Illinois Travel Guide

Planning a trip through the Midwestern USA? There’s no better place to start than Illinois. Bordered in the west by the Mississippi River, the “Prairie State” fuses both rural and big-city charms to deliver the quintessential Midwest experience.

Most visitors start (and end) their Illinois visit in Chicago, the biggest city in the Midwest and the third-largest in the USA. Famed for its world-class museums and superb architectural palette, the Windy City has plenty to explore. It’s truly one of the USA’s must-see destinations, whether you’re traveling from near or far.

When you’re done with the state’s largest city, spring over to Springfield, the capital of Illinois. Discover why Illinois’s secondary nickname is the “Land of Lincoln” with a visit to the city’s famed historical sites, including Lincoln’s former home and his burial site.

With Illinois’s two biggest cities out of the way, focus on the country’s most legendary road-trippin’ road: Route 66. Stretching from Chicago to Los Angeles, the famous route finds its first strides in Illinois. Fill up the tank and ramble along, keeping your eyes peeled for classic Americana, from wacky roadside attractions to retro diners to drive-in movie theaters.

Along the way, don’t forget to dig into Illinois’s more bucolic treasures. Explore Great Rivers Country, home to quaint riverside towns, wineries, craft breweries, and farm-to-table restaurants. Or venture around the state to frolic in beautiful parks like the Shawnee National Forest, Giant City State Park, and Pere Marquette State Park.

Ready to squeeze more into your itinerary? Plan the ultimate Midwest adventure with this quick & easy Illinois travel guide, including tips for where to go, what to do, and when to visit!

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Where to go in Illinois


One of the USA’s most iconic cities, Chicago is the perfect spot to launch your itinerary through Illinois. Located on the shores of Lake Michigan, The Windy City is famed for its historic architecture, world-class museums & galleries, and cultural scene.

Start exploring Chicago at Millennium Park, the city’s most notable green space. Located in the heart of The Loop, the 24.5-acre park is home to the world-famous “Bean” sculpture, reflecting the downtown skyline.

Chicago, IL

After admiring Millennium Park, get your culture fix at the nearby Art Institute of Chicago. The world-renowned art museum holds almost 300,000 works from national & international artists, spanning several centuries.

To catch the city’s stunning architecture from (way!) above, zip up to the Skydeck at Willis Tower or 360 Chicago on North Michigan Avenue. From either observation deck, you’ll peer down upon the city’s most iconic buildings, from the Wrigley Building to Tribune Tower.

When the day draws to a close, retire to trendy neighborhoods like West Loop or River North to experience Chicago’s food & drink scene, from Michelin-starred restaurants and casual eateries to hip cocktail bars and craft breweries.

Ready to plan your trip to Chicago? Get started with these travel resources…


Embarking on a classic Route 66 road trip? Prepare to roll into Springfield. Located about three hours from Chicago, Illinois’s capital city is a popular stop on the “Mother Road,” thanks to its classic American diners and roadside attractions.

Be sure to start your journey stuffing your Springfield itinerary with classic Route 66 stops like Route 66 Motorheads Bar, Grill & Museum, Cozy Dog Drive In, and Weeble’s Bar & Grill.

Aside from its road-tripping nostalgia, Springfield is famed as the home of Abraham Lincoln just prior to leaving for Washington, DC, as the newly-minted leader.

Springfield, IL

Save time to browse the Abraham Lincoln Presidential Library and Museum and the Lincoln Home National Historic Site. Learn about the life & legacy of the 16th US President before paying tribute at the Lincoln Tomb State Historic Site.

Architecture fans should also look out for Springfield’s iconic buildings. Admire the glorious Illinois State Capitol, featuring a spectacular glass dome soaring even higher than the US Capitol in DC. Or witness the early work of one of America’s most famous architects, Frank Lloyd Wright, in the heart of the city at the 35-room Dana-Thomas House.


Only 90 minutes northwest of Chicago, Rockford is the perfect base for exploring the heart of northern Illinois. Home to just shy of 150,000 people, the city is famed for its gardens and park, featuring over 4,000 hectares of green spaces.


Get your primer on Rockford’s green reputation at the stunning Anderson Japanese Gardens. Covering five hectares, it’s one of the finest Japanese-style gardens in the nation, teeming with ponds, waterfalls, and walking paths. Even bigger is the Klehm Arboretum & Botanic Garden, spreading out over 155 acres of landscaped green space.

After finding your bliss, ratchet up the adventure at one of Rockford’s many outdoor recreation hotspots. Pound the hiking trails at Rock Cut State Park, fly through the air on a zipline at Zip Rockford, or careen through the rapids in a kayak along the roaring Rock River.

Starved Rock State Park

If you’ve only got time for one outdoor adventure in Illinois, beeline for Starved Rock State Park.  Located on the Illinois River, just 93 miles from Chicago, this popular state park showcases everything from craggy cliffs and canyons to waterfalls and streams.

Starved Rock State Park

Strap on your hiking shoes to traipse along miles of hiking trails, winding through woodlands to viewpoints like Lover’s Leap Overlook, where you’ll enjoy beautiful views over Starved Rock Dam and the Illinois River.

For an extra special visit to Starved Rock State Park, extend your stay overnight in the on-site Starved Rock Lodge. Enjoy a romantic evening cuddled up by the fireplace and enjoying the lodge’s luxurious amenities, including a hot tub and an indoor pool.


Counter Chicago’s big-city vibes with the small-town charms of Galena. Located three hours from the Windy City, Galena is among the loveliest towns in Illinois, famed for its beautiful 19th-century buildings.


American history buffs should start their Galena trip at the Ulysses S. Grant Home. Built in 1858 in Italianate style, the mansion was once home to the Civil War general and, later, the 18th President of the United States. Take a tour of the historic home, admiring the original period furnishings, and learn more about the general’s legacy.

After soaking up Galena’s historic architecture, venture outside the city to experience its natural beauty. Catch a glimpse of three states from the top of the Horseshoe Mound Preserve or breathe in the breeze off the Mississippi River at the Casper Bluff Land & Water Reserve.

Other destinations in Illinois

  • Naperville
  • Peoria
  • Evanston
  • Cahokia Mounds State Park
  • Champaign
  • Matthiessen State Park

When to visit Illinois

The best time to visit Illinois is from April to May and from September to October. The spring and fall shoulder seasons offer a great combination of pleasant temperatures, sunny skies, and smaller crowds.

Spring Sunset

Summer is the peak tourist season in Illinois. Although temperatures are warm, the crowds tend to be larger and prices higher. The summer months are also among the most humid and rainiest, making it a less ideal time to travel than the shoulder seasons.

Winters in Illinois tend to be cold and cloudy, with daytime temperatures often in the single digits and nighttime temperatures often falling below zero. Warm weather travelers should avoid visiting Illinois at this time of year.

How to get to Illinois

By air

Illinois is home to 11 commercial airports, including four international airports. Most travelers arrive in Illinois by air via Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW).

Major airlines flying into ORD and MDW from domestic and international gateways include:

  • American Airlines
  • American Eagle
  • Delta Air Lines
  • Frontier Airlines
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
  • United Express

By road

Illinois is well-connected by road to the neighboring states of Iowa, Wisconsin, Indiana, Michigan, Kentucky, and Missouri. Popular road routes to/from Chicago and approximate driving times include:

  • Des Moines, IA (5h22m)
  • Milwaukee, WI (1h56m)
  • Indianapolis, IN (3h14m)
  • Detroit, MI (4h45m)
  • Louisville, KY (5h3m)
  • St Louis, MO (4h57m)

Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.