From Chicago to Toronto

What about Ann Arbor? It's a lively university city just west of Detroit.

Go through Western NY, PA, OH, & IN. Breaking up the trip in Cleveland will mean 6 hours each way, so it's longer and different Cleveland has Rock & Roll Hall of Fame, excellent art museum, interesting neighborhoods: Little Italy, Tremont, Flats for example. Surpisingly good park systems--Cultural Gradens and Laefront Nature Preserve in the city--mMetro parks and Shaker Lakes in the suburbs. If it's summer--music outdoors at Blossom Music Center between Clevealnd and Akron

You also can break up the trip with things in various spots along the way:
Nothing much to see in Indiana unless you want to see the Studebaker Museum or Notre dame in South Bend

Toledo--one of the best and least known art museums, with excellent glass collection and a working glass studio (scheduled times on weekends) and its free

Cedar Point & Lake Erie islands: Amusement park (Cedxar point), resorty islands with wine tastings

Western NY State: Chataqua, wineries (far NE Ohio also has these near the lake in Madison & Geneva areas)

Chicago to Detroit is 4.5 hours.
Chicago to Toledo is under 4 hours.
Chicago to Cleveland is 5 hours.

Unless you visit some great areas north of I-96/Grand Rapids, which is 3 hours from Chicago, you really would be going out of the way.

If you need to do some shopping, besides downtown Chicago, which has everything from luxury to boutiques and a Nordstrom Rack and H&M/Uniqlo, there are some so outlets 1 hour east of Chicago in Michigan City, which is on I-94 to Detroit.

You could then stay a night 1 hour north of there in a cool area of lake cottages and marinas and golf, Saugatuck/Douglas, as Oct will be gorgeous weather in Michigan...lots of good apple cider and wine country too.

Sherwood Forest B&B is great, or head downtown Saugatuck.

Grand Rapids is booming downtown as well, as far as food/music go.

If you want to stay outside Detroit downtown, consider the Birmingham area, nice little downtown and shopping. Not too far to the Detroit Zoo either. The Townsend Hotel is a very nice option too...also nearby is the Somesret Mall, one the best malls in the country as far designer labels go, anchored by Nordstrom, Neimans and SFA, has Gucci, Burberry LV, Armani etc etc...just like Michigan Ave, but lower sales tax (Illinois is 10.5% vs 6% Michigan) if your spending thousands. Make sure you take the tags off everything before crossing border to Canada and Customs, or you will be delayed.

If you want more a straight shot, then head to Detroit suburb edge of city called Dearborn, and stay at The Henry, and go the Henry Ford Museum is which is excellent, and your close the trendy downtown areas now gentrifying like Mid Town and Corktown areas... (Slows Bbq)..

Downtown/Greektown area has a MGM Grand Casino that is nice is well, lots to do eat and do around there as well.

I live in Chicago, and have a summer home in Michigan, and go to Detroit monthly for work, so know the lay of the land well...I also go to Toledo and Cleveland monthly too, both nice, Cleveland Rock Roll Hall of Hame needs at least 1/2 day IMO...lot of great nostalgia there...right downtown on the lake, which downtown Cleveland is on fire too...very happening...

I would just stop at one of the quiet beach towns on the Michigan side of Lake Michigan. There are lots of outlet stores on the roads around Grand Rapids in Michigan. If you use route 69, you don't even need to drive through Detroit on the way to Toronto.

The reason most people say "Detroit" is because it is almost exactly halfway between Chicago and Toronto, and is a large city with all that entails. Visiting any other major city (e.g. Cleveland) instead requires a detour.

Without a substantial detour, your best alternatives are Ann Arbor or Toledo. Ann arbor is a college town, and usually has quite a bit going on, but if you're going during summer it can be quieter. Toledo does have a great art museum, but is otherwise an old industrial port city that's trying to revitalize.

Cleveland is probably the "best" option for things to do, and you'd pass through Niagara on your way to Toronto, but it'll add a few hours to your journey.

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