Chicago to South Dakota via I-90 W

Route Distance: 579 miles to Sioux Falls, 333 to Rapid City (912 miles total)

Suggested Time: 10 Days

Drive Time: 14 hours

Flight Options: O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) to Sioux Falls Regional Airport (FSD), Rapid City Regional Airport (RAP), Aberdeen Regional Airport (ABR) or Pierre Regional Airport (PIR)

The open road is calling Chicagoans to explore the rugged natural beauty, historic lands, and unforgettable family fun that awaits along I-90 in South Dakota. This road trip, which starts in Chicago and ends in Rapid City, will create amazing memories from start to finish. Don't forget to order your Vacation Guide before hitting the road to discover even more South Dakota adventures.

Chicago to Rochester (5 Hours, 14 Minutes)

There’s plenty to see along the way. Rockford, IL, has a great Japanese Botanical Garden and Frank Lloyd Wright-designed home to tour. Madison, WI, has a charming, walkable downtown. Rochester, MN’s Mayowood Mansion is the perfect place to stretch your legs (and, if you are traveling with kids, stop for the night).

Rochester to Sioux Falls (3.5 Hours)

A short time after you cross the state line into South Dakota, you’ll reach Sioux Falls at the junction of I-90 and I-29. South Dakota’s biggest city, Sioux Falls offers a lot to see and do, so plan on spending a couple of days here.

Things to Do in Sioux Falls

Around Town

Stroll along “Phillips to the Falls,” which unites downtown to the city’s namesake, a beautiful waterfall and surrounding Falls Park (131 E Falls Park Dr.). The buildings here are some of the oldest in the city. Find great panoramas atop a 50-foot observation tower at the Falls Park Visitor Information Center. Throughout the park, you’ll also find over a dozen sculptures.

Speaking of sculptures, the city’s SculptureWalk installment intersperses dozens throughout downtown. The vibrant installation culminates with the Arc of Dreams (300 N Cherapa Place), a stainless-steel piece that soars 85 feet into the air.

Meet animals from around the globe at Great Plains Zoo & Delbridge Museum of Natural History (805 S Kiwanis Ave.) and Butterfly House & Aquarium (4320 S Oxbow Ave). At nearby Washington Pavilion (301 S Main Ave.), art and science alike will pique your curiosity.

For super-kid-friendly fun, head to Wild Water West Waterpark (26767 466th Ave.) or Thunder Road (201 N Kiwanis Ave.) Human foosball? Yep. Human foosball.

Sioux Falls Parks & Trails

Get outdoors and take in the incredible scenery. Good Earth State Park (26924 480th Ave.) offers a rare glimpse into the lives of South Dakota’s indigenous peoples and six miles of trails. Take in the photogenic waterfall at The Mary Jo Wegner Arboretum (1900 S Perry Pl.). For one of the most dramatic landscapes in South Dakota, head to Palisades State Park (25491 485th Ave.).

Sioux Falls Restaurants

To fuel your adventure, start the day with an indulgent breakfast at Flyboy Donuts, grab some espresso and a pastry at Coffea Roasterie & Espresso Bar, or have a fun sit-down breakfast at Phillips Avenue Diner (121 S Phillips Ave.). For lunch, get your taco fix (and perhaps a mid-day cerveza) at Los Paisanos (802 E 10th St.). For a healthy lunch in the heart of downtown, head to Sanaa’s Gourmet (401 E 8th St.), a Mediterranean restaurant where you’ll find vegan as well as gluten-free items on the menu. For dinner, opt for diverse menu options in a hip setting at Bread & Circus Sandwich Kitchen (600 N Main Ave.) or spice it up with some Cajun food at Swamp Daddy’s Cajun Kitchen (421 Phillips Ave.).

Sioux Falls Hotels

From family-friendly brand names with all the familiar trappings like Courtyard by Marriott Sioux Falls (580 WaTiki Way) to the historic, boutique Hotel on Phillips (100 N Phillips Ave.), Sioux falls has the perfect base camp for your crew.

Sioux Falls to Rapid City: Fun Along the Way

Once you’re ready to head west, gear up for some serious only-in-South-Dakota fun. Rapid City is a haul (about five hours of road time), but there’s a lot of fun on the way. Hop on I-29 North before catching I-90 West toward your first adventure.

Sioux Falls to Mitchell (1 Hour)

Get ready for some folksy (okay, corny) fun, because no South Dakota road trip is complete without a visit to The World’s Only Corn Palace (604 N Main St.). The building’s façade is festooned with an ever-changing array of colored kernels. Don’t forget to pick up a popcorn ball to snack on.

Mitchell to Chamberlain (1 Hour)

Further west along I-90, delve into the lives of South Dakota’s Native American people at Akta Lakota Cultural Center (1301 N Main St.), which sits right along the Missouri River. No stop here is complete without a stop at Al’s Oasis (1000 E South Dakota Hwy 16), where the pie is always tasty and the décor makes you feel like you’re in a Western.

Chamberlain to Wall (2 Hours, 9 Minutes)

A stop at Wall Drug Store (510 Main St.) is mandatory. The ultimate roadside attraction offers hearty eats, Western art, and, of course, tons of tchotchkes. The kids will love digging for gems and spotting (and posing with) the rare jackalope. After you explore, head south down Highway 240 to get an awe-inspiring glimpse (and photos!) of the dramatic rock formations at Yellow Mounds Overlook in Badlands National Park.

Yellow Mounds Overlook to Rapid City (1 Hour)

The gateway to the Great 8, Rapid City is a hub for public art. Sculptures of U.S. presidents line the sidewalks, and visitors can walk among granite statues and buildings displaying brilliant murals in Art Alley.

Things to Do in Rapid City

The big draw here is Mount Rushmore, where the faces of four U.S. presidents tower over the surrounding hills. Snap a photo from the Grand View Terrace and stroll the Presidential Trail. Then, head for the hills (the Black Hills, that is) for a hike at Custer State Park, especially to Black Elk Peak, the highest point in South Dakota. Be mesmerized at the ancient rock formations of Jewel Cave. Delve into Native American culture and see what will soon be the world’s largest stone carving at Crazy Horse Memorial®. For kicks, as you head back to town stop by the Dinosaur Park (940 Skyline Drive).

Rapid City Restaurants

With so many ways to work up an appetite, Rapid City also has plenty of great restaurants. Fire up your day with breakfast and coffee from Alternative Fuel (512 Main St.). For a taste of Philadelphia in downtown SoDak, head to Philly Ted’s (520 Main St.). Seeking a fine-dining experience? Head to Enigma at the Rushmore Hotel (445 Mt Rushmore Rd). Or, get your guac on at ¿Que Pasa? Cantina (502 Main St.).

Rapid City Hotels

For a boutique experience, book at historic Hotel Alex Johnson (523 6th St.), where you’ll find Vertex Sky Bar, an on-site rooftop bar with amazing Black Hills panoramas. If you’re traveling with kids (or are a kid at heart), there are buckets of fun to be had at WaTiki Indoor Water Park Resort (1314 N Elk Vale Road), which is connected to five hotels, an arcade, and several restaurants.