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A Weekend in Chicago!

  • lillianhilton
  • Sep 18, 2019
  • 4 min read

Hey friends!

Over Labor Day weekend, I visited some of my besties up in Chicago! This city is nothing short of fun & fabulous and I'm here to give you the scoop on our super fun weekend!


Where to Stay

- If you're visiting and staying at a hotel, the Chicago Athletic Association is a unique hotel full of charm & history. If I had to sum this hotel up into one word, it would be regal. It offers more affordable prices, is right on the river, and has an amazing roof-level bar with an atrium that overlooks the city.

- If you're traveling with a group and staying for a few days, VRBO has many options for homes that you can rent out.

- Until this trip, I always thought hostels were exclusive to Europe, but turns out there are some here in the US, too! We stayed with our friends in a super cute neighborhood in Arlington and while we were there, we noticed that there is a hostel in Chicago. This hostel offers private rooms with an en-suite, private room with shared bathrooms & a communal bunk bed room options. If you're looking for a cheaper option for a place to stay and you're up for adventure, it could be an option for you. It's worth noting that this part of Chicago is very walkable & full of great restaurants and bars.


(from left to right: Chicago Athletic Association, a private home in Arlington, the Chicago Getaway Hostel)


What to Do

- If it's baseball season, you've got to make the time to go see a Cubs game. I am not a huge baseball fan, but even I had an awesome time at this stadium. If you're sitting in the bleachers, it's worth getting there a little early to grab your seat. There are a TON of super fun bars that you can go to before/after right around the stadium, so be sure to have your party pants on! If you're gluten free, they serve spiked seltzer here!


- My friend, who is a Chicago local, is engaged and was on the market for a dress! Even if you don't live in Chicago, it could be a super fun girls weekend if you or a friend are engaged and want to make a fun trip out of wedding dress shopping. We went to Alice in Ivory and Sarah Seven's bridal store. Sarah Seven was where she said yes to the dress; the dresses there are classic, simple & very elegant.


- The Hancock Building - on the 96th floor of the Hancock building, there is a bar/restaurant called the Signature Lounge at 96th & if offers the best view of the city with floor-to-ceiling windows. While we walked in without reservations, it's worth making them if you're in a larger group.



- Rooftop bar of Chicago Athletic Association = this bar was so fun and provided an amazing view of Lake Michigan & the famous bean statue. It's got both an indoor atrium and an outdoor balcony with seating and a fire pit. If you're looking to have a private event or a rehearsal dinner, it's an option they have available. This venue is very hip & perfect for getting a group together.


- City Winery = on Sunday, we wanted some post-brunch drinks and this was the perfect spot! They've got a huge indoor winery as well as a very large outdoor area with tables, umbrellas & a garden. If you're looking for somewhere to have a rehearsal or reception dinner, this is an awesome option. What's unique about this venue is they are the only winery in Chicago that makes their wine on the spot.


The City Winery in Chicago


- The Chopping Block Culinary School - While we didn't have time to go to a cooking class, I've read in multiple books how amazing this cooking school is. If you've got the time, there are week-long bootcamp classes (MY DREAM) and one-time classes as well. There's also the option to book as a group or for a corporate event, too.


Where to Eat

- River Roast = This restaurant serves family-style roasted meats & veggies and their food is AMAZING. If you're gluten free, they've got lots of options for you there. It's also right by the river and has options for wedding events.

- Little Goat Diner by Chef Izard = This is not your ordinary diner with greasy food; this restaurant features diner classics with a high-end spin and is perfect for brunch. If you're gluten free or have any dietary restrictions, they've got a separate menu just for you.

- Lou Malnati's = If you're in the market for iconic Chicago-style pizza, this is a must. Gluten free deep-dish pizza is also available here!

- Frances' Deli & Brunchery = This is a cute little breakfast/lunch cafe that's got a wide variety of breakfast options. If you're feeling indulgent, their cinnamon roll pancakes were quite a spectacle.



- City Winery = if you're looking to feel classy with a glass of wine and a great meal, the city winery is a great option! It's also great for if you're trying to have an event like a wedding or rehearsal dinner.



Chicago, you were amazing and loads of fun! Until next summer!


xx

Lil


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