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Top 20 Signature Travel Network Agency 5.0 Google Rating (13 Reviews)

Premier Luxury Travel Agency Serving Chicago, IL

Your Chicagoland gateway to extraordinary vacations. From luxury Great Lakes expedition cruises departing Chicago Navy Pier and non-stop Caribbean/Mexican escapes from ORD and MDW, to bespoke European tours, ocean voyages, and destination weddings—our dedicated advisors deliver VIP resort perks and 24/7 advocacy with zero added booking fees.

Request A Chicago Quote (860) 365-2857
5222 N Oakview Ave #2e, Chicago, IL 60656 | Toll-Free: 1 (888) 883-0460 | $0 Added Booking Fees
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5.0 GOOGLE RATED • 13 VERIFIED CLIENT REVIEWS

Vincent Vacations – Travel Agency Chicago

“Each place we stopped at for the night had a unique charm and was in a fantastic location. Everything went off without a hitch! Vincent Vacations made our travels effortless.”

Address: 5222 N Oakview Ave #2e, Chicago, IL 60656  •  Mon–Fri: 9:00 AM – 5:30 PM
(860) 365-2857
Connect With An Advisor

Non-Stop From ORD & MDW

Effortless direct flights from O'Hare & Midway to Cancun, Punta Cana, Jamaica, Cabo, Aruba, London, Rome, and Paris.

Sail Direct From Navy Pier

Embark on luxury Great Lakes expedition cruises right in downtown Chicago with Viking and Pearl Seas—zero airfare stress.

Signature VIP Privileges

Enjoy $100 resort credits, free daily breakfast, room upgrades, and hosted Distinctive Voyages cruise cocktail parties.

$0 Added Booking Fees

Our cruise, resort, and tour planning services are paid directly by suppliers—giving you a 24/7 advocate at zero added cost.

Curated For Chicagoland Travelers

Featured Chicago Vacation Hub & Specialties

Explore our premier travel collections designed around direct departures from Chicago, exclusive Signature Travel Network amenities, and five-star luxury partners.

Great Lakes Cruises from Chicago Navy Pier Departs Navy Pier

Great Lakes Cruises from Navy Pier

Embark in downtown Chicago aboard Viking Expeditions (Viking Octantis & Viking Polaris) and Pearl Seas Cruises. Explore Mackinac Island, Georgian Bay, Niagara Falls, and Lake Superior with zero airport hassle.

Non-Stop Tropical All Inclusive Resorts from Chicago ORD Non-Stop ORD & MDW

Non-Stop Tropical All-Inclusives

Escape Midwestern winters with direct non-stops to Sandals & Beaches Resorts (Preferred Partner), Secrets & Impression Resorts, and Atelier Playa Mujeres. Direct gateways to Cancun, Punta Cana, Jamaica, and Aruba.

Chicago Destination Weddings and Honeymoons Group Room Blocks

Destination Weddings & Romance

Full group travel management for Chicago couples. We lock in discounted guest room blocks, coordinate ceremony venues in Mexico and the Caribbean, and unlock free room perks for the couple via our romance concierge.

Ultra Luxury Ocean and River Cruises Chicago Signature Exclusives

Luxury Ocean & River Cruises

Certified specialists for Regent Seven Seas, Ritz-Carlton Yacht Collection, Silversea, Explora Journeys, Viking, and AmaWaterways. Pair seamless ORD European flights with hosted shore events and onboard credits.

Tauck and Abercrombie Kent Luxury Tours Chicago Tailor-Made Luxury

Escorted Luxury Tours & Safaris

Handcrafted small-group and private journeys with Tauck and Abercrombie & Kent (historic Chicago roots). From bespoke Italian and Swiss journeys to once-in-a-lifetime African wildlife safaris in Kenya and South Africa.

Iconic Rail Journeys from Chicago Union Station Chicago Union Station

Scenic Rail Expeditions

Depart from North America's historic rail crossroads at Chicago Union Station. Connect to the Rocky Mountaineer, Canadian Rockies luxury packages, and worldwide luxury trains including Belmond with full concierge planning.

Local Chicagoland Expertise

Meet Your Chicago, Illinois Travel Specialists

Connect directly with certified travel advisors ready to tailor your milestone vacation, luxury cruise, or tropical retreat.

Jaime Martis-Frazier Chicago Travel Agent

Jaime Martis-Frazier

Luxury Caribbean & Tropical Specialist

Specialties: Caribbean, Jamaica, Tropical All-Inclusive Escapes, Family Vacations.

Joe Merendino Chicago Cruise Guru

Joe Merendino

Cruise Guru & Worldwide Destination Specialist

Specialties: Ocean & River Cruises, Alaska, Italy, Japan, Hawaii, Mexico, Caribbean.

Lauren Bujanski Magic with Laur

Lauren Bujanski

Disney, Universal & Family Vacation Planner

Specialties: Walt Disney World, Universal Orlando, Florida Getaways, Multi-Gen Trips.

Lauren Kranick Romance Travel Specialist

Lauren Kranick

Island Escapes, Romance & Honeymoon Specialist

Specialties: Caribbean, Bahamas, Hawaii, Romantic Honeymoons, Florida Beach Retreats.

Tanya Widner Magical Planning Services

Tanya Widner

All-Inclusive, Cruise & Theme Park Specialist

Specialties: Mexico, Cancun, Riviera Maya, Caribbean, Alaska, Europe, Disney & Cruises.

Explore All 100+ Vincent Vacations Advisors Worldwide

Why Book With Vincent Vacations vs. Directly Online?

We Wait On Hold So You Don't

When airlines change flights or weather hits ORD, skip the 3-hour phone queue. Your dedicated advisor resolves rebooking directly.

Signature Exclusive Amenities

Unlock $100 resort credits, free daily gourmet breakfast, priority room upgrades, and shipboard credits unavailable through public booking engines.

Continuous Price Monitoring

If your cruise or resort announces a promotion prior to final payment, our advisors proactively re-price your itinerary to secure savings.

Frequently Asked Questions: Chicago Travel Planning

Everything you need to know about working with our Chicago travel advisory team.

As an elite Top 20 Signature Travel Network agency, Vincent Vacations unlocks exclusive VIP perks that travelers cannot obtain on their own, including up to $100 in hotel resort/spa credits, complimentary daily breakfast for two, priority room upgrades, and hosted cruise events. In addition, our dedicated advisors eliminate hold times and advocate for you 24/7 in case of flight disruptions or schedule changes.
Yes. Our advisors regularly arrange seamless non-stop luxury vacation packages from ORD and MDW to top destinations including Cancun, Riviera Maya, Punta Cana, Aruba, Jamaica, Los Cabos, Nassau Bahamas, London, Rome, Paris, and Athens.
Chicago Navy Pier is the premier US homeport for luxury Great Lakes expedition cruises. Viking Expeditions (sailing the state-of-the-art Viking Octantis and Viking Polaris) and Pearl Seas Cruises (Pearl Mist) offer 8-to-15-day voyages exploring Lake Michigan, Mackinac Island, Georgian Bay, Lake Superior, and Niagara Falls with zero airfare required for Chicagoland residents.
On the vast majority of cruise bookings, all-inclusive resort packages, and preferred hotel stays, Vincent Vacations does not charge added booking fees. Our compensation is paid directly by our luxury travel suppliers, ensuring you receive personalized concierge service, insider pricing, and exclusive perks at no additional cost.
Yes. Through our dedicated romance division AllInclusiveWeddings.com, we manage guest group contracts, secure low group deposits, provide individual travel assistance for your attending wedding guests from Chicago, and negotiate complimentary room upgrades and event credit for the wedding couple.
You can connect directly with our advisory team by calling our local Chicago office at (860) 365-2857, calling toll-free at 1 (888) 883-0460, or submitting an inquiry online through our website. We provide both phone and virtual video consultations to tailor your travel plans.

Ready To Plan Your Next Exceptional Getaway?

Whether you are embarking from Navy Pier, flying non-stop from ORD/MDW, or curating an ultra-luxury European journey, our certified Chicago specialists ensure an unforgettable experience.

Request A Chicago Quote (860) 365-2857

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