Drive from Chicago to Iowa for a few days along the Great River Road and iconic Iowa cities before heading toward South Dakota, or further along to Yellowstone National Park.
Day 1: Chicago to Davenport, Iowa
Chicago O’Hare Airport to Davenport (2.5 hours, 165 miles)
As you make your way west from Chicago, you’ll hit the Great River Road as soon as you drive over the Mississippi River into Iowa. The Great River Road National Scenic Byway runs all along Iowa’s Eastern border and offers world class vistas, charming river towns, magnificent limestone bluffs and much more. .

Arrive in Davenport
Davenport is part of the Quad Cities which encompasses four cities spanning Iowa and Illinois. Stay in Downtown Davenport to enjoy views of the Mississippi River and all it offers.
Mississippi River Visitor Center – Arsenal Island
The Mississippi River Visitor Center is located on Arsenal Island at Lock & Dam 15 on the Mississippi River. Visit from January to March to watch the bald eagles flock to the area to feed. From April through mid-December, the river is open to commercial navigation, and you can watch as boats pass through the locks. Lock & Dam tours are available during the summer.
Lunch - Celebration River Cruises – from Moline, Illinois (15 minute, 7 mile drive)
Celebration River Cruises offers specialty themed lunch cruises, dinner and sightseeing cruises. The two-hour Captain’s Narrated Lunch Cruise features a hot lunch buffet, prepared fresh right onboard. The excursion passes the Quad Cities' many historic sites, including the Rock Island Arsenal, located on a 946-acre, federal-owned island, and Lock and Dam #15, the largest roller dam in the world.

Take a trip back to the Gilded Age of silver. This one-of-a-kind museum is the world's largest collection of spoons, and includes French, German, British, Chinese & Egyptian antiquities. The rarest spoons can be seen here in Davenport.
Dinner: Front Street Brewery
Enjoy craft brews & river views. Menu items include pork nachos, peanut butter and jelly smashburgers and an Iowa classic – pork tenderloin sandwich. The brewery offers a lineup of craft brews from flagships to seasonals. Core beers include “Bucktown Stout” and “Vanilla Porter.”
Overnight: Hotel Blackhawk
Hotel Blackhawk, a Marriott Autograph Collection Hotel, is located in the heart of downtown Davenport in the Quad Cities. Enjoy the indoor pool and hot tub, sundeck, bowling alley, Rise Neighborhood Café and Bix Bistro, along with a full-service spa.
Day 2: Quad Cities to Des Moines
The paved RiverWay Trail that runs through the Iowa Quad Cities and follows the majestic Mississippi River. Hop on the trail at Credit Island Park in Davenport and continue along the riverfront through parks and historic villages. Bike rentals are available at the Quad Cities Convention & Visitors Bureau in Davenport. Board the Channel Cat Water Taxi in Bettendorf and enjoy a variety of biking trails on the other side of the river. Or cross the mighty river via the Centennial Bridge or Arsenal Bridge.
Drive to Iowa City (1 hour, 60 miles)
Welcome to the UNESCO City of Literature!
Drive (15 minutes, 7 miles)
Lunch: Walker Homestead
Located just outside Iowa City, Walker Homestead grows a variety of foods, including herbs, flowers and grapes for wine and raises animals and honey. This field-to-fork farm and winery offers a seasonal menu featuring the goodness of the farm in delicious pizzas and starter dishes like roasted veggies, hummus and focaccia.
Drive to Des Moines (110 miles, 1 hour, 40 minutes)
John and Mary Pappajohn Sculpture Park
The John and Mary Pappajohn Sculpture Park features artwork by more than two dozen of the world’s most celebrated artists. The 4.4-acre park, located within a major crossroads of the urban grid, creates a pedestrian-friendly entryway to downtown Des Moines.

Dinner: HOQ
Using produce from local farms, HoQ’s constantly evolving menu invites diners to sample global flavors inside an elegant dining space. The Des Moines restaurant carefully selected their suppliers, who provide over 90% of their ingredients using sustainable practices. The menu includes classic favorites with a twist, such as grass-fed beef burgers and steaks, free-range chicken burritos, locally raised lamb shanks, grilled cheese and a seasonal soup as well as a variety of unique vegetarian and vegan options like hummus and naan, rice and lentil crepes and more..
Overnight: Renaissance Des Moines Savery Hotels
Listed on the National Registry for Historic Hotels, the Savery offers a luxurious stay in Downtown Des Moines. It’s also located within walking distance of the East Village, Court Avenue restaurants and shops, and accessible from the downtown skywalk.
Day 3: Des Moines to Sioux Falls

The Downtown Farmers’ Market, held May-October in Downtown Des Moines' Historic Court District, supports farmers, growers and artisan food entrepreneurs from all around the state of Iowa. Visitors can explore a vibrant array of offerings, including fresh produce, eggs, meats, and more, alongside unique attractions and activities. As you depart Des Moines, drive along Interstate 80 toward the western side of Iowa, known for its Loess Hills and Lewis and Clark history. As you head west, you’ll have the option to take the White Pole Road Scenic Byway. The byway is a tribute to the early 1900s dirt road that began here and went on to become Iowa’s first certified route under the Iowa State Highway Commission. You’ll discover where westward settlers travelled the long abandoned covered wagon trail and the early railroad tracks running parallel to the route before the automobile pushed for public roads with pavement and cement bridges
Consider these stops along the way:
- Drew’s Chocolates, Dexter – This family-run shop has been selling its handmade chocolates daily since 1927! (35 minutes, 35 miles)
- Visit Stuart’s towering majesty of the domed Saints Center; admire the four-sided town clock atop the Historic Clocktower Building; marvel at the beauty of Rock Island Railroad Depot; and take an unforgettable photo at the Bonnie & Clyde Bank Robbery Site. (5 miles, 10 minutes)
- Jesse James Train Robbery Site, Adair - The Jesse James Historical Park features a large steam engine wheel marking the spot where Jesse James and his notorious gang of outlaws staged the world's first robbery of a moving train on the evening of July 21, 1873. (20 miles, 20 minutes)
Drive to Sioux Falls (3.5 hours, 250 miles)
Get back on Interstate 80 and head towards Interstate 29 in Southwest Iowa to easily make your way toward Sioux Falls. You will soon be on the Lewis & Clark National Historic Trail, which traces the Lewis & Clark Expedition through 16 states and over 4,900 miles. Iowa's leg of the trip is marked by Lewis & Clark Trail signs along Interstate 29 as it follows the Missouri River from Council Bluffs to Sioux City.
Consider some stops along the way:- Lewis & Clark Monument and Scenic Overlook – Council Bluffs Honors the expedition of Lewis & Clark and their historic meeting with the Otoe and Missouri Indians, and the overlook offers expansive westward view.
- Lewis and Clark Interpretive Center – Sioux City The Lewis and Clark Interpretive Center was built to commemorate a history of the time when Lewis and Clark's Corps of Discovery traveled through this area.
Continue your Midwest adventure toward Sioux Falls (2 hours 20 minutes, 160 miles) to head toward the Black Hills and Yellowstone National Park.
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