LUXE Serendipity magazine

By Donna Richardson

Chicago invites you to come and discover award-winning restaurants, iconic attractions, stunning outdoor spaces, a rich cultural scene, vibrant neighbourhoods, and a welcoming and inclusive Midwestern spirit. See for yourself why Chicago was honoured as “Best Big City in the U.S.” by Condé Nast Traveler’s Readers’ Choice Awards 2024 for a historic eighth consecutive year!

Festivals & Events:

Arts in the Dark (October 18, 2025), now in its 11th year, is a magical evening parade celebrating Halloween as the “artist’s holiday” and drawing together world-renowned institutions, celebrated Chicago cultural organisations, important youth programs, and aspiring artists in every field. It is a dazzling production that delights an audience of 100,000 with unique floats, spectacle puppets and creative performances – all set against the backdrop of historic State Street. (Neighbourhood: The Loop)

The 47th running of the Bank of America Chicago Marathon will take place on October 12, 2025. The race begins and finishes in Grant Park. (Neighbourhood: The Loop)

The Chicago Christkindlmarket is delighted to announce the return of its cherished holiday tradition for its 29th season at Daley Plaza in Chicago, its 4th year at RiverEdge Park in Aurora, and its return to Gallagher Way in Wrigleyville. The Chicago and Aurora locations will open on November 21, 2025, while Wrigleyville will welcome visitors starting November 23, 2025. All three markets are admission-free, featuring authentic vendors, live entertainment, and special events to create a festive holiday atmosphere. (Multiple Neighbourhoods)

Chicago Fashion Week (October 9-19, 2025) makes its return, weaving together the city’s past and present with a celebration of Chicago’s evolving fashion history. Emerging with a mission to define a ‘new look’ that places the Second City first in fashion, CHI✶FW is threading the eye of Chicago’s Loop to create a diverse tapestry of citizens from across the metro region united by a vision of a continuous, communal, and fashionable future. (Multiple Neighbourhoods)

Chicago International Film Festival (October 15 – 26, 2025) – North America’s longest-running competitive film festival celebrates its 61st edition at venues across the city including AMC NEWCITY 14, the Music Box Theatre, the Gene Siskel Film Center, the Chicago History Museum, and more. Each year, more than 100 filmmakers from around the world visit Chicago to show their films at the festival. (Multiple Neighbourhoods)

The Wintrust Magnificent Mile Lights Festival is back for its 34th year on November 22, 2025. As the largest evening holiday parade in the country, this event draws up to a million people to Chicago’s iconic North Michigan Avenue. Headlined once again by Mickey Mouse and Minnie Mouse from Walt Disney World Resort, the festival features festive floats, giant helium balloons, celebrity appearances, musical acts, and a jaw-dropping fireworks display over the Chicago River. (Neighbourhood: Magnificent Mile)

World Music Festival Chicago (September 26 – October 5, 2025) – The annual World Music Festival is your passport to musical acts from around the globe. This free, city-wide festival features over 31 artists from 16 countries at 11 venues around Chicago including the Chicago Cultural Center, Millennium Park, and Navy Pier. This festival, which has been held in Chicago for more than 20 years, embraces well-known stars and emerging artists in genres that range from traditional to contemporary. You can hear everything at the World Music Festival — from Indian classical music to Bulgarian bagpipes and Congolese funk. (Multiple Neighbourhoods)

Meetings, Conventions, & Venues:

The Obama Presidential Center – Covering 19 acres, the campus will include a fruit and vegetable garden, an athletic facility for programs and events, a premier museum, an auditorium, a branch of the Chicago Public Library, and additional amenities. The programming will encourage visitors, whether local or international, to carry the impact of their experience with them. The full campus is currently set to open early 2026. (Neighbourhood: Hyde Park)

Airlines and Airports: 

Mayor Brandon Johnson and The Chicago Department of Aviation (CDA) joined airline and local leaders in August 2025, to break ground on The New Concourse D at O’Hare International Airport, a transformative $1.3 billion project marking the first major milestone in ORDNext, the next phase of development through the O’Hare 21 capital plan, which will construct two new concourses and a new global terminal. 

●   The New Concourse D will include 19 new gates designed for narrow-body aircraft, with the flexibility to adapt 18 of those gates into nine larger gates that can accommodate wide-body planes. Current planned amenities include more than 20,000 square feet of lounge space, 30,000 square feet of commercial space, and a 450-square-foot children’s play area. 

At O’Hare International Airport (International Flights):

●   United Airlines extended its summer seasonal service to Dublin, Ireland year-round for the first time. The winter flights will be operated by a B767-300ER and the summer services by a larger B787-8. This development signals a deepening of United’s commitment to the Irish market out of Chicago, including its summer seasonal Shannon, Ireland service which started in 2023.

Sports:

The Chicago Bulls and the Museum of Contemporary Art Chicago have announced a new retail collection that reaches fans at the intersection of sport and art. This collaboration provides basketball fans and art enthusiasts the opportunity to own a piece of Chicago’s culture from two of the city’s most notable brands. Chicago artist, Cody Hudson, designed the collection which is intended to reflect the city’s unique art and sport landscape. (Neighbourhood: Near North Side) 

Accommodations:

The St. Regis Chicago has launched its new Family Traditions Package, where families are invited to embrace a curated journey of connection, creativity, and comfort from the moment they arrive. Children are greeted with handcrafted amenities and monogrammed robes, and access to the Astor Treasure Chest—a whimsical trove filled with curated board games, books, and sweet surprises inspired by the St. Regis legacy. Guests looking for an elevated family-friendly retreat can expect a concierge-curated itinerary that includes unforgettable nearby experiences like Millennium Park’s “Bean” and Crown Fountain, Maggie Daley Park’s adventure playgrounds, the Shedd Aquarium, and the Chicago Children’s Museum at Navy Pier— easily accessible via their complimentary Rivian house car.

Retreat into one of the hotel’s sumptuous rooms and suites with panoramic views of Lake Michigan and the Chicago River, and enjoy access to their signature St. Regis Butler Service, an intuitive extension that handles everything from unpacking to arranging family experiences, so guests can truly be present for every magical moment. Parents can enjoy luxurious pampering at The St. Regis Spa Chicago—the only Forbes five-star rated spa in Chicago—for tailored treatments and poolside serenity on the wellness floor. Kids can enjoy manicures and pedicures (ages 5 and up) and the heated indoor pool with sweeping skyline views. With daily breakfast, nightly milk and cookies, complimentary cribs, and child-friendly dining at on-site restaurant Tre Dita, The St. Regis Chicago doesn’t just accommodate families—it celebrates them. (Neighbourhood: The Loop)

Food and Libations: 

Ambar, which offers a modern interpretation of Balkan cuisine with a “Dining Without Limits” experience, recently opened a new Chicago location. The restaurant’s every detail expresses the deeply rooted Balkan heritage, built around award-winning food and unparalleled hospitality. Small plates transform the traditional experience of gathering around the table for a feast to enjoy grilled meats, fine cheeses, various blends of kaymak, local wines, and an expansive collection of rakia. (Neighbourhood: River North)

Class Act + Nightcap offer a unique perspective on fine dining and mixology through an immersive, communal tasting menu experience and speakeasy. The multi-room concept centres around a single 16-foot communal table, where guests can share a carefully curated tasting menu while witnessing the energy and artistry of an open kitchen. Chef Nicolai Mlodinow’s avant garde cuisine, the free flowing spirits, and the newly forged connections make every night unforgettable. (Neighbourhood: Bucktown)  

Dimmi Dimmi Corner Italian is a new Italian-American restaurant located at 1112 W. Armitage. Helmed by Executive Chef Matt Eckfeld, Dimmi Dimmi offers a fresh, feel-good take on classic Italian-American fare. The menu features homemade pasta, seasonal vegetables, and thoughtfully crafted Italian classics that celebrate warmth, community, and culinary creativity. (Neighbourhood: Lincoln Park)

Ox Bar & Hearth is a new dining destination opening in Lincoln Park in September 2025. A heartfelt tribute to seasonal Midwestern food, great drinks, and warm hospitality from Alain Uy and John Asbaty, Ox Bar & Hearth will offer a reimagined take on the neighbourhood restaurant, blending comfort with simplicity. (Neighbourhood: Lincoln Park)

Pequeño Mercat is a new café located within The Blackstone Hotel on Chicago’s Cultural Mile, complementing the hotel’s existing 

Spanish restaurant, Mercat a la Planxa. The café will offer a curated selection of La Colombe coffees, including Monaco Medium Roast and Nizza espresso, alongside Rishi teas. Guests can enjoy speciality drinks such as cortados and mochas, as well as draft lattes and cold brew on tap. The menu features freshly baked pastries, breakfast items like bagels and croissants, and savoury lunch options, including tarts and sandwiches. Seasonal desserts, along with fresh fruits and snacks, ensure a variety of options for all guests. (Neighbourhood: The Loop)

Trino is a personal interpretation of the classic steakhouse, reimagined by Chef Stephen Sandoval and Partner Oscar Sotelo, the team behind Diego and the Entre Sueños Dinner Series. Rooted in the culinary traditions of Northern Mexico, Galicia, and Argentina, Trino blends bold flavours, thoughtful technique, and high-quality cuts with a spirit of warmth and genuine hospitality. (Neighbourhood: West Loop)

Exhibitions (Immersive Art & Museums):

The Art Institute of Chicago’s new fall and winter exhibitions include (Neighbourhood: The Loop):

●  Elizabeth Catlett: “A Black Revolutionary Artist and All That It Implies” (through January 4, 2026) – A deft sculptor and printmaker, ardent feminist, and lifelong social activist, Elizabeth Catlett (1915–2012) was a defining artist of the 20th century. Across nearly 100 years—from Jim Crow segregation through the Cold War and into Barack Obama’s first term as president—Catlett remained steadfast in her commitment to both her art and her political beliefs. Bringing together over 100 works from across Catlett’s awe-inspiring career, this long-overdue retrospective showcases the significant role this revolutionary artist and radical activist played in her time and the influence she still has today. Her powerful work continues to speak directly to all those united in the fight against poverty, racism, and imperialism.

●    On Loss and Absence: Textiles of Mourning and Survival (September 6, 2025 – March 15, 2026) – Drawn primarily from the Art Institute of Chicago’s collection, On Loss and Absence brings together over 100 objects from diverse cultures dating from antiquity to today to reveal the ways people use textiles to sustain spiritual beliefs, understand death, cope with grief, remember those who have passed, and heal from trauma, both personally and collectively. 

●  Bruce Goff: Material Worlds (December 21, 2025 – May 29, 2026) – This major retrospective celebrates the unbounded creative practice of American architect Bruce Goff (1904–1982). Best known for his groundbreaking, idiosyncratic single-family homes in suburban and rural areas across the United States, Goff charted an alternative narrative for a modern architecture imbued with individuality, materiality, and fantastical invention. The first major show of the architect’s work in over 30 years, this exhibition is drawn primarily from the Art Institute’s vast Bruce Goff collection and archive. The project features over 200 works including spellbinding architectural drawings, elaborate architectural models, and a selection of Goff’s ambitious, little-known abstract paintings.

The Chicago History Museum will presentAquí en Chicago, opening October 25, 2025. In 2019, students from Instituto Justice and Leadership Academy, Rudy Lozano Campus, in Pilsen, protested CHM for the lack of Latino/a/e representation. In doing so, they stood on the shoulders of past Latino/a/es and allies who fought against cultural erasure and systemic racism. Chicago has been home to Latino/a/e communities since the 1800s and their descendants have actively carried on and protected Latino/a/e cultural heritages and traditions. Through art, photographs, interviews, clothing, personal items, everyday objects, and historical treasures, Aquí en Chicago traces the lives of Latino/a/e communities that have maintained a persistent cultural presence and flourished in Chicago and the surrounding suburbs. The exhibition is presented in both English and Spanish. (Neighbourhood: Lincoln Park)

Elmhurst Art Museumwill exhibit Shakkei Work by Mayumi Lake and Bob Faust(September 6, 2025 – January 5, 2026), the first major museum exhibition for these two Chicago-based artists whose colourful, kaleidoscopic artworks create an immersive optical experience. Featured in separate galleries, recent large-scale work by each artist will transform the space. Lake’s imagery is based on the symbolic floral motifs found in antique Japanese kimonos. Faust’s wallpapers and prints incorporate digital photographs he gathers for each project, sourced from the natural surroundings of the location where he is showing the work. Lake and Faust will also collaborate on new work for this exhibition, introduced in the centre gallery, combining their love of organic patterning and spatial design. (Neighbourhood: Elmhurst, IL)

Griffin Museum of Science and Industry presents the exciting world of one of the most beloved superheroes of all time in Marvel’s Spider-Man: Beyond Amazing – The Exhibition (through February 8, 2026). In this immersive exhibit, guests will  see rare comic books, view props and costumes from favourite Spider-Man movies, explore cutting-edge interactive installations, and take photos with life-size statues of your favourite characters, like Miles Morales, Ghost-Spider, and, of course, Spider-Man! Superfans can dive deep into the evolution of Spider-Man from his first comic book appearance to the latest TV, movie, and video games, while kids of all ages can get hands-on with drawing activities and more. (Neighbourhood: Museum Campus)

The Illinois Holocaust Museum is proud to present Experience360, a brand-new, state-of-the-art downtown satellite location now open at 360 N. State Street, in the heart of downtown Chicago’s River North neighbourhood. Visitors will be able to step into history with virtual reality, discover artefacts and stories of resilience through immersive storytelling, and participate in “conservations” with interactive holograms of Holocaust and genocide Survivors. Experience360 offers a dynamic, deeply personal way to engage with history through conversation, technology, and truth. (Neighbourhood: River North)

Museum of Contemporary Art Chicago will unveil the new exhibition Yoko Ono: Music of the Mind (October 18, 2025 – February 22, 2026) this Autumn, which presents one of the most comprehensive exhibitions to date of Yoko Ono, the trailblazing artist, celebrated musician, and formidable campaigner for world peace. This remarkable retrospective—on view at the MCA as the only US venue—traces Ono’s career since the 1950s and presents over 200 works across a variety of media including performance footage, music and sound recordings, scores, film, photography, installation, and archival materials. Participatory artworks—a key aspect of Ono’s practice—also feature in the exhibition, and visitors are invited to partake in several interactive, instruction-based artworks. (Neighbourhood: Streeterville)