Gay & Ally Travel Agents in Chicago

Georgia Stanek-Finkle

Protravel International (Chicago)

Georgia Stanek-Finkle has been selling travel since 1979 and holds a degree in Geography, Travel & Tourism, and Marketing from DePaul University. She's based in the Chicago office of Protravel International, now part of Global Travel Collection, where her advisor profile lists LGBTQ+ Travel among her own specialties, alongside Festivals & Events, Food & Wine, and Culture, History & Arts. She's also named on Protravel/GTC's dedicated LGBTQ+ Travel advisor roster, alongside two Chicago colleagues. Stanek-Finkle books through Virtuoso, the invitation-only luxury travel network, giving clients access to upgrades and amenities at partner hotels and cruise lines worldwide.

Todd Bulmash

Fora Travel

Todd Bulmash is a Chicago-based advisor with Fora Travel who brings more than 20 years of travel experience to clients, including trips through the Caribbean, Alaska, and European cities. His Fora profile lists Boutique Travel, Cruises, and LGBTQ+ Travel among his specialties. As with other Fora advisors, client contact runs through the Fora advisor platform rather than a personal phone or email listing.

Mike McMains

Tours With Mike

Mike McMains runs Tours With Mike, leading three LGBTQ Stories walking and trolley tours around Chicago — North Side, Downtown, and South Side — each tracing local LGBTQ history from the 19th century to today. Public dates are bookable directly through the Chicago History Museum, an official tour partner whose ticket includes free museum admission within a week of the tour; private tours run year-round. McMains has been featured on WGN's Daytime Chicago, in a Canadian Pride documentary series, and by Axios Chicago, Block Club Chicago, and the Chicago History Podcast. No personal LGBTQ+ ownership claim is made here — the tours' subject matter is the specialization.

Out & About Chicago Walking Tours

Out & About Chicago Walking Tours is, per the company's own homepage, "proudly LGBTQ owned and operated." Co-owners Antonio Rodriguez and Rickii Romano met at The Theatre School at DePaul University, where they earned their MFAs in acting, then spent years leading architecture tours on the Chicago River before starting their own company. Their tours tell what they call "the whole story" of Chicago, including the Great Chicago Fire and the reversal of the Chicago River, rather than a sanitized version. Romano's guide bio highlights LGBTQ+ Chicago history and culture, including Hollywood Beach, which her bio describes as "Chicago's queer beach." Booking runs through a contact form or Instagram DM.

Peter Carideo

CRC Travel, Inc.

2105 N Southport Ave, Suite 205, Chicago, IL 60614

Peter Carideo has run CRC Travel since 1990, putting the agency at 36 years in business, and has been named to Condé Nast Traveler's Top 125 Travel Specialists list every year since 2003. The agency maintains a dedicated "You Go Girl" Gay & Lesbian Travel Links page on its site and is listed in the ChicagoPride.com/GoPride LGBTQ Chicago business directory under Travel Agencies. CRC Travel's ownership itself isn't confirmed as LGBTQ+; its inclusion here reflects its long-running LGBTQ+-focused content and directory presence rather than an ownership claim. The agency's office is on North Southport Avenue in Lincoln Park.

Richard Engle

Protravel International (Chicago)

Richard Engle spent 25 years owning and operating his own Chicago travel agency before joining Protravel International, now part of Global Travel Collection, where he works as an Experiential Luxury Travel Specialist focused on vacation experience design. He plans adventure trips, family vacations, and arts-and-culture itineraries, with particular depth in Australia and New Zealand, the Mediterranean, South Africa, and South America. Engle is included on Protravel/GTC's LGBTQ+ Travel advisor roster alongside two Chicago colleagues, though his own advisor profile doesn't list LGBTQ+ Travel among his named specialties. He books through Virtuoso, the invitation-only luxury travel network.

Zoom Vacations, LLC

2338 N Monticello Ave, Chicago, IL 60647

Zoom Vacations was founded in 2002 by Joel Cabrera and Bryan Herb, who personally lead nearly all of the company's small-group tours to destinations including Bhutan, Egypt, India, Japan, South Korea, Laos, the Maldives, Morocco, Peru, Portugal, Rwanda, Kenya, South Africa, Sri Lanka, Thailand, and Vietnam & Cambodia. Purple Roofs lists it as a Gay Owned Tour Operator, and it's won Out Traveler's Reader's Choice Award for Best Small Gay Tour Provider multiple years running, plus a Travvy Award (Gold) for Best Escorted Tour Operator LGBT. Co-founder Bryan Herb served four years on the International Gay and Lesbian Travel Association board, two as chair, and has appeared as a travel expert on Travel Channel's Vacation Challenge and Logo's Bump.

Jenna Pollock

Fora Travel

Jenna Pollock is a Chicago-based advisor with Fora Travel, where her bio describes her as a New England-born, Chicago-based "queer mama" who is endlessly curious about the world. Her listed specialties include Off-the-Beaten-Path travel, LGBTQ+ Travel, and Outdoors & Nature, with expertise across the USA, Europe, and Southeast Asia. She's lived in Boston, Atlanta, New Orleans, South Texas, Chicago, London, Manila, Chiang Mai, and Muscat, and speaks English, Spanish, and Dutch. As with other Fora advisors, client contact runs through the Fora advisor platform rather than a personal phone or email listing.