Cooler weather in Chicago doesn’t mean that the city slows down. Bundle up and prepare for a weekend full of Chicago’s best with this hour-by-hour itinerary.
3 p.m. | Shopping on Michigan Avenue
Chicago’s Magnificent Mile is the perfect way to start off your trip with endless shopping
options, festive lights and horse-drawn carriages. The holidays make this iconic city gleam
and Mag Mile is just the place to experience it.
6 p.m. | Experience Dinner at the Purple Pig
The Purple Pig is one of the city’s true culinary gems. Just north of the Chicago River, this
James Beard Award-winning restaurant tops every foodie’s list. Pro tip: Order the bone marrow.
9 p.m. | See Where Comedy Legends Began
The Second City has a long-standing history in Chicago, first opening its doors in 1959.
Many comedy legends like Steve Carell, Stephen Colbert and Tina Fey are alumni of its
stage; see their roots — and some of the best up-and- coming talent in comedy.
9 a.m. | Breakfast at Circa at The Gwen, a Luxury Collection Hotel, Chicago
Start your busy morning at Circa in The Gwen. Enjoy a French press coffee with croissant
bread pudding French toast, and thank us later. (Also, you’ll need those carbs, we promise.)
11 p.m. | Ice Skate in Millennium Park
A must-see during your visit is Millennium Park with the Cloud Gate sculpture, more
commonly known as the “Bean.” Ice skate just below, snap some photos of the gorgeous
skyline, and try to stay on your feet.
12:30 p.m. | Dig into a Deep Dish Pizza
Chicago is synonymous with gooey pizza. For a quintessentially Chicago experience, try
Giordano's stuffed pizza with sausage and cheese crust one block north of Millennium Park.
Or, pick a pie at Pizano’s Pizza, whose founder is heralded as one of the original deep dish founders.
2 p.m. | Experience the World’s Best Museum
Trip Advisor recently rated the Art Institute of Chicago as the best museum in the world —
and for good reason. This winter brings photography from post-war Japan, Neapolitan crèche and master drawings, alongside an unparalleled contemporary collection (with
works from Andy Warhol, Roy Lichtenstein and Jasper Johns).
7 p.m. | Hit the Publican’s Dining Hall
Now that you’ve walked off the deep dish, order something a little more protein-heavy at
The Publican. With an emphasis on farmhouse and fisherman fare and the city’s most
thoughtful beer list, reservations are a must.
10 p.m. | Visit the John Hancock for a Nightcap
Located on the 96th floor of the John Hancock, The Signature Lounge boasts an
unforgettable skyline and an Old Town Old Fashioned to match.
10 a.m. | Brunch at Green River
Head to the 18th floor for a brunch whose beauty is its simplicity. GreenRiver’s smoked
salmon eggs benedict pairs perfectly with goodbye views of Lake Michigan, especially from the terrace.
12:30 p.m. | Relax at Bliss at W Chicago Lakeshore
Relax, restore and rejuvenate at The W Chicago Lakeshore’s Bliss Spa. You’re off to the airport soon, better decompress now with a Triple Oxygen Treatment or a movie while you