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.

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.

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, the Taste of Chicago, and Lollapalooza 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 you’re prepared for whatever Chicago’s weather throws your way.

Where to stay in Chicago

The Peninsula Chicago

Few hotels are as synonymous with The Windy City as The Peninsula Chicago. Celebrating its 25th anniversary in 2026, the property has spent a quarter century setting the standard for hospitality along the Magnificent Mile. While Chicago’s hotel landscape has changed dramatically since the hotel opened its doors in 2001, The Peninsula Chicago remains remarkably relevant—equally beloved by first-time visitors discovering the city and longtime regulars who return year after year. Its location places guests in the center of it all, within walking distance of Oak Street’s designer boutiques, the Chicago River, world-class dining, and many of the city’s most recognizable architectural landmarks.

While Chicago’s hotel landscape has changed dramatically since the hotel opened its doors in 2001, The Peninsula Chicago remains remarkably relevant.

As a family-owned brand, The Peninsula has long understood that world-class hospitality isn’t just about square footage or amenities—it’s about consistency. The hotel has maintained Forbes Five-Star status every year since 2003, a distinction few properties anywhere in the world can claim. Recently named the top hotel in the United States and recognized as one of the best hotels in the world by La Liste 2025, the accolades continue to accumulate, yet each stay remains remarkably personal. The service philosophy in Chicago draws heavily from the brand’s Hong Kong roots, blending gracious Asian hospitality with the warmth and amiability that this Midwest capital city is known for.

The hotel’s recent investment in wellness has strengthened its appeal. With two floors dedicated to a revitalized spa and wellness center, it creates a true urban retreat to dig into your wellbeing while being in the heart of the city. The accommodations at Peninsula Chicago remain among the city’s most spacious. Across 339 guest rooms—including eighty-two suites—the design strikes a balance between classic style and contemporary comfort. The iconic Water Tower Suite and Lake Suite each exceed 2,500 square feet, while the Peninsula Suite spans more than 3,000 square feet and includes a baby grand piano and a spacious private terrace overlooking Lake Michigan.

Park Hyatt Chicago

Between its impressive private art collection and award-winning cuisine, 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 premier 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 a powder room, that make guests feel right at home in downtown Chicago. These elegantly understated rooms ensure a plush, comfortable stay.

This legendary property is the ideal home base for anyone looking for immediate access to the city’s most exciting attractions and exemplary service.

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, along with craft cocktails from an extensive global collection. The lounge also invites guests into its working wine cellar that houses a specially curated global wine collection. Uncorking and sipping the rare, 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 in the midst of Chicago’s skyline.

Where to find the best Chicago architecture

In good company, woven into the American architectural tapestry alongside 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 that span a range of historical periods. This wide array of architecture is thanks to the city’s central location along key 19th-century trade routes, 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, showing how the city rose from the ashes to become bigger and better. Our personal favorite way to explore Chicago’s architecture scene is with a private guided walking tour, all arranged through your SmartFlyer travel advisor.

Smartie Scouted Chicago architecture

• Aqua Tower: One of the more adventurous designs that has 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 of 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 clock tower and plaza offer a dramatic backdrop for timeless photoshoots.

Where to Eat in Chicago

If you only planned to eat in Chicago, you could easily spend every hour of your entire weekend working your way through the can’t-miss restaurants—and still have plenty of stops left. To help you navigate the abundance of options in the Windy City, SmartFlyer’s Chicago experts assembled this neighborhood-by-neighborhood guide. Happy eating!

Gold Coast 

• RL Restaurant: One of only a handful Ralph Lauren outposts in the world, RL Restaurant is the iconic American fashion brand’s most fully realized expression of hospitality, designed as an extension of its signature Americana aesthetic. The dining room feels closer to a private club, defined by dark wood paneling, equestrian photography, and buttery leather banquettes. The menu stays intentionally classic—crab cakes, lobster, prime steaks, wedge salads—executed with a focus on consistency rather than reinvention. 
• Adalina Prime: A contemporary Northern Italian restaurant designed for long, social dinners, Adalina balances polished interiors with an energetic dining room. Truffle pasta, veal Milanese, and tableside carpaccio define the menu, which is built around shared plates and made for celebratory occasions. 

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.
• 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

• 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.
• 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 the “Prince of Pork”.
• Doma Cafe: A Croatian café that emphasizes style and a feeling of home, this is a spot for when you wish you were on the Adriatic Sea. Stop here for homemade hash browns and an espresso tonic—an ideal way to kick-start a Chicago day.
• Lou Mitchell’s: A historic downtown diner serving breakfast since 1923, Lou Mitchell’s is famous for its welcoming counter service and signature donut holes served upon arrival. This cozy spot embodies Chicago’s old-school hospitality culture.
• Shaw’s Crab House: A long-standing seafood institution with both an oyster bar and a traditional dining room, here you can expect Alaskan king crab, oysters, and New England-style seafood to define the menu.
• RPM Steak: A modern steakhouse known for its expansive wagyu program and dry-aged cuts, RPM Steak is built around indulgence and precision. Japanese A5, truffle potato purée, and seafood towers define the experience. Look forward to meals served in a sleek, high-energy dining room designed for long, celebratory nights.

• Topolobampo: Rick Bayless’s flagship remains one of the most notable Mexican tasting menu restaurants in the U.S. The experience is structured around regional storytelling, with complex moles, duck carnitas, and seasonal seafood dishes that reflect deep culinary research and technique.
• Sushi San: This fast-paced sushi bar concept, focused on quality fish in a more casual format, offers hand rolls, nigiri flights, and tuna-focused dishes that are served alongside playful cocktails, creating a balance between accessibility and high-quality ingredients.
• La Serre: A glasshouse-style dining room inspired by the French Riviera, La Serre is defined by its greenhouse architecture—olive trees, florals, and soft light. The menu leans French-Mediterranean with whole branzino, truffle chicken, and tableside pastas that emphasize familiarity over reinvention.
• Bavette’s: Packing French flair and premium prime rib, this is one of Chicago’s see-and-be-seen spots. Outfitted with sultry low lighting, red leather banquettes, live jazz, and ample glamor, Bavette’s is a sumptuous take on the classic steakhouse.
• Asador Bastian: A Basque-influenced steakhouse from Chef Doug Psaltis, Asador Bastian was originally built in 1883 and is located in what is known today as the Flair house. Come for the steak, stay for the stunning townhouse setting.
• Obelix: A Michelin-recognized French bistro from Chefs Alexia Duchêne and Jeremy Salamon, Obelix is one of the city’s most precise expressions of modern Parisian cooking. Expect rotating seasonal plates, house-made pâtés, foie gras terrine, pristine crudos, and a downstairs oyster bar is ideal for later evenings.

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.
• 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.”
• The Gage: A refined gastropub steps from Millennium Park, blending Irish and American influences, The Gage is known for its venison shepherd’s pie and fish and chips. Its extensive whiskey list anchors a menu built for elevated comfort.

• Volare: A traditional Southern Italian restaurant that has remained largely unchanged for years, Volare serves up chicken parmesan, veal marsala, and seafood pastas. Here, the menu is focused on familiarity, consistency, and warm hospitality.
• Fioretta: A theatrical steakhouse with live music, wood-fired cooking, and a strong art deco influence, Fioretta is your spot for dry-aged steaks, octopus carpaccio, and tableside presentations that define a menu built around high energy.
• Maxwell’s Trading: From Chef-Partner Erling Wu-Bower and Executive Chef Chris Jung comes a place designed for unwinding, dining, and listening to music. Ingredients are grown on the building’s rooftop urban farm, and the restaurant fosters a community-oriented, collaborative spirit, featuring a menu that blends global influences.
• Monteverde: Helmed by James Beard award-winning Chef Sarah Grueneberg, Monteverde specializes in fresh, hand-cut pastas. This Italian hotspot blends appreciation for traditional fare with an adventurous spirit for new flavor profiles.
• Sepia: Locals know this renowned Michelin-guide restaurant for taking the concept of the American melting pot and translating that into refined, hearty cuisine. The restaurant sources its rustic, seasonal menus from local artisans and sustainable practices.

Lincoln Park

• Cafe Yaya: An all-day neighborhood café from James Beard Award–winning Chef Zach Engel, this spot is where Mediterranean and French influences shape everything from morning pastries to evening small plates. The atmosphere feels effortlessly local, equally suited to a coffee and croissant as it is to a leisurely dinner paired with thoughtfully selected wines. where Mediterranean and French influences shape everything from morning pastries to evening small plates. The atmosphere feels effortlessly local, equally suited to a coffee and croissant as it is to a leisurely dinner paired with thoughtfully selected wines.
• Armitage Alehouse: Channeling the ambiance of a classic London pub, Armitage serves elevated British comfort food accented with Indian influences. The menu moves from flaky pot pies and fish and chips to curries, samosas, and richly spiced specialties, all complemented by a well-rounded list of ales and cocktails.
• 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.

Bucktown

• Mirra: Located in Bucktown, Mirra explores the intersection of Indian and Mexican cuisines through a menu that is as intellectually compelling as it is deeply flavorful. Signature dishes weave together techniques, ingredients, and culinary histories from both traditions, resulting in creative dishes like lamb barbacoa biryani and seafood-forward small plates. Executive Chefs Zubair Mohajir and Rishi Kumar lead the kitchen, bringing their distinct backgrounds and shared interest in cross-cultural storytelling to every course.

The Bear-Approved Recs

Chicago has always been a leading food city—but nothing cemented its status as a culinary destination quite like The Bear. Across five seasons, the show highlighted everything from the most upscale restaurants in the city to the sandwiches integral to Chicago’s identity. The Emmy-winning show is a tribute to the inventive, complex, and endlessly satisfying restaurant scene, and is an excellent guide to eating your way through this Midwest beacon.

• La Scarola: A Chicago institution in West Town that has been open since the late 90s, La Scarola is the home to “the best Pasta Fagioli in Chicago.” While it wasn’t featured in The Bear, they have hosted the discerning cast for a meal. What could be a better endorsement than that?
• Publican Quality Meats: A butcher shop and counter-service sandwich shop that specializes in house-made sausages, artisanal baked bread, and intimate hospitality; Publican Quality Meats is a Chicago staple. Located near the West End River Walk, it’s an ideal casual lunch spot.
• Lao Peng You: This intimate dumpling-focused restaurant specializes in handmade northern Chinese dumplings. Located in West Town, it’s a first-come, first-served establishment that happily includes no shortage of chili oil in most dishes.
• Pequod’s Pizza: A Lincoln Park institution known for its pan-style deep-dish pizza with a caramelized cheese crust, Pequod’s Pizza is a no-frills slice of deep-dish that has consistently ranked on national “best pizza” lists.

Birriería Zaragoza: A Jalisco-style birria spot known for slow-cooked beef served with rich consommé, this gem is run by the Zaragoza family and serves up rich flavors inspired by patriarch Juan Zaragoza’s home in Mexico. While they have two locations, you’ll want to head to the Uptown location, as their Archer Heights original spot is temporarily closed after a fire.

Avec: This West Loop staple is known for communal seating and Mediterranean-leaning dishes like chorizo-stuffed dates, in addition to its location in River North. Avec plays a subtle but important role in The Bear as part of the city’s chef mentorship and industry ecosystem. Off-screen, we recommend ordering a selection of their small plates.

Kasama: A Filipino restaurant and bakery that made history as the world’s first Michelin-starred Filipino tasting menu, this daytime bakery counter is just as noteworthy as its dinner service. Their longaniza sandwiches and pastries have been prominently featured in The Bear. The bakery takes walk-up orders—but the tasting menu is reservation only.

Ever: A two-Michelin-star tasting menu restaurant from Chef Curtis Duffy, Ever was featured in the “Forks” episode of The Bear. This spot represents the pinnacle of precision-driven fine dining in Chicago, with a tightly choreographed service style and multi-course menus that define contemporary American gastronomy.

Where to Drink in Chicago

After you’ve cleared your plate—whether that’s with a multi-course tasting menu or a sandwich picked up from the counter—head to one of Chicago’s numerous watering holes. An excellent mix of glamorous bars and local mainstays means you’ll have no trouble finding a craft cocktail to sip on or a refreshing beer to wash down.

• 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 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 has always been putting the best of Illinois live music on its stage.
• Kingston Mines: 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 an elevated menu featuring 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, bottled in 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 in a 1920s Art Deco apartment 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 features 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.

Where to Shop in Chicago

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 design history, you can find some truly rare items in flea markets and vintage stores.

• 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 Handmade, which feature 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 with deep backlists of rare finds collected and curated by its enthusiastic staff. The Silver Room–an institution founded on a 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 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-tos 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 discover new, cutting-edge productions that have yet to grace Broadway. Comedy fans also regard the city for its rich improv scene, which helped fuel the meteoric rise of iconic performers like Amy Poehler and Stephen Colbert.

• Chicago Shakespeare: Located on Navy Pier, this theatre focuses on reimagining classics such as Twelfth Night and Midsummer Night’s Dream for a contemporary audience. The theatre is also integral in the development of new projects, from musicals to plays.
• Goodman Theatre: This professional theatre company has been the developmental grounds for many iconic musicals and plays. An example of their pulse on the cultural zeitgeist favoring 90s remakes is a recent production of The Who’s Tommy, an iconic rock opera whose last large-scale production hit Broadway in 1993.
• Hell in a Handbag: Susan Sontag defines “Camp” as “an intentional over-the-top-ness, a slightly (or extremely) ‘off’ quality, bad taste as a vehicle for good art.” This theatre company’s eclectic mix of comedic productions mounted around the year embodies each part of that definition and is an ideal way to kick off your Chicago weekend.
• Lifeline Theatre: Lifeline Theatre reimagines books and other literary works and adapts them for the stage. Past productions include world premieres of Treasure Island, Wuthering Heights, and Frankenstein.
• Lookingglass Theatre: Founded in 1988 by graduates of Northwestern University, Lookingglass Theatre Company is a nonprofit theatre that focuses on the development of new works staged at the emblematic Water Tower. The theatre also provides theatre education to Chicago-area students and teachers through various Education and Community Programs.
• Steppenwolf Theatre: Every production that goes up at Steppenwolf guarantees performances that are both visceral and moving. Many thespians quote this ensemble as one of the leaders in physical storytelling.

Ready to take on the Windy City by storm? Contact your SmartFlyer travel advisor today to get planning.