Skip to content
  • Home
  • Blog
  • About
  • Contact
Instagram Pinterest TikTok
Hannah Willett Logo

Hannah Willett

traveling with a 9-5

  • Midwest Travel
  • DestinationsExpand
    • Europe
    • Asia
    • South America
    • North America
    • Africa
    • Oceania
  • Travel Itineraries
  • Tips & Guides
Hannah Willett Logo
Hannah Willett
traveling with a 9-5

The Ultimate Illinois Travel Guide

Illinois is famous for Chicago’s legendary architecture, world-class food scene, and lively neighborhoods. But don’t overlook the rest of the state—think small towns brimming with charm, quirky roadside stops, and scenic state parks ideal for a day away. This Illinois travel guide has everything from must-see attractions in the Windy City to lesser-known gems for travelers looking to go beyond the beaten path. Whether you’re exploring Lake Michigan’s shoreline or venturing into Southern Illinois, this guide offers a mix of travel stories and insider tips to make the most of your next adventure.

Illinois is Known For:

The Chicago Skyline and Architecture

Chicago is the birthplace of the skyscraper and home to some of the world’s most famous buildings, from the Willis Tower (formerly Sears Tower) to the cutting-edge designs of Aqua Tower and The St. Regis. Take an architecture boat tour on the Chicago River to see these stunners up close and hear the inside stories of the architects who shaped the metropolitan area.

Route 66: The Mother Road

Illinois is the starting point for Route 66, the legendary highway that runs from Chicago to Los Angeles. This nostalgic route is dotted with diners, classic motels, and vintage signs that transport you back to the glory days of the American road trip. Grab a photo at the “Begin Route 66” sign near Grant Park in Chicago before hitting iconic stops like Lou Mitchell’s diner.

Deep-Dish Pizza and Chicago Eats

You’ve heard about Chicago’s deep-dish pizza, and yes, it’s as delicious as it’s hyped up to be. But that’s not the only food Illinois has mastered. Try an Italian beef sandwich at Portillo’s or a Chicago-style hot dog (hold the ketchup!) at Gene & Jude’s. Don’t miss the city’s Michelin-starred spots either—Alinea and Girl & the Goat offer elevated, unforgettable dining experiences.

The History and Legacy of Abraham Lincoln

Illinois isn’t called the Land of Lincoln for nothing. For history buffs, the ultimate pilgrimage spot is Springfield, where you can walk in Lincoln’s footsteps at the Lincoln Home National Historic Site and explore the Abraham Lincoln Presidential Library and Museum. There’s a whole trail of Lincoln landmarks, so you can dive deep into this chapter of U.S. history.

Scenic State Parks and Hidden Nature Spots

Think Illinois is all flat farmland? Think again. With places like Starved Rock State Park and Matthiessen State Park offering waterfalls, cliffs, and incredible hiking trails, Illinois has no shortage of outdoor adventures. Further south, Shawnee National Forest is a little-known paradise, with unique rock formations and winding trails, plus the Instagram-famous Garden of the Gods.

Major Cities and Destinations

Chicago: The Heart of Illinois

Let’s be real—Chicago is the main event. Start with Millennium Park and snap a selfie at The Bean before heading over to Grant Park to see Buckingham Fountain and panoramic views of the Lake Michigan shoreline. For museum lovers, the Art Institute of Chicago and the Field Museum are must-sees, while sports fans will want to catch a game at historic Wrigley Field. Explore neighborhoods like Wicker Park for boutiques and coffee shops, Lincoln Park for family-friendly fun, and Pilsen for vibrant street art and tacos.

Springfield: Lincoln’s Hometown

Springfield is the place to go for all things Lincoln. Walk through Lincoln’s old neighborhood at the Lincoln Home National Historic Site, then visit his tomb at Oak Ridge Cemetery. The Abraham Lincoln Presidential Library and Museum brings history to life with immersive exhibits on his life and legacy. Don’t leave without trying a “horseshoe,” a local sandwich creation piled high with fries and cheese sauce.

Galena: The Perfect Weekend Getaway

Galena is a charming historic town near the Illinois-Iowa border, known for its 19th-century architecture, rolling hills, and scenic views of the Mississippi River. Wander down Main Street for antique shops, cozy cafes, and wine tasting rooms, or get active with kayaking on the river. In winter, Chestnut Mountain Resort offers skiing with a view, making Galena a year-round destination.

Rockford: Art, Gardens, and Small-Town Vibes

Just an hour from Chicago, Rockford has surprises around every corner. The Anderson Japanese Gardens are an oasis of zen, while Rock Cut State Park has hiking, fishing, and even horseback riding trails. Don’t miss Rockford Art Museum and quirky local spots like Rockford City Market for artisan goods and live music.

Evanston: Lakefront Views and College Town Charm

Located just north of Chicago, Evanston is home to Northwestern University and boasts a beautiful lakefront with sandy beaches, charming neighborhoods, and a walkable downtown. Take a stroll through the Shakespeare Garden, visit the Mitchell Museum of the American Indian, or have a picnic by Lighthouse Beach.

Top Attractions and Landmarks

The Art Institute of Chicago

One of the top museums in the world, the Art Institute of Chicago is a must-visit for art lovers. The museum’s collection spans centuries and continents from Monet’s Water Lilies to Grant Wood’s American Gothic. The modern wing, designed by architect Renzo Piano, adds a sleek touch to this Chicago classic.

Millennium Park and The Bean

Located in the heart of downtown Chicago, Millennium Park is known for Cloud Gate (aka “The Bean”), an enormous mirrored sculpture by artist Anish Kapoor. This park is also home to the Jay Pritzker Pavilion, an outdoor concert venue, and the Crown Fountain, where digital faces spout water, making it a favorite for kids in the summer.

Willis Tower Skydeck

Standing 1,353 feet above ground, the Willis Tower Skydeck offers unbeatable views of Chicago. Dare to step onto The Ledge, a glass box that extends out from the building, for a heart-pounding experience. On a clear day, you can see up to four states from the 103rd floor.

Starved Rock State Park

Located along the Illinois River near Utica, Starved Rock State Park is known for its sandstone canyons, waterfalls, and scenic hiking trails. It’s a favorite spot for Chicagoans looking to get out into nature and explore beautiful landscapes without venturing too far from the city.

Navy Pier

Navy Pier is the classic spot for family fun in Chicago, with carnival rides, restaurants, and the Chicago Children’s Museum. The Centennial Wheel offers great views of the city skyline and Lake Michigan. Navy Pier also hosts summer fireworks, festivals, and seasonal events, making it a year-round attraction.

Lincoln Park Zoo

Just north of downtown Chicago, Lincoln Park Zoo is one of the last free zoos in the U.S. Stroll through the grounds to see lions, gorillas, and other animals. The nearby Lincoln Park Conservatory is a peaceful greenhouse with tropical plants and a respite from the city’s hustle and bustle.

Cultural and Historical Sites

Cahokia Mounds State Historic Site

Cahokia Mounds in Collinsville is a UNESCO World Heritage Site and was once a major Native American city, with 120 mounds built by the Mississippian people. Visit Monks Mound, the largest prehistoric earthen structure in North America, and learn about the ancient culture that thrived here long before European settlers arrived.

Pullman National Monument

Located on the South Side of Chicago, Pullman National Monument preserves the history of America’s first planned industrial community. The monument includes historic buildings and exhibits about the Pullman Company’s role in labor rights and the evolution of the American railroad industry.

Route 66 Hall of Fame and Museum

Located in Pontiac, Illinois, the Route 66 Hall of Fame and Museum celebrates the history of the iconic “Mother Road.” The museum has vintage cars, memorabilia, and Route 66 artifacts. Don’t forget to stop by the huge Route 66 mural in Pontiac for a photo op!

Illinois Travel Tips

Best Time to Visit

Illinois offers something for every season. Spring (April-May) and fall (September-October) are great for city exploring and festivals, while summer is perfect for beach outings on Lake Michigan and state parks like Starved Rock. Winter in Chicago has its own charm with Christkindlmarket and ice skating in Millennium Park.

Getting Around

For Chicago, the Chicago Transit Authority (CTA) offers trains and buses that make getting around easy. A Ventra card covers both, and Google Maps can help with route planning. For travel to Springfield, Galena, or Illinois’s smaller towns, renting a car is the best option to enjoy the scenic roads and lesser-known spots.

Where to Stay

From luxury hotels in Chicago’s Magnificent Mile to historic inns in Galena and scenic vacation rentals near Starved Rock, Illinois has accommodations for every style. Book early for popular events like Chicago’s Lollapalooza.

Latest on the blog
  • Affordable girls trip destinations in the USA

    21 Affordable Girls Weekend Getaway Ideas the USA

    Girls’ trips don’t need to cost a fortune. Whether you’re celebrating a birthday, reuniting with your college crew, or just need a break…

    Read More 21 Affordable Girls Weekend Getaway Ideas the USAContinue

  • Palm Springs California

    9 Warm Places to Travel for Memorial Day (in the US)

    Memorial Day weekend (basically the unofficial start of summer in the US) is one of the best chances all year to take a…

    Read More 9 Warm Places to Travel for Memorial Day (in the US)Continue

  • The 12 Best Short Road Trips from Chicago (2025)

    The 12 Best Short Road Trips from Chicago (2025)

    If you’re itching for an escape from the Windy City but don’t want to spend all day in the car, you’re in luck….

    Read More The 12 Best Short Road Trips from Chicago (2025)Continue

  • Privacy Policy

© 2026 Hannah Willett

Scroll to top
  • Midwest Travel
  • Destinations
    • Europe
    • Asia
    • South America
    • North America
    • Africa
    • Oceania
  • Travel Itineraries
  • Tips & Guides
What are you looking for?
Search