The Long Weekend

The Perfect Weekend in Chicago

By Avery Carmichael

The Windy City

, Chi-Town, The City That Works—call it what you will, but Chicago is a veritable powerhouse. As the third most populous city in the United States, Chicago feels quintessentially new, with towering, reflective skyscrapers and impressive urban planning. Add its innovative food scene and artistic spirit, and Chicago is an alluring destination for all types of travelers. Here is a detailed itinerary for the perfect weekend in Chicago.

Contact Indagare for assistance planning a customized trip to Chicago.

Day 1: Art and Architecture

With such a large physical footprint and over 70 neighborhoods, Chicago has a solid roster of hotels, most of which are located downtown. We recommend the high-touch Peninsula for family-friendly amenities, the Four Seasons for magnificent views and contemporary art, and the Chicago Athletic Association Hotel for a buzzy scene.

After settling in to your hotel, explore Chicago's art museums. Begin with the The Art Institute of Chicago, where the extensive collection rivals that of The Met's. Thanks to Edward Hopper's Nighthawks, Grand Wood's American Gothic, Georges Seurat's A Sunday on La Grande Jatte and many other works, you could easily spend the whole day here. Next, get some fresh air and admire Anish Kapoor's renowned public sculpture, Cloud Gate, the centerpiece of Millennium Park (and of most millennials' Instagrams after a visit to Chicago).

The Museum of Contemporary Art (MCA)

, and the new, experiential wndr museum are ideal next stops for modern and contemporary art lovers. wndr recently played host to one of Yayoi Kusama's Infinity Mirror Rooms and will continue to host inspiring pop-ups in the months to come.

Refuel with a slice of melt-in-your-mouth deep-dish pizza at Giordano's, a five-minute walk from the MCA, before passing by the Chicago Water Tower. This late 19th-century architectural marvel was one of the few buildings to survive Chicago's Great Fire of 1871. Alternatively, head to the Skydeck, on the 103rd floor of the Willis Tower (previously named Sears) for larger-than-life views of the Chicago cityscape.

Finish the day with a show. Options include Broadway's greatest hits, like Hamilton and Dear Evan Hansen, a comedy show at Second City or a jazz concert at a local nightclub, such as Andy's or The Green Mill.

Day 2: Shopping

Head to the upscale River North neighborhood for a lively brunch at Beatrix. This café-cum-bakery is just as great for a quick coffee and croissant as it is for a hearty breakfast of eggs and bacon. Locals love its laid-back, homey feel.

After breakfast, spend the morning browsing Chicago's best shops. Begin at P.O.S.H. and peruse the shop's well-curated British and French antiques and contemporary home goods. Walk a few blocks to the Magnificent Mile, where the Chicago outpost of Barney's is located. Other favorites are Ikram, which sells high-end designer clothing for women, including the likes of Givenchy, Erdem and Dolce & Gabbana, and doubles as a lunch spot and art gallery, as well as Space 519, a concept store replete with menswear, women's apparel, organic beauty products and home décor.

Stop at Mindy's Hot Chocolate in Wicker Park for a hot chocolate pick-me-up, and continue on to Moon Voyage clothing boutique and local literary haunt Myopic Bookstore. Asrai Garden, also nearby, features gorgeous floral arrangements.

Further afield, locals love the Andersonville neighborhood for its small, local home and furniture stores, including Scout and Brimfield. Stop for a lunch of traditional Southern fare at the popular Big Jones restaurant.

This evening, join in Chicago's enthusiastic sports scene and see the famous Chicago Bears at Soldier Field, the Blackhawks and Bulls at the United Center or the Cubs at Wrigley Field. Be warned: Chicago fans can be very convincing, so whether or not you start off rooting for their team, you'll likely end the night pulling for 'da Bears!'

Day 3: Relax and Riverwalk

On your final day, indulge in a treatment at one of the city's fabulous hotel spas. The Peninsula Hotel, with its extensive relaxation area and selection of treatments, is a favorite. If you're interested in Ayurvedic treatments, Allyu Spa (not associated with a hotel) has a number of chakra-balancing treatments, among other types of massages and facials.

If you are visiting during the spring, summer or fall, head to Chicago's Riverwalk, a 1.25-mile pedestrian walkway that lines the river. Rent a kayak and spend your day paddling on the river, or head to one of City Winery's domed structures for a glass of wine with views.

Contact Indagare for assistance planning a customized trip to Chicago.