Chicagoing, Sarah Spain style! 2018

Chicagoing, Sarah Spain style! 2021

People are always asking me for the best restaurants, bars and activities in Chicago. While my recommendations do change based on who’s asking, who they’re going with, how much money they want to spend, etc. I certainly have favorites that always seem to pop up, so I figured I’d start a collection of suggestions here, adding to it as I discover new spots I love. So here’s my (always growing and evolving) list of Chicago faves. (Always call ahead in case of COVID-related cancellations.)

EAT (well)

RPM Italian
Cindy’s Rooftop
Coast Sushi
Cafe Ba-Ba-Reeba
Girl and the Goat
Union Sushi
Siena Tavern
Nico Osteria
Uncommon Ground
Mindy’s Hot Chocolate
Frontera Grill
Lula Cafe
EAT (casual)
The Fifty/50
Roots Pizza
Furious Spoon
Native Foods
Lyfe Kitchen
Silli Kori/Thai Village
Au Cheval
Big Bowl
Big Star
Edwardo’s Natural Pizza
Harry Caray’s Navy Pier (AMAZING memorabilia collection)
Harry Caray’s Water Tower (cool interactive museum, too!)
Public House

DRINK (with your date)

The Berkshire Room
The Green Mill
Buddy Guy’s Legends
RM Champagne Salon
The Sixth
Lost Lake
Violet Hour
Three Dots & A Dash
The Aviary
Chicago Athletic Association
DRINK (with your friends)
Old Town Ale House
The Fifty/50
The Hideout
Royal Palms (shuffleboard!)
Murphy’s Bleachers
Clark Street Ale House (bring your dog!)
Revolution Brewing
Headquarters Beercade
Big Star
The Green Door


Red Stars game
Sky game
Cubs game
Blackhawks game
Bears game
Bulls game
White Sox game
Fire game
Second City
Zanies Comedy Club 
Chicago Architecture Foundation boat tour
Street Fests
Harry Caray’s interactive Chicago Sports Museum
Concert at the Pritzker Pavilion
Shopping on Michigan Avenue
North Avenue Beach
Shedd Aquarium
Walk/run/bike the 606 
Walk/run/bike the lakefront 
Art Institute
Hancock Observatory
Sears (NOT Willis!) Tower Skydeck
Lincoln Park Zoo
Adler Planetarium
Buddy Guy’s Legends
Kingston Mines
The Green Mill
Chicago Shakespeare Theater
The Goodman Theatre

Steppenwolf Theatre

Garfield Park Conservatory