Planning a Trip to South Dakota: 9 Day Itinerary from Chicago

Summer 2020 was supposed to be a trip to Italy with my parents and our family. Once we realized it wasn’t going to be possible due to COVID-19, I started thinking about where we could go by car instead. After doing some research, listed below is our 9-day itinerary from Chicago to use when planning a trip to South Dakota:

*I recommend the guidebook Moon Mount Rushmore & Black Hills: With Badlands . It’s an excellent travel guide for the South Dakota area and outlines a ‘must see’ section with highlights for each area.

9 Day Itinerary – Chicago to South Dakota

DAY 1 – Chicago – Sioux Falls
This would be our longest day of driving, 9 hours, to get to Sioux Falls. From Chicago, we took I-90 the whole way. Once we arrived in Sioux Falls, we checked into our hotel and headed to Falls Park.

Falls Park is full of waterfalls located along the Big Sioux River. You will also find an observation tower, remains of an old mill and cafe in the park. We stayed overnight in Sioux Falls at the Holiday Inn.

DAY 2 – Sioux Falls – Badlands National Park – Wall
The drive to Badlands National Park should take about 4 hours but we made some stops along the way. Once you hit the road, you will see signs and stops for LOTS of attractions. We stopped in Mitchell at the Corn Palace. It’s the only Corn Palace in the world. It’s free to visit and was a good break for the kids.

From Mitchell, we continued on to Badlands National Park. Reference the national park website to learn more about the history, how the Badlands formed and park closures. Things we did in the park:
*Walked Door Trail & Window Trail. We explored the rock formations in this area.
*Drove the Badlands Loop Road to see all the rock formations and landscapes around the park.
*Drove Sage Creek Rim Road. Here we saw fields of prairie dogs and bison.

When we exited the park, we continued on to Wall, South Dakota. There are signs all along I-90 advertising Wall Drug along the way. Wall Drug is enormous! We shopped for a few things but barely scratched the surface. We stayed overnight in Wall at Best Western.

planning_a_trip_to_south_dakota_badlands

DAY 3 – Wall – Hot Springs – Custer State Park
After leaving Wall, we headed to Hot Springs to visit the Mammoth Site. This is an active excavation site and museum where research continues today about the Wooly Mammoth. We visited the dig site and saw the remains that have been uncovered. Our kids participated in the Junior Paleontology Program which I highly recommend. It’s very educational and informative.

Next, we headed to Custer State Park. Custer State Park is known for its scenic drives, lakes and historic sites. If you are planning a trip to South Dakota, I recommend spending a few days to explore what Custer State Park has to offer. We spent 3 days here because there is so much to do and see. Once we arrived, we drove the Wildlife Loop which usually takes at least an hour. We saw bison, pronghorn and burros. Try to drive this in the early morning or evening as these are the best times to see wildlife.

Around 4:00pm we checked into our cabin which was located just outside the entrance of Custer State Park. I would HIGHLY recommend this place! It was a very nice, spacious cabin and the location was perfect. At the time, I found the cabin on Rushmore Rentals website – named Morris Place Cabin 2 located in Custer, SD. Currently, I don’t see this particular cabin on their website. I have seen it on Expedia and other rental sites. If interested, I would recommend Googling ‘Morris Place Cabin 2’.

DAY 4 – Custer State Park
Today we hit the road early and drove Needles Highway to Sylvan Lake. Needles Highway is a scenic drive known for its narrow winding roads and tunnels, granite spires and spectacular views thru pine and spruce forests. There are 3 narrow tunnels along the way. The most famous is the Needles Eye Tunnel. Only one car can pass thru these tunnels at a time. There’s plenty of beautiful views and pull offs for photo ops. The drive to Sylvan Lake took about an hour with all the stops. See pictures below.

Here are a few tips to make your visit to Sylvan Lake more enjoyable:
*Arrive at Sylvan Lake (which was around 9am) and immediately rent paddle boards since you cannot reserve these in advance. It’s best to get them right when you arrive as they run out of rentals quickly.
*Start your day early to get to Sylvan Lake. The drive is much more enjoyable without fighting a traffic jam thru the tunnels. Also, the lake gets very busy as the day goes on and parking gets full. We had no problem with parking arriving at 9am and found a spot in the lot.
*We hiked the Sylvan Lake Trail. It’s an easy 1.6-mile loop with nice views of the lake. It was also a good distance to break in the kids!
Around 4pm we headed to the town of Custer for dinner. Custer is a lively town with plenty of restaurants, brew pubs and shops. After dinner we headed to our cabin for the night (pictured below).

cabin_south_dakota_planning_a_trip_to_south_dakota

custer_state_park_planning_a_trip_to_south_dakota

needles_eye_tunnel_planning_a_trip_to_south_dakota

Needles_highway_views_planning_a_trip_to_south_dakota

sylvan_lake_south_dakota_planning_a_trip_to_south_dakota

DAY 5 – Custer State Park
This morning we went horseback riding at Blue Bell Stables in Custer State Park. I made reservations 2 months in advance. We went on an hour group ride which was the perfect amount of time for the kids first time riding. My one suggestion is getting cash before you ride so you can tip the guides at the end.

Afterwards, we went into Custer for lunch and spent the afternoon at Legion Lake. Legion Lake was close to our cabin, just inside the park. You can swim, fish and boat here. It’s a nice spot for a relaxing afternoon.

DAY 6 – Custer State Park – Mount Rushmore
Early in the morning we said goodbye to our cabin and drove Iron Mountain Road to Mount Rushmore. This is a not to be missed scenic drive. It’s full of curves, switchbacks, wooden bridges, tunnels and a STUNNING view of Mount Rushmore in the distance. When we arrived at Mount Rushmore, we viewed the site and visited the museum and exhibits. It’s pretty amazing how it was constructed. We learned all about the process and history.

Once we left Mount Rushmore, we went into the town of Keystone to catch the 1880 train. The train follows the original route between Hill City and Keystone that was laid down in the late 1880s to service the mines and mills. It’s a 2-hour narrated train ride from Keystone to Hill City. In Hill City, we had a 15-minute break, then took the train back to Keystone. Honestly, I would not recommend the 1880 train. It was a long ride and ate up a lot of time.

That evening we stayed at Under Canvas, a glamping campsite in Keystone. Under Canvas has upscale glamping locations across the country. The accommodations are safari inspired tents with all the amenities such as, bathrooms with showers inside the tents, fresh towels and a wood burning stove. The main lobby is a communal space to eat meals at the cafe, sit and relax or enjoy the view of Mount Rushmore from the patio. In the evening, you can roast smores at firepits scattered around the grounds. At night, Mount Rushmore is lit up which you can see in the distance from the patio. We spent 2 nights and LOVED staying here and so did our kids. They explored the grounds and had a great time experiencing a different kind of camping. I highly recommend it!

mt_rushmore_planning_a_trip_to_south_dakota

under_canvas_planning_a_trip_to_south_dakota

DAY 7 – Keystone – Devils Tower – Deadwood
Today we left early and drove to Devils Tower National Monument. Devils Tower was the very first national monument. It’s a rock formation that was formed by magma and stands 867 feet tall. We hiked around the tower which gives views from many different perspectives. There’s lots of rocks at the base which were great climbing for the kids. It’s quite a sight to see!

devils_tower_planning_a_trip_to_south_dakota

Next, we headed to the historic town of Deadwood. In the late 1800’s, Deadwood was a lawless town known for it’s goldrush history. Wild Bill Hickok, Calamity Jane and others came looking for gold. Today, you can visit Deadwoods museums, casinos, historic sites, restaurants and more. We visited Saloon No. 10, where Wild Bill Hickok was shot while playing poker. Check times for re-enactments of this historic event as well as re-enactments of shooting outs on Main Street.

DAY 8 & 9 – Keystone – Sioux Falls – Chicago
Today we started our journey back to Chicago. We drove from Keystone to Sioux Falls and stayed overnight. The next morning we drove from Sioux Falls to Chicago which took 9 hours.

A Few Tips if You are Planning a Trip to South Dakota
*Because of COVID-19, Jewel Cave and Wind Cave were closed. If open, plan a visit.
*The chuckwagon cookout at Blue Bell Lodge was not running due to COVID-19. If open, consider making reservations.
*The 1880 town on the drive to South Dakota was closed. If open, try to make a stop here.
*Bring a cooler with food in the car. We had a snack bin in the car and food for breakfast & lunch filled our cooler. We cooked some dinners at the cabin. Bring water and Gatorade.
*When choosing places to stay, find somewhere with a washer/dryer. We did all our laundry at the cabin which was midway thru our trip.
*When staying at hotels, we always looked for ones with a pool for the kids.

Overall, South Dakota was so much more than we expected. It’s full of beautiful scenery with numerous things to do and see. It’s historical and educational mixed with the beauty of the outdoors. I HIGHLY recommend it. I hope you find this information useful when planning a trip to South Dakota. It was one of our best family trips.