Windy City Whirlwind: A Local’s Top Tips for Making the Most of Your Chicago Trip
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Take in the Skyline from Hancock Observatory
No trip to the Windy City is complete without heading up to the Hancock Observatory for a breathtaking 360-degree view of Chicago's magnificent skyline. Situated on the 94th floor of the John Hancock Center, the observatory offers floor-to-ceiling windows looking out over the city, the lakefront, and four neighboring states on a clear day.
Gaze down at the tiny yellow taxis zigzagging along Michigan Avenue, get a bird's eye perspective of Navy Pier jutting out into Lake Michigan, and spot landmarks like the Willis Tower, Wrigley Field, and Lincoln Park Zoo from up above. The views are particularly stunning at night when the city lights up. Try to time your visit for sunset when you can watch the city transition from day to night.
The observatory has free telescopes you can use to zoom in even closer. Take advantage of the Sky Tour experience, which guides you through the sights using pre-recorded commentary available in seven languages. For kids, there are scavenger hunts and interactive exhibits like building a skyscraper. On weekends, you may catch a live jazz band playing by the windows.
Beyond the views, there are fun photo ops like the ledge where you can step out and look straight down 1,000 feet. The observatory just underwent a major renovation in 2020 to enhance the visitor experience. New features include the open-air 360 CHICAGO outdoor deck and TILT attraction that uses floor-to-ceiling glass to literally tilt visitors out 30 degrees over the city.
What else is in this post?
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Take in the Skyline from Hancock Observatory
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Indulge in Deep Dish Pizza at Lou Malnati's
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Explore 'The Bean' in Millennium Park
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Marvel at Art Institute of Chicago's Collection
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Stroll Along the Lakefront Trail
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Catch a Show at Second City Comedy Club
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Bar Hop in Wrigleyville Neighborhood
- Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Savor Italian Beef Sandwiches at Al's Beef
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Indulge in Deep Dish Pizza at Lou Malnati's
No visit to Chicago is complete without digging into the city's famous deep dish pizza, and there's no better place to experience it than Lou Malnati's Pizzeria. This beloved local chain has been serving up hearty, mouth-watering deep dish since 1971. With over 50 locations scattered throughout Chicagoland, you're never far from a Lou's. But for the quintessential experience, head to one of their Chicago restaurants like the original Lincolnwood location, which still has the Malnati family's original ovens.
What makes Lou's so special is their buttery, flakey crust. It has a unique texture that's crispy on the edges yet soft and doughy on the inside. Unlike a thin crust pizza, a Lou's deep dish pie has crust that comes up the sides of the pan to form a bowl that can hold generous helpings of cheese and chunky tomato sauce. They layer mozzarella, cheddar, parmesan, and romano cheeses to make that signature gooey goodness Chicago-style pizza is famous for. Toppings like sausage, pepperoni, mushrooms, onions, and green peppers are liberally applied.
The key to deep dish is patience and restraint. These pies take 45 minutes to bake - much longer than a typical pizza. The prolonged cooking allows the crust to fry to a golden brown in the pan while the toppings get thoroughly melted and caramelized. Resist the urge to dig in immediately once the pizza arrives steaming hot on your table. Let it cool for a few minutes to allow the molten ingredients to settle. Trust me, your first bite will be so much more enjoyable without burning the roof of your mouth!
When you do take that first bite, prepare for the flavors to explode. The melding of the crunch crust, sweet tomato sauce, gooey cheese, and savory toppings is an experience every pizza lover deserves. The balance between the buttery crust and bold toppings makes this hearty pizza impossible to have just one slice of.
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Explore 'The Bean' in Millennium Park
Of all the attractions in the vast green expanse of Millennium Park, none is more iconic than Cloud Gate, affectionately known as “The Bean.” This gleaming 110-ton elliptical sculpture is an Instagrammer’s dream and a must-see for first-time visitors and returning Chicagoans alike. British artist Anish Kapoor designed the polished stainless steel sculpture to resemble a giant mirrored bean. The smooth surface beautifully reflects and distorts the Chicago skyline and clouds drifting overhead.
Approaching The Bean is an experience in itself as the sculpture changes shape and perspective. One second it looks convex, the next concave, playing tricks on the eyes. Walk around the perimeter of the sculpture and discover unique views. Stand directly under the 12-foot arch to catch a fishbowl view of the skyline upside down. Pose for fun house mirror selfies where body parts look improbably stretched and squashed.
The most popular photo op is facing The Bean head-on to capture the dead center perfect mirror reflection. Lines can get long midday but are more manageable early morning and at night when the lighting is ideal anyways. Some savvy photographers come prepared with selfie sticks or even selfie drones to get both themselves and the sculpture in one epic shot.
While you’ll inevitably spend time rubbernecking and snapping photos, don’t forget to walk through the interior chamber underneath the sculpture. The seamless shape overhead gives the impression of being inside a monolithic egg. The chamber’s acoustics produce a subtle echo effect, amplifying the chatter of other visitors exploring the space with you.
Beyond its artistic merits and photographic appeal, part of what makes The Bean so special is its accessibility. The sculpture is centered within Millennium Park, an open public space with no admission fees. Visitors are encouraged to touch the sculpture and interact with it. Kids can burn off energy running circles around it. It's also wheelchair accessible via a gently sloped ramp.
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Marvel at Art Institute of Chicago's Collection
Housed inside an iconic Beaux-Arts building perched along Chicago's Lake Michigan shoreline, the Art Institute of Chicago contains one of the nation's premier art collections. Wandering the Institute's sprawling galleries, you'll encounter iconic masterpieces from around the world spanning 5,000 years.
Art lovers flock here to glimpse Grant Wood's American Gothic, Edward Hopper's Nighthawks, and Georges Seurat's pointillist A Sunday Afternoon on the Island of La Grande Jatte. Yet what makes the Institute truly special is the breadth and quality of its holdings. The diverse collection comprises over 300,000 works spanning impressionism, postmodernism, textiles, photography, and much more.
Beyond just paintings, the galleries contain sculpture, architectural models, coins, drawings, prints, and decorative arts. Must-see highlights include the Thorne Miniature Room dioramas portraying European and American dwellings through the centuries in intricate detail. Don't miss Chagall's vibrant America Windows stained glass and the Arms and Armor hall with its Game of Thrones-esque displays.
While the Institute could take days to fully explore, even stopping into just a few galleries will overwhelm your senses. In the Modern Wing, venture through the airy, light-filled space showcasing 20th century greats like Matisse, Rothko, Pollock, and Warhol. The Rubloff Paperweight Collection dazzles with rainbow-hued glass paperweights crafted by master artists.
The expansive Impressionist collection transports you to Monet's garden at Giverny and the gritty bar scenes of Degas and Toulouse-Lautrec. Stand rapt for hours before the pointillist marvels of Seurat and Signac's luminous canvases. Don't miss the special exhibitions either like the Obama portraits or recent Frida Kahlo show.
Beyond the art itself, appreciate the Institute's stately neoclassical building. The original structure opened as the World's Fair in 1893 before becoming the museum's permanent home. Gaze up at the expansive skylights and intricate ironwork. Burn off some energy climbing the Grand Staircase immortalized in Ferris Bueller's Day Off. Fuel up at the onsite Terzo Piano restaurant overlooking Millennium Park.
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Stroll Along the Lakefront Trail
Chicago's magnificent lakefront is one of the city's crown jewels, and there's no better way to experience it than by taking a leisurely stroll along the Lakefront Trail. Running for 18 miles along the shores of Lake Michigan, this paved path offers spectacular views of the skyline while connecting beachfront parks and gardens.
On a sunny day, you'll find the trail bustling with runners, cyclists, rollerbladers, and pedestrians soaking up the sunshine and fresh lakeside air. The further north you venture, the thinner the crowds get until it's just you, the lake, and the calls of circling seabirds.
One memorable section is North Avenue Beach with its iconic rainbow pylon sculpture framing photo-worthy views of downtown. Kids can splash in the shallow water or play in the interactive funhouse fountain. Nearby, Fullerton Beach offers volleyball courts and kayak rentals for paddling along the shoreline.
Meander south to take in the beauty of Oak Street Beach's waving white prairie grasses and the historic Ohio Street Beach with its vintage bathhouse. Further along, olive green and terracotta hues mark the Milton Lee Olive Park, named for a local Medal of Honor recipient.
For an only-in-Chicago experience, check out the quirky collection of sculptures and monuments along the trail like the wiggly Crown Fountain with its twin 50-foot glass brick towers depicting spitting faces. Kids love interacting with the photorealistic visages.
Near Buckingham Fountain, artfully arranged flower beds burst with vivid blooms in the expansive Grant Park. Linger to watch the spectacular water display with its dancing streams and light show. Heading south, you'll notice more and more sailboats speckling the harbor until you reach the Museum Campus.
The Adler Planetarium's glittering granite dome catches the sun while seabirds wheel over the debris of shipwrecked ships at the Museum of Science and Industry's Underwater Archaeology site. Stay alert and you might even spot Ambrose the sea lion gliding through the waters offshore.
After taking in the sights, pop into one of the trailside ice cream shops and enjoy your cold treat al fresco on the Lakefront Trail picnic rocks. On a peaceful morning, grab a coffee and pause on one of the benches facing east across the glassy water to take in a radiant sunrise.
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Catch a Show at Second City Comedy Club
Among Chicago's myriad cultural attractions, few experiences encapsulate the city's vibrant arts scene better than catching an improv show at the legendary Second City Comedy Club. Situated in the bustling Old Town neighborhood, Second City has been honing the talents of up-and-coming comedians since 1959. The intimate, 200-seat onsite theater exudes a palpable energy even before the curtain rises.
When the lights dim, get ready to let loose and laugh yourself silly at the quick-witted cast's hilarious, unscripted skits. The performers riff off audience suggestions, weave in local references, and spoof timely topics ranging from politics to dating faux pas. You never know where the scenes will go, which is half the fun. The talented cast thinks on their feet, and no two shows are ever quite the same.
Beyond the performing antics, it's fascinating to realize you're watching tomorrow's comedy superstars in the making. The Second City stage has launched the careers of legends like Bill Murray, Stephen Colbert, Tina Fey, Keegan-Michael Key, and countless cast members from Saturday Night Live. In fact, you might catch an occasional celeb alum making a surprise guest appearance, which always brings down the house.
Before or after the show, check out historic photos lining the theater lobby illustrating Second City's star-studded history. Peruse the gift shop to pick up an "I *Heart* Chicago" shirt or witty mug to remember the laughs. Don't forget to snap the iconic Second City marquee and pose under the Old Town sign nearby.
Beyond the mainstage shows, Second City offers specialty performances like family-friendly matinees and late-night uncensored sets. Aspiring comedians can even take beginner improv classes and workshops to hone their craft. With new original shows every few months featuring fresh faces, it's worth catching a Second City performance on repeat Chicago visits. You're guaranteed new jokes and a memorable evening out.
Even locals who have seen dozens of shows return again and again and enthusiastically attest Second City is an absolute must-do. The atmosphere can't be beat, with audiences uniting around finding humor in shared everyday experiences. Laughter fills every corner of the intimate space.
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Bar Hop in Wrigleyville Neighborhood
Nestled in the shadows of historic Wrigley Field, Chicago's Wrigleyville neighborhood is a rollicking district packed with sports bars, lively pubs, and plenty of Cubby blue. Baseball pilgrims flock here on game days to join in the infectious energy buzzing through the streets and cheers echoing from the Friendly Confines. Yet you needn't wait for a home game to have an unforgettable bar-hopping experience in Wrigleyville. This always-happening neighborhood boasts one of the best bar scenes in the city.
The classic way to tap into the local vibe is by popping into Murphy's Bleachers, the iconic sports bar steps from Wrigley Field's bleachers entrance. The exterior is splashed in eye-catching Cubbie murals, while inside you'll find memorabilia plastered across every inch of wall space. Order the "Monster Basket" loaded with cheese fries and chicken tenders to fuel up for a long night ahead. Other longtime favorites near the ballpark include The Cubby Bear with its tucked-away beer garden and Sports Corner Grill for people-watching patios.
Venture down Clark Street to explore laidback neighborhood pubs packed with regulars cheering on the Cubs. Old Crow Smokehouse knocks barbecue classics and bourbon cocktails out of the park, with cubbies lining the walls stocked with over 200 whiskeys. Acre reproduces a cozy European beer hall vibe with long communal tables made for making new friends.
For beer lovers, make a pilgrimage to local favorite Hopleaf Bar. Their encyclopedic beer menustacked with Belgian ales, craft IPAs, and obscure brews could occupy you for an entire evening. Snack on their Montreal-style smoked meats, pretzels, and snacks to balance the high ABVs.
If dancing is more your speed, checkout the legendary Smart Bar known for bringing underground house and techno DJs spinning eclectic beats into the wee hours. This dark, intimate space has been the epicenter of Chicago's dance music scene for over three decades.
Crawl between lively bars clustered along Clark and Sheffield Avenues. Tributary blends tiki cocktails with live reggae and DJs. Lodge Tavern's hunter lodge decor and local crowd will make you feel like a regular. Tourist magnets like Moe's Tavern transport you to Springfield with painstaking Simpsons-themed decor. You may stumble upon roving musicians crooning Sinatra or impromptu dance parties spilling onto the sidewalks.
Windy City Whirlwind: A Local's Top Tips for Making the Most of Your Chicago Trip - Savor Italian Beef Sandwiches at Al's Beef
No visit to Chicago is complete without sampling the humble Italian beef sandwich, and there's no better place to indulge than the renowned Al's Beef in Little Italy. This unassuming spot has been serving authentic, mouthwatering Italian beef drenched in spicy giardiniera since 1938, cementing itself as a Windy City institution. Once you bite into one of these messy masterpieces, you'll instantly understand why Al's Beef proudly calls itself the "World's Greatest Italian Beef Sandwich."
While upscale versions of the Italian beef have become trendy across Chicago's restaurant scene, nothing compares to scarfing down the real deal at Al's standing shoulder to shoulder with locals at the cafeteria-style counter. Opt for the juicy Original Beef sandwich loaded with sliced beef steeped in seasoned gravy, or go all out for the king-sized Big Beef layered with even more succulent meat.
Either way, the thin-sliced, tender beef bursts with savory flavor, deliciously moist yet just shy of falling apart. Peppers provide a satisfying crunch and kick of heat to punctuate each bite. For the brave, request your sandwich "dipped" for the full experience. This entails plunging the entire sandwich into the rich gravy to achieve the ultimate level of hot, dripping, beefy goodness. Go slow and steady to keep the wonderfully messy amalgam of ingredients from disintegrating in your hands.
Beyond the iconic beef, Al's menu features Italian pork and sausage sandwiches plus sides like meatball sandwiches and crispy fries or hash browns. Wash it all down with an icy cold soda, or opt for a Goose Island if you prefer an adult beverage. Expect long lines snaking down the block at peak lunch and dinner hours. But the wait is well worth it.
The communal dining setup inside fosters an electric, dimly lit atmosphere where regulars chat shop and lively Italian wafts through the air. Once you snag your towering sandwich, pull up a seat at one of the Formica tables. Digging into that first mouthwatering bite, you'll instantly taste why generations of Chicagoans and tourists alike have made the pilgrimage to Al's Beef.
Beyond the original Little Italy location, Al's has expanded to a handful of other spots around town in recent years. But for the true old-school experience, settle in among the faded murals depicting Roman scenes at the Taylor Street flagship store. Your taste buds will thank you. Even finicky eaters and picky kids gobble up Al's sandwiches, once they get past the prospect of "soggy" bread. Sink your teeth in, and you'll discover the artistry in the perfectly orchestrated interplay of textures and flavors.