The Perfect Weekend in Chicago

Visitors with only three days in Chicago should maximize their time with ample art and food exposure. Orient yourself by taking an architectural cruise along the Chicago River or get high with a panoramic view of the city from the top of one of its fantastic buildings. Then hit up some of the world-class museums along the lakefront: A visit to the Art Institute, the Field Museum, and the Chicago Architecture Foundation can explain (in a spectacular fashion) the cultural breadth of the Windy City. See the Cubs play ball at Wrigley Field and drink a craft cocktail at one of our favorite bars. In just one long weekend, you’ll get a vivid taste of Chicago, a city second to none.

111 S Michigan Ave, Chicago, IL 60603, USA
Just imagine having 264,000 square-feet of modern art at your disposal seven days a week. That is exactly what you have if you visit the Modern Wing of the Art Institute of Chicago. Above is but one example of the funky-cool exhibits that await you in this colossal house of creativity. If you need a drink, a snack, or perhaps a fine-cuisine fix to recharge, you can also stop by the Terzo Piano restaurant that is located within the museum. The Modern Wing is a must-see for art lovers while visiting the Windy City.
2391 N Stockton Dr, Chicago, IL 60614, USA
Constructed way back in 1890, the Lincoln Park Conservatory and Gardens in downtown Chicago boasts a mind-boggling array of exotic plants and flowers. The conservatory is home to four different display houses, as well as sculptures, outdoor gardens, monuments and a tranquil fountain. The irony is that while the sprawling gardens encompass a huge swath of land, it all resides right in the middle of the bustling Lincoln Park area, yet still remains one of the hidden gems of the Windy City. It has been referred to as a botanical goldmine, and is equally entertaining for adults and children alike. This place is indeed one wicked garden. Chicago is known for lots of interesting things, but this is one hidden gem that is both fantastic and free.
7705 N Eastlake Terrace, Chicago, IL 60626, USA
Pick up your morning coffee at one of the many local coffee shops, and walk to Rogers Beach (known by locals as Lighthouse Beach). The sunrise over Lake Michigan is stunning! Locals fish off the lighthouse pier in the early morning semi-darkness. Bikers, joggers and dog-walkers on the lake-side path smile and wish you good morning as they pass. Benches in the park and on the beach give you a quiet place to relax, and a lovely view of the ever-changing, colorful water and sky. It’s peaceful and calm—the most delightfully splendid hour of your day! This is the real Chicago!
112 E Upper Wacker Dr, Chicago, IL 60601, USA
The Chicago River and Lake Michigan are two of the city’s greatest assets, and there’s no better way to experience both than with an architectural boat tour. While there are plenty of reliable options around, go with First Lady Cruises, which calls upon expert docents provided by the Chicago Architecture Foundation to reveal extensive history, culture, and style insights (for example, how the design of Willis Tower was based on cigarettes, or how the Monadnock Building on Jackson Boulevard was fabricated with 100 different shapes of brick). Book anytime between May and November for these rides, which run every day of the week and last 90 minutes.
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.
5700 S Lake Shore Dr, Chicago, IL 60637, USA
Anyone who’s into model trains should visit the Museum of Science and Industry in Chicago. Originally opened in 1941, The Great Train Story was the largest model train of its day. After being briefly shuttered in 2002 for extensive additions, this O gauge two-track train set is truly something to behold. The model stretches from downtown Chicago to the western seaboard of Seattle. The level of detail is absolutely staggering, and you can spend hours looking for such unique sites such as Marilyn Monroe in her famous white dress being caught in the wind, to King Kong (albeit on the wrong building since New York isn’t included), to the Chicago Police Department fishing a body out of the river after a hit from Capone’s fellas! And just to give some idea of the size, in the photo above (which hardly captures the immense scale) you will see a large passenger plane suspended above it. The Great Train Story currently runs 30 trains at a time, more than enough for everyone to create their own unique tale while visiting.
5219 N Clark St, Chicago, IL 60640, USA
Brimfield specializes in antique glassware, vintage signs, custom upholstered chairs and plaid blankets, pillows and furnishings of every conceivable style and design. The owners began collecting antiques in the UK in the late 1990s and opened their shop in Chicago about 8 years ago. Brimfield continues to be family owned and operated and they promise unique finds to all their customers.
1520 North Damen Avenue
The first rule of the speakeasy is that it can’t be easy to find. The Violet Hour’s door is directly across the street from Big Star. Look for the handle on the wall and the light above it, because the door mural changes frequently and cleverly disguises the space. It doesn’t take reservations, so expect to wait in line as the number of people in the bar at any time is also tightly controlled. This is good, because it won’t ever be packed! The Violet Hour isn’t a get-up-and-mingle kind of joint, which makes it the perfect dark, sexy lounge for romantic dates and quiet conversations about world domination. The cocktail menu changes frequently, so even if you’ve been before, you should go again. (And try the Finocchio Focaccia.)
809 W Randolph St, Chicago, IL 60607, USA
West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.
805 S State St, Chicago, IL 60605, USA
As you can imagine, there’s a lot of discussion over who has the best pizza in Chicago; so, here’s what I know for sure: Lou Malnati’s serves a great stuffed pizza, they’re one of the oldest pizza names in town and they have yet to franchise outside of the state of Illinois. If you come to Chicago and you want Chicago style stuffed pizza, eat the pizza you can only get here!
2800 W Logan Blvd, Chicago, IL 60647, USA
It took no time for this neighborhood restaurant from chef and owner Diana Dávila to garner major fandom. The menu—a compilation of antojos, or Mexican small plates—is a nod to Dávila’s Mexican heritage and an invitation to diners to experience the country as she did growing up. Expect that journey to unfold with the likes of fish with yellow mole, enchiladas potosinas, and an array of taco options (from beer-can chicken to butternut squash). Drinks are just as groundbreaking—opt for the Chicana, a floral and herbaceous coming together of hibiscus, mezcal, gin, Chartreuse, and maraschino.
177 N Ada St #101, Chicago, IL 60607, USA
Not only do husband-and-wife team John Shields and Karen Urie Shields share an impressive culinary background (one that entails gigs at Tru, Alinea, and Charlie Trotter’s between them), they now share two restaurants: the Loyalist, a neighborhood restaurant focused on farm-fresh fare, and Smyth, an upscale tasting-menu eatery embodying those same sourcing philosophies. It’s the latter that garnered a Michelin star within just six weeks of opening, thanks to an incredibly ingredient-focused approach that often means making key elements of dishes in-house. Dungeness crab with saltwater-poached foie gras and scrambled kani miso continues to be a favorite for diners, as is the egg-custard dessert—a brilliant and beguiling bowl of egg yolk, salted licorice, and frozen-yogurt meringue.
851 W Randolph St, Chicago, IL 60607, USA
This skin-care sanctuary just opened its doors in Fulton Market’s bustling neighborhood after spending two years in Roscoe Village, where it built an obsessive following for its handmade products. The line was inspired by the cofounders’ mission to create items free of parabens, sulfates, and dyes, and to date they’ve already whipped up soaps, scrubs, masks, and body butters. If that wasn’t enough to keep them busy, the shop also runs several wellness classes a week (including yoga and meditation), along with a six-seat mask bar, where guests can customize their own clay masks with the guidance of skin-care pros.
2780 N Lincoln Ave, Chicago, IL 60614, USA
This Lincoln Park destination, besides being one of the only designer-toy shops in the Midwest, has gained a reputation for being one of the best designer-toy shops in the world. It stocks a wildly diverse selection of vinyl figures and pop-culture collectibles from creative brands across the globe, including Kidrobot, Funko, Tokidoki, and Amuse. Still, it’s their “blind box” toys that sell fastest—customers don’t know which toy in a collection or series they’re buying until they open the box post-purchase. The shop’s other areas come with surprises, too: An adjacent gallery houses artwork, and its 1,000-square-foot space is available for private events (when it’s not hosting monthly BYOB Drink n’ Draw parties).
2657 N Kedzie Ave, Chicago, IL 60647, USA
In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”
1060 W Addison St, Chicago, IL 60613, USA
Steeped in history, loved my many, loathed by some, and sorely in need of a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to to baseball and Chicago. Snag tickets and enter the much-lauded venue, or simply meander around the area and take in the antics of locals ‘doing what they do’ on game day; you’ll be entertained regardless. And by the way, there is a game going on too, in case you didn’t notice.
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Journeys: Africa + Middle East
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