Chicago

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

Swimmers and sunbathers at Oak Street Beach in Chicago, one of the best Chicago beaches on Lake Michigan

A Beginner’s Guide to Chicago’s Underrated Beaches

Kiteboarding and frozen margaritas…on Lake Michigan?

Milwaukee Art Museum in Wisconsin

The Endless Influence of Scandinavian Design Gets Its Due in Wisconsin

Different interior and exteriors of cabins

Escape to the Woods With These Cozy Cabins

Bar at Torali, The Ritz-Carlton, Chicago

The Ritz-Carlton Chicago Just Finished a $100M Renovation

Route 66 Historic Badge

Tracing the Path of Historic Route 66, Just Outside of Chicago

The Latest

An employee at Barrels and Billets hands over a bottle of custom bourbon to a customer

The Best New Louisville Bourbon Experiences to Try

Sample Pappy Van Winkle (without going broke), bottle your own whiskey or let the pros do what they do best

The college town of Iowas City is pictured here behind the Iowa River

There’s Actually Never Been a Better Time to Visit Iowa City

It’s like a Hallmark movie set, with a brand-new art museum

A sunset on the Great Lawn at Mission Point Resort on Mackinac Island.

This Is Your Last Chance for a Perfect Mackinac Island Weekend

Late October means fewer crowds and gorgeous weather. Here's your itinerary.

View Of Trees On Field Against Sky During Autumn, Galena Illinois

The Top 5 Stays for Midwestern Fall Foliage Viewing

Get some fall color in your system with these weekend getaways

Popular

Built to Crush the Mustang, This 1-of-1 ‘60s Pontiac Is Up for Sale

The Legendary Green Beret Who Lives Like a Modern Samurai

A Guide to the Best Life Hacks From the Last 100 Years

Here’s Everything You Need to Know About “Beige Flags” in Relationships

Once a Marathon Runner, Now the World’s Strongest Man

The InsideHook Newsletter.

News, advice and insights for the most interesting man in the room.

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Fermilab in Batavia is a 6,800 acre National Environmental Research Park and many areas are open to the public.

An Unbeatable Scientific Field Trip Is Just an Hour Outside Chicago

Lake Geneva Pier with Chairs at Sunset

How to Spend the Ideal Weekend in Lake Geneva

Downtown Milwaukee

A Hotel Insider on Where to Eat Cheap (and Well) in Milwaukee

Beach against the sky in Michigan City

3 Weekend Getaways From Chicago That Require Less Than a Tank of Gas

Z Bar exterior at the Peninsula Hotel

Where to Meet Singles, Grab a Coffee and Get a Sunset Cocktail in Chicago, From a Five-Star Hotel’s Concierge

United Airlines aircraft during flight with a sunset over the ocean in the background. We take a look at the best new routes out of Chicago's O'Hare and Midway airports.

The Best New Routes at O’Hare and Midway Are Summer Vacation Fodder

Rivers and Sandy Beaches along Indiana Dunes State Park

6 Perfect Campgrounds Near Chicago for Your Weekend Getaways

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 Bean in Millennium Park

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

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The Argument for NYC's New $29 Hot Dog Is Actually Quite Compelling