It is that time of year to bundle up to explore the best of Chicago indoors and out this beautiful season. Whether practicing figure eights, playing in the snow, or staying nice and warm at one of the lively events around the city, exhilarating experiences await all winter long. Keep these possibilities in mind the next time you’re up for something to do.

Hit the Ice

Ice skating is the quintessential winter activity, and there are quite a few noteworthy spots devoted to the pastime. Over at Millennium Park, the McCormick Tribute Rink attracts beginner and seasoned skaters alike. The best part is that admission is free. The only thing you need to pay for is the skate rentals. Open through March 8, 2020, the seasonal rink also hosts free ice-skating lessons on select mornings and features a DJ on the first and third Thursday of the month.

Downtown, Maggie Daley Park provides a picturesque spin in nature with the Scenic Skating Ribbon that stays open through early March.

Finally, The Peninsula Sky Rink, located on the fourth-floor terrace of The Peninsula Chicago Hotel, offers a chic take on ice skating with music, awesome views of The Magnificent Mile, and drinks and dishes to keep everyone toasty. Plus, you’ll be skating for a good cause since all the proceeds from the rink benefit children’s charities.

Snow Days

Thrilling times are ahead when the temperature drops, and snow lovers can look forward to frolicking outdoors at the Soldier Field Sledding Hill. The vertical fun happens on the 35-foot slope located at Museum Campus, whether there is real snow or not, thanks to a snow-making machine courtesy of The Chicago Park District that will provide plenty of artificial powder. It is recommended to call (312-235-7000) ahead of time since sledding is not always available. 

Siberian Huskies, Wolves and More, Oh My!

The 14th Annual Polar Adventure Days return to Northerly Island on January 25 and February 29, 2020, offering two Saturday afternoons of outdoor adventure for the entire family. Everyone will have a blast making nature-inspired crafts, seeing Siberian huskies and wolves, and exploring the birds of prey at the Flint Creek Wildlife Rehabilitation Center. Active types can go snowshoeing if there is enough of the fluffy white stuff on the ground, or just simply sit back and sip on their hot cocoa. Admission is free.

You know they say that you haven’t been somewhere unless you take a selfie to document it, right? Well, Chicago has no shortage of photo-worthy places to strike a pose. From world-famous attractions to colorful street art and mouth-watering food, there are so many vibrant visuals that you won’t mind having on your camera roll. Here are a few places to visit that are Instagram-worthy—just don’t forget #Chicago so everyone can see!

Day or night, The Chicago Theatre downtown is hands-down a must for selfies. Why? Well, no need to tag your location with the bright red, six-foot marquee letting everyone know the location. Apart from making a good backdrop, the historic venue, which has been welcoming audiences since 1921, is a good place to watch a concert, standup comedy and other shows from some of the biggest names in show business.

Art lovers who want a shot with a Picasso should make their way to Daley Plaza. Unofficially known as “The Picasso,” the massive, untitled Cubist sculpture by the Spanish master adds an interesting aesthetic to any photograph. At Millennium Park, which happens to be the most visited destination in the Midwest, “Cloud Gate,” does exceptionally well, as the ultimate selfie-backdrop. The futuristic-looking shiny work of steel by British artist Anish Kapoor attracts plenty of photo-snappers keen on capturing the cool reflection of the cityscape.

Within walking distance, the Art Institute of Chicago is a prized place with two majestic lion sculptures always camera-ready. During the year, the two African lion sculptures are decked out to honor hometown teams as well as to get in the festive spirit for the holidays.

If it’s the Chicago skyline that you’re after, there is a great angle from the Adler Planetarium on Solidarity Drive close to the Shedd Aquarium, both part of the area known as Museum Campus. Along with the soaring skyscrapers, Lake Michigan is also visible from this vantage point.

Nothing shouts fun more than a cool pic with a Ferris wheel. Whether it’s standing below or sitting high above at nearly 200 feet, or even better with the fireworks bursting in the background, the Navy Pier Centennial Wheel has become a go-to for the perfect shot. Nostalgic baseball fans have Wrigley Field, the home of the Chicago Cubs, a popular destination for smiling sports fans since it first opened in 1914. Today, people love to stand right in front of the red and white marquee and snap a selfie to preserve their memories. 

 

Leisurely walking tours are nice and all, but some people want pure adventure. Thank goodness Chicago offers exhilarating experiences for those out there on the wilder side. Have a look at the activities that you’ll want to check off your bucket list the next time that you’re around. 

Imagine staring straight down from more than 1,000 feet above. Yikes! When the fear of heights is not an issue, give TILT 360 Chicago a try. Located on the 94th floor of 875 North Michigan Avenue, the former John Hancock building, this innovative thrill ride offers a new window to the city with a glass-enclosed steel platform that tilts groups of up to eight ever so slightly a little over the edge. It’s worth it with the amazing views of the Magnificent Mile and the skyline that you won’t quite experience anywhere else. 

Meanwhile, on the water, the Seadog Speed Boat takes passengers on a riveting ride complete with twists and turns at a super-fast pace. Also, when the cruise is not zipping away, the experience includes interesting narration about the great city that is Chicago. You should note that getting wet will probably not be super difficult during this 30-minute boat ride that certainly flies!

Now it’s possible to feel the rush of floating in the air without having to jump out of a plane at iFLY Chicago, an indoor skydiving experience at Lincoln Park. This adrenaline-rushing activity involves putting a flight suit and experiencing unforgettable body flight in a gravity-defying, vertical wind tunnel two times per visit. The activity is safe and ideal for people of all ages and fitness levels. Plus, it’s great for families and groups. 

It’s okay to humblebrag after touring downtown Chicago from a helicopter. Prime views are what to expect when you sign up for a private helicopter ride from Chicago Aerial Tours. After departing from the Vertiport Chicago Heliport terminal, you’ll get to view the famous skyline and lake from a bird’s eye perspective. Ready? 

A little on the tamer side is taking in the fireworks at Navy Pier from the comfort of your seat on the Centennial Wheel. These are not just regular fireworks, by the way. They are a colorful pyrotechnic show synchronized to music overlooking gorgeous Lake Michigan that takes place Wednesday through Sunday from Memorial to Labor Day. 

Listen up ghouls and gals, Halloween will soon be here, and there are quite a few ways to celebrate the occasion. Whether you want to dress up and show off your costume, check out something scary or go trick-or-treating, there is so much to do in Chicago all month long. So what will it be?

So Wild

Families looking for a safe alternative to trick-or-treating should head out to Lincoln Park Zoo for Spooky Zoo, taking place on Saturday, October 26, 2019. Part of the annual Fall Fest, the beloved tradition also offers other fun activities from animal enrichment experiences to a fun corn maze, and more. Older kids and grown-ups who want to learn about the zoo’s haunted history can take a thrilling tour if they dare on October 29 and 30. Led by author, podcaster, and host of Mysterious Chicago Tours, this fascinating, 75-minute walkabout reveals scary things that you probably didn’t know including its cemetery past.

Phantoms of the Opera

Don your finest costume and wear a mask for the lively Lyric Halloween Masquerade. Hosted by the Lyric Opera of Chicago, this annual affair returns for an epic night of music by DJ Metro, dancing, signature cocktails, and bites from local restaurants. Besides, it’s all for a good cause with proceeds benefiting the emerging operatic talent of The Patrick G. and Shirley W. Ryan Opera Center. It goes down on Saturday, October 26 from 8 p.m. until midnight, so be there!

Halloween Fun at Navy Pier

Of course, Chicago’s iconic destination, Navy Pier, has a few things going on in honor of Halloween. Trick-or-treaters should bring a big bag and stock up on candy courtesy of participating establishments from 2 to 6 p.m. on October 26, 27 and 31st. Meanwhile, the Haunted Maze, is bound to instill frights thanks to spine-tingling twists and turns featuring ghosts from the Capone era and other dark moments from the city’s history. New this year is Cosplay on the Pier: Halloween Fest 2019, featuring a designated cosplay photo area, costume contests, and more on Saturday, October 26, from 2 to 10 p.m. What are you going to wear?

Not for the Faint of Heart

Stories of paranormal sightings and other grisly tales are in store during the Chicago Hauntings: Original Ghost Bus Tour offered throughout the year, including on Halloween. Veteran paranormal researcher Ursula Bielski brings brave groups to notorious sites from unfortunate tragedies, including the Eastland disaster, the Iroquois Theater Fire, and the St. Valentine’s Day massacre to the Hull House, which inspired the chilling movie Rosemary’s Baby. Known as the “World-Famous Supernatural Excursion,” this 2.5 to 3-hour excursion may have you sleeping with the lights on after it’s all over.