, a girl who doesn’t like lobster) and I don’t like deviled eggs, but for some reason I just love these lobster deviled eggs.  Who says two wrongs don’t make a right?


I’ll never forget the time my husband and I were on our way to dinner when we were stopped by a couple who asked us if we knew where TGI Friday’s was. My mouth agape, I stood there stunned, unable to speak. I don’t understand the question. My brain is trying to process….TGI Friday’s? Chicago? You want to go to a TGI Friday’s while you’re in Chicago? Is that what I just heard? No clearly you must have miss-spoke. I wanted to take them by the shoulders, give them a little shake and say “you’re in Chicago man, pull it together!”

The array of restaurants which lay before you is astounding. Chicago is home to numerous James Beard award winners and Michelin starred restaurants, so how does one choose a single restaurant to recommend? It’s hard, I’m sweating bullets here.

Breakfast recommendations are easy, it’s a choice of eggs, pancakes, french toast or waffles, everyone’s got it on their menu, and lunch is easy because you’re in Chicago so of course you have to try hot dogs and pizza. But dinner, that’s a whole other beast. Do you want Steak? Seafood? French? Italian? Mexican? Asian? Irish?….and the list goes on. I could write an entire article on a single cuisine type alone, and a novel on all of them together, so to make one single recommendation…boy that’s a lot of pressure. And I’ve cracked, I can’t do it. I can’t make just one recommendation; there are too many variables. So, I’m going to lay out a few options and let you choose.

Option One – Open up that wallet

Everest Chicago
Photo by Everest

My top two ranked restaurants are: No. 1 Everest, No. 2 Sixteen.  Both are very expensive (~$150-$250 per person) and both offer a tasting menu. In addition to a tasting menu, Everest also has the option to order a la carte, but don’t do it. You definitely want the tasting menu so you can experience an array of flavor profiles. Sixteen offers a 4 course selection and an extended chef’s selection, which ended up being 16 courses and took us two and a half hours to complete. If you are planning to get the 16 course menu, arrive hungry.

Sixteen Chicago
Photo by Sixteen

Everest resides on the 40th floor of the Chicago Stock Exchange, while Sixteen resides on, yes you guessed it, the 16th floor of the Trump Tower. With expansive glass windows, both offer breathtaking views of Chicago. Everest presents a panoramic view of the city while Sixteen offers a more up close and personal view.  As far as ambiance goes, both are wonderful, it’s really just a matter of your personal preference.

While I have ranked these as my number 1 & 2, I would like to mention that I have been to each of these restaurants only once, so it is very likely that they could pull a switcheroo in exactly who finishes in first and second place upon subsequent visits. But regardless of who ranks first or who ranks second, I don’t think you could go wrong with either one of them.

Option two – Easier on the wallet

The windy city is home to some great steakhouses, so if you’re more of a meat and potatoes type of guy or gal then you’re in luck.  So far I have eaten at 25 different steak houses downtown and I have two favorites. I frequent them both often and depending on my mood, I might choose one over the other on a particular night.

STK Chicago restaurant interior
Photo by STK


Both have gorgeous interiors. STK Chicago can be described as modern chic while Prime & Provisions would be vintage opulence.  Prime & Provisions hosts a cigar bar while STK is outfitted with a DJ to spin music.


Both restaurants have an outstanding salad. STK’s shaved brussel sprout salad is A-mazing. I have never liked brussel sprouts, yet I love this salad. After eating this salad I thought, “ok I guess I love brussel sprouts now”. Um, nope. I tried them back home in Arizona, and like a five year old I was pushing them to the side of my plate so they weren’t touching any of my other food. STK’s brussel sprout salad is definitely large enough to share, if you want to that is.

Prime & Provision’s pickled purple cauliflower salad is another winner. I’ve never been a fan of cauliflower, but this salad is awesome. How do you do it Chicago? How do you make me like food I have never liked before? This salad is not quite as large as the brussel sprout salad from STK, but it is still shareable.


Prime & Provisions
Photo by Prime & Provisions

Prime & Provisions’ signature cut is their dry-aged, center-cut porterhouse, which comes at a per person price. It’s excellent. The only caveat to this dish is that because it’s a single cut of meat, everyone who is sharing should like their meat cooked to roughly the same temperature. On the plus side, the steak is served on a 600 degree plate, and because it comes pre-sliced it’s easy to leave several pieces on the plate to cook a little longer for those that want it.

My favorite steak of all time can be found at STK and it is the 16 oz. sirloin. For my entire adult life, I have been a filet girl, but then I discovered sirloin. It has so much more flavor than a filet, but is much leaner than a ribeye, making it the perfect cut of meat. Sure it’s not quite as tender as a filet but the flavor profile cannot be beat. It’s hard to find a sirloin at most steakhouses, and even harder to find one that is done right and that’s why STK is my go-to place for sirloin.


I’ve tried the creamy yukon potatoes at STK. Creamy should be in all caps, underlined and bolded on the menu. Too much butter for me, and I’m a butter lover. I’ve also had the parmesan truffle fries. They are cooked well, crispy on the outside with lots of moist potato on the inside, but I’m not a truffle lover and these were truffle city. So if you love truffles, get the fries and you’ll be happy.  I’ve also had the mac n cheese, which is a solid performer – very flavorful cheese with the noodles cooked just right, not mushy like I often get at other restaurants.  Also, the asparagus is good, but it’s asparagus… nothing too exciting there besides some interesting smelling pee at the end of the night.

I’ve had similar sides at Prime and Provision’s. I enjoyed their properly whipped potatoes with a horseradish parmesan crust. The baked potato on the other hand was not very good, it tasted water-logged. Maybe it was an off-night, but I’ve been hesitant to try it again.  If I do, I’ll be sure to update this guide.  Their decadent mac n cheese is indeed decadent, and it’s really hard to say which steakhouse has the better mac n cheese, they are both delicious. The sautéed spinach was good but again, like asparagus, not that exciting.


Ah yes, my favorite part of the meal. When we sit down at a restaurant and the waiter hands me my menu, the first section I always look at is the dessert menu. And when the dessert is not listed on the main menu, but instead is found on a separate smaller menu that they bring you after dinner, I get really grumpy.

I have actually been known to order and eat my dessert before dinner. Sometimes that dessert sounds sooo good that I know I won’t enjoy my meal because all I will be thinking about is that dessert. So I just have to get it out of, or rather into, my system. I know, I have a real problem.

Overall, I wasn’t too impressed with the desserts at STK. I’ve tried the banana cream pie in a jar: 3 out of 5 stars. I’ve had the warm baked cookie with ice cream and felt it was not good enough to be worth the calories: 1 star. And I’ve had the ice STK, which is 3 mini ice cream cones each a different flavor: 3.5 stars.  I think their best “dessert” actually comes in liquid form as their strawberry cobbler martini, very yummy indeed.

Now, Prime & Provisions, they know how to do dessert.  If I could recommend only one dessert to try in all of Chicago, it would be their tableside smores.  I know, I know, you’re probably saying, “you mean those things I ate as a kid around the campfire”? Yes, those are the one, but Prime and Provisions has taken campfire smores to a whole new level. I don’t want to ruin the surprise, so I’m not saying anything more other than, get it! Even if you don’t go to Prime & Provisions for dinner, stop in there for the smores.  Even if you don’t like smores, get it! You know how I didn’t like lobster or deviled eggs or brussel sprouts or cauliflower, but Chicago made me love them? Well I bet the same thing would happen with you and their tableside smores. I take every single guest that visits me in Chicago on a trip to Prime and Provisions for their tableside smores. But if you are really gonna fight me on this one and simply refuse to listen to me, then I have another option for you. Try the tequila lime icebox cake. It’s phenomenal. It tastes like an extra tart key lime pie but is frozen like ice cream. It’s very refreshing. But get the tableside smores.

Fried oreos from Taste of Chicago

By now you are taking your last bite of your tableside smores and you realize your Chicago food tour is coming to an end.  You’re starting to feel sad.  Yes, I know the feeling.  In times like these I like to remind myself of a quote from none other than Dr. Suess – “Don’t cry because it’s over, smile because it happened”.  Just make sure you don’t have any chocolate in your teeth first.