Chicago's 5 Most Magical Neighborhoods During The Winter Season

Chicago's kaleidoscopic personality shines during winter. As its 18 miles of lakeside trails and 8,800 acres of green lend themselves to frosty walks, and trees are adorned with glitzy lights and Christmas decorations, the city becomes a perfect playground for those chasing wintery delights.

Of its 77 recognized neighborhoods, some truly put on a show during Christmas — including candle-lit parades and giant animals recreated in LED lights. You can always count on the city to hold unique events, too, and there are plenty of activities to enjoy (both indoor and out) all season long. From ice ribbons and igloo restaurants to floating hot tub boats and traditional caroling, five neighborhoods stand out when it comes to magical winter celebrations.

Ready to explore the snowy streets of Chicago? If so, lace up your winter boots, pack your warmers, and prepare to enjoy the city in all its splendid winter glory.

The beating heart of the city, the Loop is easily one of the most exciting places to roam in Chicago year-round. Museums, architectural wonders, shops, and restaurants are contained within its modest 1.58 square miles. Small but mighty, the core of the Windy City also has a strong historic claim as the place to best celebrate the holiday buzz. While Grant Park was the site of Chicago's first official Christmas tree, adorned and displayed in public in 1913, another park within the Loop now has the honor of hosting the city's official tree.

The lighting of the official festive tree in Millennium Park is welcomed with much fanfare, and a celebration marks the occasion every year in mid-November. The wider area is also home to the Maggie Daley Ice Ribbon, the best place to enjoy frosty skates and glides. The ice ribbon stays open until early March, making it a perfect activity to enjoy throughout winter. If you visit during the Christmas holidays, be sure to enjoy a sip of mulled wine in Daley Plaza's Christkindlmarket between one skate and the other.

Another wintery highlight to be enjoyed near the Loop is the Winter WonderFest at Navy Pier. This family-friendly event with fun rides and skating galore takes place against the backdrop of the city's beloved pier, a free-to-access year-round playground right by the water. Though it's technically in Streeterville, it's a relatively quick walk from the Loop — be sure to check it out if time permits.

Whether you're after world-class shopping or simply want to soak in the seasonal atmosphere, Andersonville has you covered. As the "Shop Local Capital" of the Windy City, with amazing eateries and locally owned stores, Andersonville is the perfect place to spend your bucks, knowing you're giving back to the community. You're unlikely to find its wares anywhere else, thanks to its blend of special, quirky, and unique shops — including Andersonville Galleria (selling paintings, prints, and artisanal wares), the old-style music store Rattleback Records, and the boutique Cowboys and Astronauts. In short, if you are looking for a unique present to gift during the holidays, you should head to Anderson without a doubt.

Andersonville also celebrates Christmas a little differently: it honors its Swedish roots (which you can see in its bright blue water tower that marks the neighborhood's skyline) by kicking off the holiday season with a St. Lucia celebration. This Nordic festivity aims to celebrate light during one of the darkest parts of the year. Andersonville faithfully sticks with the traditional candle-carrying, singing, and eventual crowning of the year's Lucia. Outside of this one-of-a-kind event, Andersonville's main artery of Clark Street is adorned with festive Christmas decorations, including colorful lights and window displays. That means even if you miss out on any seasonal events, you can still enjoy a bright and cheery stroll through its streets.

If you want to enjoy a magical rooftop dining experience, head to the igloos at I|O Godfrey, located at the corner of North La Salle Drive and West Huron Street. It doesn't get any better than that for classy skyline views. Plus, the igloo pods are surrounded by a mesmerising display of lights, cascading all around you and creating that quintessential winter wonderland sensation. Whether you want to stop for a bite or simply a luminous cocktail, you can book a small or a large igloo to accommodate your party.

River North is also home to the buzzing Nutcracker Pop-Up Bar, promising tinsel-filled fun and signature cocktails to welcome the holiday season in style. This is your time to shine in front of the camera, as this pop-up bar has heaps of photo opportunities with colorful seasonal props, from reindeer and life-size Nutcrackers to glowing Santas and snowmen.

Even Three Dots and a Dash is getting a makeover for the festivities. This popular bar, normally infused with tiki, sun, and rum, has switched its tanning beds off and turned the snow machine on for winter. You will still be able to sip its signature cocktails, but there's also Christmas specials: Eggnog Grasshopper, Hot Buttered Rum, and Santa's Seahorse Saturn. Step in at your own risk for an eclectic taste of River North ... Pole.

If snowy skyscrapers and rooftop bars are not for you, and instead you want to enjoy a more laid-back, nature-inspired celebration of the winter season, then mighty Lincoln Park has the answer. With direct lake access, a sprawling green space, and even a zoo, it's no surprise Lincoln Park has accrued the title of Chicago's "Most Sought-After Neighborhood."

This tranquil neighborhood deserves its own entry thanks to the ZooLights festival, which is hotly anticipated every year. For more than 30 years, the zoo has been clad in multicolored lights, LED decorations, and unique animal-themed displays to bring a truly unforgettable twist to the venue. Entry to the celebration ranges from $7 to $20 and accommodates various concessions, but keep an eye on select Mondays during the winter calendar if you want to snag a free ticket. And while the ZooLights require a fee to view, you can still walk through the zoo for free during the day before the festivities begin.

When it comes to houses completely decked out with wintery decorations, the place on everybody's list is Sauganash. This tiny, historic neighborhood up north is often featured among the best Christmas lights displays in the city. The praise comes from various forums, too, including Reddit. When planning your walk (or drive) to marvel at the light displays, "start at the west end, Central and Pratt, [so] you leave the best lights on Longmeadow for last", recommends one local Redditor.

The best bit is that every year's decorations are different, as Sauganash residents independently decide how to style their front yards and tree-lined driveways. There is no official map or way to explore the district, so just follow the twinkling lights through the neighborhood as you see fit. It's easy to reach Sauganash from both downtown Chicago and O'Hare Airport, which is just 10 miles away from this magical, wintery hidden gem. It's a bit far from downtown compared to the other neighborhoods on this list, but if you're seeking traditional single-family homes lit up like the Griswolds' house in "National Lampoon's Christmas Vacation," it's a spot to keep in mind.

In order to come up with the list of Chicago's most magical neighborhoods during the winter season, we referenced trusted sites with a finger on the pulse of the city's latest happenings, such as ChooseChicago. As first-hand experiences are also incredibly important, we combed painstakingly through locals' tips and reviews, from Tripadvisor and Google reviews to Reddit.

Neighborhoods with events that last the length of the season, offer festive holiday decorations, and carry other highly rated amenities earned priority for this list. Much of Chicago is lit up for the winter months, however, and since it's pretty easy to get from one neighborhood to the next, it's worth exploring as many as you can.

Pricing played a role in determining the list, though most events across the city are either free to attend or charge just a small fee. Weather was not a factor — every inch of Chicago can be frigid in the winter, though no doubt its streets are quite cozy when you're bundled up, and snow is falling between the soaring skyscrapers.