15 Unforgettable Ways to Explore Chicago
Chicago stands tall as one of America’s most exciting cities, packed with amazing food, stunning architecture, and vibrant culture. The Windy City offers something for everyone, from towering skyscrapers to beautiful lakefront views. Ready to discover what makes this Midwestern gem so special? Here are 15 unforgettable Chicago experiences you simply can’t miss!
1. The Publican’s
Food lovers rejoice at this West Loop hotspot where rustic farmhouse meets modern culinary magic. The restaurant’s communal tables create an atmosphere that encourages sharing both food and conversation. Renowned for its pork-focused menu and impressive beer selection, dining here feels like joining a delicious celebration.
Many ingredients come from local farms, ensuring peak freshness and flavor. Between the honey-glazed pork chops and seafood towers, there’s something to satisfy every palate. Weekend brunch offers a more casual way to experience their culinary excellence without the evening crowds.
2. Gino’s East
Written on the walls by thousands of visitors, graffiti covers nearly every inch of this iconic pizzeria, creating a uniquely Chicago experience. The legendary deep dish here features a golden cornmeal crust that cradles layers of gooey cheese, chunky tomato sauce, and your choice of toppings.
Patience is essential – each pizza takes about 45 minutes to bake to perfection. Locals recommend ordering immediately upon arrival to minimize the wait. Founded in 1966 by two taxi drivers and their friend, this pizza institution has become a mandatory pilgrimage for food enthusiasts visiting the Windy City.
3. The Violet Hour
Behind an unmarked door in Wicker Park lies a sanctuary dedicated to the craft of cocktail making. Velvet curtains, high-backed chairs, and chandeliers create an atmosphere of Prohibition-era elegance and mystery. Mixologists work with scientific precision, hand-chipping ice and carefully measuring house-made bitters and infusions.
Their menu changes seasonally, ensuring fresh ingredients and innovative combinations year-round. Strict house rules (no cell phones, no standing at the bar) might seem fussy at first, but they preserve the intimate atmosphere that makes this speakeasy special. Arriving early helps avoid the typical wait times that form outside the hidden entrance.
4. Chicago Skydeck
Suspended 1,353 feet above the city streets, glass boxes extend outward from Willis Tower (formerly Sears Tower), offering heart-stopping views of Chicago’s urban landscape. Brave souls can step into these transparent ledges, creating the illusion of floating above the city with nothing but clear glass beneath their feet.
Morning visits typically offer the clearest views and smallest crowds. On exceptionally clear days, visitors can see four states – Illinois, Indiana, Wisconsin, and Michigan. Professional photographers are available to capture your daring moment, though personal cameras are also permitted. The elevator ride alone impresses, climbing 103 floors in approximately 60 seconds.
5. Green Mill Jazz Club
Stepping through the doors of this Uptown landmark transports visitors straight back to the 1920s. Founded in 1907, this jazz club retains its original Art Deco interior and once served as Al Capone’s favorite hangout – his preferred booth still remains. World-class musicians perform nightly on the small stage, creating an intimate experience unmatched in the city.
The cocktails follow classic recipes, perfectly complementing the vintage atmosphere. Poetry slams on Sundays showcase Chicago’s vibrant literary scene. Arriving early guarantees better seating, as this cash-only establishment fills quickly, especially on weekends when the line often stretches down Broadway.
6. Millennium Park
Cloud Gate (affectionately nicknamed “The Bean”) steals most of the attention with its mirror-like surface reflecting the skyline, but this downtown park offers much more to explore. Summer evenings come alive with free concerts at the Frank Gehry-designed Jay Pritzker Pavilion, where world-class performances unfold beneath a stunning steel trellis.
Children splash gleefully in Crown Fountain, where massive digital faces projected on glass towers playfully spout water. Winter transforms the park with ice skating and holiday lights. Lurie Garden provides a peaceful retreat amidst the urban landscape, featuring native plants that change dramatically with the seasons. The park connects directly to the Art Institute via a striking pedestrian bridge.
7. Revolution Brewing
Massive metal fists clutching grain and hops mark the entrance to Chicago’s largest independent brewery. Inside the Logan Square taproom, wooden barrels and exposed brick create an industrial-chic atmosphere where locals gather to sample innovative brews. Free brewery tours reveal the fascinating process behind their creations, from their flagship Anti-Hero IPA to seasonal specialties.
The gastropub menu elevates typical bar food with locally-sourced ingredients and beer-infused recipes. Wednesday night trivia attracts competitive crowds, while special release parties celebrate new beer launches throughout the year. Their beer garden provides a perfect summer hangout spot, though it fills quickly on weekends.
8. Slippery Slope
Neon lights bathe this Logan Square hotspot in a rosy glow, creating the perfect backdrop for late-night dancing and friendly competition. The basement level houses vintage Skee-Ball machines that bring out everyone’s playful side, with winners often buying rounds for their friends. Famous for their Tamale Guy appearances (a beloved Chicago tradition where a vendor sells homemade tamales from a cooler), this dive bar attracts an eclectic mix of locals and visitors.
Their signature shot, the Pickleback, pairs whiskey with pickle juice for a surprisingly delicious combination. DJs spin everything from hip-hop to house music as the night progresses, turning the dance floor into a sweaty, joyful celebration of Chicago nightlife.
9. Mr. Beef on Orleans
Grainy photos of celebrity visitors line the walls of this tiny, no-frills sandwich shop that inspired the hit TV show “The Bear.” Since 1979, this River North institution has served Chicago’s most authentic Italian beef sandwiches – thinly sliced roast beef soaked in savory jus, piled on Italian bread.
Regulars know the ordering lingo: “dry” (less juice), “wet” (extra juice), or “dipped” (bread completely soaked). Add hot or sweet peppers for extra flavor. Lines often form during lunch rush, but the wait moves quickly as efficient staff maintain the rapid-fire pace. Cash only policies and limited seating emphasize that this place prioritizes food quality over frills.
10. John Hancock Observatory
Cocktails taste better 1,000 feet above Chicago at 360 CHICAGO (formerly John Hancock Observatory). Unlike other observation decks, this one features a full bar where visitors can sip drinks while watching the sun set over the city grid. Adrenaline seekers gravitate toward TILT – a moving platform that angles visitors outward at 30 degrees over Michigan Avenue.
Interactive touchscreens throughout the space highlight city landmarks and provide historical context. Many locals consider these views superior to Willis Tower, particularly for showcasing the lakefront. Visiting during twilight offers the magical transition from daylight to the city’s twinkling nightscape, with fewer crowds than peak afternoon hours.
11. The Wieners Circle
Char-grilled hot dogs and cheese fries satisfy late-night cravings at this Lincoln Park institution, but the real draw is the unique customer service experience. Staff and patrons engage in playful, sometimes profane banter that has become legendary throughout Chicago. After midnight on weekends, the tiny hot dog stand transforms into performance art as inebriated customers from nearby bars match wits with the quick-tongued staff.
The Chicago-style hot dog comes dragged through the garden – topped with mustard, relish, onion, tomato, pickle, sport peppers, and celery salt (never ketchup). First-timers should observe the interactions before participating in the verbal sparring tradition. Despite the rowdy atmosphere, the food quality remains consistently excellent.
12. Oak Street Beach
Sunbathers sprawl on golden sand with skyscrapers towering directly behind them, creating one of Chicago’s most striking visual contrasts. Located at the northern end of Michigan Avenue, this urban beach offers a surprising escape from city life without leaving downtown. Beach volleyball courts host competitive leagues throughout summer, while the paved lakefront trail accommodates joggers, cyclists, and rollerbladers.
A seasonal beachside café serves refreshing drinks and light meals with unbeatable views. Morning visits offer peaceful Lake Michigan vistas before crowds arrive. The beach provides a perfect cooling break between shopping excursions on the Magnificent Mile, with rental chairs and umbrellas available during peak season.
13. Billy Goat Tavern
Newspaper clippings and vintage photos cover nearly every wall surface in this underground institution, chronicling its fascinating history since 1934. Made famous by the Saturday Night Live “Cheezborger” sketch, servers still playfully bark “No Pepsi, Coke!” at customers in homage to the classic comedy routine. Located beneath Michigan Avenue, this tavern played a crucial role in Chicago journalism history as the favorite watering hole for newspaper reporters.
The infamous “Cubs Curse” originated here when owner William Sianis and his pet goat were ejected from Wrigley Field. Simple double cheeseburgers on kaiser rolls remain the signature dish, best enjoyed with a cold beer at the well-worn bar counter where countless Chicago stories have unfolded.
14. Harry Caray
Memorabilia from Chicago’s beloved sports announcer fills this River North steakhouse, creating a museum-like atmosphere celebrating baseball history. Caray’s trademark oversized glasses hang prominently near the entrance, welcoming sports fans and food lovers alike. Prime aged steaks and classic Italian dishes attract diners seeking both nostalgia and culinary excellence.
The bar area buzzes during Cubs games, with fans gathering to honor Caray’s legacy. Famous for its collection of cursed artifacts, the restaurant displays the infamous Bartman ball that was ceremoniously destroyed to help break the Cubs’ championship drought. Reservations are recommended, especially during baseball season and on weekends when wait times can stretch beyond an hour.
15. Navy Pier
Extending nearly a mile into Lake Michigan, this historic pier has transformed from a military facility into Chicago’s most visited attraction. The centerpiece Centennial Wheel offers climate-controlled gondolas that rise 196 feet, providing spectacular views regardless of weather. Boat tours departing from the pier provide architectural commentary and fireworks cruises during summer evenings.
Crystal Gardens, a one-acre indoor botanical park, offers a tropical retreat even during Chicago’s notorious winters. Family-friendly attractions include a Chicago Children’s Museum and an IMAX theater. While some locals consider it touristy, the pier’s beautiful lakefront location and variety of activities make it worth exploring, especially during weekday mornings when crowds are thinner.
