6 Reasons to Visit Chicago in Winter

The city of Chicago is filled with public parks, breathtaking architecture, clean streets, and the beautiful shores of Lake Michigan, and gives New York City a run for its money. You should definitely visit Chicago in the winter!

There’s something for everyone and this glorious city has everything you could possibly expect: beautiful buildings, incredible food and entertainment, a colorful history (Al Capone and Barack Obama are just two famous residents), and a wide variety of art and culture.

Chicago River Architecture Tour

Imagine diving into a giant pizza pie, where skyscrapers touch the sky and the lakeshore stretches as far as the eye can see. Chicago is a city that’s like a playground for all ages, with its mix of deep-dish pizzas, towering buildings, and cool museums. If you’ve only got 48 hours to explore, that’s just enough time to get a feel for this jewel of the Midwest.  Let’s dive into our unforgettable 2-day Chicago itinerary.

6 Reasons to Visit Chicago in Winter

1. Central Location & Easy Access

Chicago is perfectly located in the heart of the U.S. for quick flights around the country. There are two international airports conveniently located with thousands of flights per day, and both are conveniently located to the downtown area. When you arrive it’s easy to find a taxi or ride-share operator, but even more convenient (and inexpensive) is the  Chicago Transit Authority (CTA) Blue Line ‘L’ Train. This train runs 24 hours a day and costs $3 – $5  to travel between downtown and O’Hare airport. The CTA Orange Line ‘L’ Train connects directly to Midway. One of the best reasons to visit in winter is you’ll have the city to yourself – no tourists, no visitors, just locals and commuters doing their thing.

 2. Chicago Architecture

If architecture is your jam, you’ll be in heaven here. It’s literally FILLED with some of the greatest American architecture and buildings. The entire city was once a muddy mess. Engineers had to actually raise the level of central Chicago in order to build the city we see today.

so many towers and skyscrapers in Chicago

You don’t have to be an architect buff to marvel at the magnificent buildings that are located all around. Marina City, The Chicago Avenue Pumping Station, Sears Tower, The John Hancock Building, Wrigley Building, Tribune Tower, the Buckingham Fountain were just some of the buildings we admired. We saw many wedding parties taking pictures with the spectacular backdrop of the buildings and sunset combo, etching this beautiful city into their special day forever.

chicago architectural river tours

Many companies offer Chicago River Architectural Tours, allowing you to experience the city’s infamous architecture from the best seat in the house – the river.

3. Chicago’s Legendary Eats

If cities had a taste, Chicago would be a bold, diverse, and utterly delicious explosion of flavors that could make even the pickiest eater’s mouth water. When we talk about food in this city, we’re not just talking about eating; we’re embarking on a culinary adventure. Eating hearty foot in Chicago in the winter is the way to really understand Chicago’s food history.

Chicago is known as one of the best cities for food in the U.S. at any time of the year. The city is known for its quintessential food staple, the infamous Chicago deep-dish pizza. The crust is higher and more crispy than traditional pizza, allowing for large amounts of cheese, sauce and toppings.

Chicago-Deep Dish Pizza

Deep dish pizza reverse-engineers the traditional pizza by serving the sauce on top of the cheese and toppings. Chicago-style deep-dish pizza is more like a cheesy, tomatoey pie with a thick, buttery crust that cradles all the toppings like a warm hug. Each slice is so hearty, you might need a fork and knife to conquer it. Whether you’re a cheese fanatic or a sausage enthusiast, diving into a deep-dish pizza is a rite of passage when visiting Chicago. It’s incredibly dense and feels heavy in your stomach, so after one or two slices, you should be full.

Have you ever heard of an Italian beef sandwich? Another treat that will heat you up quickly in winter. Imagine thinly sliced, seasoned roast beef, soaked in its own juices, and piled onto a sturdy roll. Add in some sweet peppers or spicy giardiniera for that extra kick. It’s messy, it’s juicy, and it’s quintessentially Chicago.

For those with a sweet tooth, you can’t miss out on Chicago’s take on popcorn. Picture this: caramel and cheese popcorn mixed together in the same bag. Sounds a bit odd, right? But trust me, it’s a sweet and savory match made in heaven. One bite and you’ll wonder how you ever enjoyed popcorn any other way.

4. Public Parks in Winter

The Chicago Park District manages over 600 parks throughout the city, so there really is something for everyone. These open spaces offer places to relax or work out, and many of them offer cultural programs. Millennium Park was completed in 2004 and was quickly named the top attraction in the Midwest in 2017.

millennium park - Chicago's big silver bubble, or silver bean

This 24.5-acre park is located in the heart of the city and is simply filled with culture. Frank Gehry’s Pritzker Pavilion hosts free concerts in the summer. Anish Kapoor’s 110-ton Cloud Gate (fondly referred to as ‘The Bean’). And, Jaume Plensa’s Crown Fountainare are all located there. Additionally, the Lurie Garden has dazzling flower displays all year. This photo was taken in the middle of December, you can see hanging out around the Bean in winter doesn’t scare off the locals.

5. Chicago Winter Culture

Chicago is literally seeping with culture and depending on your mood, your possibilities are endless. And because of the freezing wind and rain you might experience during a Chicago winter, there are nice warm indoor venues. The Windy City has contributed significantly to the arts and is the home to blues, hip-hop, gospel, jazz, and soul. Chicago is also the birthplace of improv comedy and home to two renowned comedy troupes: The Second City and iO Theater and five Tony Award-winning theaters. There’s a thriving fine arts scene and many world-class museums. These include The Field Museum, Art Institute of Chicago, Shedd Aquarium and Chicago History Museum.

Chicago’s culture is as layered and vibrant. This city is a beacon of diversity, where every neighborhood tells its own story. It’s a place where towering skyscrapers and serene parks coexist, symbolizing the city’s blend of progress and tranquility.

6. Winter Rooftop Views of Chicago

A rooftop dining experience is something you must-do while in this fabulous city in winter and many people rush to ‘Skydeck Chicago’ for the panoramic views and the opportunity to see four states, or TILT at ‘360 CHICAGO’ to extend out and over The Magnificent Mile and look downward over the Chicago’s skyline. London House was recommended to us and they had a full winter wonderland setup on the upper deck, where you can eat, dine and hang out in a tent with Santa. It was fantastic, and has to be one of my favorite rooftop bars ever.

London House: the rooftop bar at sunset

London House has beautiful architecture and the view from the top is incredible and it’s the perfect date night to see the skyline. We arrived just in time for sunset, and watched the city lights twinkling over the river, as the sky lit up the infamous skyline with the most spectacular sunset we’ve ever seen. Go here if you’re looking for a 2-day Chicago weekend itinerary.

What are YOUR favorite things to see in Chicago in winter?

Let me know in the comments below and join me on Instagram and X (Twitter)!

About The Author


I’m a travel and health writer, digital brand consultant, breast cancer survivor, and supermom to two boys! I keep it real and share stories of raising an active family, life after a cancer diagnosis, and family travels around the world! Each story is shared with my dry, and sometimes naughty sense of humor.

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