My Epic Windy City Adventure

Chicago, the most amazing winter city


What's up everyone! I just got back from the most amazing weekend exploring Chicago with my college roommates Megan, Sam and Emily. Despite the freezing winter weather, we had the absolute best time. Let me tell you all about it!

Meeting Up in the Windy City

My roommate Megan is actually from the Chicago suburbs, so when she suggested a girls weekend trip to her hometown, the rest of us immediately agreed. We were able to find some really cute and modern vacation rentals in Chicago on sites like Karta and booked a cool loft right near downtown.

We flew in from New York City on a Friday morning and met up at our trendy rental. After claiming beds, sprawling out on the comfy couches, and admiring the awesome skyline views from our space, we bundled up in warm layers and ventured outside to start exploring the neighborhoods. 

The freezing wind instantly slapped us in the face, but we were determined to make the most of our Chicago winter weekend!

Trendy Vibes in Wicker Park

We spent that first full afternoon wandering around the artsy Wicker Park neighborhood. We had so much fun popping into the quirky bohemian shops, cafes, record stores, and bookstores that lined the streets. 


Walking along Milwaukee Ave and Division St, I loved seeing all the cool street art murals splashed across the old brick walls. Wicker Park had such an edgy, alternative vibe compared to the more polished downtown area.

When we worked up an appetite, we dined at Big Star - a lively taco joint known for its authentic gourmet tacos loaded up with all the fresh toppings and house made salsas. The perfect fuel after hours of walking in the cold! 

Wicker Park was the ideal first taste of Chicago’s vibrant culture, food, and art scenes that we were eager to keep exploring.

Bundled Up on the Lakefront Trail

On our second day, we walked from our downtown rental all the way to Lake Michigan’s scenic Lakefront Trail. Despite the whipping winds and frigid temperatures, we were determined to see the shore. 

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Bundled up in our warmest layers, we walked for miles along the pedestrian path taking in the spectacular views of the blue icy lake and Chicago's skyline in the distance. I honestly couldn't get over how stunningly clear blue the water was even in the dead of winter!

We stopped many times just to admire the snow framing the picturesque lake, snapping pics and taking it all in. Seeing the famous Cloud Gate aka "The Bean" sculpture in Millennium Park was the perfect photo opp with the Chicago skyline behind us. Even in winter, the lakefront here is gorgeous.

After thawing out with hot chocolates back at our place, we got glammed up for a night out on the town! 

Epic Bar Crawls and Comedy Shows

That night we kicked off our bar crawls with dinner and drinks in the trendy West Loop neighborhood. Hopping between popular restaurants like Girl and the Goat and cocktail bars like The Aviary, we fueled up on gourmet food and tasty libations. 

Afterwards, we continued bar hopping along the Chicago Riverwalk downtown, dancing and laughing the night away. Seeing the glittering skyline reflections on the water was so pretty!

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Ending our epic night at Second City comedy club watching hilarious, witty improv sketches was the cherry on top. We seriously cracked up over the quick-thinking comedians and satire comedy shows. I had tears streaming down my face from laughing so hard!

Over too Soon but Left Wanting More 

Our short weekend trip flew by way too quickly, but we were left completely charmed by Chicago. From the vibrant culture, arts, and food scenes to the friendly Midwestern vibe, it's easily one of my new favorite U.S. cities!

Using Karta to find adorable vacation rentals in the heart of Chicago also made trip planning super easy and stress-free. Now I can’t wait to return to Chi-Town soon and explore more of the neighborhoods, museums, shops and restaurants. There’s still so much to uncover in this world-class city!

So that's the scoop on my awesome winter weekend in the Windy City. Let me know if you have any other recommendations for must-see spots and attractions in Chicago! I need to start planning trip #2.