The Loop is Chicago’s vibrant urban and cultural hub, named for the distinctive elevated train tracks (called the ‘L’) that loop around it. You’ll find world-class museums, on-trend shops, and boutiques, award-winning dining, and exciting nightlife within its boundaries — south and east of the Chicago River and north of Ida B. Wells Drive. Whatever you love, you’ll find it in the heart of the city.
Day 1
Breakfast
Start your weekend decadently with a trip to Stan’s Donuts for enormous sugary goodies. Or stop into Goddess and the Baker for a smorgasbord of sweet and savory treats. If you feel a little guilty afterwards, you can work off the calories at Millennium Park’s free outdoor yoga classes, available over the warm weather months. Or take a stroll along the beautiful Lakefront Trail any time of year to take in serene views of Lake Michigan.
See the sights
A guided ride with Big Bus Tours is a fun way to get your bearings and hop on and off at the sights you’d most like to explore. Or see the city’s amazing architecture on foot with a Chicago Architecture Center walking tour, or by boat on the center’s Chicago’s First Lady Cruise.
Drop into the Chicago Architecture Center box office for tour tickets, but not before you’ve explored its galleries. Building Tall, located in the Skyscraper Gallery, is a great immersion course into Chicago’s architectural legacy, as well as ground-breaking world architecture. The exhibit catalogs significant achievements in skyscraper design — particularly fitting given Chicago’s status as the birthplace of the modern skyscraper.
Lunch
Sample the extensive German-American menu and craft brew list at classic Chicago restaurant The Berghoff, which first opened its doors in 1898. Or stop into the Lockwood Restaurant at historic Palmer House Hilton to try the brownie in the place where it was invented.
Shop
Spend the afternoon browsing historic State Street. Give your wallet a workout at the fashionable flagship Macy’s State Street, housed in a landmark building. Then check out Block 37, home to a bunch of hip stores and eateries.
Dinner and a show
For dinner, pick from one of three restaurants within Italian Village, a long-time Loop favorite that’s been run by the Capitanini family since 1927. The Dearborn is a modern American tavern with a laidback vibe and refined takes on the classics.
All these spots are right in the Chicago Theatre District, where you can see a hit Broadway In Chicago performance at one of the Loop’s historic theatres. Or you can hop over to the architecturally stunning Lyric Opera to soak in some classical culture. Both the Lyric and many of the Loop’s theatres offer behind-the-scenes tours, which are a fun way to experience a little of the limelight.
If you’re in the mood for an indie flick instead, check the schedule at the Gene Siskel Film Center, named for the famed film critic and operated by the School of the Art Institute of Chicago.
Late night
Amp up your evening with a fast-paced game of ping-pong at AceBounce, followed by dancing on the 27th floor at the wildly popular Roof on theWit. You can also do some roof raising at Raised – An Urban Rooftop Bar at the Renaissance Chicago Downtown Hotel. It features a sleek indoor/outdoor lounge and private VIP greenhouse.
Day 2
Breakfast
Begin your morning with a tasty brunch. You’ll be treated to spectacular Millennium Park views and scrumptious dishes at Cindy’s, perched on the 13th floor of the architecturally stunning Chicago Athletic Association Hotel, whose building dates from 1893. Or grab early morning breakfast at The Atwood, an airy and luxurious restaurant located in the Staypineapple Hotel right on State Street.
See the sights
Get ready for some exploring at Millennium Park Campus. Begin at the Chicago Cultural Center, where you’ll see the largest Tiffany stained-glass dome in the world, art exhibits, classical concerts, dance performances, and more — and all for free.
Next, head to the Art Institute of Chicago, one of the largest and oldest art museums in the United States. Don’t miss the museum’s collection of Impressionist and Post-Impressionist art, one of the most extensive outside of the Louvre in Paris.
Lunch
In the summer, head to Millennium Park’s McCormick Tribune Plaza to enjoy outdoor dining with views of The Bean and the surrounding skyline.
More sights
From either dining spot, you’ll be perfectly positioned to explore the rest of the Millennium Park Campus, including Cloud Gate, aka “The Bean,” interactive Crown Fountain, the Boeing Galleries for outdoor art exhibits, and the Jay Pritzker Pavilion, where you may be lucky enough to sit on the Great Lawn in time for some live music or an evening movie screening.
You can also take the gleaming stainless steel BP Bridge to neighboring Maggie Daley Park, a spectacular oasis that features rock-climbing walls, a Skating Ribbon, mini golf, tennis courts, and a surreal play garden.
Evening
Explore the Chicago Riverwalk after dusk, and you’ll be wowed by Art on theMART, the world’s largest digital art projection, displayed on 2.5 acres of theMART’s Riverwalk-facing facade (Wednesday to Sunday from March through April and daily from May through December). Then stroll the Riverwalk’s coves to discover wining and dining, boat excursions, and even more public art.
Late night
Toast your trip high above the glittering city from LH on 21 at LondonHouse Chicago, a chic indoor rooftop spot with sweeping views of the Chicago River. Or enjoy late-night Belgian-inspired mussels and beer at Fisk & Co. at the Kimpton Hotel Monaco Chicago. For a little dancing thrown in, head to Cerise at the Virgin Hotel Chicago. It’s a fun-loving, playful spot overlooking the Chicago cityscape from 26 floors up.
Insider tip: Free Chicago Greeter tours
Get an insider’s look at the Loop with a free Chicago Greeter or InstaGreeter tour. Chicago Greeter pairs you with a knowledgeable local who’ll show you around the Loop or any of the city’s neighborhoods you choose. You can even pick your preferred language and theme — like architecture or food and drink. Book today.
