IFWTWA Conference Media Trip

Chicago, Illinois

October 22-25, 2026

Welcome to Chicago, named the Best Big City by Condé Nast Traveler readers for an unprecedented nine consecutive years.

The city is known for its electric big-city energy, famed restaurants and bars, a world-class cultural scene, iconic architecture, and miles of jaw-dropping waterfront. Chicago’s acclaimed museums include the lakefront Museum Campus and The Art Institute of Chicago, ranked one of the top five museums in the world by TripAdvisor

One of the country’s top dining cities, Chicago’s restaurant scene includes 23 Michelin-starred restaurants and international cuisines from around the world.  Visitors will find a packed calendar of exciting events all year long, from magical holiday traditions to major summer festivals like Lollapalooza and the Chicago Pride Parade.

Chicago’s unbeatable theatre scene includes Broadway in Chicago, iconic comedy clubs, and Tony Award-winning venues. Chicago is also home to a groundbreaking music scene known for its influence on blues, jazz, gospel, and house music. The city’s gorgeous outdoor spaces include charming neighborhood parks, the bustling Chicago Riverwalk, and sandy beaches with sweeping skyline views.

Chicago’s welcoming and inclusive spirit means every visitor feels welcome. The city’s neighborhoods are home to an array of inclusive communities, including the nation’s oldest official LGBTQ+ neighborhood. 

Finally, you can’t leave Chicago without checking out top sites and attractions, including an observation deck inside one of the world’s tallest buildings, “The Bean”, Navy Pier, UNESCO World Heritage sites designed by Frank Lloyd Wright, and so much more. Come experience what makes Chicago a place unlike any other.

Barry_Butler_Riverwalk in Chicago. Photo by Caroline Theis courtesy Choose Chicago

What Chicago Seeks from Media Participants

  • This four-day, three-night trip is for four writers
  • Writers will complete one to two articles and/or videos (depending on individual writers chosen and media outlets); Choose Chicago will discuss requirements with each writer
  • Writers will provide social media posts either during or following the trip

Itinerary:

Thursday, October 22

Writers will depart Potawatomi Casino Resort and head to Chicago. Details to be finalized. 

Start exploring Chicago and stay overnight in Chicago.

Friday, October 23 – Saturday, October 24

Choose Chicago will curate a customized itinerary once the four writers are chosen. They will review the writers’ interests and outlets and determine the best itinerary to provide the best experience for the attending writers. However, writers can expect to see some of the highlights found in these Classic Chicago Itineraries

Sunday, October 25

Depart from Chicago O’Hare International Airport (ORD) for your return home.

Chicago Millennium Park