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Road Tripping in Illinois – The Highlights

Earlier this month I visited Chicago and northern Illinois on a road trip. The goal was to experience a bit of Americana—those things so typically American, so typically traditional of one of the world’s largest countries. Road tripping with Illinois Tourism through “the heartland” of the USA, my personal plans for the trip were what you might consider basic: eat, drink, take pictures and enjoy—but the trip turned out to be much more surprising.

On the road from Chicago, northern Illinois proved to be much more interesting than expected. During other road trips I’ve taken through the state (to visit friends at colleges across the midwest), there were always lots of cornfields and long, monotonous, flat roads.

This time, though, exploring the northern part of the state from Chicago and Lake Michigan all the way to Iowa & Wisconsin, the terrain was different and the stopover cities were more interesting. Illinois is a surprisingly diverse and interesting part of America—a true melting pot of cultures, U.S. history and contemporary trends.

In partnership with Expedia, I’m sharing below the highlights from my road trip through northern Illinois, out on the open road. (Use the suggested highlights for each city listed below to plan the perfect road trip through Northern Illinois—trust me, you won’t be sorry with these recommendations!)

Road Trip through Northern Illinois


Chicago Skyline
That Chicago skyline ❤ and the amazing view from the Skydeck

My one-week holiday in Illinois began in Chicago—a city I’ve always enjoyed traveling to on more “accidental” visits, but now sits right up there as one of my favorite American cities. There’s something special about such a large city (almost 10 million people in the metropolitan area) but one that maintains that midwestern friendliness so wonderfully stereotypical of the region.

Any road trip through the midwest is likely going to include stops along America’s most famous road: Route 66. But the road actually begins right in the center of Chicago. And, in typical American fashion, it begins just steps away from a diner. Not just any diner, though. This is Lou Mitchell’s.

It’s an American institution. When entering Lou Mitchell’s, you’re likely to be greeted with a donut hole and also a small box of Milk Duds. The friendliness (and food portions!) at this diner just never stops!

Lou Mitchell's Diner
The sign outside Lou Mitchell’s. Lots of friendliness (and fried things) to be found here at the beginning of Route 66
Lou Mitchell's Diner
Pro tip: Don’t start a road trip without a belly full of food!
No visit to Chicago is complete without a visit to the free Millennium Park and the famous “Bean” — a public art sculpture by Anish Kapoor

Chicago Travel Highlights

Starting a road trip in Chicago? Don’t miss these highlights. View more Chicago travel tips here.

  • Lou Mitchell’s Diner — Big breakfasts, friendly servers (you’re greeted with a donut hole!) and the start of Route 66 • (cheap—from $8 for a large breakfast)
  • Skydeck at Willis Tower — Best place for a selfie, cool viewpoints • ($19.50 for adults)
  • Millennium Park — Green space in the center of the city, famous for that metallic bean and also home to the Art Institute of Chicago (one of the world’s best museums, no joke) • view a map at (free entrance, bring your own selfie stick)

Utica, Illinois

Utica, Illinois
On the road to Utica – this is the typical view while driving through Illinois

For those looking to quickly get out of the “big city” and head to nature, there doesn’t seem to be a better spot than Starved Rock State Park and its surrounds. Just a short drive from Chicago (under two hours, even—easy to do on a day trip), it’s a nice escape from the city.

The State Park features several different hiking trails, a trolley tour and more than a few scenic viewpoints. The Lodge, though, is where I spent most of my time. The friendly bar staff in the restaurant (with a outdoor patio looking out over the bluffs and river below) made it an easy escape from the city.

While most people visit Utica and the surrounding area (including the nearby city of La Salle) for the state park, there are enough other things to do in the area. Personally, I loved the wine tasting experience at the August Hill Winery.

Some of their wines are available in Chicago, but my favorite was one called Bride of Freak of Nature—a bubbly infused with Oolong tea. It sounds weird, I know, but it’s so, so good!

August Hill Winery
Cheap wine (and bubbly) tasting in rural Illinois — who knew?!

For the tourists, the Hegeler Carus Mansion is a private homestead turned into a restoration project. The home was built in the 19th century by the same architect of several prominent buildings elsewhere in Illinois (namely their state capitol building), but what was most interesting was the home’s historical owners: the Hegeler & Carus families.

They founded a publishing house which promoted philosophy, science and religion—often intersecting the diverse disciplines, most notably in Paul Carus’ somewhat controversial Gospel of Buddha.

The house also features what is considered to be the world’s first indoor home gym (though I don’t know if I’d trust the climbing rope today). It’s a unique little stop for a bit of weird history out of Illinois’ past.

Hegeler Carus Mansion
I dare you to drive past this on the road and not try to get inside… Can you believe this is how they used to make houses??
Starved Rock State Park
Might be cloudy, but hey — I wasn’t there for the weather.

Utica Travel Highlights

Utica and the nearby La Salle are a nice escape from the busy city life. With a handful of tourist attractions, it’s no wonder so many Chicagoans escape here for the occasional weekend break.

  • Starved Rock State Park & Lodge — Scenic waterfalls, hikes and Native American history at one of the most popular Illinois destinations. Plus, the Lodge has an amazing central lounge around a large fireplace • (rooms at the lodge are upwards from $100/nigh)
  • August Hill Winery — Unique wines available for tasting and purchase at a trendy shop & lounge in downtown Utica. Try the sparkling wines, or in the summertime, their wine slushee! • (6 tastings for $5)
  • Two Girls and A Cupcake — Roadside bakery in Utica with a funny name and a huge variety of cupcake flavors. Be warned: the owners are sassy and don’t expect any warmth from them if you mention the ridiculousness of their business name… • read the Yelp reviews — they’re hilarious ($3/cupcake, but really you’re there for the selfie)
  • Hegeler Carus Mansion — Historic home with an unique past, worth stopping in for a visit to pick up some cool historical trivia • ($10 for a 1-hour guided tour and history lesson)

Galena, Illinois

Galena, Illinois

Just minutes away from both Iowa and Wisconsin, the small town of Galena has established itself as a tourist destination for much of the midwest. It’s funny how many people talk about Galena — considering it’s a city with a population just over 3,000.

And yet, the city’s picturesque Main Street and the many historical and unique tourist attractions make it one of the best weekend getaways I’ve experienced in rural America. Many regional bands stop over in Galena to play at the legendary Miss Kitty’s Grape Escape.

Couples come for romantic getaways (and even destination weddings) and others, like me, are just looking for a bit of Americana. Galena serves it all up with a bit of style and freshness.

But don’t think just because you’re visiting “small town America,” there’ll just be the stereotypical things to do. Oh no! The bed and breakfasts here are all creative and cater to diverse clients.

The city is also home to German restaurants, hipster cocktail bars of the same ilk you’d find in Chicago, a craft whiskey distillery (serving a popular moonshine) plus all that usual American history stuff. Throw in a pretty backdrop along the Galena River and some scenic viewpoints and this is a city you just can’t miss when driving through middle America.

Galena Canning Company
So many free food samples available at the Galena Canning Company. With hundreds (thousands??) of options, it’s hard not to come away with a bottle of something.
Blaum Bros Craft Distillery
Get your moonshine fix at this craft distillery in Galena – Blaum Brothers knows their liquor having learned the trade in Scotland!
Farmer's Guest House - Galena
The home-cooked, award-winning breakfast from Farmer’s Guest House – so, so good!

Galena Travel Highlights

I can’t stop broadcasting what a special place Galena is. You might think it’s just a small town, but there’s so much more to this undiscovered destination

  • Farmer’s Guest House — Beautiful, beautiful, beautiful! Really. I cannot exaggerate the simple charm and quaint beauty of this place, the friendliness of the owners and, really, just the charm of it all. • (Rooms from $169/night)
  • Blaum Brothers Distilling Company — Craft vodka, gin and moonshine distillery with a trendy bar serving unique cocktails • ($10 for a 45-minute tour & tasting)
  • Ulysses S. Grant Home — Given to the former U.S. President as a gift from residents of Galena on his return after his presidency. The historical house is good for American history buffs. Most notable trivia is the fact that there’s a sculpture out front of his wife, Julia Grant—it’s one of only a handful of sculptures of First Ladies. • (suggested donation of $5)
  • Main Street (and especially the Galena Canning Company) — Galena’s Main Street has been consistently ranked among the most picturesque in America. There are ghost tours and other walking tours around the street, but really it’s good for a bit of shopping. The Galena Canning Company offers up hot sauces and other specialty salsas (great with chips). I couldn’t resist buying a bottle of the Sweet Bourbon Glaze. •

Rockford, Illinois

Rockford sock monkey
The symbol of not just Rockford, but of all of America: the sock monkey

Rockford is a bigger city, one that’s hard to miss when driving through northern Illinois. The city hosts a number of different events and conferences throughout the year, but there are plenty of reasons to visit as a tourist. I won’t lie… I specifically wanted to visit Rockford for one reason and one reason only: the sock monkey.

Not many people know this, but the symbol of American kitsch (the sock monkey, clearly), was invented and first produced in Rockford thanks to a Swedish immigrant who made red-heeled socks without seems—perfect for making sock monkeys!

The city is now home to a historical museum which features a small exhibition on this history, as well as other cultural contributions to the city’s history. The sock monkey exhibition was a bit disappointing, to be honest, though the gift shop had a decent range of sock monkeys available for sale (I couldn’t help myself).

Rockford Brewing Co
Sampling the local brews :)

The city has more than just American kitsch, though. There’s also a riverside brewery, Rockford Brewing Company, with a nice selection of local, craft beers available in their restaurant—and in the summertime, plenty of public events.

There’s also the Burpee Museum of Natural History (ignore the name, it sounds silly) where you’ll find two truly impressive dinosaur fossils: a young T-rex (Jane) and also a near complete Triceratops fossil (Homer). Both are strangely impressive, as anyone who has visited Sue in Chicago’s Field Museum might attest.

Stumbling upon these in a small but surprising museum makes it all the more surreal—there were dinosaurs wandering around America at one point (these two particular fossils come from Montana). Next door to the natural history museum is another cultural institution: the Rockford Art Museum which, though small, manages to put on some impressive contemporary art collections.

Frank Lloyd Wright - Laurent House
The only house that Frank Lloyd Wright designed for a physically disabled client

Rockford is also home to one of Frank Lloyd Wright’s houses. As a bit of an #architecturenerd, I made a point to visit the Laurent House—important because it was the only home Wright agreed to build for a physically disabled client. There are a lot of interesting design quirks in the house, plus the typical FLW style—look out for a photo essay on that soon. Entrance to the house is pretty particular; check their website for available tours ($15 admission).

Kegel Harley Davidson - World's Oldest Dealership
At the world’s oldest Harley dealership for a few selfies…

Rockford Travel Highlights

  • Midway Museum — Home to the sock monkey! There are other exhibitions on colonial life in Illinois as well as a large and impressive history of Rockford’s impressive past as an immigrant hub • ($7 admission)
  • Stockholm Inn — Swedish restaurant and gift store famous for their breakfasts. If you’re on a road trip, you just have to stop here and see it for yourself. •
  • Burpee Museum of Natural History — Dinosaurs! Need I say more? • ($8 admission)
  • Kegel Harley Davidson — Looking for that bit of true Americana while on the road? There’s nothing more American than the Harley. This dealership claims to be the world’s oldest. Stop in for their gift shop and diner to get a few photos of yourself on the back of a Harley! •

Illinois - Road Trip
Out on the open road…

To see more of Illinois beyond the places mentioned above, take a look at these pictures over on the Expedia Viewfinder gallery—everything from the Anderson Japanese Gardens in Rockford to Sue (the dinosaur) in Chicago!

  1. Aww this makes me homesick for my state! And, fun fact, I volunteered at Midway Village as a kid! My mom made me a dress, and I spent my Saturdays there. During the summer you can’t miss the Civil War reenactments!

    • Adam says:

      Awww! How cool that you used to volunteer at Midway Village – I took a lot of selfies there, haha.

      All-in-all, it was a fantastic trip – reminded me so much of growing up in Texas and some of the other road trips I’ve been on, but this one felt just a bit more cool. There were a lot of quirky and cool things to see on the road

  2. looks like there is plenty to do!

  3. Ginger says:

    I also recently visited Chicago ! Got my tickets at travelagentinla

  4. Uzungöl says:

    Great tips. Thank you for this sharing.

  5. Sia Sharma says:

    Hey Adam
    Great road tips Experience shared …Thanks for Sharing with us…

  6. maxi says:

    Great tour deals that really work for a lifetime, indeed. I wish I was young as well to grab exciting travel deals with utmost ease.

  7. maxi says:

    Road tripping in Illinois seems awesome after reading this. Best information covered including Millennium Park and all has been great as well!!!

  8. Harry Connor says:

    Great photos! such colorful and beautiful places! i love it………i will try to my best for go to in this places………

  9. Ivy Kriste says:

    What a great trip!! Kudos..

  10. Alaçatı gezilecek yerler rehberine hoş geldiniz! Alaçatı’da nereler gezilir, en ünlü plajlar, tarihi yerler nerelerdir merak ediyorsanız yazımızı sonuna kadar okuyun…

    Ege’nin incisi Çeşme’nin bir beldesi olan Alaçatı, yıl boyu esen serin rüzgarı, taştan Rum Evleri, çiçek kokan sokakları, yöresel lezzetleri ve güler yüzlü insanları ile biliniyor. Tatilinizi burada geçirmek isterseniz Alaçatı gezilecek yerler yelpazesiyle de farklı alternatifler sunacak. Özellikle yaz aylarında yerli ve yabancı turist akınına uğrayan yörenin şık Alaçatı otelleri ile Ege’nin sakin denizinde yüzebilecek; unutulmaz bir tatil yaşayacaksınız.

  11. Xahid Hasan says:

    You are a great photographer. these photos are just way too cool. tnx for sharing with us.

  12. I first learned of Galena on the side of a cereal box many years ago, when it was described as “the town that time forgot.” About 15 years later, I managed to get there to find it exactly as advertised. Glad you liked it, too!

    • Adam says:

      How cool! I didn’t really think there were advertisements on cereal boxes :) It was a cute little city and definitely worth visiting on a road trip through the Midwest

  13. Surabhi says:

    Another excellent and inspiring article. I don’t thank-you near enough for changing my thoughts of travel into dreams of travel, then plans, then actions, then reality.

  14. rebecca says:

    Great pics! Would love to do a bit of the US of A

  15. Nailul says:

    This master professional.
    Fotn I think is good above
    all. Thank you for sharing

  16. Rob Fulling says:

    Being from Illinois, I apologize for the slightly boring scenery. I am so glad that you are taking away a positive view though, because many people miss that there are so many great little places when driving through Illinois.

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