Chicago in a weekend: Our Guide for Where to Eat

One of the (many) reasons for traveling to places where we haven’t visited before is to try out the local restaurants and experience the food. When we travel, we make an effort to not eat at the same location twice, and also not visit some where that we have back home. When we were recently visiting Chicago over a weekend, we couldn’t wait to try as much food as we could get our hands on. Having been centrally located on E. Wacker Drive, the majority of places we ate at were within walking distance of our hotel (with the exception of restaurants on the Navy Pier). We’ve created a short list of restaurant recommendations that we experienced and enjoyed during our stay in Chicago to share with you! If you’ve ever visited any of the restaurants on this list, we’d love to hear about your experience!

Without further ado… Chicago in a weekend: our guide for where to eat:

For Breakfast:

Corner Bakery Cafe:

This location was on Wacker Drive, and just a few steps down from where we stayed (Wyndham Grand) while we were in Chicago. The Corner Bakery Cafe was slightly different than what we were used to, in that instead of being seated/order food/eat/pay, you kind of did the opposite. Upon entering, (we must have looked like out-of-towners), the hostess directed us to stand in line to order and that she’d seat us after while we wait for our food. So, that’s what we did – we ordered, paid for our food, served our own beverage (coffeeeeeee), and were then seated. I guess that it isn’t a bad idea, as the restaurant was definitely busy – just…different. But it worked – and the food was quite delicious!




The Corner Bakery Cafe is a great place to grab a quick breakfast, but make sure you go early to beat the lines – it’s quite a popular venue! Pricing is average for the food and serving size. We certainly enjoyed it!


The Billy Goat Tavern:

Having arrived in Chicago mid-afternoon, we were at the point of being hangry (it was that extreme) so it was time to get the fastest, most delicious food we could without having to eat at a fast-food chain like McDonalds or Burger King. We found an information desk and asked where a good place to eat nearby was, and he kindly informed us about The Billy Goat Tavern. Intrigued, we followed his directions…down below the city… It was as sketchy as you think it’d be – we literally went down into the depths of Chicago via a staircase that we couldn’t see to the bottom of. But like I said – hunger was the deciding factor in this case. As it turns out, our stomachs made a good decision, because The Billy Goat Tavern ROCKS! We were greeted at the door and asked what we wanted. Having admitted that we’ve never eaten there before, the lady who greeted us told us to get the “CHEEZBORGER! You want doublecheez!” – it wasn’t a question, it was what she had the chefs make for us. But it turned out to be DELICIOUS, so it’s all good. Once receiving our “cheezborgers”, we were directed to a counter where we could add our toppings of mustard, ketchup, pickles and onions, if we so chose.





We highly recommend checking this place out if ever you’re looking for a good, greasy “cheezborger” for cheap! (And, don’t be intimidated by the location. All of the best places look a little rough around the edges!)


If you’re on the hunt for traditional, Chicago-style, deep dish pizza, Giordano’s is where you want to go! The location we went to was at Navy Pier, and the line-up was HUGE, and then there was an hour wait once you put your name on the waitlist for a table. Pro tip: once you put your name on the waitlist, you do have the option of pre-ordering your pizza right then and there. It will save you even more wait time, so we highly suggest that you do this step. Once we finally got in (we spent our time waiting by wandering around the pier, so it didn’t feel that long) we were seated and waited for our order of the deep dish Chicago classic – pepperoni, mushrooms, green peppers and onions. We decided on a small, and were SO glad that we did. It was so massive that we couldn’t finish it all and ended up taking it back to our hotel with us.



To be honest, this pizza was probably the most delicious that we’ve ever had. We’d go back here again and again. The price is right, considered that the serving sizes are MASSIVE. Definitely worth a visit if you’re in Chicago!

America’s Dog:

Alongside with the traditional must-eat pizza, you for sure have to try a traditional Chicago-style hot dog on Navy Pier! We visited America’s Dog and it did not disappoint. It was set up as a standard food-court, walk-up type, but our orders came out fast, and were so delicious.


If you’re ever in the mood for a quick bite to eat in between your…escapades (ha!)… we definitely suggest a stop here! It’s inexpensive and takes no time – great for on-the-go types!


The Purple Pig:

Okay, where do we start with this one? The Purple Pig is a tappas style restaurant was recommended to us by the same guy who suggested The Billy Goat Tavern. It specializes in cheese, “swine”, and wine, with other fantastic dishes as well. One thing to note here is that it does not take reservations, so be prepared to wait, as this place is very hard to get into without having to wait. When we decided to dine here, we had our name added to the waitlist and went for a stroll down the magnificent mile to kill some time and see the sights. Once we came back and were seated, the wait staff were lovely. Because we hadn’t previously visited this style of restaurant, they explained the menu, and helped us pick out a wine to suit our taste preferences. Keeping in mind that all dishes were meant to be shared, we tried to get a bit of everything (some of which we ate before remembering to take a photo – whoops!):


The Purple Pig was a great experience overall. Very fancy, gourmet dishes. Excellent staff. The price point was higher, but worth every dollar. You should definitely check this place out if you’re going to be in the city, and have an appreciation for masterly crafted cuisine!

Mercadito / La Mez Agave Lounge:

Last on our list, but definitely not least, is Mercadito/ La Mez Agave Lounge. Originally, a friend of Alicia’s had suggested Mercadito, as she and her husband had been and loved it. Always interested in dining suggestions, we decided that Mexican cuisine would be a great idea, and we’d have our last meal in Chicago there. Unfortunately, we didn’t think to plan ahead (we were in a bit of a pizza coma at the time of planning) so we failed to make reservations. We had decided to walk down to the restaurant around 8:30, hoping it would be a bit less busy, but it was actually quite the opposite upon our arrival. Being waitlisted (again – learn from our mistakes, friends!) the hostess had suggested that if we wanted to go down to the “bar” downstairs, we could have a few drinks down there while we wait for a table to open up. The hunger had hit, but we decided to wait for a table at La Mez, beneath the ever-popular Mercadito. Turns out, it was a fantastic idea. We ordered (very expensive) drinks at the bar and enjoyed them while talking with our bartender, she passed us a menu to look over – they served the same food downstairs as they did upstairs. She had informed us that there was a group of people who were about to pay and as soon as they left, she would save the table for us so that we could place our order. Finally being seated, we dove right in and got guacamole and delicious salsa verde. For our main dish, we ordered tacos (because duhhh). Shrimp and carne tacos, to be specific!


Mercadito, and more importantly La Mez Agave Lounge has DELICIOUS Mexican food. We would go back in a heartbeat. The prices were pretty average, considering the quality and food portions, and the atmosphere was a lot of fun! We definitely recommend it…but do yourself a favour and MAKE RESERVATIONS!

–The Calkins’

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