Go Big in Chicago: History, Home Runs, and Hot Slices
- SAMPLE ITINERARY
- 5 days ago
- 4 min read
Updated: 4 days ago
Big-shouldered and big-hearted, Chicago is one of America’s truest cities. It’s a place where food is a point of pride, sports are a shared language, and history spills out onto sidewalks, ballparks, and neighborhood bars. Built by immigrants and fueled by ambition, Chicago is also where historic Route 66 officially begins—pointing west and setting the tone for the American road trip.
The itinerary below leans into the Chicago that locals love most. It’s an authentic mix of iconic and everyday, polished and gritty—proof that one of America’s greatest cities still knows how to surprise you. Come hungry. Come curious.
Classic Chicago Activities
Here are just a few ways to soak up the character of this epic city. Think of these as Chicago's Greatest Hits—icons, classics, and a few crowd favorites. 😉
Take a Private Food Tour
Book a private food tour and you’ll quickly learn this city does way more than deep dish (though yes, that will absolutely make an appearance).
Chicago offers a wide range of customizable, guide-led food tours that dig into the city’s Italian-American roots, hopping between iconic pizzerias and old-school red-sauce joints while sharing the neighborhood stories behind every slice. It’s part history lesson, part walking feast, and proof that Chicago’s food scene runs deep—and cheesy.
Catch a Game at Wrigley Field
Even non-baseball fans feel it here. Catching a game at Wrigley Field is less about the score and more about the ritual: ivy-covered walls, neighborhood rooftops, seventh-inning singalongs, and generations of loyalty packed into one historic park. If the Cubs aren’t in town, a guided ballpark tour still delivers that unmistakable Chicago baseball energy.
Chicago baseball lore: Before TV, some say lunch breaks and workday routines shifted so fans could catch afternoon games—because when baseball called, Chicago answered.
Get to Know Gangsters, Ghosts & Chicago Legends
Chicago doesn’t just tell its history—it dramatizes it. The city offers a wide range of guided walking tours that dive deep into its Prohibition-era underworld that shaped Chicago’s larger-than-life reputation.
Most tours explore the Loop and River North, led by expert storytellers who know how to balance hard facts, colorful characters, and just enough grit to keep the past feeling thrillingly alive.
Wander Through The Art Institute of Chicago
You can’t come to Chicago without stepping into Art Institute of Chicago. Home to everything from American Gothic to Monet’s water lilies, it’s one of the most important art museums in the world—and proudly Midwestern at heart.
The modern wing alone is worth the visit, but the real magic is how the museum blends global masterpieces with a strong sense of American identity.
Where To Stay
From iconic landmarks to design-forward standouts, these stays place you at the center of the city's energy.
The Drake Hotel (Iconic)
Sitting regally on Michigan Avenue since 1920, The Drake Hotel is pure old-school glamour. Think sweeping lake views, legendary afternoon tea, and a guest list that once included everyone from Hollywood stars to world leaders.
Staying here feels like stepping into Chicago’s grand past—without sacrificing modern comfort.
The Robey (Distinctly Chicago)
For something cooler, edgier, and very now, check into The Robey in Wicker Park.
Housed in a landmark Art Deco building, this boutique hotel blends industrial design with neighborhood soul. Bonus points for the rooftop views and the feeling that you’re living like a local—just with better sheets and cocktails.
The St. Regis Chicago (Designer Luxe)
Rising along the Chicago River, this architectural showstopper pairs jaw-dropping skyline views with refined rooms, an indulgent spa, and sophisticated dining just steps from the city’s cultural core.
It’s a polished contrast to Chicago’s historic hotels—perfect for travelers who like their deep dish with a side of design.
Must-Eat Restaurants
Chicago is a true food town. These are just a few of the spots locals love to recommend and visitors should experience at least once.
Lou Mitchell’s
A true Chicago classic and longtime gateway to the city, Lou Mitchell’s has been fueling locals since 1923. It’s famous for hearty, old-school breakfasts—omelets the size of your plate, thick-cut bacon, and house-made pastries.
This is the kind of place where history, hospitality, and comfort food collide.
Au Cheval
Yes, the wait can be long. Yes, it’s worth it.
Famous for its no-frills, ultra-decadent burger (add the egg), Au Cheval is a rite of passage for food lovers.
It’s classic Chicago dining energy—unpretentious, indulgent, and obsessed with doing one thing exceptionally well.
The Purple Pig
Mediterranean-inspired, nose-to-tail, and wildly popular for good reason, The Purple Pig turns shared plates into a full-blown experience.
It’s a favorite among locals for celebratory meals, long lunches, and introducing visitors to Chicago’s more playful, chef-driven side.
This sample itinerary is just one way to experience Chicago, and we’ve got plenty more — tailored to your budget, travel style, and sense of adventure. Whenever you’re ready, we’ll help you build the Chicago Statescation that fits you perfectly.
Ready to Design Your Very Own Statescation?
We’ve got the ideas and the hookups. Reach out to see what we can build together.
