If you’re looking for an affordable winter weekend getaway and can handle a bit of cold weather, the windy city might be the place for you! I’ve visited the city once a year for the past three years (all between October and December) and am still wanting more! While it’s most commonly known as the place to hit up in the summer, I would without a doubt recommend this time of year as well! Between the delicious food and easy-going atmosphere, it takes the cake for one of my favorite U.S. cities.
Willis Tower Skydeck - Standing at close to 1,500 feet high, the famous Willis Tower Skydeck is a Chicago staple. After taking an elevator to the top, you’ll find a variety of incredible views of the city while standing on a unique glass box ledge.
Millenium Park - Modern architecture and landscapes make up another one of Chicago’s iconic sights. This is also where “The Bean” is located, and let’s be real, did you really go to Chicago if you don’t have a picture with The Bean? Don’t be fooled though, there is much more to see as you stroll around!
Christkindlmarket - Last year I stumbled upon this cutesy market while walking the streets. I’m telling you, walking is the best way to see things! The German based market offers tons of yummy holiday treats and artisan goodies. The pop up is located at Daley Plaza and opens on November 15th every year.
Michigan Ave - Shopping, shopping and more shopping. No matter how you choose to explore Chicago, you’ll end up crossing paths with Michigan Ave aka “The Magnificent Mile”. Whether you’re window shopping, looking for a designer handbag, or just trying to soak in the history of Chi town- there is something for you to discover here.
Navy Pier - While it is less lively in the colder months, taking a walk down Navy Pier is a great way to get a view of the beautiful Lake Michigan!
Portillo’s - Always my first stop in the city, the world famous hot dog and Italian beef restaurant. I seriously think about the Italian beef sandwich on a regular basis. (THAT good)
Cindy’s Rooftop - Cindy’s is all the vibes and more: a cozy spot with good cocktails and an even better city view. Just make sure to make reservations!
Eataly - With a major Italian population, it’s only right that this two-story food hall brings the tastes of Italy to the city. Enjoy bites from a variety of places while sippin’ on some fine wine.
Giordano’s - There are a million different pizza spots in the city and while I’ve tried a handful of them, I always end up back at Giordano’s. The deep dish is unmatched.
The Hampton - A great brunch destination with some insta-worthy backgrounds. This restaurant is perfect for groups and a good time.
Wrigleyville - The area that surrounds Wrigley Field, known as Wrigleyville is completely filled with different bars. This is a great location for bar hopping and mixing up the scene.
Federales - Perfect place to watch a sports event or start off your night with a group.
Studio Paris - If you’re looking to dance the night away, head to River North. You’ll find a few different clubs and some open later than others. Studio Paris is my personal fave!
My favorite thing about traveling to Chicago is that I’ve learned you can really make it your own. I’ve had an upbeat/fast-paced trip full of going out and partying but I’ve also enjoyed a chill weekend of trying out new food spots and soaking in the views. I loved each one equally and that’s what makes it so special!