Aah…… Chicago! One of my favorite city’s. Chicago will always hold a special place in my heart……… so many wonderful, crazy, fun memories. And………. I am still creating them!
I actually just got back from Chicago last week. I went there to celebrate my birthday, which happens to be on New Year’s Eve. I know…………. FUN day to have been born. I love it so much! Always a party!!
I love to stay in the Gold Coast area whenever I go home now. I don’t need a car and I can walk pretty much anywhere I want to go. If I need to go to Lincoln Park or Evanston or anywhere else further away, I just get an Uber. This past trip though I stayed downtown the entire time. The weather was perfect! Yes, it was cold! But I am always prepared for that.
For me, the weather was quite mild. During the day it was very sunny and the temp averaged around 30-35 degrees most days. It got a little colder at night. As long as you have warm clothes, proper boots, scarves, and a nice pair of gloves you’ll be fine. It even snowed a few times which made me very happy. 80/90 degrees everyday can get a little boring!
Chicago happens to have some of the best restaurants. There were quite a few new places that I wanted to visit. It’s always so hard packing everything in – in such a short period of time, but I managed to get around to several new spots.
My favorite place and one that I sometimes will visit daily maybe just for a Dirty Martini and some Tuna Tartare is Hugo’s Frog Bar. This place is so lively and has the best food. Whenever I have dinner there, I always order the same thing – the Planked Lake Superior White Fish. I can’t get this in Florida so………….. They used to have Tuna Tartare on the menu, but took it off several years ago. However, they are so incredibly generous that whenever I go in and ask the chef to make it special – they always do! How nice is that? I had it on New Year’s Eve and as always, it was incredible!!!
Tuna Tartare 
Planked Lake Superior White Fish
Hugo’s is where I had my very first Dirty Martini! It is now my favorite drink. I love it with blue cheese stuffed olives. To me, that’s a meal! I even have a martini glass in my home with Hugo’s Frog Bar on it! It’s displayed on a glass shelf where I have all of my favorite things……… all cocktail/bar related things. People always get a kick out it whenever they see it for the first time. A lot of funny things displayed and they’re mostly gifts I’ve received from friends and family.
So whenever I travel anywhere, I always make a little list of places I want to go. This time there were so many new places I wanted to hit – I needed to do a bit of planning because technically it was still the holiday’s and some places were going to be closed for New Year’s.
I stayed a Aloft Mag Mile this time. It’s a new boutique (Marriott) hotel just steps away from Michigan Avenue. We walked pretty much everywhere. The only reason we ever took an Uber was because of the shoe situation (wearing heels) or if it was late and the temp dropped a ton and we were just a little too cold. The hotel was fantastic – it had just opened in October. The lobby was HUGE and had lots of funky furniture spread out to lounge on. There was a fire place, a gorgeous super long bar, a snack area where you could purchase coffee, pastries, snacks in the morning.
There was always music playing and in the evening every night there was live music! It was great! I became really good friends with the bartenders………… one in particular ……… Gabriel. He was fantastic and made the best cocktails. This was the first time ever that I just tried all kinds of new drinks. I usually stick with my usuals. I think I drank more than I ate this trip!
Aloft Lounge Area 
Lounge Area and Bar 
Aloft Lounge Area 
Aloft Re-Fuel Area 
Gabriel Shakin It Up! 
We spent a lot of time at the bar! Every single day before heading out and after getting back at the end of the night (if it was still open)! It was such a chill spot!! The music and the staff……… the decor and the vibe was just so on point. We loved it! We got a ton of reccomendations from Gabriel. He told me about this new spot called Aster Hall. Aster Hall had just opened in November. It’s this amazing upscale food hall located on the 5th and 6th floors of the 900 North Michigan Avenue building. They have about sixteen unique food vendors where guests can find local food, international cuisine, classic cocktails, curated wines, artisan coffee and juices. On the lower level are upscale stores in case you want to go shopping. It’s a really gorgeous building.
The lounge is on the 6th floor. There was really nice jazz playing. Opposite the bar area was a huge area for lounging – all around the floor to ceiling windows. There were tons of seating areas with sofas, chairs and coffee tables. Closer to the bar there were several high tops. The first time I went I was so overwhelmed by the menu of places you could eat, I decided to head to the lounge and have a cocktail while deciding what I wanted for lunch.
After about 3 hours, I still hadn’t decided! However, I had made several new friends at the bar! I knew the entire staff by the time I left. Tim was one of the bartenders. He made me some awesome drinks. Some I’ve never even heard of! It was a blast! My nephew Joseph ended up meeting me there. Funny thing is I never ate. I just drank the entire time! My nephew Joseph wanted to take me to a place he loves to go to so we had a few drinks at Aster Hall then ventured on.
900 Michigan Avenue 
After Aster Hall, we went to this place called 8 Bar. 8 Bar is a martini lounge that’s on the first floor of Maple and Ash……….. a steak and seafood eatery…………. another restaurant in the Gold Coast Area. Enjoyed a few apps and some cocktails!
Smoked Salmon 
Lollipop Lamb Chops
I did go back to Aster Hall the next day with my niece’s though. We had lunch this time and it was fantastic. If I still lived in Chicago, I would be spending many days here in the lounge! They even have a dining room sized table with charging stations down the middle. People would come in, plug in their laptops and work while sipping on coffee or whatever. I could totally see myself doing this often.
When you get to the 5th floor, there are several kiosk stations with printed menu’s nearby. You check out the menu and go on the kiosk to order whatever you want. There are several numbered stations. You can order a burger from one station and fries from another. You pay electronically once you’ve completed ordering. The computer prints out a receipt and there is a number next to each station you ordered from. You pick up your food and find a nice comfy spot to eat. There are tables and comfortable booths all over. You can even take your food up to the lounge and sit anywhere you like. The bar will serve you drinks.
The lounge had a really nice wine/cocktail menu (book) and each page has a quote at the top. I love this one!
Another new place I had the chance to check out was Wells Street Market. This 10,500 sq. ft. Urban Food Hall is located in the Chicago Loop area. There are about 9 fast-casual restaurants plus a full-service bar and a specialty floral shop.
I already had plans to have dinner at The Purple Pig one evening however, the same chef/owner Jimmy Bannos also has a place in the Wells Street Market called Piggie Smalls. I had lunch at Piggie Smalls and met the General Manager, Andrew Bannos (in the picture below). Lunch was amazing as well as the service. I am a huge fan of Greek/Mediterranean food so this was a treat! I had a Gyro (w/ pork and lamb) and the Greek Fries…….. OMG!!!!
Greek Fries
Greek American Gyro
The Purple Pig has been on my list of restaurants to visit for a few years. For the life of me, I don’t know why it took me so long to finally make it happen. In any event, it was worth the wait. It was within walking distance to my hotel which was great. The place was packed – as I had expected it to be! We were able to get a few seats at the bar after not having to wait too long. I love eating at the bar sometimes. It was so busy and lively and everyone seemed to be having a really good time. We made some new friends at the bar and the guys working behind the bar were great as well! They made recommendations on wine and cocktails and food. We just took our sweet time……. starting out with drinks/wine and then a few appetizers. I LOVED the menu!!! So full of new and innovative things I had never tried before and if I had, the way they prepared the dishes were gonna be very new to MY palate. For instance, I cook beets all the time! I love them. I even cook the beet greens instead of throwing them away like most people do. The Purple Pig had beets on their menu…….. I believe the dish was described something like: Salt Roasted Beets with Whipped Goat Cheese and Pistachio Butter…… REALLY??? I ordered them…….. and they were out of this world!
Salt Roasted Beets
We also had Crispy Pig’s Ears with Kale, Pickled Cherry Peppers and Fried Egg, House Made ‘Nduja with Giardiniera and Tetilla Cheese and a plate of Risotto with Portuguese Sausage and Clams. Everything was exceptional! The food, the drinks, the staff/service, the vibe, all of the other diners…….. it was an awesome night – kind of like one big party! We all know how much I love a party! I can’t wait to go back!
House-Made ‘Nduja w/ Giardiniera and Tetilla Cheese 
Risotto w/ Portuguese Sausage and Clams 
Crispy Pig’s Ears
The Purple Pig Bar 
The Purple Pig Open Kitchen 
Amazing Team at The Purple Pig!
These are just a handful of my favorite places. Also, just in a very teeny tiny area of the city! Chicago is HUGE and of course, there are way more places to visit and lots of lots of fun things to do. This short trip was strictly to celebrate my birthday and that is exactly what we did! We only stayed in the Gold Coast Area.
Several years ago while walking down Oak Street I saw this sign on a building that read: Fig & Olive. I was with my best friend Becky. I’m sure my face lit up as I just assumed this was a gourmet store of some sort that probably sold really nice Olive Oils and stuff. We went inside, but it was just a very small entry way. You had to take an elevator upstairs…………. and when the elevator doors opened………………….. WOW!!!!! This is what we saw……………..
Fig & Olive Bar
Ever since that day, Fig & Olive is always on the list of places to stop whether it be for just an afternoon cocktail, brunch or dinner! There are actually 2 levels to the restaurant and they even host private parties. When we were there it was New Year’s Eve (daytime) and they were setting up for the big night. It looked absolutely stunning!!! I took my niece there – she had never been. Now she wants to have her next birthday party here and I don’t blame her!
Eataly Chicago is HUGE! With 63,000 square feet of space, you will find dozens upon dozens of your favorite culinary items for sale, at least 20 different restaurants and bars where you can find breakfast, lunch, dinner, wine, Champagne, pastries, charcuterie, pizza and pasta and fresh breads. You can find fresh pasta to cook at home or already prepared for you! It’s at least 3 or 4 stories tall……… I can never remember. They also have seminars, classes, wine tastings and will even host private events for you. The staff is incredible and there is always someone nearby to help or answer any question you might have.
Butternut Squash Gnocchi 
Fried Portobella Mushrooms w/ Garlic Aioli
One of the open kitchens at Eataly 
Prime Dry-Age Tomahawk Ribeye 
Fresh Seafood
I have a very long list of things to do and places to go in this wonderful city that I am lucky enough to have grown up in. I keep it on my computer because I often have friends that have never even been to Chicago and always ask me for recommendations. I keep this “spreadsheet” updated at all times – it’s even color coded with places, phone numbers, addresses and notes of a little history. It’s full of museums, jazz clubs, theaters, spas in addition to all of the great places to eat and drink. Still…….. these are just a handful of the places that I know about and frequent! There are a ton!!!!!!
I’ll be doing more blog posts on Chicago because there is so much more to write about and I fly home whenever I get the chance. For now, this will have to do.
On my last night in town I did get to visit RPM Italian! It was everything I expected and more. The decor, the ambiance, the service and the food and drinks…………… incredible! Make a reservation though if you plan to go!
RPM Bar
Tuna Tartare 
Octopus
Shrimp Scampi 
Carbonara
It was an amazing super long birthday weekend! Can’t wait to go back!! I really hope you get the chance to visit – especially if you never have before. Be sure to check out some of these places! Trust me – you won’t be disappointed!!
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Looking to have a Great time in Chicago on your visit?! Tammy is the Go To person for all the Great spots! No doubt, one of the best visits I had in the city and I’m only 30 minutes away!
You’re so funny! Can’t wait to do it again Cole!!! 🙂