Menu

The Chicago Loop is the vibrant urban heart and downtown cultural epicenter of the Windy City, named for the distinctive elevated (‘L’) train tracks that loop around it. Here you’ll find world-class museums, on-trend shops, award-winning dining and exciting nightlife within its boundaries—south and east of the Chicago River and north of Congress Parkway. The holidays are a great time to visit, with lots of festive sights, sounds and happenings throughout the Loop. Follow our Do the Loop weekend itinerary to experience the best this lively area has to offer. You’ll find that everything is within easy walking distance, or close to CTA transportation.

DO THE LOOP

Before you arrive, book a room at a Chicago Loop hotel. Some of the many choices include the boutique Kimpton Gray Hotel, housed in a historic office building and featuring lauded Latin cuisine in its Boleo year-round rooftop restaurant. The pet-friendly Hyatt Centric The Loop Chicago boasts the seasonal AIRE rooftop bar with panoramic city views. The Palmer House A Hilton Hotel is an elegant Loop stalwart that has been hosting visitors for more than 140 years; check out the historic lobby mural during afternoon tea at its Lockwood Restaurant & Bar.

Chicago Loop Alliance - Palmer House 

DAY 1

Gear up for the day with a cup of coffee from Chicago's own Intelligentsia (with two Loop locations) or Goddess and The Baker, known for its yummy desserts (think layered rainbow cake). Or start the morning with a healthy veggie scramble and berry smoothie at Peach and Green.

Then it's off to do some sightseeing. A narrated ride with the Chicago Trolley & Double Decker Co. is a fun way to get your bearings and hop on and off at the sites you'd like to explore. Or view the city’s amazing architecture on foot during a Chicago Architecture Foundation walking tour.

For lunch, head over to Miss Ricky's Diner at Virgin Hotels Chicago and dig into comfort food like buttermilk fried chicken and waffles. Or, sample the extensive menu of German-American fare and a craft brew at The Berghoff, open in the Loop since 1898.

Spend the afternoon shopping on historic State Street. Give your wallet a workout at the fashionable flagship Macy's State Street. Then check out Block 37, home to hip stores like the Chicago Design Museum Threadless Artist Shop and tasty bites from Latinicity Food Hall and Lounge. And don't miss the apothecary potions and lotions at Merz Downtown, located in the Palmer House.

For dinner, choose from one of the three restaurants housed within the Italian Village, a long-time Loop favorite that's been run by the Capitanini family since 1927. You'll be right in the Chicago Theater District, where you can see a hit Broadway in Chicago play on the stage of a classic theater; or a dance performance by the critically acclaimed Joffrey Ballet Chicago at the historic Auditorium Theatre of Roosevelt University. If you're in the mood for an indie flick, check the schedule at the Gene Siskel Film Center, operated by the School of the Art Institute of Chicago.

Or amp up your evening with a fast-paced game of ping-pong at AceBounce, followed by dancing 27 stories up at the wildly popular ROOF on theWit, rated one of the Top 3 Rooftop Bars in the World by Travel + Leisure. Or raise the roof at Raised-An Urban Rooftop Bar at the Renaissance Chicago Downtown Hotel, featuring a sleek indoor/outdoor lounge and private VIP greenhouse.

Chicago Loop Alliance - Breakfast

 

DAY 2

Begin your morning with a delectable brunch. You'll be treated to spectacular Millennium Park views and sumptuous dishes at Cindy's, perched atop the Chicago Athletic Association Hotel. Or go for the Italian dishes, such as the lemon ricotta crespelle, at Tesori Trattoria & Bar.

Then get ready for a whirlwind day exploring the Millennium Park Campus. Begin at the beautiful Chicago Cultural Center, which offers a variety of free arts programs and tours of its magnificent architecture. Next, head to the Art Institute of Chicago, known for its breathtaking pieces that include one of the largest collections of French Impressionist works in the world.

Have lunch at the European-style Toni Patisserie & Café, serving made-from-scratch sandwiches, like the croque monsieur, and delectable desserts. Or opt for the authentic Jamaican dishes, including jerk chicken, at Mr. Brown's Lounge, adjacent to the Hard Rock Hotel Chicago.

Afterwards, stroll through Millennium Park, Chicago’s downtown playground for the arts. View the awesome multimedia Crown Fountain (featuring projected faces of everyday Chicagoans), snap a selfie with Anish Kapoor’s huge reflective Cloud Gate sculpture (affectionately known as The Bean), and catch a performance at the Harris Theater.

Take the gleaming stainless steel BP Bridge to reach neighboring Maggie Daley Park, a spectacular 20-acre oasis that features a winding Skating Ribbon (ice skate rentals are available).

Loop Alliance Custom Content Body Image 3

You can't leave the city without experiencing Skydeck Chicago in the Willis Tower, one of the tallest buildings in the world. When you reach the 103rd floor Skydeck Chicago (the highest observation deck in the United States), you'll be awed by the jaw-dropping city views. For a real thrill, step out onto The Ledge, a glass balcony that extends four feet beyond the building some 1,353 feet up in the air.

For dinner, watch the chefs works their delicious magic in the display kitchen at the Roanoke Restaurant and Club, turning out specialties like rotisserie farm-raised chicken and brick-oven pizzas. Then head out for cocktails and toast your trip high above the glittering city lights from LH on 21 at the historic LondonHouse Chicago, a chic indoor rooftop spot with sweeping views of the Chicago River.

To celebrate the festive season in style, check out Holidays in the Loop brought to you by the Chicago Loop Alliance.

Spend a Weekend in the Chicago Loop - Brought to you by Chicago Loop Alliance.
(Photo Caption:Palmer House Hilton, Tesori Trattoria & Bar and Macy's on State Street)