Happy Wanderer Travel and Tours
888-277-7697 Ext/Pin# 0697
happywanderertravel@gmail.com

Chicago, Illinois (17 offers included)

from $3,700.00 (USD)
Per Person
Nights: 10
Price Per Night:$370.00 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Berlin, Niagara Falls/Toronto, Toronto, Ottawa, Montreal, Stowe, New York
Allow us to introduce Canada and America, you might have heard of them. Enjoy the sights of the Midwest and the North as you drive through scenic countryside and quaint towns. Feel the spray on your face at the thundering Niagara Falls, wander cobblestone alleyways in Old Montreal, enjoy a Chicago-style hotdog in the Windy City and have a meal with an Amish family in Berlin, Ohio. With this 11-day tour, you and North America will be best buds in no time.
from $3,439.00 (USD)
Per Person
Nights: 10
Price Per Night:$343.90 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Berlin, Niagara Falls / Toronto, Toronto, Ottawa, Montreal, Stowe, New York
Escape the crowds, embrace the snow and enjoy the magical festivities of Christmas on this 10-day winter adventure through the USA and Canada. Check out the Windy City, dine with an Amish family in small-town Ohio, experience the misty magic of Niagara Falls and skate along the frozen Rideau Canal in Montreal. Explore eclectic and French-infused Montreal, try your hand at sleigh riding in snow-covered Stowe, and finish up among the bright lights and skyscrapers of New York. Along the way, there’s a slew of winter festivals and Christmas markets to explore.
USA Road Trip: Epic East Coast
18-to-Thirtysomethings
from $3,059.15 (USD)
Per Person
Nights: 8
Price Per Night:$382.39 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. Ready to cross a whack-load of items off your must-see list? This 21-day circuit through the East Coast of the United States leaves no stone unturned. Feel the thunderous roar of Niagara Falls, dig into deep dish pizza in Chicago, and explore the Home of Blues, Soul & Rock 'N' Roll in Memphis. And since this tour starts and ends in New York City, you can book in extra time to party...
Private: Intro To Chicago
Private and Personal
from $411.00 (USD)
Per Person
Location(s): Chicago
You will enjoy Chicago even more if you learn where, when, and why.
Nights: 15
Price Per Night:$196.60 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – Pontiac – Springfield – International Route 66 Mother Road Festival, Springfield – St. Louis, St. Louis – Branson, Branson – Arcadia – Oklahoma City, Oklahoma City – Elk City – Amarillo, Amarillo – TucumcAri – Albuquerque, Albuquerque, Albuquerque – Albuquerque Balloon Fiesta – Gallup – Winslow – Williams, Williams. Excursion To Grand Canyon National Park...
16 Days, featuring: Chicago
Nights: 11
Ship: Le Champlain
Itinerary: Chicago, Illinois, USA, , Traverse City, Michigan, USA, , Detroit, Michigan, USA, , Toronto, Canada

The Great Lakes have played a vital role in the history and culture of North America for centuries... and this cruise invites you to explore the storied waters of Lakes Michigan, Huron, Erie and Ontario – and some of the unique cities and towns that have grown along their shores – with a 7-night voyage between Chicago and Toronto aboard Le Champlain, plus two-night stays at your choice of premium hotels in these great anchor cities!

Full Day Private Tour Of Chicago
Private and Personal
from $1,423.00 (USD)
Per Person
Location(s): Chicago
This full day tour will show you just about every inch of Chicago!
from $1,889.00 (USD)
Per Person
Nights: 9
Price Per Night:$209.89 (USD)
(based on double occupancy, for comparison only)
Location(s): Chicago, Chicago – St. Louis, St. Louis – Paducah – Nashville, Nashville, Nashville – Memphis, Memphis. Visit To Graceland, Memphis – Indianola – New Orleans, New Orleans
10 Days, featuring: Memphis–indianola–new Orleans
USA Road Trip: Highlights of America
18-to-Thirtysomethings
from $4,461.65 (USD)
Per Person
Nights: 8
Price Per Night:$557.71 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. Got a month, a camera, and a sense of adventure? Then sign yourself up for this 29-day road trip through the United States that leaves no stone unturned. You'll hit the big cities, like New York and Los Angeles, and spend time in stunning natural settings like the Grand Canyon and Yosemite. In between, visit a community arts project in Detroit and join a line-dancing party at a cow...
USA Road Trip: New York to Orlando
18-to-Thirtysomethings
from $2,166.65 (USD)
Per Person
Nights: 8
Price Per Night:$270.83 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. From beaches to barbecue to the blues, this 14-day road trip through the East Coast of the United States ticks all the boxes and then some. Experience Detroit's cultural resurgence at a community art project, dig into deep dish 'za in Chicago, and follow the footsteps of music legends like Elvis Presley and Johnny Cash in Memphis. You'll leave with a full stomach and an even fuller...
USA Road Trip: LA to New York
18-to-Thirtysomethings
from $7,436.65 (USD)
Per Person
Nights: 8
Price Per Night:$929.58 (USD)
(based on double occupancy, for comparison only)
Location(s): Los Angeles, Los Angeles/San Diego, San Diego/Lake Havasu City, Lake Havasu City/Grand Canyon, Grand Canyon, Grand Canyon/Monument Valley, Monument Valley/Las Vegas, Las Vegas, Las Vegas/Zion National Park, Bryce Canyon NP/Moab...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. While you won't get to see all 50 states on this epic 56-day American road trip, you'll get closer than most Americans do in a lifetime. Between stunning national parks (Yellowstone, Yosemite) and game-changing cultural hotspots, you'll dig into the tastiest eats and visit iconic landmarks like the Golden Gate Bridge and the Statue of Liberty while filling your feed with some jealo...
from $2,619.00 (USD)
Per Person
Nights: 7
Price Per Night:$374.14 (USD)
(based on double occupancy, for comparison only)
Location(s): Detroit/Dearborn, Detroit – Frankenmuth, Frankenmuth – Mackinac Island, Mackinac Island, Mackinac Island – Tunnel Of Trees – Charlevoix – Petoskey, Petoskey – Grand Rapids, Grand Rapids – Chicago, Chicago
8 Days, featuring: Grand Rapids–chicago
Nights: 11
Ship: Le Champlain
Itinerary: Toronto, Canada, , Detroit, Michigan, USA, , Traverse City, Michigan, USA, , Chicago, Illinois, USA

The Great Lakes have played a vital role in the history and culture of North America for centuries... and this cruise invites you to explore the storied waters of Lakes Michigan, Huron, Erie and Ontario – and some of the unique cities and towns that have grown along their shores – with a 7-night voyage between Chicago and Toronto aboard Le Champlain, plus two-night stays at your choice of premium hotels in these great anchor cities!

from $2,464.15 (USD)
Per Person
Nights: 8
Price Per Night:$308.02 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville/San Francisco, San Francisco/Yosemite National Park, Yosemite National Park/Sierra Nevadas...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. Why choose between the East Coast and West Coast when you can hit both in two weeks? This 14-day tour takes you from New York City to Los Angeles with some incredible stops in between. Explore the country music capital of Nashville (hello honky-tonks!), catch a glimpse of San Francisco's Golden Gate Bridge, and hike the trails of Joshua Tree National Park. It's the most epic way to...
USA Road Trip: New York to Nashville
18-to-Thirtysomethings
from $1,104.15 (USD)
Per Person
Nights: 6
Price Per Night:$184.03 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. Take a week, an empty stomach, and a burning desire to see the East Coast and you've got one helluva road trip. On this speedy seven-day tour through the United States, you'll discover the best of the region's music, culture, cuisine, and history. Witness the resurgence of Detroit by visiting a community-based outdoor art project, dig into deep dish pizza in Chicago, sip your way t...
USA Road Trip: New York to LA
18-to-Thirtysomethings
from $7,436.65 (USD)
Per Person
Nights: 8
Price Per Night:$929.58 (USD)
(based on double occupancy, for comparison only)
Location(s): New York City, New York City/Niagara Falls, Niagara Falls/Detroit, Detroit/Chicago, Chicago, Chicago/Louisville, Louisville/Nashville, Nashville, Nashville/Memphis, Memphis...
Now's the time to explore the United States on your terms with this tour that's affordable for young travellers. If you're the type of traveller that doesn't do things in halves, this all-encompassing 56-day road trip through the United States has your name written all over it. You'll embark on two comprehensive circuits along the East and West coasts with a flight in between (fewer long drives means more time doing fun stuff). What makes this journey even better is the company you'll keep-a ...
from $99.00 (USD)
Per Person
Location(s): Chicago
Are you aware of the Art Institute of Chicago and its influence on the world stage?