SkinnyPig Travels: Chicago, IL (What To Do & Eat)


I finally visited Chicago! This has been on my list for ages, and it took me 34 whole years to get there. Crazy, I know.

The attraction of Chicago (for me) was actually the same reason I stayed away from it for a while. Hear me out. As a New Yorker, I’m drawn to places that are different, and everyone says the same thing about Chicago: great city, great food scene, lots to do! And you know what else is like that? New York City.

So…I guess you could say I never felt the need to rush there. But after many years of food blogging and constantly hearing about the food, I decided it was time to go. The verdict? LOVED IT. If I had to live somewhere else for a bit, it would probably be there. Just not during the winter because it sounds worse than NYC and I can’t even imagine that.

I stayed at The Godfrey Hotel, courtesy of HotelTonight, and once again they came through in the clutch with a fantastic option at a solid price. Big room, friendly staff, and super convenient location just a couple blocks from Portillo’s (famous for their hot dogs and Italian beef sandwiches). Highly recommend. Oh and the rooftop in that hotel was BUMPIN. Every. Single. Night. It’s apparently a big deal.

Below is a list of what I did/where I went in Chicago. Mimic this itinerary (at least for the food) and you won’t be sorry. I’m sure there’s also plenty I missed, but that’s just a good excuse to go back.

What To Do & Eat: Chicago, IL

  1. Portillos – I was STARVING when I got off the plane, so I literally went to Portillo’s and Au Cheval back to back. A little bang bang to start off the trip. It was aggressive, but I regret nothing. I got the Chicago dog at Portillo’s and cheese fries. The cheese sauce had that radioactive-yellow/orange color, so you know it was good. The hot dog had that snap in the casing that you just don’t see much around these parts with our dirty water dogs, and it’s topped with a pickle spear, peppers, tomato, and relish. Really tasty but a lot going on. 100% hit the spot though.
  2. Au Cheval – hands down one of the best burgers I’ve ever had in my life. Double patty, thick bacon, cheese, pickles, aioli, and an egg. It’s just executed perfectly, every layer. Go around 3-4 pm and sit by yourself at the bar, you’ll probably wait less. I only wiated 45 mins. If you’re with people, just put your names down and go across the street to La Josie for a drink like I did. Well worth the wait, I promise.
  3. Wendella Architecture Boat Tour – Get your tickets here, and I’m told this company does the best one. This was super cool and interesting if you like learning about the history and buildings of Chicago. I’m a nerd so I really liked it.
  4. Piggie Smalls Gyro Shop – fast casual spot for a quick Greek-inspired pick me up. The Greek fries with feta powder were AMAZING. I don’t even know that feta powder existed til now.
  5. The Purple Pig – same owners as Piggie Smalls, but this is their more popular sit-down restaurant. Highly pork and meat centric, and I recommend pretty much anything here. Bone marrow was “a must” from everyone who told me about it, but I think I liked the turkey leg confit the best.
  6. Air & Water Show – this only happens one weekend out of the year apparently, and I happened to be there for it!¬†We watched the Air & Water show on a boat with friends and it was by far one of the coolest things I’ve ever done. I had zero clue this was even a thing, but I’m glad I was told about it. The boats tie up together (like yacht week but less ratchet), and you watch the planes do all sorts of tricks in the air. I felt like I was watching scenes from Top Gun.
  7. Flight Club – what’s the first rule of Flight Club? ALWAYS TALK ABOUT FLIGHT CLUB BECAUSE IT’S AWESOME. I loved this place. It’s a darts club mixed with a restaurant and bar! They have wait service and you can reserve an Oche (evidently this is what a dart board is called) for you and your friends. Really fun for a group! Not to mention the food was really good; tempura green beans and al pastor skewers and cotton candy? I’ll allow it.
  8. Ina Mae Tavern – located in the trendy area of Wicker Park, Ina Mae is a Cajun-inspired joint with really yummy brunch! Think fried shrimp & oysters (only way I will eat oysters), grits, thick cut bacon, and beignets.
  9. Girl & The Goat – this is another one that lives up to the hype. Make a reservation well in advance of your trip! I made mine literally about a month before, and it was for 5:30 on a Sunday. Early bird special status, but honestly one of the best meals I’ve had in a long while, from start to finish. And you know how I feel about consistency. Stephanie Izard is the owner/chef, and she was the first female winner of Top Chef Season 4 (2008).
  10. Wrigley Field – clearly a must-visit. There are a bunch of places around here to eat as well, I just had to go early around 10 am, so there wasn’t much eating to be done by that point. Definitely more of a lunch/dinner place.
  11. Skydeck Chicago – if you have a fear of heights like I do, now is the time to conquer it! You can purchase tickets in advance here, but be prepared to wait. I went on a damn Monday at noon and it was still a crazy line to get in. Go early. And try to go on a non-foggy day because that’s kind of a buzzkill.
  12. Lou Malnati’s – famous for their deep dish pizza, I ordered a personal size to go because we literally didn’t have time prior to this to sit and eat it AT the restaurant…but I think I fucked up. I ordered the butter crust, which I’m thinking may not be deep dish? If you look at the photos you can see – the crust was way too thin to be deep dish! But regardless, it was delicious.
  13. Pizano’s – this was DEFINITELY deep dish, but it was not nearly as tasty as the Lou Malnati’s in terms of sauce, cheese, and overall flavor. But they also had fried ravioli on the menu so I wasn’t exactly complaining.

PSA – make sure you set aside at least an hour and change for deep dish pizza. I didn’t realize that it takes these pies roughly 45 mins to make and cook through because they’re so damn thick. Therefore I ended up missing the one I really wanted to try because I didn’t account for nearly enough time. SIGH.

Portillos, Au Cheval, and Piggie Smalls Gyro Shop

The Purple Pig and Flight Club

Ina Mae Tavern, Lou Malnati’s, and Pizano’s

The Bean, Air & Water Show, and Architecture Tour

Girl & The Goat and The Godfrey Hotel

Skydeck Chicago and Wrigley Field

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