The Windy City. Home to Second Street comedy, which has produced some of the greatest comedians of our time. Home to the Cubs, the Bears, the Blackhawks and the Bulls, not to mention the real animals at the Lincoln Park Zoo. Once a town that paled in comparison to St. Louis, it’s now the third-largest city in the U.S., and it’s just five hours away.
For the major tourist attractions, try Navy Pier and its soon-to-be-new giant Ferris wheel (the old one is heading to Branson). The area is a little kitschy, but the views of Lake Michigan are gorgeous. For the quintessential big-city feel, stay and shop on Michigan Avenue, aka the Magnificent Mile, where you’ll find giant Nike, Apple, Lego and Chanel stores.
Shedd Aquarium: St. Louis has nothing like the Shedd Aquarium with its 32,000 animals and sweeping views of Lake Michigan. Don’t miss the show at the Oceanarium’s amphitheater, where you’ll see beluga whales and dolphins do tricks. Then go below and see them swimming and interacting with one another and guests. Admission is $39.95 for an adult “total experience” pass, which includes shows. The website says the waiting line for tickets can be two or more hours, so order online at sheddaquarium.org
SkyDeck Chicago and 360 Chicago: Want to get a bird’s-eye view of Chicago? These observatory towers offer stunning views. SkyDeck Chicago is Willis Tower’s version (Willis is the former Sears Tower and for 25 years the tallest building in the world). Its highlight is a clear glass ledge, surrounded by windows, that you step out on, 103 stories above the city. On a windy day, you can reportedly feel the building sway. Exhibits and a short movie on architecture round out your visit. $19.50 adults. TheSkyDeck.com. The Hancock Tower features the Observatory (or 360 Chicago), which has a 360-degree view of the city, up to four states, and a distance of over 80 miles from the 94th floor. The Observatorhas Chicago’s only open-air SkyWalk (wear a jacket; it gets windy). New this year is an attraction called Tilt, where you lean out over Michigan Avenue in glass-enclosed cases ($7 extra). $19 adults, 360Chicago.com. If you don’t like elevators packed with people, these attractions may not be for you (though the elevators do move really fast).
The parks: You may not automatically think of parks when you think of Chicago, but maybe you should. It’s the parks along the shoreline of Lake Michigan that bring you beaches and fun in the summer. Millennium Park, with its stunning artwork, brings you concerts (along with Grant Park) and ice skating, right in the heart of downtown. And a new addition to the parks system, the 606, a 2.7-mile elevated trail (like Manhattan’s High Line), takes you from one neighborhood — Bucktown, Humboldt Park and Logan Square —to the next amid great views and temporary art installations. chicagoparkdistrict.com, the606.org
PLACES TO STAY
The Palmer House a Hilton Hotel: In the middle of the Loop, the theater and arts district and just a couple of blocks from Millennium Park, you’ll find the historic Palmer House. From the minute you walk in, the elaborately frescoed lobby, painted by Frenchman Louis Pierre Rigal, will take your breath away. The 1,641-room hotel feels surprisingly homey and comfortable. It also feels surprisingly new and hip, with its posters of Hollywood icons hanging throughout. The décor is modern, yet the doors and doorknobs, molding and other features give it an old-world feel (the hotel was built in 1871, making it the longest continually operated hotel in the U.S.). Our room was quite large, and reasonably priced. We got the $166 Chillcation package (available through April 30), which included half-price parking and a free breakfast for two in the elegant Lockwood restaurant. palmerhousehiltonhotel.com
Peninsula Chicago: If you prefer to stay along Michigan Avenue, the Peninsula is a French Deco work of art on the same block as Tiffany & Co. and Banana Republic. The AAA Five-Diamond establishment is all about luxury, from comfy slippers to its award-winning spa. Rooms start at $530 a night. chicago. peninsula.com
PLACES TO EAT
Chicago-style pizza: This city is known for its deep-dish pizza baked with a high edge and deep surface, lots of cheese and chunky tomato sauce (and often, but not always, a cornmeal crust). There are any number of places to get this pizza, but favorites are Gino’s East with its graffiti-covered walls and Giordanos’s with its classic charm. Their signature restaurants are just off Michigan Avenue, but both have multiple locations.
Big Jones: Is it odd to send you to a Southern restaurant in Chicago? Not when the restaurant is Big Jones and the chef is Paul Fehribach, a scholar of Southern cuisine whose recipes reach back beyond the usual suspects to dishes from the early 20th and even the 19th century. You don’t need to know any of that to enjoy incredible breads, fried catfish, pimento cheese and more — especially fried chicken to rival any you’ve eaten in the true South. bigjoneschicago.com
Topolobampo: Rick Bayless is the rare celebrity chef who has maintained a level of excellence at his restaurants while still churning out cookbooks and TV programs. Actually, “maintain” is the wrong word, because Bayless and the staff at his high-end Mexican restaurant Topolobampo are constantly innovating, reaching deeper into the many regional variations of the country’s cuisines to create thrilling new menus. If you don’t want to splurge on Toplobampo’s tasting menu, you can enjoy the more casual — but always packed — Frontera Grill or the fast-casual Xoco. rickbayless.com
America’s Cup: The first America’s Cup freshwater race in the event’s 164-year history takes place in Chicago, June 10-12, acws-chicago.americascup.com
The Chicago Blues Festival: June 10-12, chicagobluesfestival.us
The Chicago Jazz Festival: Sept. 1-4, jazzfestival2016.com
Lollapalooza: July 28-31, lollapalozza.com
Chicago Food + Wine Festival: August (dates not set), chicagofoodandwinefestival.com
Chicago Gourmet: Sept. 23-25, chicagogourmet.org
Ian Froeb of the Post-Dispatch contributed to this report.