With the latest Chicago flights deal, which unfortunately the timing doesn't work with a school aged child and a teacher wife, we were considering doing a ROAD TRIP to Chicago come summer instead. Any must sees, drives, eats, etc on route to Chicago by CAR? Plenty of info on Chicago itself but nothing for the drive there.
Will be traveling with a 3 & 6 y/o. Was planning to go south to Yellowstone, then east through Mt. Rushmore. Not hung up on another route on the return tri… See more

With kiddos stopping at an epic water park in the Wisconsin Dells could be loads of fun!

Will certainly look into it!

Haha you are brave to go on a long road trip with such young ones. Yellowstone is amazing, I would definitely recommend spending a few days there. So much to see!

We certainly LOVE our road trips! My wife and I have done even longer road trips before but nothing like this with the kiddos. Our eldest has had a few road trips under her belt and can easily sleep 10+ in the car at a time! The 3 y/o has done a few also, including overseas flights too but this one will be a challenge. Do wish us luck, haha! And yes, we plan on spending a few days in Yellowstone, possibly (again?) on the return trip just to let the kiddos stretch out their legs a bit.

Yes to Wisconsin dells!! We just did the drive from Calgary to New Jersey this summer. Loads of fun. Mount Rushmore, Hill City, Sturgis (we went during motorcycle rally and it was AWESOME).

I would have spent a few nights just in the Mount Rushmore area. It’s beautiful.

We only have to be in Chicago for one specific day but otherwise, the entire itinerary is up in the air. What else is there to do in the Mt. Rushmore area other than the obvious scenery?

Check out Sylvan Lake in Custer State Park. Great swimming lake with hikes all around.
Wall Drug mentioned below.
Deadwood is fun for a visit. Has a re-enactment of a shootout in the street during the day.
You can do a mine tour near Deadwood as well and pan for gold (costs extra but kids like it).
Lots of caves around there too.

Nya Lynn I agree. Such a beautiful area with so much to do.

We went through Yellowstone and Mt.Rushmore in early August and the crowds are horrendous. It took us over an hour and a half to go from the gate at West Yellowstone to the first campground which is less than 5 miles
. Be patient and turn down the lesser travelled roads within the park and you will be pleasantly surprised at the “smaller” Old Faithfuls that you’ll find without the hundreds of other people. The Black Hills in South Dakota are beautiful.

I second Wisconsin Dells! so fun!

Wall Drugs near Rushmore. So much more than a drug store.

There’s a splash park in the middle - extra clothes are helpful.

Also if you are interested there is a wonderful KOA campground near Rushmore. https://www.tripadvisor.ca/Hotel_Review-g54645-d619113...
TRIPADVISOR.COM
Mount Rushmore KOA at Palmer Gulch Resort

Devil's tower would be on your way to Rushmore as well. Deadwood is an interesting stop as well. I also second the wisconson dells recommendations.

If you want a day or two of great local food and pretty little towns, plus dairies and farms you can visit, Door County, Wisconsin is absolutely idyllic.

Jen I agree with Door County!!!!

Wall Drugs and Crazy Horse.

We also did the church in the hills
https://www.chapel-in-the-hills.org/
CHAPEL-IN-THE-HILLS.ORG
Chapel in the Hills, Rapid City, SD

Crazy horse is a must. You Can maybe call ahead and ask when they're doing a blast for it. They only do them every so often, so it's really interesting to be there when it happens.

Download road trippers app. You can say how far off route and what your interested in and it will show lots of little gems along the road.

We drove from Calgary to Chicago and back one April several years ago. We went through Montana and North Dakota and the drive was relatively boring, but we were told that going through Canada would be even worse. That's a long drive and we were not prepared for toll roads in Chicago and didn't have any cash on us. We had to use smaller roads which extended our trip by hour and a half.
On our way back we stopped at Wisconsin Dells - a resort city - and can highly recommend the area. We drove back through South Dakota and made a stop at Mount Rushmore and it was fun.
The trip is doable but requires some planning.

Go to RoadTripAmerica. All sorts of info.

Free activities- beaches in Chicago are great and free! Oak Street and North Ave. Beach highly recommend. Lincoln Park Zoo downtown is free. Go to John Hancock Building to the 96 floor for the best view of the city (you can get a drink if you want). Of course Millennium Park to see the bean and fountain, but also there are free concerts there throughout the summer.
Not free- Lots of various boat tours, including kayaking and Navy Pier can be fun, esp to do the ferris wheel.
Field Museum and Shedd Aquarium are great and a good spot for kids. Another great museum that is not on the main museum campus is Museum of Science and Industry- very interactive! Loads to do

Free: beaches are awesome in Chicago. Recommend Oak St and North Ave. Millennium Park- see the Bean, the fountain and free concerts going on there all summer. John Hancock 96th floor for the best view of city. Lincoln Park Zoo is also free.
Not free but recommend: boat tour, Museum Campus (spec Shedd Aquarium and Field Museum), also Museum of Science and Industry is very interactive. Navy Pier is also fun!

Alexandr Yevlash

We just did Yellowstone to Chicago this summer! Spend plenty of time in Yellowstone and Mount Rushmore, I wish we had spent longer in both areas! We stopped in Belle Fourche to see the geographical centre of the USA. Also Deadwood South Dakota is somewhere to stop too!
Wall Drug is fun to stop by. Devils Tower is pretty amazing to see. Minneapolis is a cool city to stop at too, Betty Dangers country club is a great place for dinner while there. Also go get a Juicy Lucy burger from Matts Bar.
When in Chicago, go to the Navy Pier and tour Wrigley Field. Also go see the bean in the millennium park and do the architecture river boat cruise.
Hope this helps! Have fun

Charlott great list!!

I second the architecture boat cruise.

Alexandr Yevlash

Crazy Horse Memorial .....just south of Mt Rushmore. Also if you are an AMA member they have an excellent free travel guides with alot of sights.

Lots of great suggestions for things to see and do. One piece of advice is to ensure that you time your arrival in Chitown to avoid rush hour.

Wisconsin dells with kids. so fun.