Maggie Daley Park

Rooftop venues in winter The Gwen Hotel’s terrace (above) on the fifth floor features an iceless rink for a little curling competition, as well as a cozy wood-paneled cabin that offers a rustic living room with an electric fireplace. Waiting for your turn? Grab a hot cocktail and park yourself at a communal table or the lounge seating near a fireplace or heat lamps to keep warm. 521 N. Rush. 312-377-3770. TheGwenChicago.com/curling

The sleek 13,000-square-foot VU Rooftop is located 22 floors high next door to McCormick Place, providing stellar views of downtown and three different indoor spaces, each with its own vibe and windows galore. A tasty menu of sharable plates will cure your hunger, and firepits, couches and a well-made cocktail or glass of red make the outdoor patios all the more comfortable. 133 E. Cermak. 312-528-0191. VURooftop.com

Touring the Pedway system Here’s your chance to stay warm and delve deep into Chicago history and architecture. Get the best of both worlds exploring the “city under the city,” better known as the Pedway system beneath Chicago, with the renowned Chicago Architecture Center. This unique set of underground pathways includes 40 downtown blocks of shops, art, restaurants, architecture and a few of the city’s famous historic and contemporary structures. The 1.5-mile walking tour costs $15 and is two hours in duration. 312-922-8687. Architecture.org

Explore YOUR GUIDE TO CHICAGO INSIDER’S Chicago Insider: Q&A with Chicago Detours founder Amanda Scotese

Q: Five-star reviews are the norm. What do you think makes Chicago Detours so popular?

A: I think it’s because we have the best guides in the city — they are fun, passionate, and they create an educational and interactive dynamic to the tours.

Q: Do you have a tour that’s perfect for a chilly day? A: Our Loop Interior Architecture Tour is a popular one. We stay mostly indoors, and you get to discover the beauty inside warm buildings. Guests all learn about the Pedway system, which are passages that can be helpful for navigating the city during cold weather.

Q: Give us a fun fact or anecdote from one of your tours that always surprises your guests.

A: On the 1893 World’s Fair Walking Tour, it’s fun to share with guests all the inventions and foods that debuted at the World’s Fair. Things we take for granted today have their origins at this grand Chicago event — like Wrigley Juicy Fruit gum and zippers! Q: What is your favorite building to showcase? A: That’s a tough one because I love so many different styles. I’ll say the Intercontinental Hotel on our Historic Chicago Walking Bar Tour. We learn about reading the features of the building on the outside — with its eclectic imagery from across history — and then share a hidden little corner of the building inside with incredible architectural details.

INSIDER PROFILE

Chicago Detours provides guided walking and bus tours of Chicago architecture, culture and history to both public and private groups, providing a fresh, insider perspective you won’t find elsewhere. 312-350-1131. ChicagoDetours.com

CHICAGO CRIME TOURS

The history of Chicago’s crime underworld is a vast one, and there’s no better way to learn about some of the city’s most famous criminals, mobsters and gangsters than jumping aboard Chicago Crime Tours’ luxury, climate-controlled bus. Explore a host of historic crime scenes like Holy Name Cathedral, the Biograph Theatre and the site of the St. Valentine’s Day Massacre, and get insights on the famous names like Capone, Dillinger, The Untouchables, Frank “The Enforcer” and so many more. 312-888-6224. ChicagoCrimeTours.com