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Cloud Gate to Cocktails: The Definitive Chicago Sightseeing & Dining Guide
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items From historic, old-school pizzerias to the absolute latest in high-end dining, this is your expertly curated guide to the best of Chicago's table. We're celebrating the legendary flavors, the cozy spots, and the incredible chefs that define the city'...
Map
Sections
6
Dining: Breakfast & Brunch Icons
Sightseeing & Iconic Attractions
Dining: Chicago Classics & Comfort
Dining: Upscale & Modern
Dining: Global & Seafood Focus
Sweet Treats
Dining: Breakfast & Brunch Icons
Start your day right with Chicago's most famous and highly-rated brunch and breakfast spots. These locations are known for signature dishes, generous portions, and often have a line—but they are worth the wait!
The go-to spot for a famous, classic downtown breakfast and brunch. Famous for their huge menu of pancakes, waffles, crepes, and omelets. Expect a wait, especially on weekends. Vibe: Bustling, Casual. Price: $$ Neighborhood: The Loop/Millennium Park ...
Wildberry Pancakes & Cafe
A gourmet breakfast sensation famous for its innovative, signature French Toast Flight (four different daily flavors). This is a must-try for a unique brunch experience. Vibe: Lively, Creative. Price: $$ Neighborhood: Lincoln Park.
Batter & Berries
A popular, cozy neighborhood spot known for its delicious, soul-satisfying breakfast and lunch dishes. It’s perfect for a less touristy, more local brunch feel. Vibe: Cozy, Local Gem. Price: $$ Neighborhood: South Side (Bronzeville).
Honeybear Cafe
Sightseeing & Iconic Attractions
The "Cloud Gate" portion of your adventure begins here. This section covers the absolute must-see landmarks, architecture, and world-class cultural institutions that define the city of Chicago. Plan your route to capture that perfect photo and absorb...
The ultimate Chicago photo-op. This is the heart of the city's public art scene, featuring the iconic reflective sculpture (The Bean), Lurie Garden, and the Crown Fountain. Vibe: Lively, Iconic. Neighborhood: The Loop.
Cloud Gate (The Bean) & Millennium Park
Arguably the best sightseeing experience in the city. A professional tour guide will lead you down the Chicago River, providing history on the city's most famous and innovative buildings. Tip: Book tickets in advance, especially during the summer.
Chicago Architecture River Cruise
Home to one of the world's most impressive collections, including American Gothic and works by Monet, Van Gogh, and Picasso. Vibe: Cultural, Must-See. Neighborhood: The Loop.
The Art Institute of Chicago
Stand 1,353 feet in the air on a glass box extending 4.3 feet out from the side of the former Sears Tower. This offers a thrilling, panoramic view across four states on a clear day. Vibe: Thrilling, Tourist Destination. Neighborhood: The Loop.
Skydeck Chicago
Dining: Chicago Classics & Comfort
A tribute to the flavors that made Chicago famous, this section highlights essential local foods and institutions. From old-school pizzerias and legendary fried chicken to the best burgers in America, these are the places you simply must experience.
You cannot leave Chicago without trying deep-dish pizza! Lou's is famous for its Buttercrust and signature sausage patty, offering a perfect introduction to this iconic style. Vibe: Casual, Family-Friendly. Neighborhoods: Multiple locations (The Loop...
Lou Malnati's
A Chicago staple for two things: the Italian Beef sandwich (get it dipped with hot peppers!) and a Chicago-Style Hot Dog (never, ever with ketchup). Expect long lines that move fast. Vibe: Fast Casual, Essential. Neighborhoods: Multiple locations.
Portillo's
Worth the wait for one of America's most famous burgers. Order the Single Cheeseburger (which has two patties) or the Double Cheeseburger (three patties). This spot offers an elevated, cozy, diner-style atmosphere. Vibe: Trendy, Elevated Diner. Price...
Au Cheval
If you're looking for the best saucy fried chicken in Chicago, look no further! This is a South Side staple, famous for its legendary, crispy fried chicken and Mumbo Sauce—a true local obsession. Vibe: Local Gem, Casual. Neighborhood: South Side.
UNCLE REMUS
A legendary Chicago institution! Harold’s is famous for its crispy fried chicken served with Fries and a generous dousing of their signature Mild Sauce. This is quintessential Chicago street food. Vibe: Local Icon, Casual. Price: $ Neighborhoods: Mul...
HAROLDS CHICKEN - 129 W 87th St, ...
A highly popular national chain known for its massive menu and huge slices of cheesecake. A reliable choice for large groups and varied tastes. Vibe: Casual, High Volume. Price: $$ Neighborhood: Multiple locations (Magnificent Mile, etc.).
The Cheesecake Factory
For authentic, old-school Chicago thin-crust pizza that tastes exactly the way you remember it. This Northwest Side legend has been serving up delicious pies since 1952. Vibe: Nostalgic, Casual. Neighborhood: Northwest Side.
Frank's Pizzeria & Restaurant
A spot famous for its bold flavors and New Orleans-style spice in a contemporary setting. They've earned notoriety for their incredible take on Southern classics. Vibe: Cozy, Flavorful. Neighborhood: West Town.
Cleos
A slice of New Orleans Southern comfort right here in Chicago! This diner serves up classics like shrimp and grits and decadent chicken and waffles all day in a bright, modern, yet cozy atmosphere. Vibe: Modern Diner, Cozy. Neighborhood: Hyde Park.
Roux
Dining: Upscale & Modern
Reserve a table at one of the city's premier dining establishments, perfect for date nights, celebrations, or an unforgettable culinary splurge. This section features Chicago’s best steakhouses, concept restaurants, and high-end dining experiences.
One of Chicago's most acclaimed steakhouses, known for its sexy, dimly lit, speakeasy-style ambiance and fantastic classic cocktails. This is the spot for a sophisticated, classic experience. Vibe: Speakeasy Chic, Romantic. Price: $$$$ Neighborhood: ...
Bavette's Bar & Boeuf
An acclaimed, upscale Southern-inspired restaurant in Hyde Park led by Chef Erick Williams. Known for elevated, comforting dishes, impeccable service, and a beautiful, contemporary setting. Vibe: Fine Dining, Elevated Southern. Price: $$$$ Neighborho...
Virtue Restaurant
Get dressed up for a true Chicago dining experience in the Gold Coast. This trendy, upscale steakhouse delivers on drama and serves classic cuts and seafood in a luxurious, energetic setting (often with a complimentary champagne toast). Vibe: Luxury,...
Maple & Ash
Get ready for an electrifying night of open-fire cooking! This West Loop gem is inspired by the grand, rustic grilling traditions of Argentina. The massive, custom-built parrilla (grill) dominates the scene. Vibe: Rustic Chic, High Energy. Price: $$$...
El Che Steakhouse & Bar
Chicago is a Michelin destination. Kasama is a 1-Michelin Star spot serving innovative Filipino tasting menus, or for a true bucket list splurge, consider Alinea (3-Michelin Stars) for molecular gastronomy. Vibe: World-Class, Innovative. Price: $$$$ ...
Kasama
A chic, modern night out that seamlessly blends amazing food and great wine. This Illinois-born concept features an upscale casual restaurant, full-service bar, and a Napa-style tasting room all in one. Vibe: Upscale Casual, Wine-Focused. Price: $$$ ...
Cooper’s Hawk Winery & Restaurant
Dining: Global & Seafood Focus
If you want dinner to be an absolute adventure, book a table! This is Chef Stephanie Izard's playful, inspired take on Chinese-American cuisine, served up in a super-chic setting. Must-Try: The Goat Egg Rolls. Vibe: Playful, Chic. Price: $$$ Neighbor...
Duck Duck Goat
A unique and flavorful twist by fusing Italian and Creole cuisines. This is where the richness of traditional Italian meets the bold spice of New Orleans. Vibe: Stylish, Fusion. Price: $$$ Neighborhood: West Town.
Provare Chicago
Put on a bib and get messy! This vibrant, nautical-themed spot is all about a customizable, fun seafood boil served right in a bag. Vibe: Fun, Casual, Messy. Price: $$ Neighborhood: South Loop.
Lowcountry South Loop
A Chicago favorite that brings the fun, messy, authentic seafood boil experience right to the city. Highly celebrated for its lively, casual atmosphere and customizable bags of seafood. Vibe: Lively, Casual. Price: $$ Neighborhood: South Side.
Two Fish Crab Shack
For incredible Cajun and Creole flavors, this spot feels like a full-on Louisiana getaway! The perfect place to treat yourself to giant portions of fried seafood, gumbos, and famous crawfish dishes. Vibe: Festive, High Energy. Price: $$$ Neighborhood...
Pappadeaux Seafood Kitchen
Serves up amazing seafood with a serious South Side vibe. This local favorite is known for its lively, festive atmosphere, delicious platters, and R&B music that just makes you feel good. Vibe: Local Gem, Lively. Price: $$ Neighborhood: West Side...
Joe Willie's Seafood and Bar
Sweet Treats
Save room for dessert! From historic bakeries that have stood the test of time to Chicago's most decadent new dessert spots, satisfy your sweet tooth with these local favorites.
A popular spot known for its incredible cakes, cupcakes, and other decadent baked goods, perfect for satisfying that post-dinner sweet craving. Vibe: Casual, Sweet Shop. Neighborhood: West Side.
Sugar Shack
Roeser's isn't just a bakery—it's a Chicago institution! This incredible family-run spot has been crafting stunning cakes, cookies, and tortes since 1911, making it one of the oldest and most beloved bakeries in the city. Vibe: Historic, Classic. Nei...
Roeser's Bakery