City Guides 06.14.2023

Chicago Weekend Guide

Chicago is a testament to the rich history that has long graced the American Midwest, on display through iconic landmarks, diverse neighborhoods, and a resilience that continues to shape its vibrant art and design identity. Here’s what to do this weekend to experience the best of Chicago.

Known as an architectural titan in the American design sphere, Chicago’s evolution from a small trading post in the 18th century to a bustling metropolis continues to delight, drawing over thirty million visitors each year. Founded in 1833, the city’s idyllic spot on the coast of Lake Michigan facilitated its growth as a transportation hub and a center for industry and commerce. As a city that has had to rebuild again and again throughout its lifetime, its grand architectural designs and intuitive urban planning are a sight to behold. Let’s take a deep dive into how to explore Chicago’s rich culture and how its history permeates into its must-see stops today.

How to prep for a trip to Chicago

Chicago is designed to be a walkable metropolis with plenty of sights to take in, seen with a quick glance at its impressive skyline. Much like New York, Chicago was built on a grid system with the intersection of State and Madison Streets as the midpoint of the grid. This means you’ll be able to easily find your way around the city and back to a home base when tracing what to do this weekend in Chicago.

The city is also home to a plethora of seasonal activities and festivals. The Chicago Blues Festival (June 2024), the Taste of Chicago (June 24 at Humboldt Park, July 15 at Pullman Park, August 5 at Marquette Park), and Lollapalooza (August 3-6) bring famed musicians and chefs north for summer; on the other hand, winter ushers in the Christkindlmarket wonderland. While springtime and summer in Chicago offer temperate climates filled with blossoming tulips and sunshine on Lake Michigan, The Windy City becomes truly, well, windy during the autumn and winter. Therefore, we recommend packing plenty of urban chic layers so that you’re prepared for whatever Chicago’s weather throws your way.

Where to stay in Chicago

Between the impressive private art collection and award-winning cuisine it houses, Park Hyatt Chicago exudes contemporary chic. This legendary property is the ideal home base for anyone looking for immediate access to the city’s most exciting attractions and exemplary service. In addition to being located next to the iconic Magnificent Mile, the hotel is also home to delicious dining options and premiere wellness facilities – all adding to the growing list of what to do this weekend in Chicago.

Park Hyatt Chicago offers 198 rooms – including thirteen elegant suites – each appointed with deep soaking tubs and sleek window benches with views of the Water Tower, Lake Michigan, and Chicago’s Gold Coast. Suites offer apartment-style layouts with separate living areas, as well as a range of residential features such as a kitchenette and powder room that make guests feel right at home in downtown Chicago. These elegantly understated rooms ensure a plush, comfortable stay.

The dining options at Park Hyatt Chicago are a particular highlight for a weekend outing. Their main dining area, NoMI, is named for its iconic location on North Michigan Avenue. NoMi’s team treats guests to an array of French-inspired American cuisine by Executive Chef Terence Zubieta. NoMI Lounge offers a more relaxed experience and Chicago’s best sushi alongside craft cocktails from an extensive global collection. The lounge also invites guests inside their working wine cellar that houses a specially curated global wine collection. Uncorking and sipping on the rare and unique curated wines is a particularly satisfying experience here with all wines vetted by sommelier Jillian Riley Looking for an open-air experience? Check out the NoMI Garden outdoor terrace and dine under in the midst of Chicago’s skyline.

Where to find the best Chicago architecture

In good company woven into the American architectural tapestry with the likes of New York’s Chrysler Building and Seattle’s Space Needle, Chicago is renowned for its distinct palette of hypermodern and old-world buildings. From River North to Logan Square, there is an impressive array of eye-catching facades harking back to a span of time periods along the historical spectrum. This wide array of architecture is all thanks to the city’s central location in key trade routes during the 19th century, as well as its ability to rebuild after the Great Chicago Fire of 1871 which leveled nearly 17,500 buildings.

There are a couple of ways to explore this city’s architectural marvels: one popular option for what to do this weekend in Chicago is to hop onto a boat tour along the famed Chicago River. With departures around the clock, rain or shine, your knowledgeable guide will take you through an incredible breadth of history that outlines how the city rose from the ashes to build bigger and better. Our personal favorite way of exploring Chicago’s architecture scene is via a private guided walking tour, all arrangeable via your SmartFlyer travel advisor.

Smartie Scouted Chicago architecture

Aqua Tower: One of the more adventurous designs that have graced Chicago’s running portfolio of skyscrapers, Aqua Tower was designed by architect Jeanne Gang. Its undulating facade stretches eighty-seven stories of residential living.
Bahá’í House of Worship: With roots back in the late 19th century, this is one of nine Temples of Light in the world – located just a brief drive from the city center. The building blends neoclassical, Gothic, and Renaissance elements together into a striking modern marvel for various faiths to convene.
Chicago Architecture Foundation: For a one-stop-shop for all things Chicago architecture, this nonprofit’s headquarters are just as design-forward as the history it preserves. Exhibitions range from spotlights on the evolution of urban housing to spotlights on sustainable construction.
Hyatt Headquarters: Constructed in 2017 as the hotel brand’s fourth headquarters, this striking building contains pieces of hospitality history and blends them into a hyper-modern setting. The LED blades in the lobby showcase a range of digital art from local artists.

Marina City: A variety of films featured these towers constructed in the 1960s for their distinct spiral design. The City of Chicago now recognizes Marina City as an official landmark of and the tallest building in the world made of reinforced concrete.
Merchandise Mart: As one of the largest commercial centers in the world, this Art Deco masterpiece is home to four million square footage of offices, entertainment, and dining. Just walking through its ornamental lobby is a testament to the American history it has stood through, from the Depression Era to its recent renovation in the summer of 2023.
The Rookery: A historic office building completed in 1888, The Rookery is considered one Burham and Root’s masterpiece buildings. Guests often frequent this building for its ornate atrium and a blend of Moorish design philosophy.
Willis Tower: Once known as the Sears Tower – one of the tallest buildings in the world – this 110-story skyscraper houses five floors of fine dining and shopping experiences. Willis Tower is also home to an exhilarating Skydeck that places you high above the Chicago skyline.
Wrigley Building: The commercial center needs little introduction as this iconic clocktower and plaza offers a dramatic backdrop for timeless photoshoots.

Where to eat and drink in Chicago

Food

North Chicago

BOKA: Head to Lincoln Park for seasonal farm-to-table American food. For over twenty years, Chef Lee Wolen has continued to serve up hyper-seasonal tasting menus that have garnered the restaurant multiple awards, including several highly-coveted Michelin stars.
North Pond: A charming restaurant nestled within Lincoln Park offering a farm-to-table approach. Situated at the edge of a pond, North Pond serves creative and flavorful dishes in a picturesque setting, making it a beloved weekend spot for diners seeking a taste of nature in the heart of Chicago.

Magnificent Mile

Alpana: Spearheaded by female sommelier Alpana Singh, this restaurant leads with a wine-inspired cuisine that beautifully pairs flavorful dishes with equally flavorful vinos. Singh’s goal is to reverse the pairing methodology and bring wines to the forefront of her menus.
Bistronomic: Enjoy French bistro classics comprised of ingredients from local Midwestern farms. Bistronomic’s delicious menu items include Ahi Tuna Tartare, Housemade Country Pate, Organic Amish Chicken, and the Grilled Cheese Du Jour.
Le Colonial: A French-Vietnamese restaurant with glittering, gold interiors. You can find sanctuary in this buzzy hotspot in their private dining area, perfect for your a group weekend celebration in Chicago or simply dinner for two.
Les Nomades: Chef Foland Liccioni and Mary Beth Liccioni proudly serve up a classic, fine French dining experience. Think duck pâté, Sautéed Dover sole, and artisan cheeses.
Maple & Ash: Led by a 2-Michelin-starred chef, this upscale Chicago steakhouse has a sophisticated ambiance and impeccable service. This is an excellent choice for private dining, often frequented by nationally-renowned sports teams when playing in town.
Tzuco: This Mexican restaurant highlights Chef Carlos Gaytán’s favorite Mexican dishes and is located on the Gold Coast of Chicago. Caytán is the first Mexican Michelin-starred chef and is known for combining the best of Mexico with French haute cuisine.

River North

Brindille: Carrie and Michael Nahamedian grace Chicagoans with their sleek take on Parisian cuisine. Every drink and dish is carefully curated, from their seasonal menus to their distinct dessert, absinthe, and after-dinner spirits.
Frontera Grill: This Chicago mainstay has served delicious Mexican dishes since the late 1980s. The festive interiors of Frontera Grill match the vibrant flavors bursting from their tangy tomatillos and fiery chiles.
Kostali: If you’re looking for a taste of the Mediterranean this weekend in Chicago, then look no further than this elegant restaurant. Recipient of a James Beard Award, chefs Carrie and Michael Nahabedian serve up coastal delights like roasted sea bass and squid ink risotto.
Le Select: On the flip side of Les Nomades, Le Select embodies the modern French dining experience with its glammed-out interiors and sumptuous dishes. Their upstairs bar is a delight, as well as their duck leg confit for dinner.
Purple Pig: A blend of Italian, Greek, and Spanish flavors all unified under the restaurant’s Michelin star, The Purple Pig’s menu is curated by Chef James Beard. Food critic Dana Cowin dubbed this spot dubbed the “Prince of Pork ”.

West to East Loop

Alla Vita: Looking for family-style delights? If so, then check out one of our favorite picks for Italian comfort food, expertly elevated by Executive Chef Lee Wolen’s traditional take on pasta and more.
Avec: This is a wine-focused restaurant featuring Mediterranean classics with an American Midwestern twist. Try the chorizo-stuffed Medjool dates and the swordfish and mussel tagine.
AVLI on the Park: Tucked away in the Lakeshore East neighborhood, this neighborhood gem offers a seasonal rooftop area. Executive Chef Nikolaos Kapernaros curates delicious Greek menus, bringing his cooking experience from the Culinary Institute of Rhodes to the shores of Lake Michigan.
Bazaar Meat: Underneath sparkling, crimson chandeliers, this restaurant invites you to a tasting menu that weaves from raw dishes like the prized vaca vieja and the ribeye aged to perfection. No matter how many times you visit Bazaar during your venture for what to do this weekend in Chicago, no two meals will be the same.
Cindy’s: Both a buzzing bar with rooftop views of the Loop and a top-tier restaurant, this establishment is a must-visit. Be sure to spot the original Andy Warhol hanging above their fireplace mantle in their private dining area.
Momotaro: Located in the West Loop’s Fulton Market District, Momotaro features specified stations for sushi and Robata. They also have tasty gluten-free options like A5 Miyazaki Steak.
Rose Mary: A vibrant restaurant blending the flavors of the Mediterranean and the Adriatic regions with a modern twist, Rose Mary has stylish decor and an eclectic menu. Chef and Owner Joe Flammoffer memorable Croatian dining that captures what Flamm coined “Adriatic drinking food.”
Sepia: Locals know this renowned Michelin-starred restaurant for taking the concept of the American melting pot and translating that into refined, hearty cuisine. The restaurant sources their rustic, seasonal menus from local artisans and sustainable practices.

Drink

Bar Mar: Sip on creative cocktails like the Salt Air Margarita with Milagro Blanco tequila, orange liquor, and lime topped with sea foam. Chef José Andrés’s also serves up brilliant renditions of iconic seafood classics-like fried calamari and lobster rolls.
Carol’s Pub: Looking for a taste of classic country pubs during your weekend in Chicago? Check out this local haunt, which reopened in 2021 and always putting the best of Illinois live music on its stage.
Kingston Mine’s: No visit to Chicago is complete without a visit to this mainstay blues bar. Founded in 1968, a night here leaves little question as to why this spot continues to be frequented by musicians near and far.
Kumiko: This minimalist den brings the art of Japanese bartending to the Loop. Julia Momosé serves up an elevated menu with some of the finest saké and savory small plates such as flash-seared mackerel.
LÝRA: This is the place to go for dancing after dinner. Located in the West Loop, this Greek establishment features a wraparound patio and live DJs every weekend.
Map Room: A bar decked out in vintage maps and travel decor, Map Room is sure to ignite your wanderlust. Locals love this watering hole for its twenty-five beers on tap originating from the breweries of the Windy City to the fields of Japan.
Milk Room: For those looking for drinks a little off the beaten path, Milk Room has you covered. Beverage director Paul McGee has curated a menu of rare spirits from Fernet Branca bottled in the 1950s to Cherry Heering from the 1970s.
Mother’s Ruin: This New York City haunt has found its way to Avondale and also brought all its charm with it. Signature cocktails include tongue-in-cheek blends like the Slushy du Jour and the Plot Twist.
Simone’s: If MacGyver could create a bar, it would look something like this. Simone’s space is designed and decorated using a variety of different resources like a bowling alley lane and high school science lab desks (and yes, their drinks are just as crafty).
Sparrow: Taking advantage of Chicago’s eclectic architecture, this bar is located within an Art Deco apartment from the 1920s and makes rum the star of the show.
The Violet Hour: Infused with Prohibition Era charm, this speakeasy is located in the heart of Wicker Park and is home to a rotating, seasonal cocktail list. Look out for their mural guiding guests to the entrance, as well as their house rules to help keep things classy.

An overview of the Chicago shopping scene

Chicago offers a range of shopping experiences, from the Magnificent Mile’s upscale boutiques, flagship stores, and luxury brands to Wicker Park’s independent boutiques and local artisans. Though, a lesser-known hidden gem amongst the city’s glamorous retail scene is its secondhand shopping scene. Thanks to the Windy City’s eclectic and vibrant history with design, you can find some truly rare finds in flea markets and vintage stores.

Our top neighborhoods for Chicago shopping

Andersonville: When it comes to shopping from locally-sourced shops, there’s no better place to start than in Andersonville. Located on the north side of Chicago, this vibrant neighborhood is known for Chicago-only vendors such as the Andersonville Galleria and Milk Handemade, featuring quirky home decor and artisanal crafts. Strolling along Clark Street is a treat in itself: just window shopping is sure to give you a taste of Chicago’s ever-burgeoning art scene bleeding into its fashion.
Hyde Park: There’s a reason why this is one of the most well-known cultural hubs in the States. With the esteemed University of Chicago nearby, Hyde Park is a must-visit to unlock your inner scholar. Its maze of boulevards contains 57th Street Books, a labyrinth of books containing deep backlists of rare finds collected and curated by their enthusiastic staff. The Silver Room – an institution founded on the mission to curate a shopping experience that reflects Chicago’s global community – also offers one-of-a-kind apparel, apothecary, accessories, books, and gifts.
Pilsen: This neighborhood is known for its vibrant Mexican heritage and is lined with trendy bars, family-owned taquerias, and distinctly Latin American shopping. There are a variety of vintage shops clustered near the area’s main stretch on 18th Street such as Pilsen Vintage and Knee Deep Vintage. If you’re looking to bring home a piece of Mexican-American artistry, Mestiza is the place to go. Two Latine entrepreneurs founded this colorful boutique was founded by to support socially conscious shopping and local artists.
Wicker Park: Chicago’s art community thrives here with its indie shopping, vintage stores, record shops, and more. Exciting storefronts that blend edgy design with cozy Brooklyn coffee shop vibes dot the intersection of Milwaukee, Damen, and North Avenues. One particular highlight is Shuga Records, an indie music label and record store that offers a wide range of vinyl tagged with recommendations from its friendly staff. Asrai Garden and Una Mae are our go-to’s for unique contemporary clothing labels and curiosities.

Best theatre in Chicago

Looking to find a unique evening outing for what to do this weekend in Chicago? While many will cite New York City for the Great White Way and its vibrant Off- and Off-Off-Broadway community, Chicago is where thespians flock to in order to discover new, cutting-edge productions yet to grace Broadway. Comedy fans also regard the city for its rich improv scene that helped in the meteoric rise of iconic performers like Amy Poehler and Stephen Colbert.

SmartFlyer picks for a night at the theatre