Why This Road Trip from Winnipeg to Chicago Should Be on Your Bucket List
One chilly evening in Winnipeg, I was lounging on my couch, scrolling through social media, when I saw a friend’s photo of deep-dish pizza in Chicago. Now, I loved pizza like anyone else, but this—this was a work of art.
I could almost taste the gooey cheese and savory sauce through the screen. So, I started thinking, “What if I drove to Chicago? How hard could it be?”
The Windy City had always been on my list—its stunning skyline, rich history, and, of course, that pizza. But flying seemed too easy; I wanted an adventure, a chance to see the changing landscapes, meet new people, and discover hidden gems along the way.
So, armed with a playlist full of road trip tunes, I set off, brimming with excitement and curiosity. What would I find on this journey—quirky roadside attractions, charming small towns, or maybe a hilarious mishap or two?
Well, spoiler alert: I did! From nearly running out of gas in a tiny town to finding a diner with the best pie ever, the trip was full of surprises.
So, if you’re ready to hear about my escapades and get some tips for your own adventure, buckle up! Let’s hit the road from Winnipeg to Chicago together.
How long is the drive from Winnipeg to Chicago?
The direct drive from Winnipeg to Chicago covers 863 miles (1,389 kilometers) and usually takes about 13 hours and 50 minutes under normal traffic conditions.
Best Places to Stop on a Drive From Winnipeg to Chicago
Treasure Island Resort & Casino
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Website: http://www.ticasino.com/
Location: 5734 Sturgeon Lake Rd, Welch
Contact: +18002227077
Operating hours:
- Check-in time: 4 pm
- Check-out time: 11 am
Treasure Island Resort & Casino is a huge resort with three hotel towers, boasting a total of 788 rooms and suites—the second-largest hotel in the state, if you can believe it!
What really sets it apart are the amenities. The casino is a hive of activity with over 1,800 slot machines, bingo, poker, table games, and even pull tabs.
If you’re looking to unwind, you can dive into The Lagoon indoor water park or melt your stress away at the soothing Wave Spa.
And when hunger strikes, a variety of restaurants and bars are at your disposal, ensuring that every craving is satisfied. Plus, for those road-tripping in an RV, there’s a dedicated park to accommodate your journey.
Jacob Leinenkugel Brewing Company
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Website: https://www.leinie.com/
Location: 124 E Elm St, Chippewa Falls
Contact: +18885346437
Operating hours:
- Sunday to Wednesday: 10 – 6 pm
- Thursday to Saturday: 10 – 8 pm
Jacob Leinenkugel Brewing Company has a storied past that stretches back to 1867 when it was founded by Jacob Leinenkugel, an immigrant with a dream.
This isn’t just any brewery; it’s a piece of history, being the oldest in Chippewa Falls and the seventh oldest in the United States.
Leinenkugel’s is renowned for its traditional beers and shandies, which have gained a loyal following.
For those interested in a deeper dive into their rich 150-year history, the brewery offers tours that provide a glimpse into how six generations of the Leinenkugel family have maintained their brewing legacy.
Minnesota Marine Art Museum
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Website: https://minnesotamarineart.org/
Location: 800 Riverview Dr, Winona
Contact: +15074746626
Operating hours:
- Tuesday, Wednesday, Friday to Sunday: 10 – 5 pm
- Thursday: 10 – 8 pm
The Minnesota Marine Art Museum (MMAM) is a nonprofit museum that focuses on our deep connection with water, showcasing some truly impactful visual arts.
Initially, they focused on traditional marine paintings and folk art, but their collection has grown to include works from big names like Turner, Renoir, Monet, Van Gogh, Picasso, O’Keeffe, and Cassatt.
It’s quite impressive, especially when you see the masterpieces up close!
Plus, they offer special programs for both adults and kids, making it a perfect stop for the whole family.
Riverside Park
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Website: https://www.nycgovparks.org/parks/riverside-park
Location: R25M+R3, New York
Contact: +12128703070
Operating hours: Monday to Sunday: 6 – 1 am
Riverside Park is one of those spots that instantly makes you feel at ease. It’s been a local gem since 1911 when it was first known as Levee Park.
Here, you’ll find wandering through scenic trails and wide-open spaces, where you can unwind and breathe in some fresh air. And if you time your visit right, you might even catch a lively event like Riverfest.
But one of my favorite ways to enjoy the park is to take a leisurely stroll along the riverwalk. It’s a great way to appreciate the beauty of the La Crosse West Channel Bridge while sipping coffee.
Noah’s Ark Waterpark
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Website: https://www.noahsarkwaterpark.com/
Location: 1410 Wisconsin Dells Pkwy, Wisconsin Dells
Contact: +16082546351
Operating hours:
- Monday to Thursday: 10 – 6 pm
- Friday and Sunday: 10 – 7 pm
- Saturday: 10 – 8 pm
Noah’s Ark Waterpark in the Wisconsin Dells is America’s largest outdoor waterpark, spread over 70 acres of pure fun. Trust me, it’s worth the detour, especially for families!
They’ve got more than 51 water slides catering to every thrill level. If you’re a daredevil, go for the heart-pounding Scorpion’s Tail and the Black Anaconda.
But if you’re with little ones, don’t worry—there are plenty of laid-back, gentler slides for them, too. And speaking of relaxation, nothing beats drifting along the lazy river or catching some waves in one of their two wave pools.
Just when you thought it couldn’t get any better, they also have these 4-D Dive-In Theater. It’s such a cool experience to watch a movie while floating in the pool.
Plus, there’s no shortage of food options, from quick snacks to sit-down meals.
Just a heads-up: the park typically opens from Memorial Day weekend through Labor Day. It’s a good idea to check their website for the latest on hours, rates, and tickets before you go.
The House on the Rock
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Website: http://www.thehouseontherock.com/
Location: 5754 WI-23, Spring Green
Contact: +16089353639
Operating hours: Monday to Sunday: 9 – 3 pm
The House on the Rock isn’t just any old roadside attraction; it’s a one-of-a-kind architectural marvel that will leave you in awe.
Imagine a sprawling, Japanese-inspired home built right into a massive 60-foot rock formation—it’s a sight you won’t see anywhere else.
But the real kicker, though, is the sheer variety of stuff they have inside. We’re talking about the quirkiest displays, including some really impressive robotics, curiosities, and full-scale replicas.
Each exhibit offers a new surprise, keeping you captivated for hours.
If you love discovering the unusual and unexpected, The House on the Rock is going to blow your mind.
Where to Eat During the Winnipeg to Chicago Road Trip
River Jams
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Website: https://www.river-jams.com/
Location: 2940 109th St, Chippewa Falls
Contact: +17158613041
Operating hours:
- Sunday to Tuesday: 11 – 10 pm
- Wednesday to Saturday: 11 – 12 am
Must-order menu items:
- Shrimp Dumplings
- Jammin Burger
- Fish Tacos
Price range: $$ – average
If you’re in the mood for some tasty bites by the water, go for River Jams. This waterfront diner was founded by four friends who couldn’t get enough of the outdoors, good company, and the stunning Chippewa River.
Their mission? To give you an unforgettable time with mouthwatering food and top-notch service.
Now, if you’re wondering what to order, let me give you a couple of tips.
Their Fish Tacos are out of this world. Think fresh cabbage, zesty pico de gallo, and a tangy lime pepper crema, all wrapped up in white corn tortillas, served with a side of chips and salsa.
But if you’re more of a burger person, the Jammin Burger is a dream. It’s got caramelized onions, a delicious bacon jam, creamy mascarpone, and cheddar cheese, all on a perfectly toasted bun.
Believe me, it’s as good as it sounds!
Lake City Social
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Website: https://www.lakecitysocialwi.com/
Location: 644 Wisconsin Dells Pkwy, Wisconsin Dells
Contact: +16082539109
Operating hours: Monday to Sunday: 11 – 9 pm
Must-order menu items:
- Chicken Wings
- Grilled Sirloin Medallions
- Prime Rib Sandwich
Price range: $$ – average
Lake City Social is an American eatery where families gather for hearty dinners and friends catch up over great food.
And speaking of eats, one dish people keep raving about here is their Chicken Wings.
These are not your average wings—deep-fried and doused in your choice of sauce, whether you’re into classic House Buffalo, smoky BBQ, sweet and spicy Asian Ginger, or even something with a real kick like Ghost Chili Pepper or Nashville Hot.
They come with ranch or bleu cheese dressing, too, just the way we like it.
For something a bit more substantial, the Grilled Sirloin Medallions are a must.
It’s nine ounces of tender sirloin, grilled to perfection, and served with a decadent red wine butter sauce, mushrooms, and onions. Add in loaded mashed potatoes and fresh veggies, and you’ve got a meal that’s truly memorable.
And don’t forget to check out their drinks! They’ve got some refreshing cocktails and a nice selection of local beers, which is always a plus.
Where to Stay During the Winnipeg to Chicago Road Trip
Aloft Harlem
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Website: https://www.marriott.com/en-us/hotels/nyclh-aloft-harlem/
Location: 2296 Frederick Douglass Blvd, New York
Contact: +12127494000
Operating hours:
- Check-in time: 3 pm
- Check-out time: 12 pm
If you’re searching for a stylish and comfortable place to stay, check out the Aloft Harlem. This modern 3.5-star hotel offers a range of amenities designed to make your stay enjoyable.
Their rooms are not only comfy and clean but also feature signature Aloft beds that promise a great night’s sleep. You’ll also find walk-in showers and big 42-inch LCD TVs, perfect for unwinding after a busy day.
The social scene at Aloft Harlem is where the hotel truly shines. Their 24/7 grab-and-go café/bar is ideal for a quick snack or coffee fix anytime.
For a more relaxed vibe, W XYZ Bar offers a fantastic selection of handcrafted cocktails, and the cozy courtyard is a great spot to hang out and meet fellow guests.
Oh, and if you’re traveling with a furry friend, you’ll be pleased to know that Aloft Harlem is pet-friendly!
Fairfield Inn & Suites Winona
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Website: https://www.marriott.com/en-us/hotels/lsefw-fairfield-inn-and-suites-winona/
Location: 925 Bruski Dr, Winona
Contact: +15074742500
Operating hours:
- Check-in time: 3 pm
- Check-out time: 12 pm
For a comfortable place to lay your head, Fairfield Inn & Suites is another pretty solid option. Whether you’re traveling solo or with a group, they offer a variety of rooms to suit your needs.
You can opt for a king room with a cozy sofa bed for some extra space, or go for a room with two queen beds if you’re traveling with family or friends.
When it comes to amenities, they’ve got the essentials covered: air conditioning, flat-screen TVs, free Wi-Fi, and even irons to keep your clothes looking sharp.
And if, like me, you can’t start the day without a good breakfast, you’re in luck. They offer a free continental and hot breakfast—just make sure to check the schedule since the hours vary between weekdays and weekends.
For some downtime, you can enjoy their indoor pool or hot tub, and if you’re feeling energetic, there’s a fitness center ready for a quick workout too.
They also provide laundry facilities if you need to freshen up your clothes and offer free coffee and tea to keep you refreshed throughout the day.