Chicago Winter Adventure – 48 Hours in Chicago

Are you thinking of visiting Chicago during the winter months? Today I’ll be sharing my own adventure of visiting Chicago in the winter and how I spent 48 hours there. It’s all about where to stay, what to see, do, and eat, as well as how to get around.


As a travel enthusiast always seeking new adventures, I recently found myself with a 48-hour window to explore the vibrant city of Chicago during the winter season. Kristal has been contemplating leaving Portland and heading to a bigger city, and Chicago was her first “big city” of choice. So with tickets booked, we decided to spend a weekend in Chicago.

With a rich tapestry of cultural experiences and a mesmerizing cityscape, Chicago in the winter is a true gem waiting to be discovered. Today I’ll be taking you on my whirlwind journey as I share my firsthand account of how to make the most of 48 hours in the Windy City during the chilly winter months, especially if you’re visiting in December.

48 Hours in Chicago

Getting There and Getting Around: Embracing the Chill

Transportation Options

We flew into O’Hare, but you do have a choice of either O’Hare (ORD) or Midway (MDW), and then getting into the city was a breeze. If flying is not your thing, you can always grab a coach bus or Amtrak. While I haven’t experienced Amtrak on my own, I’ve heard that the ride into Chicago can be convenient and scenic, and watching the breathtaking landscape as you approach the city is spectacular.

Chicago in Winter

Once we landed, we opted out of taking Uber and grabbed a train (the Blue Line) into the city, as our hotel was within walking distance of the train. I have to admit that Chicago’s transportation system can rival NYC. The CTA (Chicago Transit Authority) fares are also very reasonable, as you can get a full day of unlimited rides for $5 or a week for $20. Be sure to purchase your Ventra Card (which enables you to get on the buses and trains) at the airport.

Once in Chicago, navigating the city was a breeze. The CTA buses and trains offer an efficient way to get around, and rideshare services (Uber and Lyft) are readily available if you prefer a more personalized travel experience. Or, if you’re up for the adventure, you can also consider renting a Lyft bike and biking around the city.

Lyft Bike Chicago

Where to Stay

Arlo Chicago

Arlo is pretty much central to almost everything. It’s within walking distance of many modes of transportation (buses and trains), Millennium Park and the Bean, museums, the riverwalk, and lots of eateries. Lately, I’ve been finding myself not spending tons of money on hotels, as I’m simply there to sleep, not hang out. The rates were pretty reasonable for being so central, and the room was “roomy” and comfortable. Check-in was at 4 p.m., with a check-out time of 11 a.m.

Arlo Chicago

Day 1: Exploring Cultural Gems

Morning: Field Museum and The Art Institute of Chicago

My first morning in Chicago began with a deep dive into history and art at the Field Museum. Home to a fascinating array of exhibits, including Sue, the world’s most complete T. rex skeleton, the museum offered a captivating start to our day.

Field Museum

Following this, we made our way to the Art Institute of Chicago, a haven for art enthusiasts. The museum’s extensive collection boasts masterpieces from various eras and cultures, providing an immersive experience for visitors. The iconic “Bean” sculpture in Millennium Park, located within walking distance of the institute, added a modern touch to our cultural exploration.

Art Institute of Chicago

Currently, as of the time of our visit (December 2023), the “Bean” was under construction, but if you’re visiting around Christmas, consider taking a turn on the skating rink and checking out the Christmas tree. While the tree pales compared to the tree at Rockefeller in NYC, it is still beautiful.

Millennium Park

Afternoon: Chicago Cultural Center

For a midday break, we decided to head to the Chicago Cultural Center, a hidden gem in the heart of the Loop. The stunning architecture and free cultural events made it a delightful stop. After all, who doesn’t love the word free and everything it entails? We marveled at the world’s largest Tiffany stained-glass dome before enjoying a quiet moment in Preston Bradley Hall.

Chicago Cultural Center

Day 1 (Continued): Evening Adventures

Evening: Navy Pier

As the sun set, we made our way to Navy Pier, a winter wonderland adorned with sparkling lights and festive decorations. The Ferris wheel, though chilly, offered breathtaking views of the city skyline against the winter night. With seasonal events and a variety of dining options, Navy Pier provided the perfect setting for an enchanting evening.

Chicago Navy Pier

Night: Chicago Bulls Home Game at the United Center

To cap off the night, we couldn’t resist the allure of attending a Chicago Bulls home game at the iconic United Center. The electrifying atmosphere, passionate fans, and sheer energy of the game made it an unforgettable experience. Whether you’re a basketball fan or not, catching a live Bulls game is a quintessential Chicago experience. What made it even better was that the Bulls actually won, playing against the New Orleans Pelicans. It was a close game (120–114), but exciting nonetheless.

Chicago Bulls Game

Day 2: Winter Wonders and Wellness

Morning: Christkindlmarket Chicago

Waking up to a crisp winter morning, we decided to head to the Christkindlmarket Chicago, a festive European-style market that magically transforms Daley Plaza. With the Chicago Christmas market lauded as one of the best in the US, I just had to go. The aroma of spiced mulled wine and the sound of holiday tunes filled the air as I explored stalls offering handcrafted ornaments, wooden toys, and delectable treats. It was a charming way to kick off the day.

Christkindlmarket Chicago

Afternoon: Garfield Park Conservatory

The Garfield Park Observatory is a verdant oasis nestled within the heart of the city. It is free to enter, but prior registration is highly recommended. Home to a stunning collection of plants from around the globe, this botanical haven offers a tranquil escape from the urban hustle and bustle. Take a leisurely stroll through lush gardens, breathe in the fragrant blooms, and marvel at fascinating flora from tropical rainforests to arid deserts. Don’t forget to snap a few photos amidst the vibrant greenery for your Instagram feed!

Garfield Park Conservatory

Day 2 (Continued): Evening Adventures

Evening: Fashion Outlets of Chicago

No trip is complete without doing a bit of shopping. The Fashion Outlets of Chicago, located just minutes from downtown, boasts over 130 designer outlets, offering everything from high-end fashion and luxury brands to trendy apparel and accessories at unbeatable prices. Browse through the latest collections from renowned designers such as Gucci, Prada, and Burberry, or score deals on coveted brands like Nike, Coach, and Michael Kors. Whether you’re hunting for designer steals or seeking to refresh your wardrobe with the season’s hottest trends, this upscale outlet mall delivers a truly exceptional shopping experience that’s sure to delight fashion enthusiasts and bargain hunters alike.

Night: Soul Cycle Class

After indulging in the winter delights of the Christkindlmarket and doing a bit of shopping at the Fashion Outlets of Chicago, we decided to balance our Chicago experience with a Soul Cycle Hip-Hop class. Located in the trendy West Loop, the class provided an invigorating workout against the backdrop of Chicago’s urban landscape. It was a perfect way to stay active and warm up during the chilly winter day. Although, if I’m being honest with myself, it also showed me that I was not as in shape as I thought I was, but I’ll get there.

Soul Cycle

Places to Eat


WILDBERRY Pancakes & Cafe: Located at 130 E Randolph St., Chicago, IL 60601

We had brunch, and if you want one place to eat in Chicago, then definitely make it WILDBERRY Pancakes & Cafe. WILDBERRY is a delightful culinary haven in the heart of downtown Chicago and less than a 5-minute walk from Arlo. With its inviting atmosphere and mouthwatering menu, WILDBERRY promises a memorable brunch experience for all who enter its doors. From fluffy pancakes to savory skillets, their offerings showcase a creative twist on breakfast classics, catering to a variety of tastes.

Coupled with friendly service and a central location near Millennium Park, Wildberry Brunch Chicago is the perfect destination to start your day in the Windy City.



sweetgreen: Located at 150 N Michigan Ave., Chicago, IL 60601

We decided to have something simple for lunch, and while sweetgreen isn’t exclusive to Chicago, it was conveniently located near Arlo, as most of our eateries were. sweetgreen is more than just a salad spot; it’s a culinary destination that celebrates fresh, wholesome ingredients and sustainable sourcing practices. From signature salads bursting with seasonal produce to hearty grain bowls and nourishing plates, sweetgreen’s menu is brimming with flavorful options to satisfy every palate.


Giordano’s: Located at 130 E Randolph St, Chicago, IL 60601

We wanted to try Chicago’s Deep Dish Pizza, and Giordano’s was recommended. Deep-dish pizza is definitely an acquired taste, because I was not impressed. I come from New York City, and there is actually a rivalry about whose pizza is better, and I definitely have to give New York the honors. I decided on a personal deep-dish pizza and ended up leaving half on my plate because I couldn’t get over biting into such a “deep” pizza.

Time Out Market Chicago: Located at 916 W. Fulton Market, Chicago, IL 60607

Time Out Market Chicago is currently one of the seven Time Out Markets around the world. I had the chance to visit Time Out Market Lisboa in Portugal and was very impressed. Time Out Chicago, not so much.

Time Out Chicago is a bustling culinary destination offering a diverse selection of gourmet cuisine and cultural experiences under one roof. With a vibrant atmosphere and an array of food stalls curated by local chefs and artisans, Time Out Market invites visitors to indulge in a culinary adventure like no other. From mouthwatering street food to elevated fine dining, there’s something to satisfy every craving. Whether you’re seeking a quick bite to eat or a leisurely meal with friends, Time Out Market Chicago promises a memorable dining experience in the heart of the city’s dynamic Fulton Market district.

Time Out Market Chicago

Sweet Treat / Dessert

JARS Sweets and Things: Located at 216 N Peoria Street, West Loop, Chicago, IL 60607

We wanted to try something local, and Jars Sweet and Things was recommended as we were told it originated in Chicago.

JARS Sweets and Things is a delightful confectionery haven offering a delectable array of treats to satisfy any sweet tooth. From artisanal chocolates to indulgent desserts, JARS promises a sensory delight with every bite. Their creative creations are crafted with care and attention to detail, showcasing a blend of traditional flavors and innovative twists. Whether you’re in the mood for a classic chocolate truffle or a whimsical dessert jar, JARS has something to delight every palate. With its charming ambiance and mouthwatering offerings, a visit to JARS Sweets and Things is sure to be a memorable experience for all dessert lovers.

JARS Sweets and Things

In Conclusion: A Winter Wonderland Awaits

As I concluded my 48-hour winter journey through Chicago, I couldn’t help but marvel at the city’s resilience and vibrancy, even in the face of the winter chill. From cultural excursions to sports spectacles, festive markets to invigorating workouts, Chicago has proven to be an all-encompassing destination for a memorable winter weekend.

While I had a great time in Chicago, if you intend on staying in the Windy City for more than 48 hours, or even if you do spend 48 hours, the best way to experience Chicago is with CityPASS®. I’m always touting CityPASS® as one of the best ways to visit a city, because not only do you get to visit some of the city’s top attractions, but you save money while doing so.

Chicago Millennium Park

For those seeking a brief escape to the Windy City, the key to maximizing the experience lies in embracing the season’s unique offerings. From the iconic museums and cultural centers to the lively sports scene and festive markets, Chicago in the winter is a tapestry of experiences waiting to be explored.

Whether you’re an art enthusiast, a sports fan, or someone simply in search of winter wonders, Chicago’s diverse offerings ensure that your 48 hours in the city are filled with unforgettable moments. So, bundle up, hit the streets, and let the magic of Chicago in the winter unfold before your eyes.

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