If you are going out on a Sunday night, then one of two things may have happened: You are passing through a city at an inopportune time, or you are someone who likes to go out when everyone else stays in. There is a certain kind of pleasure in everyday, off-peak travel that is easy to revel in. Your options are a little more limited, but the crowds have dispersed and you have the city to yourself, even in the waning summer months.
If you are in downtown Chicago on a Sunday night, take a walk through Millennium Park when the crowds have thinned out a little bit. Instead of dining downtown, take advantage of the light traffic and jump in the car service of your choice and drive up scenic Lake Shore Drive to Andersonville. This neighborhood is home to the Hop Leaf Bar, where you can enjoy a selection of artisanal beers while eating a great burger.
From here, a short car ride or a 20-minute walk south on Broadway gets you to the legendary Green Mill Cocktail Lounge. On a Sunday night, things may just have quieted down by 10 p.m., so sit and nurse a drink for the rest of the night while listening to that evening’s house band.
Read This Next
#TrazeeTravel
Insta FeedSlideshow
Sep 8, 20268 Must-Visit Libraries Around the World
It’s time to start dreaming of your next trip. Here are eight must-visit libraries around the world.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
North America
Sep 8, 2026New Upscale Italian Restaurant and Bar Opens in NYC’s West Village
Last month, New York City’s West Village welcomed a new restaurant and bar with some seriously promising dishes and drinks. Floradora is the newest concept from Cody Pruitt and Jacob Cohen, the team also behind Libertine, Chateau Royale and Capitaine.
Destinations / North America
Sep 7, 20265 Unique Glamping Getaways to Take Across the South This Autumn
Did you know glamping accounted for 29 percent of all camping experiences in 2025? The elevated camping experience lets you both enjoy the great outdoors with some comforts you don’t get from just sleeping in a tent.
Sponsored Content
TAP Air Portugal: A Milestone Year
From small airline to global success, TAP Air Portugal turns 80 and better than ever.
Asia
Sep 7, 2026Canopy Opens First Hotel in Southeast Asia
Hilton’s Canopy brand made its debut in Southeast Asia. New Canopy Bangkok Sukhumvit opened last month.

ShareThis