24 hours for the Mainstreamer
Chicago's Virgin Hotel is located near the heart of the Loop and within walking distance of the Magnificent Mile. Start your day at the hotel's in-house diner, Miss Ricky's, where you can dine on decadent chicken and waffles or a stack of pancakes. Breakfast is served all day, so you can always come back for more.
Journey to the 103rd floor of the Willis Tower and enjoy the view before mustering all of your courage and steping onto the Ledge. The glass cube structure extends over the side of the building, making you feel as if you’re suspended 1,353 feet off the ground. Try not to lose that breakfast.
Catch a bus to Millennium Park, a 24.5-acre greenspace which features Frank Gehry's Pritzker Pavilion and serpentine bridge; sculptor Anish Kapoor's 110-ton Cloud Gate (a.k.a. “The Bean”); and Jaume Plensa's Crown Fountain, with its ever-changing array of locals' faces spewing water very five minutes in the summer months.
Walk north to the Michigan Avenue Bridge and board the Chicago Architecture Foundation River Cruise, a one-and-a-half hour tour of beautiful buildings lining the Chicago River. The tour docent will delve into the city's storied architectural history while you kick back with a drink and enjoy the sights.
Head to River North and eat lunch at this über-efficient local chain, which offers authentic Chicago dogs. The juicy dog comes on poppyseed bun steamed to perfect softness and with a generous helping of thick-cut tomatoes, onions and a hefty pickle slice.
Leave the Loop and catch the Red Line to Wrigleyville, the home of historic Wrigley Field. Buy tickets in advance or take your chances with the scalpers lining the streets before entering the Friendly Confines and knocking back an Old Style in the bleachers. If the Cubs aren't in town, you can take your pick of the area's various sports bars.
Head back downtown for a quick stop at Water Tower Place, a mall situated on Michigan Avenue that hosts the usual selection of apparel retailers as well as the American Girl Place and a Lego Store.
Once you've worked up an appetite, walk down the street and get some deep-dish pizza at this Chicago institution. You'll probably want to order an appetizer while you wait for your gooey pile of cheese, sauce and topping to cook.
Even if you know nothing about improv, chances are you've heard of Second City. This is the place that put both sketch and improvised comedy on the map while launching the careers of Tina Fey, Chris Farley and John Belushi. Make reservations for a main stage show and you could see the next great Chicago comic.
Chicago may not be a tropical getaway, but you can pretend you're on the beach by paying a visit to River North cocktail bar Three Dots and a Dash. Enjoy a delicious (and strong) cocktail or team up with some friends and sip on a punch bowl.
You've got one more stop on your intinerary: Singing and dancing at the Original Mother's. This Division Street bar offers nightly karaoke and a dance floor that is usually packed with late-night revelers. Even if you don't make it to 4am, you can at least sing "Sweet Caroline" before you turn in for the evening.
The new Virgin Hotel is a dream hotel for people into design and technology, with an app to control the room temperature, a pour-over coffee setup in each room and a Tesla to give free rides to guests. The press release about the hotel said the bed “functions as a playpen and traditional bed," so interpret that as you'd like.