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  • Destination: Rallies | Nationwide & International RV Tours
  • Duration: 8 days

September 07 – September 14, 2017

Two Person / RV $4,295
One Person / RV $3,595
Additional Guest $2,095

September 06 – September 13, 2018

Two Person / RV $4,595
One Person / RV $3,795
Additional Guest $2,195

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C’mon babe…Let’s paint the town!

From its famous skyline, food and people, to its historic architecture and storied mob past, Chicago is more than just a name. Around here, it’s an adjective. And, it’s a place worth exploring, if only for a taste of that “Chicago-style”. Adventure Caravans RV Tours and Rallies is ready to introduce you to the Windy City and all she has to offer. So, hold on to your skirt, and let’s go!

Chicago’s picturesque skyline reflects onto the waters of Lake Michigan. Its looming skyscrapers flash the sparkle of dawn’s break. But, at night, they take on a darker quality, towering ominously, like deceitful beacons against Chicago’s midnight sky. Their outline is imposing, simulating a mob of gangsters assembled on the darkest of alleys, out to settle a score or two. Such is the impression of the entire city, a bright, vibrant metropolis, full of life, and hurried movement. Its unassuming people carrying-on their innocuous daily routines, however, aptly conceal a nefarious past, one hidden deep in the sinister underbelly of the city’s streets. Adventure Caravans RV Tours and Rallies reveals the secrets of Chicago’s mafia past so well, you’ll suspect us of clandestine ties to the mob!

Set in the jazz era of Chicago’s 1920s and 1930, while still in the grip of prohibition, the exploits of gangsters such as Capone, Dillinger, “Baby Face” Nelson, and Moran are drawn out for you in an informative and engrossing narrative and tour. It exposes the root of their infamy, including their corrupt exploits, their convoluted manipulations of both the innocent and those with something to hide, their ways of skirting the city’s legal system. And, in an effort to better serve their wayward exploits, they were also known to have turned more than a few cops rogue. We scour the streets for their regular haunts, gambling dens, brothels, as well as the “spots” purposed for carrying out their macabre reprisals and the demise of the retched. Today, only the sites remain, but their haunting echoes continue to resonate the salaciousness and depravity of times gone by.

It’s time to shake off Chicago’s scintillatingly macabre past to explore a present-day that is equally as engrossing and more dynamic than ever! For that, we head off to the Loop in the city’s central business district in search of Macy’s at State Street. The retail chain’s main mid-western location is appropriately located in the acclaimed Marshall Field & Company Building. Recognized as the second-largest retail store in the world, this celebrated structure was built in 1892 and has enjoyed its place on the National Register of Historic Places and its distinction as a National Historic Landmark since 1978. The building boasts two famous outdoor fixtures, well-known street-corner clocks situated along the building’s perimeter, but its most celebrated feature remains the intricate architecture of its spectacular Great Hall. Visible from the 5th floor and above, this intricate atrium is brandished with multiple ornately designed balconies, which were affixed in stages over the course of more than twenty-years. The atrium’s pièce-de-résistance is an elegant vaulted glass ceiling exquisitely adorned by Louis Comfort Tiffany ethereal mosaics. Its totality is truly a sight to behold.

A visit to one of Chicago’s distinguished skyscrapers is next on our expedition. The 108-story Willis Tower is still most commonly referred to as the Sears Tower, its name when it was given the notable distinction of Tallest Building in the World, a title it held for almost a quarter of a century. In 1972, a sky-deck was opened to visitors, a direct result of its one-time record-breaking height. Located on the 103rd floor, the feature allows for an unparalleled 360˚ view that expands over the entire state of Illinois, Lake Michigan, and on a clear day, reaches even beyond to its neighboring states, Indiana, Michigan, and Wisconsin. Retractable glass-enclosed balconies were added during a 2009 renovation, making the experience even more thrilling. When extended from the building’s structured perimeter, the all-glass boxes, aka The Ledge, give passengers the rare sensation of floating 103 stories above ground in frozen animation. The experience is not for the weak of heart. To alleviate any cardio-shock caused by The Ledge, the risk-factor to our next activity is markedly lower, making the choice obvious…shopping!

Likened to France’s celebrated Champs-Elysée, the Magnificent Mile, located along North Michigan Avenue, is Chicago’s shopping and lifestyle mecca, featuring unique shops and major name retail houses, whose offerings cover a comprehensive spectrum of products. Thanks to the building boom of 1969, the 100-story John Hancock Center skyscraper was built on the northern end of the avenue, and then in 1976, the Water Tower Place, housing over 100 shops, multiple theaters and restaurants, opened to the public, just adding to the areas list of things-to-do. An additional boom in the late 1980s saw two additional high-rises, 900 N. Michigan Avenue building and Park Tower, take their place along the popular hub.

Navy Pier, located on Lake Michigan, near downtown, was named in honor of the veterans of WWI, and was once considered the world’s largest pier. The Headhouse, one of the pier’s two major attractions, houses the Chicago Children’s Museum, and Gateway Park, which features a fountain with 240 computer-operated jets. The second major building is the Auditorium, also referred to as the Hall, which has an elaborate Grand Ballroom and a half-domed ceiling that stands 100 ft. high. Among the many other popular attractions on the pier are the giant Ferris Wheel and musical carousel with its 36 hand-painted animals, a seven-story, 525 seat Shakespearean theater complex, and the Navy Pier Aeroballoon, a helium balloon that seats up to 18 people and floats above the lakefront to admire the city’s skyline.

The Navy Pier is also the launching point of many of Chicago’s premiere boat trips, from romantic dinner cruises to a speeding water craft, even an array of chartering opportunities. The Architecture Cruise Tour on the River awaits us to embark on a journey laden with striking views found along the river. The tour highlights both commercial and residential architectural design variations by well-known architects, including Mies van der Rohe, Bertrand Goldberg, and Skidmore, Owings and Merrill. The vessel serves up a visional feast as it seemingly floats between some of the most beautiful buildings in the world, offering spectacularly modern views of massive skyscrapers, as well as highlighting the stunning beauty of time as reflected by the more historic structures of the past.

Adventure Caravans RV Tours and Rallies always dedicates time to some enjoyable leisure activities, too. In honor of the most highly anticipated pastime among our adventurers, eating, our scheduled lunches and dinners are carefully chosen to impress the taste-buds and uplift the spirit. Among the week’s scheduled epicurean ventures are a Gospel Brunch at the House of Blues, dinner at a surprise downtown restaurant, and a lunch at the famous Portillos restaurant.

In one of our featured culinary adventures, however, it is the locals’ lead we follow during the Chicago’s Food Lovers Walking Tour, featuring samples of the city’s notable favorites, including deep-dish-pizza, hot-dogs-sans the ketchup, and Italian beef. Stroll through one of the city’s food hubs, stopping at prime eateries to sample their choice offerings, burning calories almost as soon as they are consumed. Adventure Caravans RV Tours and Rallies later recognizes our adventurers’ second favorite pastime, laughter, by heading over to one of Chicago’s premiere comedy clubs, where we settle in, and prepare to dispel some hefty belly-laughs made easier by our earlier sampling indulgence.

 As if this weren’t enough, our tour of the Windy City also includes visits to such celebrated attractions as are the Home and Studio of Frank Lloyd Wright, “Bean” Millennium Park, the Museum Campus featuring the Field Museum of Natural History, Adler Planetarium, Shedd Aquarium, the Lincoln Park Zoo and Conservatory, and Wrigley Field. Before the end of our Chicago tour, however, we also head downtown to indulge in a Famous Chicago Pizza Dinner, an enjoyable way to replenish the energy reserves necessary for the titillating treat that follows…a Broadway Show! Yes, dinner and a show, Chicago-style, is a must-do prior to ending our magical week in the Windy City.


Day 1
● Orientation & Get Acquainted Party
Day 2
● The Loop Luxury Motorcoach Transportation
● Chicago’s Food Lovers Walking Tour
● Architecture Cruise on the River
● Navy Pier
● Willis (Formerly Sears) Tower
– Skydeck Chicago Observatory & The Ledge
Day 3
● Untouchables Motorcoach Tour
● The “Bean” Millennium Park
– Lurie Garden
– Jay Pritzker Pavilion
● The Magnificent Mile
360 Chicago – Formerly John Hancock Building
Day 4
Chicago Blues done Wright & Chicago Neighborhoods
– Luxury Motorcoach Transportation
● Visit Frank Lloyd Wright’s Home & Studio
● Gospel Brunch at House of Blues
● Downtown Chicago Tour
Day 5
● Northside Luxury Motorcoach Transportation
● Wrigley Field Tour
● Lunch at Local Restaurant
● Elk’s National Headquarters & Memorial
● Museum of Science and Industry
Day 6
● The Chicago Coast Luxury Motorcoach Transportation
● Museum Campus
– Field Museum of Natural History
– Adler Planetarium
– Shedd Aquarium
● Famous Chicago Pizza Dinner – Downtown
● Broadway Show
Day 7
● Chicago Historic Downtown Luxury Motorcoach Transportation
● Federal Reserve Money Museum
● Historic Theaters Tour
● Macy’s on State Street – Formerly Marshall Field’s
● Farewell Dinner at Downtown Chicago Restaurant
Day 8
● Hitch-up Continental Breakfast, Hugs & Good-byes

Please note: Itinerary may change due to Chicago Cub’s Schedule and availability of date & time sensitive tickets.

Tour Features

Click Here to View What is Included In Every RV Rally

– Architecture Cruise on the River
– Go Chicago Pass



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Experience the Adventure


  • “This was our first tour and it exceeded our expectations!”
    Chris & Barb Christian
  • “There wasn’t a thing or subject they [the Wagonmasters] wouldn’t bend over backwards to find out, get, or inform us about, and all with a cheerful and professional manner, no matter how tired.” “The thing we liked best on this tour was the variety and frequency of extra curricular activities, such as cultural tours, eating out, socials, games.” “We were led through and shown some of the most spectacular scenery we have ever seen.”
    Tom & Charlu Choate
  • “This trip fulfilled our once-in-a-lifetime desire and more. It was top notch and we will (and already have) recommended it to many!”
    Dale & Cheryl Curtis
  • “Excellent schedule—it rocked!  Food was excellent!”
    Ralph & Ruth Johnson
  • “Fabulous scenery, lots of wildlife, great weather and a great group of caravanners! I loved it!”
    Dee & Kelvin Capozzi
  • “Exciting tours, delicious dinners, close to speedway—good seats. It was all good.”
    Rick & Gail Davies


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  • “Excellent trip and leaders!”
    Len & Carole Adams
  • “We like the combination of enroute stops, free days to explore and planned AVC tours/activities. We thoroughly enjoyed the whole tour.”
    Winston & Linda Norris
  • “The thorough coverage of Alaska provided memories for a lifetime!”
    Allan & Pat Hagerstrand
  • First let me say that Barbara and I enjoyed the rally.  We would give it a solid 10+ points.  We look forward eagerly to our next adventure.  We would enthusiastically recommend Adventure Caravans to friends or strangers.  It was fun!

    Frank & Barbara McCollum
  • “I would recommend this type of Alaska experience to everyone!”
    Dale Jobe & Carol Colburn
  • “The entire team did a very good job. They were so helpful and lots of fun to be with. They bent over backwards to accommodate us. It was a great rally. The Rallymasters were lots of fun and so efficient. We had a very good time.”
    Jim & Jan Dawes
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