Road Trip Itinerary Ideas from Chicago

With the addition of our new puppy, Gambit, to the family, traveling for a week or more seemed unfair, unless we could take him with us. Gambit’s young age and planned rabies vaccination date prevented us from meeting many of the certifications required to take him abroad for the travel dates we were aiming for. His cute face, and his proven road warrior status made us confident that a long road trip with Gambit would be a great adventure. As a result, we started researching possible road trip itineraries.


I thought I’d share a few of the road trip itineraries with you all. Of course, feel free to modify these itineraries to fit your travel needs and preferences. Please add any recommendations or suggestions for other readers in the comments below.

Criteria. Our trip would start and end in Chicago, IL. We were looking to take 7-14 days off and not have more than 8 hours of driving a day if it could be helped, or if we did have to drive more than 8 hours in a day, we’d be out of the car for the full day after. We also did not want to repeat any part of the tour on the way back home. Our primary goal was to see some national parks and camp, but not spend the entire trip in one park or place.

Each itinerary starts with the full version we explored. Under each itinerary I added modification suggestions if you are looking to drive more aggressively or need to shorten the trip length. Itineraries one and two head east to Acadia National Park and include Canada, itinerary three heads west to Yellowstone and includes four national parks, itinerary four heads south and includes five national parks, and itinerary five heads north with optional national parks and Canada.

Acadia_National_Park,_ME_(16243110897)Itinerary 1: East to Acadia National Park and Canada

  • Number of Days: 11 days (6 days include driving)
  • Countries and States: US: Illinois, Indiana, Ohio, Massachusetts, New Hampshire, Maine, Michigan, and either New York or Pennsylvania and Connecticut (based on route choice), Canada: Quebec, Ontario.

Day 1: Drive from Chicago to Cedar Point, Sandusky, OH (5.75 hours) or drive to Cuyahoga Valley National Park (5.25 hours)

Day 2: Enjoy Cedar Point Amusement Park or Waterpark  or Cuyahoga Valley National Park.

Day 3: Drive from your Ohio stop to Boston (10.5-11 hours*).
*Route through New York is on average 20 minutes faster than route via
Pennsylvania and Connecticut due to traffic and road conditions.

Day 4: Explore Boston

Day 5: Drive from Boston to Acadia National Park (4.5 hours);
Spend the morning in Boston or afternoon in Acadia National Park

Day 6: Explore Acadia National Park (Here are some park insider guides from a fellow blogger and from National Geographic)

Day 7: Drive from Acadia National Park to Montreal (6.25 hours)
Spend morning in Acadia National Park, or afternoon in Montreal.

Day 8: Explore Montreal

Day 9: Drive from Montreal to Toronto (5 hours), or from Montreal to Niagara Falls (6.75 hours)

Half day in either Montreal or Toronto. Don’t forget, Niagara Falls is just 2 hours outside of Toronto!

Day 10: Explore Toronto or Niagara Falls.

Day 11: Drive from Toronto to Chicago (6 hours) or Niagara Falls to Chicago (8.25 hours)

Modification Options: Looking for a shorter version of this itinerary? Skip the stop and day at Cedar Point and drive from Chicago to Boston on day 1 instead. Drive time 15 hours. Days 8 or 10 can also be condensed so you are in Montreal or Toronto for a half day instead of a day and a half. You can also skip Toronto or Niagara Falls entirely and drive from Montreal to Chicago. Drive time 13.25 hours.

1024px-Montreal_Skyline_-_Jul.09_(3791024434)Itinerary 2: Extended variation of Itinerary 1.

  • Days: 13 (7 include driving)
  • Countries and States Visited: US: Illinois, Indiana, Ohio, Massachusetts, New Hampshire, Maine, Michigan via Upper Peninsula, and either New York or Pennsylvania and Connecticut (based on route choice), Canada: Quebec, Ontario.

Day 1-9: Follow Itinerary 1

Day 10: Explore Toronto or Niagara Falls.

Day 11: Drive from Toronto to Mackinaw City, MI (7.25 hrs via Michigan, 8.5 hours via Upper Peninsula) or Pictured Rocks National Lakeshore, from Niagara Falls (7 hours).

Day 12: If in Mackinaw City, take ferry to Mackinac Island, MI. If at Pictured Rocks National lakeshore, explore the park.

Day 13: Drive from Pictured Rocks National Lakeshore, MI to Chicago, IL (6.75 hours) or Mackinac City to Chicago (7 hours).

Optional Variation: Mackinac Island and Pictured Rock National Lakeshore can both be included if you add one- two extra days depending on the amount of time you want to have at each stop. Drive time between the two points is 2.5 hours.

Itinerary 3: West to Yellowstone National Park

  • Days: 13 (8 include driving)
  • States visited: Illinois, Wisconsin, Minnesota, South Dakota, Wyoming.

Day 1: Chicago to Wyalusing State Park, WI (Alan’s and my favorite state park) (4 hours)

Day 2: Explore Wyalusing State Park

Day 3: Drive from Wyalusing State Park to Sioux Falls, SD (5 hours)
Visit Falls Park for excellent views of waterfall.

Day 4: Sioux Falls, SD to Rapid City, SD (Just under 5 hours)

Day 5: Visit Mount Rushmore, Custer State Park, and Crazy Horse Memorial, outside
Rapid City, SD

Day 6: Drive from Rapid City, SD to Yellowstone National Park, WY (7.2 hours)

Day 7: Yellowstone National Park, (National Geographic Article)

Day 8: Drive to and explore Grand Teton National Park (9 min drive)

Day 9: Drive from Grand Teton National Park to Wind Cave National Park, Custer County,
SD (7 hours)

Day 10: Explore Wind Cave National Park

Day 11: Drive to and explore Badlands National Park (2 hours)

Day 12: Drive from Badlands National Park to one of many beautiful state parks near La
Crosse, WI (8 Hour drive)

Day 13: Drive from La Crosse, WI to Chicago, IL (4 hrs 19 mins)

1024px-Clifftops4-7-07Itinerary 4: South to the Great Smokey Mountains

  • Days: 11 days (6 include driving)
  • States Visited: Illinois, Indiana, Ohio, Pennsylvania, Maryland, Virginia, North Carolina, South Carolina, Tennessee, and Kentucky

Day 1: Drive from Chicago, IL to Cuyahoga Valley National Park, OH (5.5 hours)

Day 2: Explore Cuyahoga Valley National Park

Day 3: Drive from Cuyahoga Valley National Park, OH to Shenandoah National Park, VA (5.25 hours)

Day 4: Explore Shenandoah National Park

Day 5: Drive from Shenandoah National Park to Congaree National Park, SC (7.5 hours)

Day 6: Explore Congaree National Park

Day 7: Drive from Congaree National Park to Great Smokey Mountains National Park, TN (3.5 hours)

Day 8: Explore Great Smokey Mountains National Park

Day 9: Drive from Great Smokey Mountains National Park to Mammoth Cave National Park, KY (4 hours)

Day 10: Explore Mammoth Cave National Park

Day 11: Drive from Mammoth Cave National Park to Chicago, IL (6 hours)

Alternative version: To save a couple days, combine days 6 and 7, to give a half day at Congaree National Park in the morning of Day 6 and then travel to Great Smokey Mountain National Park that evening. Days 9 and 10 can also be combined to drive to Mammoth Cave National Park the morning of day 9 and explore the park that afternoon.

1024px-Pt_Betsie_lighthouse_Frankfort_MichiganItinerary 5: North Along The Great Lakes Circle Tour

The Great Lakes Circle Tour is a designated scenic route around the five great lakes of the U.S. and Canada. Each lake has its own circle tour, or they can be combined for a longer expedition.  If time or distance is of concern, feel free to break your road trip down to just the southern half of Lake Michigan by catching the ferry in Ludington, MI or Manitowoc, WI. Itineraries can be as short as a few days, or as long as weeks. It’s up to you.

Having Chicago as the starting point, the Lake Michigan Tour is the most accessible Great Lake.

We definitely recommend the stops in Holland, MI; Green Bay, WI (Go Pack!); Sheboygan, WI; Mackinac Island, MI; Traverse City, MI; and Door County, WI. There are also some great spots that are just off the scenic route that can be easily added, like Pictured Rocks National Lakeshore in the U.P, or Peninsula State Park, Ephraim, and Fish Creek in Door County, WI. A stop in Milwaukee’s Historic Third Ward is also nice for brews and eats before returning to Chicago.


Poochie on dashboardAdditional Road Trip Resources: is a site that combines the mapping capabilities of Mapquest, with the point of interest details of Trip Advisor. It is an excellent resource for ensuring you don’t miss any great stops along your route.  You start by entering in your road trip starting point and the location that will be your furthest from home, and it will map the route and highlight possible stop ideas along the way.

At first, I found this site to be a miracle worker, but once I started planning with it, I found it too commercialized and the filters not narrow enough to plan my entire trip on it. This site is associated with Trip Advisor’s sales company, Viator, and it’s a bit too in my face with non-personalized stop options, but it can still be an excellent resource to see if there is anything off the beaten path to see along the way of your trip once you’ve selected your main points. There is also an ap if you want to do any impromptu stops during your road trip. also has some itinerary ideas in their Roads and Rides section, like their Route 66 guide, or Appalachian Trail route. 

Lonely Planet

I am often a big advocate of the Lonely Planet travel guides. They not only include insider details on prices and site access, but sample itineraries and maps. Naturally, Alan and I went to our local library looking for Lonely Planet USA road trip guides when researching this vacation.

We found a Lonely Planet Road Trip Lake Michigan from 2005 and were quite disappointed when we opened it. Not only was the Lake Michigan guide more of a restaurants and hotel guide for the local cities, but it only covered the mainland Michigan side of Lake Michigan. It left out three quarters of Lake Michigan coast; the upper peninsula, Wisconsin, Indiana, and Illinois were not included in the maps or guide details.

We also explored Lonely Planet’s USA’s Best Trips book. It offered four recommended itineraries in the Great Lakes region: Route 66, a classic American byway; Michigan’s Gold Coast, full of beaches and beer; Along the Great River Road, which follows the Mississippi River from Minnesota to Louisiana; and Highway 61, the blues music roadway of America.

I hope you found some inspiration and helpful resources for your upcoming road trip. If you have any recommendations or suggestions for road trips, please be sure to list them in the comments!


Credits: Article by Acacia Thornton. Images of Gambit, and Poochie on Dashboard by Acacia Thornton. All rights reserved.  Header image By Bureau of Land Management; image of Acadia National Park By heipei from Deutschland;  image of Montreal By Emmanuel Huybrechts from Laval, Canada; image of lighthouse by Belle montano-zygmunt; all licensed under [CC BY 2.0] via Wikimedia Commons; image of Grand Tetons National Park by Jon Sullivan and image of the Great Smokey Mountains by Aviator31, via Wikimedia Commons are in the public domain. 

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