Midwest & Great Lakes Self Drive Holidays
Discover a region of vibrant cities, charming small towns, lakefront scenery and wide-open prairies, America’s friendly and fascinating heartland.
The Midwest & Great Lakes region stretches across America’s heartland, offering a blend of spectacular freshwater coastlines, historic cities and timeless rural landscapes. Home to the five Great Lakes — the largest freshwater system on Earth — the region boasts sandy beaches, lighthouses, island communities and scenic byways that feel worlds away from the bustling cities nearby. Explore Chicago’s striking skyline and deep-dish dining scene, wander through Milwaukee’s breweries, cruise along Michigan’s golden lakeshores or discover the Scandinavian heritage of Minnesota and the peaceful countryside of Iowa and Nebraska. With its mix of vibrant culture and laid-back charm, this region reveals a different, refreshing side of the USA.
Beyond its natural beauty, the Midwest is rich in history and Americana. Drive a stretch of legendary Route 66 from Chicago through Illinois and Missouri, explore the motorsport heritage of Indianapolis, or dive into the musical roots of Kansas City and St. Louis — the birthplace of barbecue and jazz. Michigan’s Upper Peninsula offers rugged wilderness and waterfalls, while Ohio blends urban attractions with idyllic Amish Country. Whether you’re exploring university towns like Madison and Ann Arbor, following the Great River Road along the Mississippi, or circling crystal-clear lakes on a summer road trip, the Midwest & Great Lakes region delivers adventure, authenticity and warm hospitality at every turn.
Can’t decide on the perfect route? No problem—Our UK based Travel Experts will craft a tailor-made road trip just for you, ensuring you experience the very best of this incredible region.
Why Route 66 through us?
We’re not just another tour operator offering Route 66 holidays. We know the road, the people, the buildings and the experience. We’re passionate about America's “Mother Road”… and once you’ve driven it, you will be too.
Historic Accommodation
We want you to experience the real feel of Route 66 and you’ll stay in restored historic hotels and motels in some locations. Should you prefer modern hotels we are happy to swap these for you.
Authentic Experience
Route 66 is not about driving on the interstate, it is about taking your time on the original route. We’ll tell you the best way to enjoy the trip by stopping at the best locations, diners and museums
We give back to Route 66
We’re active members of several state Route 66 associations and try to help those businesses which make the trip so special. You can help too by eating in a family run diner instead of a burger chain
Niagara Falls & The Great Lakes
Popular Trip!
Discover all five Great Lakes, Niagara Falls, Toronto, Chicago and New York City on this 16-night self-drive holiday. A remarkable journey through freshwater wonders, iconic cities and scenic landscapes across the USA and Canada.
16 nights from £2,699pp
including flights
Lincoln Highway East
New for 2026!
Journey along the eastern section of the historic Lincoln Highway from New York City to Chicago, exploring Amish Country, Gettysburg, Pittsburgh, Ohio and Indiana — a perfect blend of American history, small towns and scenic highways.
14 nights from £2,199pp
including flights
Route 66 Holidays
Choice of 2 & 3 Week Itineraries
Explore our extensive range of Route 66 self-drive holidays from Chicago to Los Angeles. Click the button below to view our dedicated Route 66 itineraries page and start planning your journey along the legendary “Mother Road.”
14 nights or more from £2,299pp
including flights
Speak to a Travel Expert
Our team have travelled extensively across the USA & Canada to ensure that they can give first hand, unrivalled experience when discussing our holidays.
Call: 01234 938066Enquire NowBook Virtual AppointmentWhy choose RouteTrip USA?
Clients rate us 5/5 through Feefo
We’re multi-award winners
Your trip is fully ATOL Protected
Our support is second to none