A Road Trip From Chicago to Seattle

We’ve compiled a great road trip from Chicago to Seattle, covering some of the best American towns, cities, and landmarks.
Written by Michelle Ballestrasse
Reviewed by Carrie Adkins
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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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Key trip details

Chicago, IL to Seattle, WA
​​Distance: 2,075 miles
Driving time: 31 hours
Suggested length of trip: 4 to 5 days
This is definitely a trip that requires some rest along the way, so why not take advantage of the drive and get the most out of every stop? Feel free to add time to any city on the way there or back.

Itinerary

  • Chicago, IL—1 day
  • Madison, WI—One half to 1 day
  • Sioux Falls, SD—1 day
  • Deadwood, SD—1 day
  • Bozeman, MT—One half to 1 day
  • Seattle, WA—1 to 2 days

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!

Where to eat in Chicago

  • Joe's Seafood, Prime Steak & Stone Crab
    ($$$): If you’re looking to treat yourself and splurge on excellent seafood, Joe’s is where to go. Their seafood platter is a crowd favorite.
  • Wildberry Pancakes and Cafe
    ($$): 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.

What to do in Chicago

The Art Institute of Chicago
  • 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.

Stop in— Madison, WI

147 miles, 2.5 hours
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.
To get to Madison, follow the I-90 W until you reach US-12 W/US-18 W, where you can take exit 263.

Where to eat in Madison

  • Naples 15
    ($$$): For a splurge with Italian flair, Naples 15 serves up gourmet steak, seafood, and authentic wood-fired pizza.
  • The Old Fashioned
    ($$): 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.

What to do in Madison

The Madison State Capitol building downtown
  • Explore 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.

Stop in— Sioux Falls, SD

435 miles, 6.5 hours
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.
Continue on the I-90 W, then take exit 6 from the I-229 S.

Where to stay in Sioux Falls

  • The Historic Victorian Inn
    : Located in the heart of downtown Sioux Falls, this well-maintained B&B was originally built in 1888. The rooms are comfy and cozy, and its central location makes it a great starting point for exploring the city. Cost per night: from $447.

Where to eat in Sioux Falls

  • 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, serving up impeccably delicious steak, seafood, and 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. This wicked diner is decked out with an entirely retro interior.

What to do in Sioux Falls

Sioux Falls
  • 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

385 miles, 5.5 hours
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.
To reach Deadwood, follow the I-90 W to SD-34 W/SD-79 S/I-90BL/Lazelle St and take exit 30.

Where to stay in Deadwood

  • The Lodge at Deadwood
    : This lodge has everything you need for a night of rest and relaxation. They have simple, luxurious rooms and there are two award-winning restaurants and even a casino on-site. Cost per night: from $151.

Where to eat in Deadwood

  • 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.

What to do in Deadwood

Custer State Park
  • Visit 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!
Pro Tip If you choose to head out on this road trip during winter, be aware that driving on South Dakota roads can be another adventure in itself. Be sure to take your time on icy or snow-covered roads and prep accordingly!

Stop in—Bozeman, MT

430 miles, 7 hours
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.
Take the US-212 W and I-90 W until you reach S Church Ave in Bozeman!

Where to stay in Bozeman

  • Gallatin River Lodge
    : This secluded stay is located just west of Bozeman, and offers jacuzzi suites and fantastic dining options all in a luxurious and comfortable package. Cost per night: from $425.

Where to eat in Bozeman

  • 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.

What to do in Bozeman

Gallatin River
  • 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.
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Arrive in—Seattle, WA

677 miles, 10.5 hours
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.

Where to stay in Seattle

  • Watertown Hotel
    : This contemporary, colorful stay is located to everything you might want to see or do in Seattle. Its bright and unique interior won’t be like any hotel you’ve seen before! Cost per night: from $174.

Where to eat in Seattle

  • 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
    ($$): Transforming local produce into Mediterranean cuisine is Lola, located in the heart of Belltown. We recommend visiting them for brunch!
  • Serious Pie
    ($$): 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.

What to do in Seattle

The Space Needle seen from Gas Works park
  • 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 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 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 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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