Illinois Vacation Guide

There’s far more to Illinois than a simple visit to the Windy City of Chicago. Though Chicago is a fantastic destination for gourmands and lovers of the arts and culture, it should serve as a jumping-off point for further explorations and adventures in this incredible and diverse state. Chicago is, after all, the famous starting point of Route 66, which all but encourages travelers to venture further west into what Illinois loves to call “the middle of everything.”

From quick weekend getaways to week-long itineraries jam-packed with adventures, you’ll find many great things to do in Illinois. Moreover, choose a Bed and breakfast in Illinois, and you’ll have a welcoming home away from home to share as you venture around the state.  

Venture your way to the charming, historic town of Galena, the second most visited destination in Illinois, or see the sights along Illinois’ portion of the Great River Road as it navigates along the Mississippi River. Head to popular state attractions like Starved Rock State Park or explore the state’s remarkable historical figures in the Capital city of Springfield. Wherever you go in Illinois, adventure awaits – and so, too, does a welcoming Bed and Breakfast in Illinois!

Things To Do In Illinois

Even if you leave the vibrant city of Chicago out of the picture, there are still more than enough things to do in Illinois to pack a vacation itinerary. From venturing into Illinois State Parks for one outdoor adventure after another to navigating your way through the state’s rich tapestry of history and culture, we know you’ll love every second of your time in Illinois.

Outdoor Enthusiasts

It’s never been easier to get off the beaten path in Illinois than by visiting one of the many Illinois State Parks. Within the incredible network of parks, which includes the famous Starved Rock State Park, there are lush forests filled with hiking and biking trails. Add to that a vast network of rivers perfect for boating and paddling adventures, not to mention the rolling hills of Illinois’ Driftless Area, and it’s easy to see why nature enthusiasts love visiting this great state. 


The Shawnee National Forest alone has more than 400 miles of impressive hiking trails, not to mention the stunning Garden of the Gods. If water-laden adventures are more your thing, don’t miss a rafting trip on the Vermillion River or the stunning bayou-like natural paradise found on the Cache River in southern Illinois. Wherever you go, it’ll feel like you’re a world away from the hustle and bustle of downtown Chicago.

Illinois 1

Food & Drink

There are plenty of iconic foods in Illinois, many of which are associated with Chicago. Take the famed deep-dish pizza, Chicago dogs, or even cultural specialties like pierogies and Italian beef sandwiches. Food lovers could enjoy one feast after another in Chicago alone, but the love of food extends far beyond the Windy City. 


Where other Midwest states, particularly Wisconsin and Minnesota, have excelled in the craft beer scene, wineries in Illinois have flourished. Today, there are more than 150 wineries and tasting rooms around the state, with tourism driving more expansion to the industry as years go by. If you live by the slogan “Rosé All Day” in the summer, you’ll love getaways to Illinois, as Rosé is the official state wine.

Illinois 2

Arts & Culture

While many of Chicago’s leading arts venues are internationally recognized, including the famed Art Institute of Chicago and the city’s vibrant jazz & blues venues, there’s far more to Illinois’ arts & culture scene that is worth exploring. 

Head to central and southern Illinois and discover the Land of Lincoln. History comes alive in Springfield, home to more sites dedicated to the life and legacy of this famed American President than any other place in the country. Meanwhile, in charming Galena, get to know the life and legacy of another American President, Ulysses S. Grant.

Alternatively, enjoy a relaxing summer afternoon outdoors listening to modern-day Thesbians at the Illinois Shakespeare Festival in Bloomington or visit the ornate Robert Allerton Park in Monticello. 

Illinois 3

Best Time to Visit Illinois

Though you might think of summer as the best time to visit Illinois, the heat and humidity makes this season slightly less attractive than the cooler seasons of spring and fall. Spring can be cool still, but by fall, not only does the state transform under the vibrant colors of the season, but the weather stays relatively warm and markedly less humid, making it an ideal time to travel. 

Summer is also a much busier time of year to be in Illinois, particularly in Chicago, which means much larger crowds. However, despite the heat and humidity, summer also brings many vibrant festivals and fun. 

With heavy snows and plenty of winds, tourism drastically drops off in Illinois in the Winter. Even so, winter in Illinois offers the adventurous traveler plenty of perks, including fewer crowds, cheaper lodging, and still plenty of things to do in Illinois, both inside and out.

Illinois 4

Winter in Illinois

Illinois 5

Spring in Illinois

Illinois 6

Summer in Illinois

Illinois 7

Fall in Illinois

Top Destination Cities in Illinois

There’s no doubt that Chicago is one of the top cities to visit in Illinois. From the city’s vibrant arts & cultural scene and the scenic shores of Lake Michigan to the alluring shops and gourmet restaurants, there’s much to love about the Windy City. However, no trip to Illinois should include only a visit to Chicago, as there are many more great things to do and places to see around the state. We’ve highlighted three more great cities below, all worth adding to your itinerary.

Illinois 8

Galena

One visit to the historic downtown of Galena, Illinois, where most of the buildings are listed on the National Registry of Historic Places, is all it will take to fall in love with this small town. Surprisingly, though the population of Galena is just over 3,000 people, it’s the #2 most visited destination in Illinois. 

Here, you’ll find a historic Main Street lined with independently owned boutique shops, art galleries, restaurants, and historical attractions, not to mention a brewery and a couple of wineries. The Galena River flows through the heart of town and is suitable for paddling, or there’s hiking or biking along the neighboring Galena River Trail, too. 

Galena is situated in Illinois’ Driftless Region, meaning it’s characterized by rolling hills and beautiful valleys – a departure from the otherwise flat Midwest. With plenty of wine tasting, great restaurants, and natural scenic beauty, it’s the perfect place to enjoy a relaxing and romantic getaway with your special someone.

Illinois 9

Springfield

Springfield is not only the state capital of Illinois but also the birthplace of American President Abraham Lincoln. History lovers will admire attractions like the Abraham Lincoln Presidential Library & Museum, Lincoln’s Tomb, and the Lincoln Memorial Garden.

There’s also plenty in Springfield for lovers of the outdoors, including several fantastic golf courses, a variety of biking trails such as the Lost Bridge Trail, and so much more. And, of course, don’t forget to check out the exciting roadside attractions along this stretch of the famed Route 66.  

Illinois 10

Rockford

In northern Illinois is the city of Rockford, known as the city of gardens and rivers. It’s a fantastic place to spend a few days, particularly if you want outdoor adventure. Here, you’ll find the Forest Preserves of Winnebago County, known as one of the best park systems in the state. There are over 10,000 acres of rivers, lakes, and forests, all of which are ripe for outdoor adventures. Another great place to explore is Rock Cut State Park, which is perfect for boating and birdwatching. 

We can’t mention Rockford without mentioning the gorgeous gardens you’ll find here, including the Anderson Japanese Gardens, the Klehm Arboretum, and the Nicholas Conservatory & Gardens

Rockford is also home to some fascinating museums, including the Burpee Museum of Natural History, home to several fantastic dinosaur exhibits, and the Rockford Art Museum.

Best Places To Stay In Illinois

Like other great midwest destinations, Illinois is filled with one extraordinary adventure after another. Though there are plenty of great places to stay in Illinois, you’ll be best served by choosing a small and independently operated Bed and Breakfast in Illinois, like those found under the Midwest Association of Independent Inns. 

Throughout the state, you’ll find a unique array of Inns, cottages, cabins, historic mansions, and other unique lodging options, all of which share one thing in common: The same dedication to excellence in hospitality that you’ll find throughout the rest of our Midwest Association of Independent Inns. Our properties go far beyond offering a simple place to stay, so the next time you plan a trip to Illinois, don’t forget to book a room at a leading Bed and Breakfast in Illinois.

Illinois 11

Hotel Galena

Illinois 12

Hawk Valley Retreat & Cottages

Illinois 13

Cloran Mansion Bed & Breakfast

Illinois 14

Timmermann House Bed & Breakfast