When vacationers go to San Francisco they often pair it with a side trip to Napa Valley or the California coast or Yosemite (or all 3.)

I'm thinking of going to Chicago for a week's vacation and need ideas for side trip to pair it with. Or better yet a loop trip out of and returning to Chicago. I'd like to see some nice scenery.

Any suggestions?

What time of year?

If you put Chicago side trips into the search feature here, you will get the back threads on this. There are several. Be aware that driving/traffic is much easier going West or South rather than going East or North from Chicago, IMHO and lots of others.

Chicago is a whole lot bigger than SF, and there is enough to do here that to me it is not comparable to the Napa Idea. Not that it can't be done, but the practicality of it is just different. My favorite places with good scenery are hard drives under either winter or construction. LOL!

Some easier ones would be Starved Rock area, which has more all the time for visitors, including a Utica water park now- plus some Indian tale places that certainly are not flat. Or hilly Galena with that scene if it appeals.

My favorite is MI- all the way- but time of year is important to all this as well. And length of time for the loop too.

3rd week of April.

3 day loop.

How about flying into Chicago, driving thru Ricine, Milwaukee, Sheboygan and up into Door County staying in Egg Harbor or Fish Creek and then flying out of Green Bay?

April is iffy for weather, but it may be nicer South than North. How about a trip to Springfield to see the new Abraham Lincoln Presidential State Library and Abe's haunts too. Vintage plus entertainment! The ride is easy/doable/flat and the traffic is rarely a concern in that direction- so you would not be spending all your time driving. Everyone who has gone gives it a rave. Lots of high tech surprises. Also it would not be crowded, IMHO and lodging would be reasonable- not Graduation time yet for colleges etc.

Either that or maybe something around Milwaukee, but that is not my "ken" despite going maybe 3 or 4 times in the last 15 years. It's not festival times- but the brewery tours are always fun, IMHO.

All the really spectacular places are too far to do a leisurely 3 day loop or are apt to be cold/rain then, actually. How do you feel about places like the Dells and waterpark cities, LOL!

My favorites are all in MI, but in April- it will not be snowmobile, swimming, or wine harvest or much else open on the big Lakefront itself yet. Most of the closer MI locations don't open full boat, even in the restaurant category, until May. But it is still probably worth a trip to Warren Dunes, or any of the big dunes in IN, if you have never seen them.

And a drive vacation going to the Northern part of MI or WI or MN would not give you the same thing at all as an entire week in Chicago plus a 3 day junket would.

If you have not been to Chicago before, do some research on the neighborhoods, theatre, museums, sports or whatever. Besides downtown and the tourist areas, there are more SF size neighborhoods in Chicago than is realized. And maybe 20 something smaller ones too. Some are so different from one another that you will THINK you have left. I just did this with D.C. I was there 7 full days and did not see 1/2 the neighborhoods there, either.

Chicago's are DIFFERENT from each other and from the logistics of SF. Go to Hinsdale, Brookfield (Zoo) and the natural beauty surrounding that area. I just recently spent an entire day near Oakbrook in their natural/historical preserve seeing an ancient waterwheel mill and immense beauty in nature. They (these parks/Nat. preserves) are numerous in Chicago proper too. These places are rarely highlighted anywhere.
There is no need to drive eons to see "less" in actuality. A full week in Chicago will only skim the surface, frankly.

Starved rock is a cliff where Native Americans chose to starve rather than surrender. That area and the one around Galena are VERY hilly and the Illinois River valley is beautiful.

Go down and the see the real Chicagoans fishing for smelt. Smelt season opens Apr. 1 and they are all down there in nets and it is better than a jazz festive, IMHO. Although that might be at its end by the time you come. People will teach you more than you want to know if you show up for that. Go to Hyde Park. Go to GSU in Park Forest and see the biggest ground sculpture park in the USA- never toted on anything because of where it is. Perfectly safe.

Take a ride to Gold Coast and North of Lincoln Park. Go to a ballgame and feel the atmosphere. In April there is pure hope.

All the real woods, like Door, or most of MI- are doable but you are going to do more driving than enjoying. And not easy driving either.

I'm been in a log jam of cars in Napa and this is totally different. Massive 16 plus wheelers as far as you can see will surround you. And in April or Aug. they never end.

Not to say it can't be done, but it is nothing like a ride to Napa.

And lastly, one real to do would be to the Chicago Botanical Gardens in Glencoe- in April that might be a real real winner. And the Bai Hai Temple on the way. And maybe a race at Arlington too that day, if they are open.