If you follow me on instagram (and if you don’t, what are you waiting for?!) you probably noticed that I recently was in Chicago for a girls’ weekend with my sister and my two cousins. Ya’ll we had the best time!
Ever since we all finished up with school, we’ve started taking a girls’ trip every year or every couple of years. This year, we picked Chicago. Part of the reason we picked Chicago was to catch one of New Kids on the Block’s shows during summer tour.
And OMG…the show was amazing! If you are a Blockhead, there may still be time to check out one of their concerts (they are about halfway through the tour). This tour may be one of my favorites yet…just everyone having a great time. Even if you aren’t a Blockhead, Boys II Men and Paula Abdul opens for them, so if you grew up in the 90s, I think you’d enjoy yourself!
But, I digress. Back to Chicago. If you are planning a trip to Chi town (and if you aren’t, you need to!), I’ve got you covered!
Where to Stay?
We stayed at the newly renovated Blackstone, which is part of Marriott’s Autograph Collection. And I have to say, this may be one of my favorite hotels I’ve ever stayed in. First, Helen, the night manager, was absolutely fantastic. She was always taking care of us, especially after our flights were severely delayed getting in (my sister and I didn’t make it to the hotel until 3 am – not fun). My favorite part of the hotel though was the absolutely adorable lobby. I loved the furniture!
I especially loved this bar hutch in the middle of the lobby. On the weekends, the bar hutch “opens” as Timothy’s Hutch, with a bartender serving craft cocktails out of the hutch and a bar cart. Super adorable!
The location of the hotel is pretty outstanding too. The hotel is off of Michigan Ave (a/k/a Magnificent Mile), and about 0.5 miles from the famous “Bean”.
Where to Eat & Drink?
Boy do you I have you covered! I did quite a bit of research before we left, and most of the list was made up of restaurants and bars. What? I know what I like. And I like to eat and drink my way around a city!
This is a must see. Cindy’s is located at the Chicago Athletic Association, which was about half a mile from the hotel. The restaurant has amazing sky-lights so that if you are eating inside, you can still enjoy the view. There is also a bar outside so that you can enjoy the view and have a cocktail.
The menu is set up to share plates with friends, which I love because you get to try more! If you are going for brunch, I’d recommend the quiche – seriously may be one of my absolute favorite quiches ever. I’d also recommend the Howl at the Jun cocktail – so amazing. If you sit at the bar, ask for Donnie K. – he was a real treat!
A word to the wise, if you want to go, go early. The first time we tried, there was a 45 minute wait just to get upstairs (and then there was an additional wait once you are upstairs). We went back on Saturday morning around 11 am. There was an hour wait for a table but we were able to find some seats at the bar.
If you can’t make it into Cindy’s, the Drawing Room, on Floor 2, was super cute too. They serve craft cocktails and lite bites.
We stopped by Hampton Social for brunch (are you noticing a trend?!) and was not disappointed. They have an extensive Rosé selection as well. Even better than the food was the atmosphere – the restaurant opens up on 2 sides and has a ton of different seating options from couches, tables, to hammocks. You may also recognize the “Rosé All Day” sign…one of the most instagrammed places in the City!
Time and time again, I was told if we wanted deep dish pizza, then Lou Malnati’s was a must. I’ve recently given up (or limited) my cheese intake, so I don’t think I was able to fully enjoy all the goodness, but the pizza was pretty delicious. I loved the Lou’s salad as well.
Xoco is one of Rick Bayless’ restaurants and is right next door to Frontera Grill, another one of his restaurants. Xoco is a bit of a quicker option and I’d highly recommend going for happy hour – can’t go wrong with $5 margaritas and $5 guac and chips. We strategically picked Xoco for an early dinner before the concert…best decision ever.
If you ever watched Giuliana and Bill Rancic’s reality show, then you’ve heard of RPM Italian. Located in the River North neighborhood, RPM Italian is as much about the “scene” as it is for the food. I’d recommend that you make a reservation as far in advance as possible. If not, you might end up like us and eating at 9:45 pm.
I think Chicago may be mildly obsessed with doughnuts. And why shouldn’t they be?! If you like doughnuts, then Doughnut Vault should be on your list. Their buttermilk doughnut is what made them famous…and…believe me, it didn’t disappoint.
If you are looking for truly the most unique cocktail bar, then Three Dots and a Dash is a must. Named as one of the World’s 50 Best Bars by Drinks International, Three Dots and a Dash is an underground tropical tiki and craft cocktail bar. The creativity with the drinks is nothing like I’ve seen before. Each drink is in a different custom pottery glass, and is filled with fruits, herbs, and toys. Yes, toys. Backscratchers, mermaids, gold coins…you name it, they incorporated it.
The drinks are strong, so buyer beware. I have a feeling this bar is one of those places that you go into and may not come out of!
What to Do?
Architecture Boat Tour
Even if you are not a huge architecture fan, I promise you’ll enjoy spending 90 minutes cruising the waterways of Chicago and learning about all of the different buildings. We used Shoreline Excursions, which was great. A lot of people recommend First Lady, which is a tour group that partners with the Chicago Architecture Foundation, so you may want to check them out too.
Millennium Park is probably best known for “The Bean,” but has a variety of other public art as well. During the summer months, check out the website for public events.
Shopping in Lincoln Park
If you are looking for something other than Magnificent Mile for shopping, check out Lincoln Park. There are a ton of cute locally-owned shops. If you are looking for a breakfast place, check out Toast. Summerhouse Santa Monica was also on our list of places to check out…but in the middle of the day during the week, the wait was over an hour! Lesson learned…make reservations!
What are some of your favorite places to check out in Chicago?