Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Take in the Stunning Views from Willis Tower Skydeck

No trip to Chicago is complete without a visit to Willis Tower and its Skydeck for breathtaking views of the Windy City. At 1,450 feet, Willis Tower remains the second tallest building in the U.S. after One World Trade Center. The tower was originally called Sears Tower when completed in 1973 since it was built for Sears. In 2009, London-based Willis Group Holdings purchased the naming rights.

Once the world's tallest building, Willis Tower boasts Skydeck on the 103rd floor where visitors can step out onto glass boxes called The Ledge that extend 4.3 feet outside the skyscraper's steel frame and look straight down 1,353 feet. Talk about vertigo! Even visitors not daring enough to venture onto The Ledge can take in stunning 360 degree views of Chicago, Lake Michigan, and four different states on a clear day. Skydeck's digital screens identify Chicago landmarks easily.

Arrive early, ideally when Skydeck opens at 9am, for thinner crowds. Purchase tickets online in advance since they can sell out. Expect airport-level security screening. The lines move fast though. Bring identification; security will check it. Once at the top, take time to observe minute details only discernible from such heights - the shadows cast by skyscrapers, the tiny sailboats dotting the lake, and the miniature cars crawling along highways.

Peer down at Chicagoans and tourists appearing like ants on sidewalks from such grand heights. Spot the patios of downtown eateries and imagine indulging on the al fresco cuisine. Glimpse the city's many green spaces. Pick out the encircling blue water of Lake Michigan. And don't forget the mesmerizing skyline itself with iconic buildings like John Hancock Center, Trump Tower, and Tribune Tower in clear view. The height makes Chicago appear boundless.
On hazy days, the views disappear into an opaque blur. But even clouds enveloping the skydeck can prove interesting to watch. Be sure to stop by both the north and south sides since the vantage points differ slightly. Take lots of photos but maintain a firm grip on cameras and cellphones so nothing accidentally falls over the edge! Selfie sticks are banned. Visitors can step onto The Ledge for photos of feet floating in mid-air with breathtaking backdrops. It makes for fun social media posts!

What else is in this post?

1. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Take in the Stunning Views from Willis Tower Skydeck
2. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Explore The Art Institute of Chicago
3. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Catch a Cubs Game at Wrigley Field
4. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Stroll Along the Magnificent Mile for Shopping
5. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Take an Architecture River Cruise on the Chicago River
6. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Chow Down on Deep Dish Pizza at Lou Malnati's or Gino's East
7. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - See Comedy and Improv Shows at Second City
8. Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Experience Blues and Jazz at Green Mill Cocktail Lounge

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Explore The Art Institute of Chicago

No Chicago visit feels complete without a pilgrimage to the Windy City’s immense trove of art - the Art Institute of Chicago. It ranks as one of America’s oldest and largest art museums as well as one of the best. Many flock to admire iconic paintings like Grant Wood’s American Gothic and Edward Hopper’s Nighthawks. However, the museum’s permanent collection spans 5,000 years of creativity from cultures worldwide. You can easily spend hours, if not days, wandering its two buildings packed with captivating works.
The Art Institute first opened in 1879, just a couple years after the devastating Great Chicago Fire. Originally part of the city’s world exposition, it eventually transitioned into a fine arts museum. The current structure dates from 1893 for the world’s Columbian Exposition. Its neoclassical design boasts an elegant Beaux-Arts facade. The interior dazzles with skylights and vaulted galleries. The Modern Wing addition opened in 2009, increasing the museum’s footprint by a third.
Don’t rush your visit. Allow ample time to soak in its diverse displays spanning Impressionist, Post-Impressionist, American, Old Master, Modern, Contemporary, Asian, African, Islamic, and Native American art. Some must-sees include Hopper’s hauntingly lonely Nighthawks painting of late night cafe patrons and the pointillist beauty of Seurat’s A Sunday on La Grande Jatte capturing Parisians lounging alongside the river Seine on a lazy afternoon.

Of course, snap the iconic American Gothic couple with their dour expressions, stoic stances, and pitchfork. Georges Seurat’s Bathers at Asnieres depicting a sunlit riverbank scene brims with Impressionist beauty. Stand rapt by Van Gogh self-portraits as well as his amber-hued Cafe Terrace at Night. Pop Art highlights include Warhol’s campy take on Marilyn Monroe along with Lichtenstein’s war-themed Whaam! with its explosive onomatopoeia.
Beyond the most recognized works, take time to admire lesser known gems. Marvel at the Thorne Miniature Rooms intricately showcasing European and American decor through the centuries. Photographers flock to natural light illuminating the airy Modern Wing. Foodies relish the museum’s upscale Terzo Piano restaurant overlooking Millennium Park. The Museum Shop tempts with artistic souvenirs.
Visit the Art Institute website before you go to discover current special exhibits plus events like artist talks and film screenings. Sign up for free daily gallery tours. The Movies at the Museum program spotlights art-related cinema on Thursday evenings. And don’t miss the museum’s special late Thursdays when it stays open until 8 pm. Download the free app as your guide for extra exhibit details and wayfinding assistance.

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Catch a Cubs Game at Wrigley Field

No trip to the Windy City is complete without catching a Cubs game at the iconic Wrigley Field. Baseball fans relish the opportunity to visit the cherished “Friendly Confines” and cheer on Chicago’s beloved Cubbies. Even non-sports fans can appreciate the ballpark's old-school ambiance and lively atmosphere.

Wrigley Field first hosted the Cubs back in 1916 and stands as the National League's second oldest ballpark behind Boston’s Fenway Park. Located in the bustling Lakeview neighborhood, the ivy-adorned brick and steel stadium oozes classic charm. Visitors eagerly pose with the iconic red Wrigley Field marquee sign out front on Clark and Addison Streets.

Inside, the ballpark dazzles with its old-timey manually operated scoreboard dating from 1937. No flashy video screens or obnoxious sound effects here. Instead Wrigley oozes nostalgia with organ music and fans tracking every pitch and play on the vintage scoreboard. The hand-turned numbers thrill traditionalists.

Another trademark is the outfield walls smothered in ivy planted back in 1937. Balls disappearing into the vines become automatic ground rule doubles. When the ivy turns red in fall, it makes a picturesque backdrop for batting practice. The cozy retro-chic ballpark only seats 41,000 fans, making it one of baseball’s most intimate. Seats line the outfield wall so daring fans sit mere feet from action.

Visitors insist the Wrigley experience offers an engaging blend of people-watching, sport, and community. Expect a diverse crowd united by Cub fandom. Superfans arrive dressed in blue and white jerseys with “W” flags and foam finger hands. The energized atmosphere simply begs participation in traditions like singing “Take Me Out to the Ballgame” midway through the 7th inning stretch.

For the best experience, score bleacher seats to join the most boisterous fans. But any spot lets you glimpse ivy walls and the iconic red scoreboard. If attending a day game on a sunny afternoon, don’t forget the sunscreen! Night games allow cooler conditions but sacrifice Wrigley’s cherished sun-soaked glow.

Timing is key for an optimal visit. Peak season runs May to September. Prices spike for big matchups against rivals like the St. Louis Cardinals. For affordable tickets, target weekday games in April or September when kids are back in school.

Insider tips: arrive early to wander the stadium, catch batting practice, and admire nostalgic touches like vintage signage. Savor stadium eats like Chicago hot dogs, nachos, and local Goose Island brews. Pose by the Harry Caray statue commemorating the legendary Hall of Fame broadcaster. And stop by the Cubs’ History Museum to trace the team’s colorful past.

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Stroll Along the Magnificent Mile for Shopping

No Windy City visit feels complete without some retail therapy along the Magnificent Mile. This bustling stretch of Michigan Avenue dazzles visitors with seemingly endless shopping opportunities through 13 blocks from the Chicago River to Oak Street.

The Magnificent Mile lays claim to 460 retailers representing luxury names to more affordable national chains. Shoppers can meander for miles while slipping into elegant emporiums and brand name flagships. Or grab some fresh air while ducking in and out of the mix of high-end giants, smaller indie boutiques, and national retailers.

Chicago’s climate means the Mag Mile transforms with the seasons. Spring welcomes back sidewalk cafes perfect for people watching amid blooming planters. Summer months lure travelers seeking air conditioned respite inside expansive department stores. Window shopping feels more inviting on balmy evenings with the street aglow from the city’s vibrant lights.
Once autumn hits, trees lining the Magnificent Mile display leaves shifting to warm shades of amber, orange and burgundy. Holiday atmosphere arrives each winter when twinkling lights get strung across streets and frosted wreaths adorn gleaming storefronts.

For savvy travelers seeking deals, late summer promises plenty of sales during back-to-school season. And winter lures bargain hunters searching clearance racks after Christmas. But any time of year, patient shoppers can discover steals at chains like Gap or Forever 21. Deep-pocketed spenders often gravitate toward the Mile’s luxury giants.

Big names include Apple, Burberry, Cartier, Gucci, Hermès, Louis Vuitton, MaxMara, Rolex, Tiffany & Co., and more. Visit their Magnificent Mile flagships for the ultimate brand experience. Inside sprawls multiple levels and departments amid upscale, gallery-esque settings. Though make no mistake - their elite price points cater to the affluent set, not discount denizens.

Beyond the bold-faced designers, Chicago-based department store mainstays like Macy’s enthuse shoppers with their epic multi-floor emporiums. Those needing some retail fuel can unwind with a snack at the mall-like food courts of Water Tower Place and Chicago Place. Or sit down for a full lunch or dinner at scenic eateries like The Cape Cod Room.

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Take an Architecture River Cruise on the Chicago River

Gliding along the Chicago River surface offers a glorious perspective of the Windy City’s storied architecture. River cruises provide an engaging orientation to downtown and the magnificent building diversity lining the riverside. Your guide will enlighten passengers about the signature structures defining Chicago's iconic skyline as you gently cruise past.
Luxury skyscrapers, elegant bridges, vintage warehouses and remnants of the city’s past unfold as you admire creative feats of engineering and design over the centuries. Cruises typically last around an hour and many options exist. You could opt for a daytime tour, a twilight cruise or specialty architecture-themed outing.

Leisurely tours by boat reveal charming angles of the city’s treasures otherwise impossible to experience on land. Cruising at tranquil paces lets you truly admire the towering landmarks. With enlightening audio commentary from your guide, Chicago’s architectural treasures tell their tales as you float by.

Gaze up at acclaimed modern marvels like the curving corncob shape of Marina City with its dual 61-story towers or the John Hancock Center tapered black frame soaring 1,128 feet. Identify Chicago’s early architectural roots in the charming red brick Monadnock Building, once the tallest structure in the Loop when built in 1891.

Your guide will regale you with the backstories behind the iconic Tribune Tower and Wrigley Building lined with Gothic details along the river. Learn to recognize the Chicago windows dotting structures, shaped like a huge center pane flanked by narrow slits for light. Spot engraved faces and other ornamental detailing carved into facades from prior eras. Wave to the Trump Tower’s riverside Jenga-like apartments with balconies stacked askew.
Cruising at night enhances city views, with illuminated buildings glowing against darkened skies. Some twilight cruises synchronize with creative light displays projected onto certain buildings. Structures may erupt in radiant colors, patterns or images timed with lively music.

During holiday seasons, cruising the glittery riverfront at night reveals festively adorned architecture. The Wrigley Building gleams wrapped in oversized ribbons and bows each Christmas. Riverside towers sprout evergreen garlands bedecked in lights several stories tall. And some seasonal cruises incorporate hot cocoa, cookies and carolers to amplify that festive spirit.

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Chow Down on Deep Dish Pizza at Lou Malnati's or Gino's East

Chicago lays proud claim as the birthplace of deep dish pizza, so sampling the Windy City’s signature pie proves essential. Lou Malnati’s and Gino’s East stand as local legends renowned for serving up the city’s sauciest, cheesiest, and most mouthwatering deep dish.

The flaky crusts manage to stay crispy despite their heaping, inch-thick toppings. The chunky tomato sauce simmers hours for maximum rich taste. And the bountiful cheese pulls stringy, gooey strands with each drippy bite. Just come hungry and ready to get messy!

Lou Malnati’s icon status owes gratitude to its founding father, Louis Malnati, known for perfecting Chicago-style deep dish techniques in 1940s city pizzerias. His son eventually launched the family’s seminal restaurant bearing the Malnati name in 1971. Today, the chain has over 50 Chicagoland locations staying true to the original family recipe.
The signature Lou Malnati’s deep dish experience means choosing between two tribulations: patience for carryout if opting to devour back at your hotel or long lines if dining in. Some tourists take out pizzas for hotel room feasts. But the heavenly aromas torment taste buds during the drive. Plus you miss out on admiring the from-scratch kitchen’s handiwork as they assemble pies, building up edge-to-edge fillings atop oozy cheese bedding the flaky, buttery crust.
Inside bustling Lou Malnati’s restaurants, the delectable pies fresh from the oven simply necessitate that first ooey, gooey cheese pull for the ‘gram. Beyond their signature deep dish, diners praise Lou’s for thin crust and menu additions like Chicken Vesuvio entrée, Chicago-style Italian beef sandwiches, and Italian sausage soup swimming with pasta.
Equally beloved, Gino’s East opened its first pizzeria location back in 1966 and also stakes claim as a deep dish trailblazer. While Lou Malnati's serves up a more buttery crust, Gino's East is known for a slightly crisper cornmeal-dusted exterior that some locals favor. Gino’s boasts its secret spice blend sprinkled atop each pie for an extra aromatic flavor boost.

Their flaky deep dish crusts get naturally “caramelized” to a golden hue from the cast iron pizza pans used. Gino’s charmingly graffitied interior walls encourage creative doodling while awaiting your meal. When your pie arrives, dive into stringy mozzarella giving way to rich marinara at the base.
Beyond their famous deep dish, Gino’s also lures Chicagoans craving cracker-thin crust pizza, char-grilled burgers, and Italian classics like chicken parmesan and spaghetti Bolognese. Streamline the takeout process by placing online orders in advance for carryout or delivery.

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - See Comedy and Improv Shows at Second City

What better place to laugh until it hurts than comedy’s ancestral home, Chicago’s legendary Second City? Comedy connoisseurs know this trailblazing troupe launched comedic icons from Alan Arkin to Tina Fey. Visiting Second City allows experiencing the theater where Chicago-style improv all started.

Since 1959, Second City has nurtured raw talent into ‘SNL’ stars, sitcom legends, and Oscar winners through its immersive improv training. Seeing a show in their intimate, historic Old Town theater offers encountering comedy at its source. Countless quotable sketches first ignited here before going viral nationwide.

Expect an ever-changing lineup with the theater’s next breakout talents. Rotating casts stage new original revues every few months. Scene stealers regularly get cherrypicked for SNL and sitcom fame. Writers generate fresh material drawing from Chicago’s buzzing current events and newsmakers.

Performers exude infectious energy and quick wit. With only a suggestion from the audience, they rapidly create scenes and characters. Laugh lines land with pinpoint precision. Running gags and inside jokes reward regulars. Even shows late into a revue’s run still feel fresh thanks to improvised riffing.

Travelers craving comedy while in Chicago can choose among Mainstage shows or more intimate options like cabarets in The Second City E.T.C. space. This smaller venue allows enjoying improv with a drink in hand at your café table seat. Acts often welcome audience members onstage for impromptu participation in sketches - always a rip-roaring good time.
Second City’s alumni pedigree means visitors may catch rising talents right before their big break. Reviewers of recent shows excitedly predict cast members who seem destined for imminent fame. Devoted alumni also remain devoted fans, often spotted chuckling in the audience at their alma mater theater.
Beyond live shows, comedy fans can also take Second City’s backstage tours. These upbeat walking tours make stops on the historic mainstage while guides share insider anecdotes. You can even snap that iconic mainstage photo of you mugging by the vintage brick backdrop.

Additional highlights include handling props and costumes to appreciate Second City's hands-on production. Guides reveal inside stories of how legendary sketches came together but often departed wildly from their scripts. You may recognize revived costumes and sets from vintage SCTV footage. Comedy history buffs savor this behind-the-scenes access.
Classes allow fully immersing yourself in the Second City experience. Aspiring comedians can sign up for improv workshops and intensives to unlock their humor potential. Second City coaches put new students through classic theater games to build improv muscles. Sign up for stand-up comedy classes to polish punchlines and delivery with guidance tailored to each participant's strengths.

Windy City Wonders: The Ultimate Chicago Travel Guide for Food, Fun, and Accommodations - Experience Blues and Jazz at Green Mill Cocktail Lounge

No trip to Chicago feels complete without reveling in some blues or jazz at Green Mill Cocktail Lounge, a Windy City cultural institution. The historic Uptown lounge has served as an iconic Chicago jazz nexus since opening its doors in 1907, hosting legends from Al Capone to Billie Holiday. Today, Green Mill nurtures Chicago's vibrant jazz scene by spotlighting both legends and emerging talents seven nights a week.

Stepping inside Green Mill feels like a jazzy time warp thanks to the vintage venue's lovingly preserved retro décor and ritzy vibe. With antique lamps throwing a moody glow across its dark wood panels, tufted leather banquettes, intimate candlelit tables, and long oak bar, the lounge transports guests back to the 1920s heyday of Prohibition-era Chicago nightlife.

The lively crowds dress to impress, further enhancing the speakeasy ambience. Hip urbanites, nostalgic older couples, and curious tourists mingle and sway shoulder-to-shoulder in the packed, narrow space. A multi-generational roster of jazz enthusiasts unites each weekend to drink in the sensational sounds.
Late night owls relish Green Mill's headliners heating up the intimate stage with improvised sax solos, finger-flying piano numbers, and soulful vocals floating through smoky air. Patrons feel the music's raw energy pulsing through the cozy, dark booths and barstools. Locals chat knowingly of upcoming acts destined for acclaim while tapping toes to sultry rhythms.
Beyond jazz bands, Green Mill hosts intimate events like the nationally acclaimed poetry slam on Sunday nights as well as Friday night sets from local blues musicians. Guitar greats get the crowd on their feet while powerfully unleashing bluesy riffs and growled vocals.

Rather than kitschy tourist-trap reproductions, Green Mill's bookings offer the real thing — passionate artists devoted to their craft. Jazz buffs find the curation and audio quality as enlightening as any great museum or theater performance.

While embracing its spirited past, Green Mill also keeps ages-old traditions alive. Patrons still enter under the iconic glowing green neon cocktail sign first erected in the 1930s. Waiters serve drinks from the same mahogany bar Capone once bellied up to for a stiff cocktail. And the vintage wall mural advertising "Music & Entertainment Nightly" still sets the scene.