Chicago Weekend Fun

Ahhh Fall weddings. Last weekend I had the pleasure of a attending a beautiful wedding in the suburbs of Chicago in a cute little town called Saint Charles.
Having been to Chicago once before, I was somewhat familiar with all that downtown has to offer but hadn’t spent more than 24 hours there and wanted to take advantage of being back. I flew in Thursday night so I could spend Friday exploring downtown and brunch Saturday morning before my hour drive to Saint Charles.
Whether you’re in Chicago for a wedding or a weekend getaway, here is a compilation of sites to see and some of the best restaurants, treats and cocktail lounges you can easily hit in 48 hours!

SITE SEEING

Cloud Gate
Located in the heart of downtown Chicago in Millennium Park, Cloud Gate is a giant reflective sculpture dubbed ‘The Bean’ because of it’s bean shape. This massive work of art was inspired by liquid mercury and weighs 110 tons! It’s famously one of the most photographed landmarks in downtown due to its reflection of the Chicago skyline.
In addition to the bean, there are a ton of activities and additional things to see in Millennium Park.

Navy Pier
One of my favorite areas of downtown Chicago is Navy pier on Lake Michigan. Open year round, this 3,300 foot pier offers a lot of fun activities including a giant ferris wheel, a children’s museum, AMC movie theater, Shakespeare theater, beer garden, shopping center, indoor eating hall and more!
See more info here.

Architecture Boat Tour
Although it was highly recommended and one of the most popular activities in Chicago, I didn’t have time for an architecture boat tour but will mostly definitely do this next time I visit! Cruise along the Chicago River for a live tour and learn about Chicago’s historic landmarks, hidden gems and how the skyscraper was invented. You can even go on a sunset dinner boat tour!
Get tickets here.

Willis Tower

Formally known as the Sears Tower, Willis Tower is 110 stories high and you can ride an elevator all the way to the top to view the Chicago skyline through glass walls and floor enclosures for MILES. I’m terrified of heights so this wasn’t on my list of things to do, however, tickets start at only $22 and it looks pretty cool.
Get tickets here.

Chicago Theater
The Chicago theater is one of the most iconic landmarks in the city so of course I had to get a photo in front of it!
View upcoming comedy and music shows at Chicago Theater here.

The River Walk

One thing that makes downtown Chicago unbelievable beautiful is the Chicago River that feeds into Lake Michigan. It runs throughout different parts of downtown with the river walk being a pedestrian walk way lined with restaurants, bridges, fishing piers and boat docks. You can easily walk this path while you’re out sight seeing.
The Flamingo Wall
Located at 601 N Wells street, I was blown away by this huge work of art and couldn’t pass up the opportunity to take a photo in front of a giant pink flamingo! I have a special place in my heart for anything pink so naturally I was convinced this wall was placed here just for me. =)
If you’re looking for more murals in Chicago, check out this Guide to Chicago murals.Lake Front Trail (Lake Michigan)
If you walk East of Millennium Park, you will eventually run into Lake Front Trail, a paved walking path along Lake Michigan. It was a PERFECT October day and I was stunned to see how blue the water was! Living in NYC, it was refreshing that such a peaceful and beautiful view was such a short walk from the hustle and bustle of the city.

Magnificent Mile
Although it’s not technically not a site to see, Magnificent Mile is the premier shopping destination in downtown Chicago full of upscale stores, beautiful hotels and cool restaurants. You will most likely run into it at some point while you’re out exploring the city but should definitely check it out!

DINING & DRINKS

Brunch at The Hampton Social

If the words ‘Rose all day’ exist in your vocabulary, you HAVE to brunch at the Hampton social! Classic brunch options, a raw bar, lobster rolls and fish tacos are staples on their menu. You cant go wrong with anything you order.

Stan’s Donuts

After site seeing for several hours, I was craving something sweet and definitely needed an afternoon pick me up. I sadly have a gluten intolerance so Stan’s donuts was perfect because they offer gluten free and even vegan donuts! They also have the most delicious cold brew coffee which paired nicely with my GF blueberry and chocolate donuts. (DO NUT judge me for ordering 2!!) Stan’s was a sweet excuse to rest my feet before venturing out for more site seeing.

Deep Dish Pizza at Giordano’s

Chicago is famously known as the original creator of deep dish pizza. Even among the locals, Giordano’s is the most famous pizza place in the city. I was excited to know they have gluten free thin crust pizza as well!

Dinner at Avec or Girl & The Goat

Noted as two of the most popular restaurants in Chicago, I would suggest dining at one or both of these places.

Tiki Cocktails at Three Dots & A Dash 

This was my ultimate favorite find in downtown Chicago! I stumbled upon this place as a last minute ‘google maps’ find and it was a memorable experience to say the least. A back alleyway with a lit tiki torch is the entrance to this speakeasy tiki bar and the ambiance takes you to a tropical paradise with a menu full of mai tais and tropical cocktails. I was literally OBSESSED! Not to mention, each cocktail is served in their own unique glass.

SHOP MY STYLE:Look #1 (Cloud Gate)
SheIn Jumpsuit $13
Moonlight Gypsy Miami Sunglasses $16
Zara Faux Suede Biker Jacket $89.90
SheIn Velvet Bow Bag $11
Steve Madden Heeled Sandals $49.95
Kendra Scott Sophia Drop Earrings $50

Look #2: (Navy Pier)
Moonlight Gypsy Embroidered Flower Boho Sweater $48
Zara Pink Mid-Rise Skinny Jeans $39.90
Moonlight Gypsy Miami Sunglasses $16
Moonlight Gypsy Velvet Quilted Shoulder Bag $50
SheIn Flat Boots $60
Kendra Scott Sophia Drop Earrings $50