Sweet Home, Chicago

In April 2022, Do by Melissa HowsamLeave a Comment

Share this Post

Plan your next getaway Chicago-style. 

Either you love Chicago, or you’re wrong. As a Raleighite who once transplanted there for two years, my heart is def stuck in a Chicago “loop”—and I guarantee the city won’t let you down.

Whether it’s your first time, or you’ve bean there, done that… the Windy City promises to make you a pretty big fan (had to). Speaking of fans… Cubs, Bulls and Bears—oh, my! On April 7, you “better get ready for a brand-new day,” as “baseball season’s underway.” Or hit up some Bulls action at United Center. (And come fall, have a Field Day cheering on da Bears at Soldier Field.) 

Beyond sports, the Second City is teeming with culture, art, luxe retail, beautiful architecture (!), and plenty to do and drink and eat (too many to name to be frank).

Essentially, in the famed words of Anthony Bourdain: “They do things big… BIG I tells ya: Mike Ditka big. Michael Jordan big. Bill Murray big. Oprah! It’s one cultural Mount Everest after another.” Fact on facts. Here, from Wrigleyville to Downtown, we get you “in the loop” on the top must-do’s the next time you blow into the city.

The Bean

Do It Up

Wrigley Field

The boys of summer are back! L-evate your experience and take your game day next level (literally) above the Friendly Confines while singin’ “Go, Cubs, Go” from your seats on the surrounding Wrigley rooftops. Then live like a local post-game and head to a nearby Wrigleyville pub for a(nother) Old Style. “Hey, Chicago, what do ya say. The Cubs are gonna win today!” wrigleyrooftopsllc.com

Chicago Architecture Foundation Center River Cruise

If it’s Frank Lloyd Wright, how can it be wrong? Seriously, if you haven’t been on this bucket-list tour through the Chicago river on Chicago’s First Lady ooh-ing and ahh-ing over the world’s best architecture (hey, “Corn Cobs”!), well, it’s a boat time. It’s billed as the No. 1 thing to do in the U.S. by TripAdvisor for a reason. architecture.org/tours

The Bean

Selfies here or you weren’t in Chicago. Officially called Cloud Gate (cool beans, right?), this iconic work of art anchoring Millennium Park in the Loop is a must-see for its famed skyline reflections and surrounding greenspace. millenniumparkfoundation.org 

Magnificent Mile

If you were born to shop, the Mag Mile is your Shangri-la (luxe fashion & hotels! delectable dining!). But for nonshopaholics, it’s still worth the stroll for beautiful architecture, historic landmarks (Chicago Water Tower, Wrigley Building…)—and people-watching, natch. themagnificentmile.com

Skydeck + Glass Ledge

Whatcha talkin ’bout Willis Tower (aka formerly known as the Sears Tower)? Live life on the (l)edge at the Skydeck and Glass Ledge for views spanning up to four states (!)—and ’Gram posts you won’t regret. theskydeck.com

Chicago Riverwalk

The Riverwalk is a vibe. Make time to meander this 1.25-mile stretch across the south bank of the Chicago River dotted with sublime alfresco dining and drinking affairs interspersed with public art, museums and plenty of places to play (kayaking!). chicagoriverwalk.us

Shedd Aquarium “Look nature in the eye” from this perch on the shores of Lake Michigan in the heart of downtown Chi-Town—housing 32,000-plus marine creatures, including sharks, sea lions and belugas. You’re whalecome. sheddaquarium.org


Answering Tom Hanks’ profound question of what the tide could bring (“Wilson!’) is this must-hang beach bar situated on North Avenue Beach behind the uberpopular volleyball courts serving (ahem) live tunes, DJs and drinks, natch. A seasonal treat, max the fun by renting a cabana—then walk over to Lincoln Park or Gold Coast and bar-hop. Hey, when in Chi-Town… castawayschicago.com

Navy Pier

Trademarked as the People’s Pier, this 3,300-foot-long national treasure on the shoreline of Lake Michigan in Streeterville is its own eat, drink, play destination with plenty of events (think witnessing high-adrenaline flying sailboat racing come June), shopping, culinary adventures aplenty, cultural experiences… NTM more people-watching. And adrenaline junkies, be sure to hit up the immersive flight ride FlyOver when it debuts this fall. navypier.org

Porto | Jordan Balderas

Nibbles & SIPS

 Slice, Slice, Baby

Giordano’s, Gino’s East, Lou Malnati’s. No matter how you slice it, Chicago is a deep-dish haven with plenty o’ upper-crust OG faves. And newcomer Peanut Park in Little Italy—from a pizza maestro whose family has decadeslong ties to the Italian dining scene—shines in a city full of standouts. Fun fact: Get Lou Malnati’s delivered to Raleigh for a cross-country taste of “home sweet home, Chicago.” peanutpark.com; loumalnatis.com 

The Signature Lounge at the 96th

Primo cocktails perched 96 floors above the city on the Mag Mile in the historic 875 North Michigan Ave (formerly the John Hancock Center)? Yes, please. Find a better sunset—we’ll wait. signatureroom.com


Of all the virtues, this one reigns supreme… Chef Erick Williams has earned a loyal following for his Southern American cuisine in Hyde Park—and for good reason. virtuerestaurant.com


Topping everyone’s best lists right now is this 2022 James Beard semifinalist Filipino-inspired resto/bakery in West Town serving up some of the city’s best pastries and breakfast sandwiches in the morning, and a new Filipino tasting menu at night. kasamachicago.com

The Wiener Circle

You don’t score your own fan site or cameo in The Breakup for nothing. Open for “curbside abuse” and high-quality street food, relish in this iconic hot dog stand with a side of insults. Vince Vaughn sightings possible. You’ll frank us for the memories. (Inside tip: Do not order ketchup.) wienerscirclechicago.com


This passion project from chef Marcos Campos and owner Daniel Alejandro Alonso is a Michelin-starred love letter to the Atlantic Coast of Spain and Portugal—and has amassed a cult following for its seasonal expressions, delectable seafood, wine, culinary cocktails… and “dreamy dining room.” Don’t miss the tasting menu. portochicago.com 


Chicago Fire fans lookin’ for Molly’s Bar are gonna wanna belly up at the real-life Bucktown version, nee 1934, where all those bar scenes are filmed. lottiespub.com


For a night on the rocks, hit up this “not a whiskey bar” punk-rock venue in Lincoln Park “that serves a whole lotta whiskey”—like more than 800 lotta (plus cult classic movie screenings, local art displays, fests and more). For house party vibes, hit up the second floor, complete with pool table and Addams Family pinball machine. Rock on. delilahschicago.com

Bar Sótano

Salud! Star chef Rick Bayless whisks you from the beaches and Big Bus tours into the heart of Mexico for a welcome respite—“where chiles transform from a single-note spice to a symphonic full-body experience” and authentic cocktails aplenty promise to be the agave to your mezcal. And talent doesn’t fall far from the tree… as this sup spot sits beneath Michelin-starred Topolobampo from his daughter. We say, make room for both! rickbayless.com


Taking your trip to new heights is this hotel rooftop resto and open-air terrace with Great Lakes beach house year-round vibes overlooking The Bean with pano views of Millennium Park, Lake Michigan, the Art Institute of Chicago and beyond—dishing seasonally rotating fam-style comfort food, biodynamic wines and can’t-miss cocktails with large-format apothecaries. cindysrooftop.com

Tagueria Chingon

If you’re in the mood for Mexcellence—everyone is constantly taco about this top-notch taco spot from the owner of a beloved French restaurant. taqueriachingon.com


We fancy like… if a fancy multicourse meal is what you’re craving, the newly revamped Oriole is worth the price. oriolechicago.com

Z Bar

Post up on the Mag Mile’s Peninsula Hotel rooftop to live the luxe life at this new swanky lounge, which never fails to attract an equally swanky crowd with its iconic vistas and inspo from the world’s culinary and cultural riches. zbarchicago.com


If you’re looking to get funked up, perf pairing found. No pour decisions in this brand-new natural wine bar in the Loop, serving up some of the city’s most inviting and hard-to-find natural wines from around the globe. goodfunkchicago.com


For some Asian persuasion, this gorge lounge/Japanese dining bar in the West Loop dishes nips and sips with equal reverence in a serene setting. barkumiko.com

Lazy Bird

Situated beneath the hip Hoxton Hotel, this intimate sip spot dedicated to classic cocktails and the occasional live music (Thu.–Sat. evenings) is the basement bar we didn’t know we needed. No egrets.

Hungry for more?

Armitage Alehouse: English pub in Lincoln Park worth the pint

Superkhana International: Fab modern take on Indian cuisine that counts Lula Cafe chef/owner Jason Hammel as one of its founders

Rose Mary: Top Chef’er Joe Flamm’s white hot West Loop Croatian restaurant

Con Todo: Bienvenidos to Jonathan Zaragoza’s first solo project—Mexican food in Logan Square.

Smyth & The Loyalist: Tried and true—and still hot

See our other recent RDU Direct Destination getaway stories for some fun in DC, Miami Beaches, Scottsdale and Salt Lake City

Share this Post

Leave a Comment