Oh Chicago….

Good morning and ugh I can’t believe it’s happy Monday! Is that really a thing.. happy and Monday together?!  It’s usually not in my book but there are only 3 (including today) Monday’s until Christmas and that seriously blows my mind!  The season is already flying by and I’m not ready for that!  I headed to Chicago for the weekend to shop a bit and see the famous Chriskindlmarket to add more to the Holiday season! PSA – this post is LONG and includes a lot of pictures so grab a cup of coffee and snuggle up 🙂


I went with a girlfriend on Friday morning and got back Sunday morning.  It was a quick trip but honestly, we did so much that I felt like it was the perfect amount of time!

As soon as we got into town Friday, we headed to our hotel, Wyndham Grand to drop our luggage off (it was 9 am after all) so we could hit the town and to our amazement, our room was ready!  The hotel was the perfect location for us, right by Michigan Ave and still close to Millenium Park and the market!


After dropping our stuff off, we set out to find breakfast because seriously… I thought we were going to starve to death!! Our flight was at 6 am so we left the house around 4 am which didn’t leave much time to eat – and who wants to eat at 4 am anyways?! I just wanted to sleep!


We ate at Wildberry Pancakes and Cafe and it was so good! The wait was an hour (literally thought I was going to keel over! #firstworldproblems) and they said that’s usual.. week day or weekend so we figured it must be good! Let me tell you.. it was so delicious and the service even better!  Definitely a place I’ll go back to!  Also, it’s right across from Millenium Park and the famous “bean” so we walked right over there to waste some time while waiting!


Of course, we took some obligatory “bean” photos!


Have you ever seen anyone so pale?! Haha!

After eating, we headed to shop on State St and ran into the market!


Such fun and cute store fronts for the holidays!

I loved how big Macy’s was.. and the building itself inside was so pretty!


I mean, only 9 floors, complete with a liquor store at the bottom floor.. no big deal!

 It was chilly so we of course had to get a cute take home mug with hot cocoa (or spiced wine if that’s your thing.. I’ll take regular wine, thanks!).  We finished up shopping a little more and headed back to the hotel to get ready for an early dinner!


We met my girlfriend’s niece for an early dinner (and some Rosé) at The Hampton Social with the famous “Rosé all day” sign!

I had the crab cakes (yum!) and a few glasses of Rosé because #whynot?!  Gayle had the mussels which were also pretty great!  Her niece had the Prosciutto flatbread and said it was fabulous!

Definitely recommend stopping by here for some sweet Rosé!


After dinner, we headed back to the hotel (so early!) and decided to get in our Christmas pajamas and watch Hallmark movies!  After getting up at 3 am, that was exactly how I wanted to end my night!

Saturday, we started our day with some breakfast and a Mimosa – because I was on vacation, duh at Southwater Kitchen.  The restaurant was right by the hotel and had a cute atmosphere with hints of Christmas!


To be honest, this wasn’t my favorite restaurant.  The food was just OK and the service wasn’t that great but it’s convenient if you’re staying right in that area!

After breakfast, we set out for the train (we took the train from the airport into the city versus a cab as well) to head over to Wicker Park for some shopping.


We shopped up and down the four or five streets and then walked a little bit around the neighborhood.  The houses were so cute, y’all!


I could totally see living in that area and heading down to the little coffee shops and bars on the daily!


And speaking of local bars… we stopped by The Southern for some more drinks (Mimosas for me, Baileys and coffee for Gayle) and a snack.


The service was great and the food/drinks even better!  She had the Biscuits & Blueberry and I had the Pretzels (I know, shocker!).


The area was so cute and I’m sure there were a ton more things that we missed! Next time, Wicker Park, next time!


This old phone booth no longer had a phone in it but was where you put in your code to get into one of the apartments!  I thought that was pretty sweet 🙂 Although, I’m sure it gets annoying when people are taking pics and you just want to get in!

And because we clearly like to eat… we had to try Stan’s Donuts before we headed back downtown!  It was seriously the CUTEST little place ever!


And the donuts were so yummy – no joke.. one of the bests! #donutsaremylovelanguage

When we got back downtown, we headed over to Michigan Ave to do more shopping!


The stores were so Christmasy and I really need to know how I can get all that garland at our house?! 🙂 I mean, that’s natural right?!


And I’ll take this Christmas tree too 🙂 Of course everyone wouldn’t move out of the way so I could get a really good picture of this gorgeous tree.. I mean, is that really too much to ask for?!


After we finished up shopping (and walking what felt like 802 miles) we walked a little more back to the hotel to relax a little before dinner!  Of course, we had the Hallmark channel on the whole time in the hotel because those Christmas movies… ugh obsessed is an understatement!

I swear my eyes are open…

We went to Italian Village for dinner and while it was another hour wait (we got there around 8 and were sat around 9).. it was definitely worth it!  The restaurant was so unique – they had it set up to resemble a little Italy village – separate rooms for different parties (tables for 2-4 not just large) and the paintings on the wall were so authentic as well!


I had the Three Cheese Tortellini (although these looked like Raviolis) and it was just yummy!!  Even though I was stuffed from the Caesar salad (prob one of the best I’ve had!) and bread… I managed to eat it all 🙂 Gayle had the lobster fettuccine and the lobster was to die for!! No joke.. it was prob some of the best I’ve ever had!

After dinner, we headed back to the hotel and watched another part of a Christmas movie then headed to bed – we had to be up around 6 the next morning to get to the train and airport so no crazy night for us!

Thanks for a fun weekend, Chicago!  Urine smelling trains and all 🙂

What fun things did you do?! Anything Christmasy?

Hope y’all had a fun weekend and are ready to tackle today and make this Monday yours!



12 thoughts on “Oh Chicago….

  1. Leslie Z. says:

    Oh my gosh. I feel like I need to go ahead and purchase a plane ticket to Chicago for next year. All of that food made me so hungry! It looks like you had an incredible time and you looked fabulous! 🙂 Cheers to only 2 more Mondays left!

    Liked by 1 person

    • happilyevergriedls says:

      Umm yes you totally need to!! 🙂 And hope for snow because that would have made the weekend perfect! I can’t believe it’s only 2 Mondays away.. where has the time gone?! I’m not ready for it to be over!


  2. tractorsandglam says:

    What a FUN weekend! I would love to go to Chicago one day. I have flown in there many times but never stayed and always think it looks beautiful. Glad you had so much fun!

    Liked by 1 person

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