Chicago

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

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

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”

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Tyler in Chicago designer Ten Speed Hero kit

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

One of our favorite Chicagoland cyclists shares his favorite rides around the city

Warren Dunes State Park

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

From “riverbaths” to mint juleps to the best beaches on Lake Michigan

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

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

A complete guide to the pandemic-appropriate five-star isolation of your dreams

farmstead exterior

10 Perfect Airbnbs for Escaping Chicago This Holiday Season

From a tiny farmhouse for two to a “family compound” that can accommodate 16

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100 Ways to Live to 100: A Definitive Guide to Longevity Fitness

Larry’s 50 Funniest Grievances on “Curb Your Enthusiasm,” Ranked

The 17 Best Luxury SUVs: A Complete Buyer's Guide

Oral Sex Is Still Taboo. This Dating App Wants to Change That.

Are Sports Illustrated Swim Readers Ready for Radical Inclusivity?

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

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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

The Kinney House

Five Frank Lloyd Wright Homes You Can Rent Near Chicago

Train Movement

The Chicago Gyms Where You Can Try All the Biggest Fitness Trends for 2020

What would drive a man to drive 1,000 miles around a Great Lake long after summer's end?

The Case for Taking a Winter Road Trip Around Lake Michigan

Swissôtel Chicago

Stash Your In-Laws in One of These 7 Holiday-Themed Chicago Hotels

Chicago Camping

It’s Not Too Late: A Brief Guide to Fall Camping Near Chicago

last minute getaways

7 Last-Minute Summer Getaways for Chicagoans

The 7 Hiking Trails Every Chicagoan Should Know

The 7 Hiking Trails Every Chicagoan Should Know

A Weekend in Minneapolis, Possibly the Midwest’s Ideal Summer City

A Weekend in Minneapolis, Possibly the Midwest’s Ideal Summer City

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