Top Things to Do in Chicago

It’s always a good time to travel to the dynamic, hospitable, foodie-centric metropolis of Chicago. But flying in the midst of a late January polar vortex with temperatures plummeting to 21 below zero made me aware of why airfares and hotel prices were so affordable in Chicago this time of year.

I needn’t have worried. The temperatures crept back up, the city returned to its normal, functional self and there were no more warnings to minimize breathing or talking due to frigid air. My canceled flight was rebooked and Chicago in January and February turned out to be just as friendly, the architecture by greats like Louis Sullivan, Frank Lloyd Wright and Mies van der Rohe just as beautiful, the exhibitions just as spectacular and the food just as memorable.

Traveling to Chicago this year? You’d be wise to make your first stop the 363-room St. Jane Hotel (formerly the Hard Rock Hotel), a stylish, sleek boutique hotel drenched in local atmosphere housed in the Art Deco 1929 Carbide and Carbon building on Chicago’s bustling Loop.

Chicago is a city renowned for its architecture (and in the spring and summer months, the Chicago Architecture Foundation River Cruise down the Chicago River is a must) and this stunning building allows you to sleep and dine in a piece of history, from the elaborately stamped brass elevator doors to the dramatic black granite and 24K gold ornamentation on the building’s facade. Design fans will appreciate how well the Chicago-based, female-owned Simeone Dreary Design Group bestowed an ultra on-trend sensibility to the public areas and private rooms. Touches of millennial pink, gorgeous statement light fixtures and a sleek Seventies-meets-Art Deco vibe balance chic and cozy. A jewel box hotel with a winking sense of humor (check out the brass monkey lamps in the lobby), the St. Jane offers next-level comfort and killer views. From our corner room outfitted with high ceilings and classic crown molding we could see Lake Michigan and the Loop and felt at-one with the pulse of this vibrant, architecturally gifted city.

Opened in July 2018, the Michigan Avenue hotel is centrally located a short walk from Millennium Park (and Anish Kapoor’s famous “Bean” sculpture), the Art Institute of Chicago featuring a fascinating Dawoud Bey exhibition through April 14 and the interactive American Writer’s Museum where you could while away a good afternoon with bookish friends and family. In fact, winter is a great time to see the city’s incredible museum’s which are toasty and filled with interesting people.

Named for Nobel Prize-winning Hull House-founder and philanthropist Jane Addams who helped the city’s poor (rooms include a biography of Addams for visitors wanting to delve deeper) the hotel has a luxurious, hip ambiance and an incredibly attentive staff that keep things down-to-earth and accessible. The pricier, bespoke Tower at St. Jane offers 33 rooms for a more high-end hotel experience including a lounge and outdoor space and gorgeous views of the city’s skyline.

In the past hotel restaurants have often been forgettable, but the demands of culinary-savvy guests are carving out a niche for spaces like Free Rein, formerly helmed by chef Aaron Lirette (who left the restaurant February 18). Lirette received a Michelin star at the now defunct GreenRiver and delivered a unique foodie experience without guests ever having to leave the comfort of the St. Jane. An adjacent lounge with pool table means you could spend a whole lovely, wintry evening inside. As with the hotel itself, the staff at Free Rein is friendly and the ambiance unstuffy. The elevated American fare with French influences includes poached duck eggs with a decadent pecorino fonduta that will make you want to lick the bowl—but it's served with lardo toast for sopping so you won't need to. The unexpected addition of trout roe to tagliatelle with country ham and parmesan dashi is uber satisfying and classic cocktails like the Last Word as well as inspired in-house creations make it a great spot to grab a drink with friends. The cozy dining room opens to a café with huge windows to watch Michigan Avenue passersby, where guests can grab coffee, breakfast and lunch during the day.

There are plenty of walkable spots worth checking out too, from the scruffy but solid Mexican street taco spot, home to pierced and tattooed hipster waiters Broken English Pub (with additional locations in Lincoln Park and Old Town) to the sophisticated brunch at Mercat a la Planxa. The menu features Catalan flourishes and a open, airy La Veranda dining room with sweeping views of Grant Park in the beautiful 1910 Blackstone Hotel (take a walk through the glam lobby to take in the modern-meets-old school velvet and gilt décor). Don’t miss a twist on the typical decadent brunch staple, the Mercat Benedict with tangy chorizo, truffle hollandaise and a buttery brioche or the Piparrada Omelette with grilled asparagus, manchego cheese and a red pepper sauce that will banish all thoughts of ketchup for good.

A certifiable foodie town, you’ll be out of luck if you don’t plan far ahead for favorites like chef Paul Kahan's gorgeous casual fine dining Blackbird or The Girl and the Goat which require far in advance reservations for anyone who hopes to check out Stefanie Izard's family-style globally-inspired menu. Equally hot, but perhaps a bit more accessible is a local friend's recommendation HaiSous. Helmed by a husband and wife team in the largely Hispanic Pilsen neighborhood, HaiSous is buzzy on a Saturday night, full of well-dressed groups and couples and inventive Vietnamese food (natch, a James Beard semi-finalist for Best New Restaurant) and cocktails you will miss when they're gone. The interior and exterior of this stylish spot is by co-owner and architect Danielle Dang of Den of Lions Design whose husband is HaiSous's Chef Thai Dang.

Chicago is filled with great independent bookstores, from Wicker Park’s maze-like, stuffed-to-the-gills Myopic Books to Michigan Avenue’s brilliantly curated, elegant new and used book emporium The Dial Bookshop ensconced on the second floor of the Richardsonian Romanesque Fine Arts Building where Frank Lloyd Wright once had an office. If history or film is your thing, make a point of taking in a movie at the restored 1929 Music Box Theatre, which features a comfy lounge for a pre- or post-film cocktail, an in-house ghost and a solid run of repertory and first-run offerings.

A city known for its theater and comedy scenes, you can experience a very affordable night out and a young, anarchic group of performers with The Neo-Futurists. Day-of ticket prices are determined by a roll of the dice and each evening’s performance of their signature "The Infinite Wrench" sketch comedy-meets-anthology line-up is determined by audience vote. At this experimental hot spot an evening of short skits in the group’s repertoire runs from the absurdist to the genuinely poignant. The millennial-minded group is caring and thoughtful despite their punk rock energy, offering trigger warnings to audience members if they need one.