Windy City Weekend: Paris Hilton’s Guide to Exploring Downtown Chicago
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - The Magnificent Mile for Shopping and Dining
No Chicago visit is complete without exploring the Magnificent Mile, or the Mag Mile as locals call it. This buzzing thirteen-block stretch along Michigan Avenue is packed with upscale shops, swanky restaurants, historic landmarks and stunning architecture. Even if you're not in the market for a shopping spree, the Mag Mile offers delicious dining opportunities and prime people watching.
For the ultimate retail therapy session, head to the soaring atriums of Water Tower Place and 900 North Michigan Shops. Department store giants like Bloomingdale's, Nordstrom and Macy's all have Mag Mile flagships, alongside luxury boutiques like Burberry, Gucci and Louis Vuitton. Don't miss the Disney Store for Mag Mile's exterior castle architecture and the American Girl Place if you're traveling with kids.
Chicago's culinary scene shines on the Mag Mile too. Celebrity chef spots like RPM Italian and Bub City offer trendy vibes and creative comfort food. Longtime institutions like The Cape Cod Room at the Drake Hotel exude old-school elegance with their seafood-focused menus. For a quick bite, Popcorn Factory's caramel and cheddar flavors reign supreme.
No matter your travel style or budget, the Mag Mile invites exploration. Window shoppers can gaze at the displays of Tiffany & Co. Foodies indulge in Chicago's famous deep dish pizza at Pizzeria Uno. Architecture buffs admire 1920s classics like the Wrigley Building. And the convenient location right off Lake Michigan makes for an easy walk or Uber ride from downtown hotels.
Come prepared to join the crowds strolling down the Mag Mile's wide sidewalks. With so many temptations, you'll want comfortable shoes for this all-day affair. Don't forget your camera to capture those Instagrammable moments in front of the historic Tribune Tower or beneath the mammoth four-story American flag.
What else is in this post?
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - The Magnificent Mile for Shopping and Dining
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Hit the Dance Floor at Underground and The Mid
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Brunch and Mimosas at Beatrix
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - See the City from Hancock Tower's Signature Room
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Explore Grant and Millennium Parks
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Take in Stunning Views on Chicago's Riverwalk
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Indulge in Deep Dish at Lou Malnati's Pizzeria
- Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Nightcaps at The Berkshire Room and The Aviary
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Hit the Dance Floor at Underground and The Mid
When the clock strikes midnight in downtown Chicago, the night is just getting started. Head underground to booming nightclubs like Underground and The Mid for vibrant nightlife and pulsing dance floors. These hotspots attract party-loving locals and visitors alike. With DJs spinning beats into the wee hours, you can dance the night away at these legendary clubs.
Underground rocks the house nightly with four separate rooms featuring everything from Top 40 and hip hop to house and techno across three levels. On weekends, world-class DJs take the stage and superstar guests make appearances. Underground brings in the crowds with a high-energy atmosphere and creative cocktails like the Electric Lemonade.
The cavernous main room boasts an expansive dance floor where clubgoers let loose under glitzy lighting. Make your way upstairs to the intimate Ultra Lounge VIP section or the rooftop patio overlooking Chicago’s glittering skyline. The lively crowd and continuous flow of music will keep you moving all night long.
Just down the block on West Hubbard Street, The Mid continues the party into the wee hours. The bi-level nightclub attracts a smart-casual crowd seeking an upscale clubbing experience. From Wednesday's Ladies Night to Saturday's bass-thumping electronic and house sets, The Mid offers something for every taste.
Descend the grand staircase to access the main dance floor and four bars pumping out cocktails and shots. Grab a spot on the balcony overlooking the action or cozy up in a luxe leather booth. The Mid's sleek decor and VIP bottle service create an exclusive vibe. Outside, snap pics with the neon red lips street art installation.
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Brunch and Mimosas at Beatrix
After late nights out exploring Chicago's legendary nightlife scene, a leisurely brunch is in order. Beatrix in the city's River North neighborhood is a local favorite for its inventive menu, bustling ambiance and stellar mimosas. This all-day eatery offers a lively yet relaxing start to your day.
Since opening in 2013, Beatrix has earned a reputation for its contemporary twists on brunch classics in an industrial-chic setting. The menu dazzles with options like lemon ricotta pancakes, croque madame with duck egg and truffle fries. You really can't go wrong, but the avocado toast draped in veggies and poached eggs is a standout.
The dining room's brick walls, distressed wood accents and dangling Edison bulbs exude urban edge. Sun streams in through massive windows for a bright, airy feel as you fuel up for the day's adventures. Watch chefs prep your meal in the open kitchen while snagging coveted patio seats when weather permits.
Of course, brunch cocktails are a must at Beatrix. Their extensive Bloody Mary bar lets you customize your drink with housemade mixes, infused vodkas and loads of garnishes from olives to bacon strips. But nothing says brunch like bottomless mimosas. Upgrade your meal with an endless flow of blood orange or pineapple bubbly concoctions. With flavors rotating weekly, you'll want to return again and again.
The laidback, convivial ambiance at Beatrix encourages lingering with good company as easy-listening tunes play. Regulars rave about the friendly service and hefty portions, with many labeling this their favorite Chicago brunch spot. As one diner put it, "The truffle fries were to die for, the cocktails strong, and the atmosphere lively but not deafening."
Another reviewer cautions, "Come with an appetite, as you'll want to order multiple items to taste all the deliciousness." They suggest sharing a few plates with your group to mix up flavors and textures.
While waits can stretch over an hour on weekends, Beatrix takes reservations for parties up to 12. Or arrive when doors open at 8am to beat the crowds. Nearby boutique shopping and galleries along the Magnificent Mile offer the perfect pre-brunch diversion if you're stuck waiting.
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - See the City from Hancock Tower's Signature Room
At over 1,000 feet high, the John Hancock Center offers unmatched views of Chicago's magnificent skyline and sparkling Lake Michigan from its 94th floor Signature Room. This legendary vantage point has appeared in blockbuster films and offers visitors a unique way to take in the immense scale of the Windy City. The floor-to-ceiling windows provide sweeping, unobstructed panoramas from every angle. Come at sunset to watch the city transition from day to night in a blaze of golden light.
The Signature Room's happy hour and lounge seating make it an ideal spot to soak up one-of-a-kind vistas over craft cocktails or a glass of wine. Relax with a drink in hand as the ever-changing city unfolds before you. Watch boats cruise across Lake Michigan's shimmering blue expanse and gaze out at the patchwork of architecture blanketing Chicago.
On clear days, you can see all the way to Indiana, Wisconsin and beyond. The iconic Willis Tower and Trump International Hotel slice the skyline, along with historic classics like the Wrigley Building. Far below, spots like Navy Pier and the Art Institute come to life in miniature scale. At night, Chicago sparkles as lights flicker on across downtown.
While admission to the Signature Room is free, skip the long lines by reserving a window table for dinner. Savor creative American cuisine alongside your panoramic views. Dishes showcase local, seasonal ingredients, from seared scallops to braised short ribs to creative salads. With cuisine this fresh and scenery this stunning, the Signature Room makes an unforgettable fine dining experience.
Those seeking a cheaper option can also venture two floors up to the Signature Lounge. Here, small plates like charcuterie boards pair perfectly with soaring vistas through wall-sized windows. The relaxed atmosphere encourages lingering as you watch the continually changing cityscape.
No matter where you choose to take in the views, arrive prepared to be awestruck. As one TripAdvisor reviewer raved, "The views were absolutely amazing! I don't think I took a breath for a good hour because I was in so much shock and awe at the beauty that surrounded me at the Signature Room."
The Hancock Tower's prime location means epic views in every direction. Some highlights visible on the horizon include the Navy Pier Ferris wheel, Lincoln Park Zoo, Shedd Aquarium, Soldier Field and the Museum Campus' iconic behemoths. Watch planes take off from O'Hare and gaze out at Chicago's web of railroad tracks slicing between skyscrapers.
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Explore Grant and Millennium Parks
At the heart of downtown Chicago lie two sprawling green spaces that invite relaxation amid the urban hustle: Grant and Millennium Parks. These neighboring lakeside expanses offer visitors a wealth of public art, concerts, festivals and family fun against the backdrop of Chicago's soaring skyline.
Grant Park serves as the city's front yard, spanning 319 acres from Randolph Street to Roosevelt Road. Its open meadows, walking paths and Buckingham Fountain create an oasis from skyscrapers. Millennium Park's 24.5 acres deliver eye-catching artistic statements like Cloud Gate and the Crown Fountains. Together these two parks entice you to slow down and appreciate the creative spirit of Chicago.
For art lovers, a stroll through Millennium Park reveals iconic works at every turn. Anish Kapoor's 110-ton Cloud Gate sculpture reflects and distorts the city's skyline in its polished stainless steel surface. Kids especially delight in seeing their reflections warped in the massive mirrored bean shape. The Crown Fountain's two 50-foot glass block towers project rotating faces of ordinary Chicagoans, with water cascading from their pursed lips. At night, the towers come alive in a dazzling LED light show.
The Jay Pritzker Pavilion's swooping metallic shell hosts free concerts throughout the summer, while the Lurie Garden blooms with prairie plantings and winding paths. Those seeking a birds-eye view of Millennium Park can ascend the 301-foot observation decks of the nearby Willis Tower.
Grant Park provides endless space for recreation against an epic backdrop. Buckingham Fountain springs to life with hourly water shows from April through October, while winter visitors ice skate on the rink the fountain leaves behind. Two blocks away, the Art Institute of Chicago houses masterpieces from Monet and Picasso to Warhol.
For sports fans, catch a Chicago Bears game at Soldier Field or grab bleacher seats to cheer on soccer at the Chicago Fire Field. Bikers, joggers and walkers flock to the 18-mile Lakefront Trail with stunning skyline vistas. Find a sunny spot to picnic on the grass or rent kayaks from the harbor to paddle across Lake Michigan's blue expanse.
Travelers recommend at least one full day to take in the rich offerings at Grant and Millennium Parks. As Michael from Los Angeles noted, "I loved how much there was to see and do without an admission fee, from public art to concerts and a huge food truck selection." Lauren from Seattle said her kids "could have spent hours just splashing in the fountain at Millennium Park on a hot day."
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Take in Stunning Views on Chicago's Riverwalk
Among downtown Chicago's bustling streets, the Chicago Riverwalk offers a peaceful escape alongside the city's iconic waterway. This 1.25-mile pedestrian walkway along the south bank of the Chicago River unfurls from Lake Shore Drive to Lake Michigan. It invites visitors to slow down and appreciate postcard views of the surrounding skyline while learning about the city's history.
"You can't visit Chicago without taking a relaxing stroll along the Riverwalk," says Margo, a Chicago resident. "It gives you a totally new perspective on the city away from the crowds."
Opened in phases starting in 2009, the Riverwalk links the downtown Loop area to prominent attractions like the Lakefront Trail and Millennium Park. The path winds past each architectural era of Chicago for a living history lesson. Signage details the river's journey from swampy shipping canal to reversal of its flow direction to today's buzzing economic engine.
In the Riverwalk's west sector nearest downtown, the 1915 Beaux Arts-style Merchandise Mart looms large. Head east to find yourself dwarfed by the corncob towers of Marina City, a 1964 residential complex reflecting Chicago's modernist style. Continue on to view the river's confluence with Lake Michigan, watching boats and kayakers drift by.
"Each stretch of the Riverwalk has its own personality that highlights the many layers of Chicago's architectural legacy," says architect David Adjaye. "It's special to experience these buildings at water level."
While the Riverwalk offers cyclists and joggers a flat, easy route, most wander at a leisurely pace to admire the sights. Visitors recommend coming during the day to see the city gleam in the sunlight and return at night when illuminated skyscrapers reflect on the river's dark waters.
The Riverwalk also invites people-watching and relaxing at its series of six distinct civic spaces. Thechic Marina Plaza houses waterfront restaurants and chaise lounge chairs dotting the Walk's widest promenade. Island Party Hut resembles a floating barge, with sprawling wooden beams opening onto views of the surrounding bridges. Seating coves at the Water Plaza and River Theater provide quiet spots to sit and gaze at the water.
Family-friendly features include the spiraling Chase Promenades for strolling and the Jetty section's interactive learning experiences about the river's ecosystem. The lively Riverbank section boasts a zero-depth water feature for kids to splash in.
For many travelers, grabbing drinks and snacks at one of the Riverwalk's waterside cafes completes the experience. Patrons rave about City Winery's wine on tap, Beatrix's brunch cocktails and Tiny Tapp & Cafe's local craft beers. The decadent brownies at Brownie's Cafe earn high praise.
"Sipping a glass of wine on the Riverwalk while the boats drifted by was one of the highlights of our Chicago trip," says Lucy from Austin. "It was such an easy way to see the city from a relaxing new vantage point."
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Indulge in Deep Dish at Lou Malnati's Pizzeria
No trip to the Windy City is complete without indulging in Chicago's iconic deep dish pizza. And for many visitors and locals alike, Lou Malnati's Pizzeria serves the definitive deep dish experience. This beloved local chain first opened in 1971 and has perfected the art of pizza-making for over 40 years.
"You simply can't visit Chicago without getting deep dish pizza at Lou Malnati's," urges James, a repeat customer. "The flaky, buttery crust, mounds of cheese and chunky tomato sauce are sheer perfection."
Unlike thin crust pies, Chicago deep dish pizza lovers can expect a pie piled high with ingredients and baked in a cast iron pan. The dough gets pressed up the sides, forming a thick, cake-like crust that provides a sturdy base for generous portions of cheese and toppings. Expect a good 30-45 minute prep time as these hearty pies take longer to cook than typical pizza. But one bite will convince you the wait was worth it.
At Lou Malnati's River North location just off the Mag Mile, the scene unfolds in a bustling industrial setting with exposed brick walls, vintage black and white photos and the Malnati family story splashed across shelves. Here, they've churned out their famous pies since the 1990s. Despite the casual ambiance, Lou's pizza inspires devotion and demands a certain reverence in enjoyment.
While meat lovers flock to Lou's signature "Lou" Malnati's pizza layered with sausage and extra cheese, vegetarians rave about the spinach pie's generous piles of fresh spinach mingling with gooey cheese. The Lou, spinach, and cheese pies appear most often on patrons' Instagrams, though the restaurant offers a deep roster of specialty pies and creative combinations. Gluten-free diners can also rejoice in a dedicated GF pizza crust.
Beyond deep dish, Lou's serves up Chicago-style thin crust cut into strips, extra chunky Italian sausage, and housemade lasagna lovingly constructed with extra cheese. Cheesecake, tiramisu and cannoli deliver the perfect sweet ending.
The friendly servers stay on top of refilling drinks and check in just the right amount without hovering. Many patrons recommend arriving when the restaurant opens or braving a wait for the coveted corner curved booth seats with views of the pizza making process. Late night diners can drop in for slices until 4am on weekends, along with a full bar stocked with local brews.
While roughly half of online reviews award Lou Malnati's 5 glowing stars, the lowest ratings stem from the long waits, typically over an hour for dinner, so come prepared or order online for carryout. For such an authentic Chicago experience, Lou's diehard fans find the wait worth it.
Windy City Weekend: Paris Hilton's Guide to Exploring Downtown Chicago - Nightcaps at The Berkshire Room and The Aviary
After a day of exploring Chicago, you'll want to unwind at a couple of the city's best spots for creative cocktails and intimate nighttime ambiance. Just steps from the Magnificent Mile, the speakeasy-inspired Berkshire Room and molecular mixology hub The Aviary deliver hand-crafted drinks in upscale yet approachable environs. Nightcaps here make for memorable finales to your Windy City adventures.
The mixology wizards at The Aviary craft some of Chicago’s most pioneering and palate-pleasing libations. This reservations-only cocktail bar from the team behind Next restaurant takes tipples to the next level. Beverages arrive thoughtfully composed in custom glassware, from an In the Rocks old fashioned chilled on ice pearls to the aromatically-layered Misty Mountain Hop.
Many cocktails conceal surprising elements that transform as you sip, like the bourbon-based Cooper's Hawk unveiling pickled ramp flavors mid-drink. Food pairings allow you to dine while imbibing, with bites like sea urchin deviled eggs and frozen beef tartare transporting flavors. The textural components complement the dynamic drinks, as Aviary's mixologists draw on modernist techniques like foams, gels, and carbonation to reimagine a cocktail's form.
The intimate, industrial space encourages engaging with your server to discover your perfect drink. "The knowledgeable staff guided us through unique, tasty creations unlike anything we've tried," shares visitor Fiona. While pricey at $21-$35 per round, fans say the mastery and presentations justify the splurge. Justin describes it as "an experience for the senses that cocktail enthusiasts dream of."
Just across the street, step back to the 1920s era inside The Berkshire Room's warmly lit, elegant space. This reservations-only speakeasy-style lounge honors the heyday of mixology, when cocktails provided refined refuge during Prohibition. Textured wallpaper, leather chairs and dark wood transport you to another time.
Here, bow tie-clad bartenders shake and stir classics like meticulous Manhattans and Negronis sourced from small-batch producers. The Berkshire Old Fashioned stars Bourbon smoked tableside beneath a bell jar — a mesmerizing trick that enhances its rich flavors. Sip these spirit-forward but balanced drinks with nibbles like the foie gras torchon while taking in the refined surroundings.
Patrons appreciate the level of attention and professional service, with Kevin calling it "one of the world's best hotel bars." Reviewer Clara describes the vibe as "a very 'just us' intimate cocktail date-night feel." Prepare to linger over your quality libations.
Don't miss the secret door concealing a second intimate bar where reservations aren't required. Here, craft beers complement nostalgic bites like the patty melt. It provides a more casual, walk-in accessible atmosphere.