Eat: Allis
Named for Charles Allis — a turn-of-the-century industrialist, art collector, and philanthropist — this welcoming space is perfect for morning pastries, afternoon tea, or a craft cocktail during happy hour. The restaurant and lounge feature an expansive art collection and views of Green Street through floor-to-ceiling windows. Grab a bite from the all-day menu in the lobby area, or a drink at the marble bar and relax upstairs in the lounge on couches perfect for snacking or working.

Stay: Chicago Athletic Association Hotel
Borrowing its name from the elite men's club that once occupied the building, the Chicago Athletic Association Hotel is a 241-room Venetian Gothic gem. While the rooms have been updated with modern amenities, tons of original flourishes remain, and join a game room, Shake Shack, and rooftop bar and restaurant on the grounds.

Recharge: 4 Letter Word Coffee
Originally hailing from Istanbul, the Logan Square coffee shop specializes in Turkish-style drinks. Their 20-seat cafe offers an intimate spot to enjoy a local pastry and a pour over. When seating is sparse, their standing tables provide a place to perch for a quick shot of espresso.

Eat: Doughnut Vault
Widely considered one of the best doughnut shops in the country, this offshoot of Gilt Bar serves up freshly made treats every morning — until they inevitably sell out. Expect a line out the door, quaint brick interior, and $1 cups of coffee.

Eat: RL Restaurant
Located next to Ralph Lauren's flagship store on Michigan Ave., the RL Restaurant brings the brand's American roots to the dinner table. Home-grown classics like seafood, steaks, salads, and sandwiches take their place alongside delicious cocktails in an upscale, club-like atmosphere where everyone receives members-only treatment.

Wear: Garb: Logan Square
A laid-back day in one of Chicago's most compelling neighborhoods lines up perfectly with this ensemble from Ralph Lauren. From head to toe, you'll be more than prepared for whatever elements you encounter thanks to essential spring layers and reliable suede boots — while the military duffel with full-grain leather accents ensures everything stays organized when you make your way home.

Shop: Diversey Wine
Specializing in wines with grapes farmed organically and fermented naturally — also known as natural wine — this Logan Square wine shop has the best selection of natural wines in the city. In addition to the low-intervention wine you can purchase to take home, Diversey offers $10 tastings every Sunday hosted by the winemakers themselves.

Cut: Blind Barber
If a haircut or beard trim is on your list during your stay in the Windy City, Blind Barber offers both, plus quite a bit more. In addition to the grooming services and a full line of products, the Fulton St. location offers a bar and lounge that is located behind a discreet door at the back of the barbershop. The door opens to a '70s themed rec room — complete with burnt-orange leather sofas, glass-block windows, and a low-lit dance floor. In addition to drinks, they offer a menu highlighted by more than 20 grilled cheese sandwich options, along with tacos and crispy chicken wings.

Eat: Bellemore
Head by chef Jimmy Papadopoulos, the West Loop restaurant infuses old-world glamour and modern American cuisine. The vintage manor vibes are the result of soft blush hues, wicker seating, and a pair of stuffed peacocks above the marble bar. But it's not all about the aesthetics. The fare is equally as impressive with a menu that includes grilled vegetable soup and rich oyster pie topped with osetra caviar.

Shop: Studio 6F
Studio 6F — named for the hex code for the color white — is far from a typical home store. Offering exclusive in-house designs, hand-picked vintage items, and pieces from custom makers, they creatively package them together to create a cohesive decor.

Wear: Garb: Second City
Exploring the Windy City requires the right look, and this collection from Ralph Lauren checks every box. The Cotton Twill Jacket is perfect for a cool spring morning, while the popover, cap, sunglasses, and Sullivan Slim jeans keep things casual and comfortable during a full day riding the 'L'. The navy and black canvas duffel completes the look and serves as a landing spot for all your gear and Chi-Town souvenirs.

Sip: Fox Bar
Tucked behind saloon doors on the mezzanine level of Chicago's Soho House, this cozy, craft-beer and cocktail lounge has a speakeasy vibe but no required membership. The West Loop watering hole offers a rotating drink list, along with small bites and comfort food from the kitchen. And to pair with the vintage decor and dim lighting, Fox Bar has a well-stocked vinyl library and regular DJ nights to add to the laid-back ambiance.

Sip: Young American
Located in Chicago's Logan Square, Young American is a neighborhood bar and kitchen offering snacks and small plates served late into the night. In addition to the craft beer and cocktails on the menu, drinkers preferring to relax without alcohol can order a CBD-infused cocktail or have CBD added to any spirit-free drink. Each of the food options is mouth-watering, but it would be a shame to miss out on the Goth Bread: made with activated charcoal, leek ash, cheese, butter, egg yolk, and the dark, aptly named "nighttime sauce."

Recharge: Metric Coffee
Located in Chicago's Kinzie Industrial Corridor, Metric Coffee serves a variety of seasonal, house-roasted specialties along with cold brews, cold-pressed juices, and pastries. There are a few spots to chill and enjoy your brew but the streetside counter is ideal for those on the go.

Eat: Tied House
Being tied to a historic landmark like Schubas Tavern can be daunting but Tied House answers the call with style and upscale comfort food. While it takes on a modern form, the Lakeview eatery pays homage to the legacy of its neo-Gothic neighbor with its brick detailing and the interior's pressed tin ceiling. The Debbie Gold-led kitchen doesn't disappoint, serving a mix of small plates and refined bar food.

Stay: The Robey
Housed in a 200-foot-tall 1920's skyscraper, The Robey honors the area's architectural past across its 89 tastefully minimal rooms. Conveniently situated between Wicker Park and Bucktown, it also houses multiple lounges, a cafe, and a rooftop pool.