Chicago, America's “Second City,” is home to several captivating museums, theaters and nature centers; its bustling downtown Loop; and, of course, its miles of Lake Michigan shoreline. Riding the famous “L” train is a good introduction to the city. And, if you’re a baseball fan, a pilgrimage to Wrigley Field is a must. (Airlines: American, Frontier, Southwest, United)
When to go
Spring. You need to be of hardy stock to visit Chicago during its legendary winters. The warmer months are perfect for exploring its history.
What to do
Learn all about Chicago’s past at the Chicago History Museum, where you can revisit the Great Fire of 1871 and take in seldom-seen images shot by suburban nanny and legendary street photographer Vivian Maier. You can’t miss the Chicago Architecture Center River Cruise Aboard Chicago’s First Lady, which points out skyscrapers like the Willis Tower along with Navy Pier and the Wrigley Building. And what would your visit be without a stroll in Grant Park, enjoying Millennium Park, Buckingham Fountain and the waters of Lake Michigan?
Where to eat
So many choices, but here are three. Check out one of the 57 Lou Malnati’s Pizzeria locations for classic Chicago deep-dish. Chef José Andrés’ Bar Mar and Bazaar Meat, meanwhile, mix the best of both worlds, with a fun seafood bar and meat emporium. The Berghoff has been family-owned for more than a century, with staff members working there for generations and serving up traditional German food like wiener schnitzel, along with American faves and more.
Where to stay
Enjoy an aura of history at the Hilton Palmer House, which recently celebrated its 150th anniversary. The building was originally a wedding gift from Potter Palmer to his beloved Bertha, who, of course, helped put Sarasota on the map. Or try a boutique experience at the Allegro Royal Sonesta Hotel in the heart of the theater district. An easy family-style option is the Embassy Suites downtown, where you can book a suite and enjoy an indoor pool.
A few other recommendations...
A book to pack
Carl Sandburg’s Chicago Poems. This 1916 collection is a memorable introduction to the Windy City’s rep as a gritty, hard-working industrial and agricultural center—“The City of Big Shoulders.”
A movie to watch
Sure, you could watch the movie version of Bob Fosse’s murderous Chicago, but for something more upbeat, how about John Hughes’ Ferris Bueller’s Day Off from 1986? It’s a love letter from the director to his adopted city.
A record to put on
Well, duh, anything by the band Chicago, but especially perhaps Chicago II, which delivers both the classic “25 or 6 to 4” and “Colour My World”—a mandatory prom dance song in Chi-town and beyond back in the day.