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🌭 Chicago's Loop, River North & the Lakefront: Deep Dish, Skyline Views & Downtown Classics

32 items

Mikey Stark

My first-timer's game plan for downtown Chicago — deep dish, Italian beef, and Chicago dogs in River North, the Bean and the Art Institute in the Loop, then river cruises, skyline decks, and lakefront walks out to Navy Pier. These are the spots I act...

Map

I always order the deep dish with the Buttercrust and lean sausage here — it's my go-to pie when friends visit Chicago for the first time.

Lou Malnati's Pizzeria

I make the pilgrimage to the original 1943 basement spot where deep dish was born — order the Numero Uno and settle in for the wait.

Pizzeria Uno

I grab a cheesy stuffed pizza here right after a Millennium Park stroll since it's steps from the Bean.

Giordano's

I get a Chicago dog dragged through the garden plus a chocolate cake shake at this Prohibition-themed River North favorite.

Portillo's & Barnelli's Chicago

I order my Italian beef hot and dipped at this no-frills counter that inspired The Bear — just know it's lunch only and closed Sundays.

Mr. Beef on Orleans

I head down to lower Michigan Ave for a ‘cheezborger, cheezborger’ and a cold beer at the dive made famous by SNL.

Billy Goat Tavern (The Original)

I book this old-school Tuscan steakhouse in a wooden frame house under the L tracks for a steak and chicken alla Joe the way Chicago did it in 1941.

Gene & Georgetti

I save Gibsons for big nights out — the bone-in steaks and the giant slice of cake are pure Rush Street swagger.

Gibsons Bar & Steakhouse

I stop in for a martini and chicken Vesuvio surrounded by Cubs memorabilia at this River North institution.

Harry Caray's Italian Steakhouse

I come here dressed up for the Mama DePandi's bucatini pomodoro and a buzzy River North dinner.

RPM Italian

I still think Rick Bayless's colorful flagship pours some of the best margaritas and regional Mexican dishes in the city.

Frontera Grill

I grab a schnitzel and a house root beer or a stein at this German classic that's been in the Loop since 1898.

The Berghoff Restaurant

I start road-trip mornings at this Route 66 diner with the free donut holes and a fluffy omelet — just note it's closed Mondays and Tuesdays.

Lou Mitchell's

I share a bunch of Mediterranean small plates and the famous milk-braised pork shoulder right on the Mag Mile.

The Purple Pig Restaurant

I love ducking down the alley entrance into this underground tiki bar for a flaming rum punch.

Three Dots and a Dash

I head up to the 13th floor of the Chicago Athletic Association for cocktails with a killer view over Millennium Park and the lake.

Cindy's Rooftop

I wander all five floors of the world's biggest Starbucks — the roasting cask and espresso martinis upstairs are worth it.

Starbucks Reserve Roastery

I grab a pour-over from Chicago's hometown roaster here before walking across the street to the Bean.

Intelligentsia

I always leave with a bag of the Garrett Mix — caramel and cheddar together sounds wrong but it's so right.

Garrett Popcorn Shops

I could spend all day with the Impressionists, American Gothic, and Nighthawks here — the lions out front are a must photo, and it's closed Tuesdays.

The Art Institute of Chicago

I get here early to snap a selfie in the Bean before the crowds, then splash past the Crown Fountain faces.

Cloud Gate

I pop into this free landmark just to stare up at the world's largest Tiffany glass dome in Preston Bradley Hall.

Chicago Cultural Center

I like catching the fountain's water show in Grant Park with the skyline behind it — it's the Married… with Children opener in real life.

Clarence F. Buckingham Memorial Fountain

I walk the Riverwalk with a glass of wine from one of the cafes and watch the boats glide under the bridges.

Chicago Riverwalk

I tell every first-timer this 90-minute architecture boat tour is the single best thing to do in Chicago.

First Lady

I step out onto the glass Ledge 103 floors up in Willis Tower for the ultimate stomach-drop photo.

Skydeck Chicago

I go up 94 floors at sunset for lake-and-skyline views, and I dare friends to try TILT.

360 CHICAGO

I ride the Centennial Wheel and walk to the end of the pier for the best skyline view from the lake.

Navy Pier

I check out whatever bold exhibit is up at the MCA, then hang on the big front steps — note it's closed Mondays.

Museum Of Contemporary Art Chicago

I walk the base of this Gothic tower hunting for the embedded stones from the Great Wall, the Parthenon, and more.

Tribune Tower

I always pause at the castle-like Water Tower that survived the Great Chicago Fire of 1871, and the free City Gallery inside is a nice bonus.

Chicago Water Tower

I snap the iconic glowing marquee on State Street, and I recommend the behind-the-scenes tour if you have time.

The Chicago Theatre