Chicago

Events, dining, nightlife, menswear and regional travel for the Windy City gent.

Rivers and Sandy Beaches along Indiana Dunes State Park

6 Perfect Campgrounds Near Chicago for Your Weekend Getaways

Don’t you dare waste a single summer weekend

Fountain Square is a mix of vintage and contemporary. With throwback antique stores and duckpin bowling visitors can experience the past. Meanwhile, new restaurants and music venues draw new crowds to this thriving neighborhood on the Southeast edge of the city.

Why Your Next Weekend Getaway Should Be to Indianapolis

Chef Concierge Phillipe Gills

Concierge Confidential: Navigate Chicago’s Best with The Langham Chicago’s Philippe Gills

Where to Try Your Hand at Winter Olympic Sports in and Around Chicago

Where to Try Your Hand at Winter Olympic Sports in and Around Chicago

View from the Willis Tower Skydeck in Chicago

A Veteran Chicago Hotel Concierge Shares All Her Windy City Secrets

The Latest

The Bean in Millennium Park

25 Very Fun, Very Chicago Things to Look Forward to in 2022

Weather and pandemic permitting

The Bell Bowl Prairie in Rockford

Why the Prairie State May Soon Lose a 1,000-Year-Old Prairie

An ancient Illinois ecosystem is under threat of being plowed under for good

Frank Lloyd Wright’s 1908 Meyer May House is one of the master’s finest Prairie Style residences, built for a local clothier in Grand Rapids.

A Weekend in Grand Rapids, An Underrated Hub for American Design

Three hours from Chicago, Grand Rapids offers everything from a Frank Lloyd Wright masterpiece to a decorated history of furniture manufacturing

These Are the 5 Best New Hotels in Chicago for 2021

These Are the 5 Best New Hotels in Chicago for 2021

There’s a rooftop bar just waiting for you to show up

Popular

Is This the “Most Baffling Blow Job Scene” in TV History?

Turn Your Regular Grill Into a Smoker in 5 Easy Steps

The Best American Whiskey That Isn’t Bourbon or Rye

Ex-Super Bowl QB Brad Johnson Is the Anti-Tom Brady on Social Media

Baz Luhrmann’s “Elvis” Is So Stupid, It Almost Feels Like Parody

Subscribe to Insidehook Chicago

Recommendations on where to go, what to do, who to see and what to wear in the Windy City.

Keep Reading

Door County, WI

Everything You Should Do During Your Weekend Getaway to Door County

How to Have an Extremely Sophisticated Weekend in Milwaukee

How to Have an Extremely Sophisticated Weekend in Milwaukee

Frank Lloyd Wright’s Life Magazines Dream House is one of the best Airbnbs on Lake Michigan in 2021. This rental is pictured at dusk on Lake Michigan

The 20 Best Airbnbs on Lake Michigan, The Third Coast of the United States

Cabin on a private island

5 Secluded Cabins and Campgrounds Near Chicago to Help You Get Back to “Normal”

Tyler in Chicago designer Ten Speed Hero kit

Is This the Year You Become a Badass Chicago Road Cyclist?

Warren Dunes State Park

Three World-Class Midwestern Road Trips for When You’re Ready to Leave Chicago

The 20 Best American Hotels to Visit for the Holidays in 2020

The 20 Best American Hotels to Visit for the Holidays in 2020

farmstead exterior

10 Perfect Airbnbs for Escaping Chicago This Holiday Season

The Forge

Chicago Now Has a Giant Outdoor Jungle Gym for Adults

cook county hospital

An Iconic Chicago Building Gets a New Lease on Life

The "Greetings from Chicago" is one of the city's most popular murals

Behold, The Ultimate Chicago Outdoor Mural Crawl

still bend schwartz house

How and Where to Responsibly Rent a Summer House Near Chicago

Show More

Recommended

Suggested for you

Is This the “Most Baffling Blow Job Scene” in TV History?

Turn Your Regular Grill Into a Smoker in 5 Easy Steps

The Best American Whiskey That Isn’t Bourbon or Rye

Ex-Super Bowl QB Brad Johnson Is the Anti-Tom Brady on Social Media

Baz Luhrmann’s “Elvis” Is So Stupid, It Almost Feels Like Parody

Which TikTok Sex Claims Are Legit? We Asked a Sexpert.