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Latest Chicago Travel Packages & Deals

We serve customers all over the USA! Contact us for a custom curated vacation package for your preferred dates, budget, airline & more.

16-night Niagara & Great Lakes Treasures Cruise

Price: $16,290 - # of Days: 16 days

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9-night Great Lakes Treasures Cruise

Price: $8,995 - # of Days: 9 days

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7-Nights Mackinac Island & The Great Lakes

Price: $3,799 - # of Days: 7 days
Experience life in the fast and slow lanes as you venture to where the automobile was born and where it’s been banned since 1898. This tour of Mackinac Island and the Great Lakes gets your engines revving with a visit to Detroit’s Henry Ford Museum to explore where past innovations have fueled the i...

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11-night Cruising the Great Lakes: Chicago to Toronto Eastbound Cruise/Land Package

Price: $13,290 - # of Days: 11 days

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11-night Cruising the Great Lakes: Toronto to Chicago Westbound Cruise/Land Package

Price: $12,990 - # of Days: 11 days

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5-Nights Waldorf Astoria Chicago

Price: $2,451 - # of Days: 5 days
Waldorf Astoria Chicago Voted 2016 Reader's Choice ‘Best U.S. Hotel’ by Condé Naste, Waldorf Astoria Chicago offers Parisian-inspired elegance in an urban sanctuary for an unforgettable stay. The destination is now in the TripAdvisor Hall of Fame, receiving outstanding traveler reviews and a Trip...

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Chicago Travel Packages

Chicago is the largest city in the Midwest, known for its soaring skyscrapers, sandy lake beaches, public parks and museums. Located on the shores of Lake Michigan, Chicago is a world-class city offering plenty of iconic attractions, diverse neighbor...

Categories: US Cities

Chicago offers everything anyoen could look for in a vacation destination including: historic landmarks, museums, sightseeing, shopping, and accommodations for every budget. Chicago is considerably different from many other vacation spots in the U.S. It is filled with history, culture and modern sophistication at the same time. Chicago has attractions and activities for a family on vacation, someone visiting for business, or a couple searching for romance. Scenic tours, amusement and fun centers including DisneyQuest, ESPN Zone, and Six Flags Great America, are here to thrill. Museums, shopping, fine dinging, and educational attractions including: The Hancock Observatory, The Shedd Aquarium, and the Chicago Academy of Science are here to entertain.

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Chicago Travel Agents

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Tanya Widner

Tanya's Magical Planning Services, Specializing in Disney and Universal

Destination Specialties
United States
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Lauren Bujanski

✨ Magic with Laur ✨

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Categories: Us Cities > Chicago


Chicago is the largest city in the Midwest, known for its soaring skyscrapers, sandy lake beaches, public parks and museums. Located on the shores of Lake Michigan, Chicago is a world-class city offering plenty of iconic attractions, diverse neighborhoods and a great variety of entertainment options including baseball, music concerts and theater.

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This massive city is home to nearly 3 million people and is a major urban center with neighborhoods and cities stretching into an extensive metropolis. Chicago was first incorporated as a town in 1833. The city experienced a rushed growth, but was all but destroyed in the Great Chicago Fire of 1871. The tragedy provided a new chance for the city to reevaluate its plan for growth. The city quickly began to rebuild and this is where many of Chicago's most legendary architectural feats were born. Today, Chicago is seen as an example of excellent urban planning in the creation of the city as well as its notable architecture.

Chicago is a city of many names including The Windy City, The City of Big Shoulders and The City of Neighborhoods. When planning your trip to Chicago, travelers will surely want to discover the great diversity of the city that is found in its plethora of neighborhoods. The signature skyscrapers and office buildings can be found in The Loop. A visit to Michigan Avenue in the heart of the city is an absolute must, as it's the main area for shopping in Chicago with many stores, restaurants and museums. Wicker Park/Bucktown is a great neighborhood to find off-the-beaten-path shopping and restaurants as well as edgy nightlife spots and a hip vibe. Since Chicago is home to such diverse cultures, there are great pockets of the city to discover other cultures including Chinatown and Greektown.

Chicago locals love this city and it shows. When the weather is nice, head to beach of Lake Michigan, a popular place to enjoy the water while still being in the heart of the city. The city is so large and so diverse that it has much to offer for every kind of traveler. Sports buffs will want to go to a Cubs game at Wrigley Field where they'll be immersed in the local sports culture of Chicago. Foodies generally hit up Hubbard and State Streets where there are great restaurants around every corner. The city is also known for its lively music scene. Indie-rock fans should visit the Wicker Park/Bucktown neighborhood for good music venues.

Quick Facts

  • Climate:

    From June to August, temperatures range from 70-90° F; from September to November, temperatures range from 40-60° F; from December to March, temperatures range from 15-35° F and in April and May, temperatures range from 40-65° F

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Categories: Us Cities > Chicago

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    Our motto at Vincent Vacations is, we go so you know! We want to ensure you have the BEST experience, whether it's a river cruise, or a corporate group incentive trip, we want to ensure your vacation is a success.

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    Many of our travel agents have been in travel since 2002! With Vincent Vacations, all travel components are taken care of - this includes accommodations, air, transfers, tours, activities, insurance, contracts, EVERYTHING.

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    Debt free and in business since 2013. Vincent Vacations has agents in Dallas, Kansas City, Houston, Shreveport, Little Rock, Roswell, Oklahoma City and more locations.

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    Travel agents can help save time and stress by doing the research and handling all your bookings for you. An experience travel agent is best at finding great deals and packages, as well as providing you with helpful information and tips. They can also help you plan special activities and experiences that you may not have thought of on your own. All in all, using a travel agent can be a great way to make sure you get the most out of your trip.

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    About Us

    In travel since 2002, and in business since 2013, our travel team serves clients all over the US! Planning a vacation away from home takes a great team. We have taken the time to build a team of dedicated, smart, hard-working personnel who are each committed to excellence and service. We work side-by-side, creating and ensuring INCREDIBLE vacation experiences for you and your group. Our store front in-office team, and our travel consultant independent contractors, work all around the US.

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