A Road Trip From Chicago to Seattle

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  • Chicago, IL
  • Madison, WI
  • Sioux Falls, SD
  • Deadwood, SD
  • Bozeman, MT
  • Seattle, WA
  • Fast way back
  • Scenic way back
  • Roadside assistance
If you take this road trip from the Midwest to the West Coast, you’ll have a chance to travel through some of the most scenic regions in the country. This road trip clocks in at over 2,000 miles, meaning you will see a whole lot of countryside, bustling cities, and historic towns.
The Midwest is infamous for its chilling temperatures and heavy snowfall during the winter, so it’s best to give this trip a pass in the winter months. Being further north means that the summer temperatures shouldn’t be too severe, so spring, summer, and fall are all ideal for this particular trek.
This trip is a long one, so be sure to budget for some hotels and plan out some rest stops to take a break from driving. And make sure that you’ve got not only great car insurance to cover you in any accidents, but also roadside assistance from Jerry, so you can get back on the road as quickly as possible, no matter what the road throws at you (or your car).
Get ready to discover some of the best-in-the-West stops on this Chicago to Seattle road trip!
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Start in— Chicago, IL

The Windy City has a well-earned reputation as the best big city in the US, thanks in no small part to its diverse culture and amenities. There’s more to do here than can be done in a day, so give yourself at least a few days to get as much out of Chicago, Illinois as you can. The list below is just a small sample of things to see, do, and eat!
An aerial view of Chicago and its many skyscrapers. Lake Michigan is in the background.
Chicago, Illinois

Eat here

  • Joe’s Seafood, Prime Steak & Stone Crab: If you’re looking to treat yourself and splurge on excellent seafood, Joe’s is where to go.
  • Wildberry Pancakes and Cafe: Wildberry earns its reputation as the best place in Chicago to score breakfast or brunch. Its status as a local favorite means it can get crowded, so plan accordingly.
  • The Purple Pig: Chicago may not be known for a Mediterranean climate, but that doesn’t mean it’s lacking in any Mediterranean flavor. The Purple Pig is an acclaimed local restaurant serving up classic Mediterranean cuisine with style.

Do this

  • The Art Institute of Chicago: Made popular by Ferris Bueller’s Day Off, but made legendary by its collection of works from the masters, including Picasso, Seurat, and Wood.
  • The Field Museum of Natural History: One of the largest museums of its type in the world, the Field Museum features a vast collection of natural artifacts from around the globe, including Sue, one of the biggest and most complete T-Rex skeletons.
  • The Magnificent Mile: If you’re looking to get some major shopping done, you can’t go wrong with the Mag Mile, a stretch of Michigan Avenue that features over 450 shops.
  • Lincoln Park Zoo: Not only one of the oldest zoos in the country but also one of the few that has free admission. And if that isn’t enough, the zoo features over 1,100 animals across 200 species.
  • Wrigley Field: True baseball fans can’t give historic Wrigley Field a miss when they pass through Chicago, as it is one of the oldest and most iconic baseball stadiums in the country.
Fans pack the Wrigley Field to watch a baseball game.
Wrigley Field, Chicago

Stop in— Madison, WI

The capital of Wisconsin isn’t the biggest city you’ll ever drive through, but it’s worth the stop for its vast and diverse food scene, as well as its nightlife and shopping.
The Wisconsin State Capitol building is illuminated against the last of a pink sunset.
Madison, Wisconsin

Eat here

  • Naples 15: For a splurge with Italian flair, Naples 15 serves up gourmet steak and seafood.
  • The Old Fashioned: A great place to pick up some classic American fare, and a cocktail…an old-fashioned, let’s say.
  • Graze: True to name, this is the place to go when you want to sample a wide variety of the cuisine Madison is known for, including their famous cheese curds.

Do this

  • Downtown Madison: The cultural and economic hub of Madison, and Wisconsin by extension, the downtown area features the highest concentration of the area’s food, shopping, and nightlife.
  • Chazen Art Museum: A major cultural center in Madison, this extensive art museum features artists from America and Europe, including Rothko, Dali, and Warhol.
  • Henry Vilas Zoo: It may not be the biggest zoo in the world, but Henry Vilas is one of only ten zoos in the country with free admission. It features a range of animal exhibits that includes polar and grizzly bears, seals, and rhinos.
  • Olbrich Botanical Gardens: For a moment of peace and tranquility, take a walk through this vast natural conservatory, featuring hundreds of species of flowers, and one of only six traditional Thai sala (pavilions) to be found outside of Thailand.
A yellow Chinese-style structure sits across the water at the Olbrich Botanical Gardens.
Olbrich Botanical Gardens, Wisconsin

Stop in— Sioux Falls, SD

The best little city in the West, Sioux Falls, South Dakota is also frequently described as the healthiest. And thanks to a resurgence in artistic interest at the beginning of the 21st century, it’s now an extraordinary hub of art and culture.
Dark water tumbles over a series of boulders at Sioux Falls. On the right, tourists watch the scene.
Sioux Falls, South Dakota

Eat here

  • Minerva’s: Treat yourself at Minerva’s, where American cuisine is served with classic elegance
  • Carnaval: Grab a taste of Brazil in this excellent steakhouse, whether it’s steak, seafood, or lamb.
  • Phillips Avenue Diner: Sioux Falls may be known for its healthy living, but that doesn’t mean you can’t treat yourself to some diner food done right.

Do this

  • Butterfly House and Aquarium: A beautiful tropical conservatory featuring over 800 free-flying butterflies, and hundreds of marine fish and corals.
  • Sioux Falls Bike Trails: If you’re on a health kick, swap out four wheels for two and take a tour on one of Sioux Falls’ dozens of available bike trails through urban and wildlife regions.
  • SculptureWalk and Arc of Dreams: This walking tour takes you to over sixty sculptures scattered throughout the downtown area and ends at the Arc of Dreams, a landmark sculpture dedicated to dreamers of the past, present, and future.
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Stop in—Deadwood, SD

A former gold rush town and a major site of the old West that attracted some of the legends of yore, Deadwood is a great stop thanks to its convenient proximity to major historical monuments. You may have also heard of Deadwood thanks to the HBO TV series that is based on its tumultuous history.
A fish-eye view of tan-colored buildings in downtown Deadwood, South Dakota. A tree-covered hill is behind them.
Deadwood, South Dakota

Eat here

  • Mavericks Steak and Cocktails: Combining classical elegance with Old West flair, this incredible steakhouse and bistro is a great place to gamble and dine.
  • The Deadwood Social Club: A steakhouse with Italian flavors and farm-to-table sensibilities, be sure to finish off your meal with one of the chef’s immaculate homemade desserts.
  • Chubby Chipmunk: Chocolate is a universal love language! The Chubby Chipmunk may have a name that makes you laugh, but their hand-dipped chocolates will make you sing.

Do this

  • Mt. Rushmore: The “Shrine of Democracy” carved into a sacred Lakota mountain range is one of the most iconic and recognizable monuments in the country.
  • Mt Roosevelt Monument: A historic tower on the outskirts of Deadwood, this stone monument was built in honor of Theodore Roosevelt, a close friend of Deadwood’s sheriff Seth Bullock (the one featured in the show, yes).
  • Custer State Park: This massive wildlife reserve is not only famous for its incredible scenery and herds of buffalo, but also Crazy Horse Memorial, Wind Cave National Park, and Jewel Cave National Monument.
  • Adams House: An elegant Queen Anne style home converted into a museum of the old west, featuring artifacts from legends like Calamity Jane, Wild Bill Hickock, and the Black Hills gold rush.
  • Mount Moriah Cemetery: The final resting place of prominent figures of the Wild West, including Wild Bill, Seth Bullock, Calamity Jane, and Potato Creek Johnny.
  • Historic Old Town: Deadwood’s historic downtown area brings the glory of the old west back to life in full color. You can experience it firsthandーdown to gambling and drinking!
A white RV drives through a road bordered by lush trees. Mount Rushmore is in the background.
Mount Rushmore, South Dakota

Stop in—Bozeman, MT

Bozeman may not seem like a big city, but it’s certainly big by Montana standards. It’s a low-key city that combines nature with technology. Its proximity to Yellowstone National Park makes it a convenient stopping point as well.
Snow-covered mountains in Bozeman stand behind a frosty field and trees.
Bozeman, Montana

Eat here

  • Montana Ale Works: Not only a source of eclectic, casual eats, but also, true to its name, a wide variety of locally-brewed craft beer.
  • Blackbird Kitchen: A haven for modern, clean cuisine, and more importantly, a lengthy list of wines of every color and specialty craft beers.
  • MacKenzie River Pizza: If you like your food simple, no-nonsense, and big on flavor, MacKenzie has you covered! Stop here for massive, savory pizzas and burgers.

Do this

  • Yellowstone National Park: The oldest and possibly most famous national park in the world, Yellowstone is home to more natural wonders than we could possibly fit in a single list. Try to spend more than a day here to experience as much as you can.
  • Ziplining at the Gallatin River: Zip through Montana’s incredible landscape across a number of different lines, including through forest canopy and over the scenic Gallatin River.
  • American Computer and Robotics Museum: The tech center of Bozeman, this unique museum uncovers the long history of computers, from the early Greek Antikythera mechanisms to the first Apple computers to the future of artificial intelligence.
  • Museum of the Rockies: If Sue back in Chicago didn’t whet your appetite for dinosaur bones, the Museum of the Rockies should be on your list, as it features the most dinosaur remains of any museum in the country, including the largest T-Rex skull ever found.
  • Palisades Falls: An easy 1.2-mile trail located south of Bozeman in the Hyalite Recreation area leads you up to the Palisades, a towering 80-foot tall waterfall that flows year-round.
A lake reflects a view of a mountain and clouds overhead at Yellowstone National Park.
Yellowstone National Park
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Arrive in— Seattle, WA

Seattle, Washington gained its notoriety as the birthplace of grunge, the home turf of bands like Nirvana, Soundgarden, Alice in Chains, Pearl Jam, and more, but it was also an early nurturing ground for prolific jazz musicians like Ray Charles and Quincy Jones. But Seattle has more to offer than amazing music–it is a city overflowing with culture, good food, and a whole lot of quirk.
The silhouette of the Seattle skyline divides the sea and a low pink sunset.
Seattle, Washington

Eat here

  • The Pink Door: This famed Seattle eatery is the perfect metaphor for the city at large—eclectic, innovative, and welcoming. Come enjoy the Italian-inspired American cuisine and the unusual entertainment, including tarot, cabaret, and much more.
  • Toulouse Petit Kitchen: Bringing the flavors of the Big Easy to the Emerald City, Toulouse Petit offers up a full day’s menu of Creole and Cajun-inspired cuisine.
  • Lola: Transforming local produce into Mediterranean cuisine is Lola, located in the heart of Belltown.
  • Serious Pie: Pizza is no joke in Seattle, and Serious Pie knows it best, with homemade crusts made daily and topped with a variety of innovative ingredients in combinations you won’t find anywhere else.

Do this

  • Chihuly Garden and Glass: One of the major collections and exhibits by famous glass artist Dale Chihuly, located at the base of the Space Needle, this massive collection of glass sculptures captures Chihuly’s careful dedication to intricate yet organic forms.
  • The Space Needle: There really is no reason to go to Seattle if you’re not going to check out its famous Space Needle, a vital component in the cityscape. Its observation deck gives you a full 360 view of the surrounding city, mountains, and Puget Sound, and its new glass floors are definitely not for the faint of heart.
  • The Modern Pop Culture Museum: The MoPOP museum is a must for pop culture nerds everywhere, featuring hundreds of iconic exhibits and artifacts from popular movies and musicians, including The Lord of the Rings, Star Wars, Terminator, and Alien.
  • Pike’s Place Market: The oldest and certainly most famous open-air market in the United States, Pike’s Place is a veritable smorgasbord of local produce, coffee, seafood, and artisan products.
The top of The Space Needle breaks through a line of low-hanging clouds.
The Space Needle, Seattle

The fast way back

Take I-94 E and I-90 E to save time. Make sure you plan around rush hour traffic when you pass through Minneapolis.

The scenic way back

Take I-84 E and I-80. This route adds a few extra hundred miles but also takes you through a few more states that you missed on the way to Seattle, including Utah and Nebraska.
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Why you need roadside assistance

This particular drive isn’t a quick trip that can be done in a weekend; you’re covering seven states and several thousand miles. That means plenty of opportunity for breakdowns, and not always in convenient locations.
So roadside assistance is definitely one of the most important tools you can take with you on this trip. That’s where Jerry steps up to the plate. Jerry now features an independent roadside assistance program that covers everything you need for a safe journey:
  • Emergency assistance
  • Towing
  • Fluid and fuel delivery
  • Winching
  • Mechanic advice
  • Rental reimbursement
  • and more!
And you get it all for just $6.99 for one car.
If you’re thinking it’s time to switch insurance carriers, Jerry can handle that, too! Jerry’s first job is finding you affordable insurance coverage tailored to your needs and budget.
It’s still easy and free to find the right policy, including ones that offer roadside assistance. Just sit back and let Jerry do all the work, so you can focus on planning your next road trip without worrying about shopping for coverage.
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