Chicago will always hold a special place in our hearts. Hi Love founder Melissa grew up in the nearby suburb of Glen Ellyn, and Chicago is where Hi Love first began and where she still calls home today. From its iconic architecture and vibrant neighborhoods to its incredible food scene, there’s so much to LOVE about the Windy City.

In this Chicago travel guide, we’re sharing some of our favorite things to do, places to see, restaurants to try, and hotels to call home during your stay. Whether it’s your first visit or you’re returning for another adventure, we hope our personal favorites inspire you to experience some of the magic that makes Chicago so special.

And now you can take a little piece of Chicago with you wherever you go. Our new Chicago Print Pouch celebrates the city Hi Love Travel calls home, featuring playful illustrations of some of our favorite Chicago landmarks and icons:

• O’Hare International Airport — One of Chicago’s two major airports and a gateway to the city.
• The Green Mill — A historic Uptown jazz club known for live music and its Prohibition-era past.
• Lincoln Park Zoo — A beloved, free zoo located in the heart of Lincoln Park.
• The Magnificent Mile — Chicago’s iconic stretch of Michigan Avenue, lined with shops, restaurants, and architectural gems.
• John Hancock Observatory — Now known as 360 CHICAGO, offering incredible views from one of the city’s most recognizable skyscrapers.
• Wrigley Field — The historic home of the Chicago Cubs and one of baseball’s most legendary ballparks.
• Navy Pier — A lively lakefront destination featuring rides, restaurants, entertainment and beautiful views.
• Lake Michigan — The sparkling waterfront that shapes Chicago’s skyline, beaches and way of life.
• The Chicago Riverwalk — A scenic waterfront path filled with restaurants, public art and unbeatable city views.
• United Center — Home of the Chicago Bulls and Chicago Blackhawks.
• The Loop — Chicago’s bustling downtown district, named for the elevated train tracks that encircle it.
• Field Museum — A world-renowned natural history museum and home to SUE, the famous T. Rex.
• Shedd Aquarium — A lakefront aquarium filled with marine life from around the world.
• Millennium Park — A favorite downtown gathering place and home to Cloud Gate, better known as “The Bean.”
• Willis Tower — An unmistakable Chicago skyscraper featuring the thrilling glass-floored Skydeck.
• Soldier Field — The historic lakefront stadium and home of the Chicago Bears.
• Museum of Science and Industry — An interactive museum filled with fascinating exhibits, inventions and hands-on discoveries.
• Grant Park — Often called “Chicago’s front yard” and home to the beautiful Buckingham Fountain.
• Art Institute of Chicago — One of the world’s great art museums, famously guarded by two bronze lions.
• Midway International Airport — Chicago’s second major airport, located on the city’s Southwest Side.

Whether you're visiting Chicago for a weekend getaway or you're a local planning a staycation, packing the right bags can make exploring the city even more enjoyable. We always recommend bringing a lightweight tote for traveling to and from the city; it easily doubles as a shopping bag for The Magnificent Mile, a farmers market stop, or even a gym bag if you're squeezing in a workout. Multi-functional zipper pouches help keep everything organized while traveling and transition effortlessly into a chic clutch for lunch or sightseeing. A versatile crossbody purse is perfect for dinners, rooftop cocktails, Broadway shows, or an evening stroll along the Chicago Riverwalk. And for daytime adventures, nothing beats a comfortable belt bag, backpack, or sling bag that keeps your essentials close as you explore museums, neighborhoods, parks, and miles of beautiful lakefront trails. The best travel bags are the ones that work just as hard as you do: lightweight, versatile, and ready for wherever the day takes you.

Whether you're planning your first Chicago weekend getaway or have loved the city for years, we hope this guide inspires you to explore its iconic landmarks, incredible restaurants, vibrant neighborhoods, and beautiful lakefront. To celebrate the city we proudly call home, we created our new Chicago Print Pouch, featuring hand-illustrated Chicago landmarks and icons. Perfect for organizing travel essentials, cosmetics, tech accessories, or everyday necessities, it's a functional keepsake and a unique Chicago souvenir that lets you carry a little piece of the city wherever your adventures take you. If you visit any of these favorite spots, tag @hilovetravel on Instagram—we'd love to see your Chicago adventures and your Hi Love favorites along the way.