From the starchitecture of Millennium Park to that red-hot restaurant scene in the West Loop and down along a truly impressive Riverwalk, the Chicago of today is a very different city from the Chicago of even fifteen, twenty years ago. Not that there was anything wrong with the old Chicago, far from it—it may not have glittered quite so urgently, it may not have been quite so visitor-ready, but there was always this quiet authenticity, a sturdiness, a rooted quality that you won’t find—not yet, anyway—when you’re hanging around the new, streamlined, shiny version of a city that seems eager to forget its roots as hog butcher (and grain futures trader) to the world. Looking to catch a glimpse of classic Chicago? That’s easy—it’s all around you. Here’s your guide to the best day ever in—if you’re asking our opinion—the best Chicago.
Morning coffee at The Monadnock.
Tall, dark and handsome, this early Jackson Boulevard skyscraper—designed in two phases by Burnham & Root and Holabird & Roche—was the biggest office building in the world in its time (the late 1800s). It remains one of the most striking commercial structures standing in the United States today. Hidden in the part of the Loop too many visitors never see, the Monadnock’s ground-floor, block-long shopping arcade is a vintage marvel, filled with nicely-done shops and anchored by a bright, warm café belonging to local coffee legend Intelligentsia. You couldn’t ask for a better start to a Chicago morning. 53 W. Jackson Blvd.
Go get breakfast at Lou Mitchell’s.
Head west along Van Buren Street—under the ‘L’ tracks—and you’ll find yourself in the middle of a seriously classic Chicago scene: The daily flash flood of bankers and traders, bursting out from the suburban rail station, sweeping past the donut shops, the liquor stores, the dimly-lit Italian dives, and into the LaSalle Street financial district. Cross over the Chicago River, and you’ll find yourself at Lou Mitchell’s, one of the Midwest’s most iconic breakfast joints. Lou’s has hosted presidents, it’s on the National Register of Historic Places and they have great waffles and omelets. 565 W. Jackson Blvd.
Ride the Green Line to the Garfield Park Conservatory.
Ready for a real adventure? Head up Jefferson Street and catch the Green Line ‘L’ westbound—this will bring you to a part of the city that barely registers with many Chicagoans, let alone visitors. It’s their loss—right at the helpfully-named Conservatory station, you’ll find one of the country’s finest glass-covered gardens. Finally recovered from a once-in-a-lifetime hailstorm a few years back, you’ll lose track of time in the conservatory’s thoughtfully-designed environments, representing everything from bone-dry desert to the lush tropics, all year round. Don’t miss the permanent Dale Chihuly glass installations tucked away in the pretty Persian Pool, just one of the many highlights of this 4.5 acre, indoor-outdoor complex. Admission is free. 300 N. Central Park Ave.
Go eat a chicken pot pie at The Walnut Room.
Is it time for lunch, yet? It’s not Marshall Field’s department store anymore—ugh, Macy’s, whatever—but give the new overlords some credit, because the 17,000 square-foot dining room at Fields’ former State Street flagship lives on, serving up that famous Walnut Room Salad (the toasted sesame dressing remains a staple in some Midwestern households) and delectable chicken pot pies, based on an 1890 recipe. The room is remarkable (come early and get a seat by the window, looking out to State Street) but this is by no means a fancy place—come as you are. Fun fact: The Walnut Room was the first restaurant ever opened in a department store, back in 1907. 111 N. State St.
See the world’s largest Tiffany glass dome (and much more).
You could go stand inside the Chicago Cultural Center and stare up at this beauty until your neck hurts and you’d have gotten plenty from your visit to what used to be the city’s central public library, but there’s so much else going on inside this neo-classical complex dating back to 1897. One of the city’s most impressive public spaces, the center buzzes with events and top-notch installations and exhibits. Located just across the street from Millennium Park, it’s a crosswalk away from your selfie-at-The-Bean moment. 78 E. Washington St.
Book a tour with the Chicago Architecture Foundation.
There are river cruises and then there is the one you take with the Chicago Architecture Foundation, where they actually know their history and other cool details you won’t learn with the other guys. Stop in their terrific Michigan Avenue shop to check out your options; regularly scheduled and affordable walks are available as well. Make time for at least one of their tours. 224 S. Michigan Ave.
Explore a vertical artist’s colony.
The Fine Arts Building on Michigan Avenue looks a lot older than its 120+ years and is a marvel on its own, but it also happens to still be a hive of creativity. Visitors are encouraged to explore the building at will—go ahead, poke your nose in any open doors, who knows what you’ll find. Make sure to ride the manually operated elevators, walk the staircases and check out the murals, too. This is one of the last things people expect to find in the money-driven Loop and among the best. 410-418 S. Michigan Ave.
Stop for an afternoon pick me up in the Loop’s oldest building.
Ask a Chicagoan for directions to Pickwick Lane and they’ll likely look at you funny, but it’s totally a real thing—at the end of the narrow, cobbled alleyway is Pickwick Coffee Roasting Co., one of the Loop’s most appealing cafés. Like most self-respecting Chicago coffee spots, they roast their own. Cookies, scones and tea (for non-coffee-having-types) are also available. 22 E. Jackson Blvd.
Clean up your act at Merz Apothecary
It’s been a staple of the North Side Lincoln Square neighborhood since 1875, but there’s no need for a long ‘L’ ride. They’ve got an outpost at the equally vintage-y Palmer House hotel, making for a potent one-two punch of old schoolness. Their vast collection of bath, body and skin care product and helpful staff could convert any skeptic—men will feel right at home. Even if you don’t need anything, poke your head in for a second. (It smells great in here.) 17 E. Monroe St.
Cocktails at The Drake
A civilized relic at the top of the Magnificent Mile, one of the city’s most iconic hotels hasn’t lived up to its potential in decades now, but it’s still here, and, in small doses, The Drake can be terrific. Choose from a selection of bars at which to order a classic cocktail, then settle in for a serious study of the Gold Coast neighborhood and the people who live there. Our pick would be the Coq d’Or, is a piece of history within a piece of history—it’s been open since the end of Prohibition. 140 E. Walton Pl.
Dinner at Gene & Georgetti
Two of Chicago’s most favorite things—slabs of red meat and giant portions of decent Italian-American cooking —come together for your dining pleasure under one, very old roof. You can eat more up-to-the-minute food at your pick of other restaurants in town, but they won’t have the ambience, the white-apron service and the all-around atmosphere of this River North classic, now in business for roughly 75 years. It’s magic. 500 N. Franklin St.
Booking a trip?
If you’re looking for the lowest airfares to Chicago, start by noodling around on CheapFlights or BookingBuddy—both will compare multiple sites at once, saving you a lot of running around. When you’re ready to book, we recommend Orbitz or Expedia—both offer 24-hour cancellation policies, allowing you to lock in the lowest fare while you finalize your plans. (As always, read the fine print first.) Just on here looking for the best Chicago hotel deals? Start by searching TripAdvisor, or Hotels.com, but don’t book anything without a stop at Priceline, where you can save up to 60% on any given night by taking advantage of their Express Deals feature. (This simple tool has probably saved us—no joke—thousands of dollars, over the years.). Finally, if you need a rental car, begin your search by swinging wide to get a sense of the market—BookingBuddy lets you check pretty much every site worth knowing, with just a couple of clicks.