For the fifth straight year, readers of Condé Nast Traveler have named Chicago the #1 Best Big City in the U.S. Five times is no fluke, especially with more than 800,000 readers voting.
And, really, in any season, it’s easy to see why. There’s never a bad time to visit the Windy City. Even in a snowstorm, Chicago is beautiful.
After countless visits – literally dozens and dozens over the past nearly 40 years – I’ve come to love the day trip, especially using Amtrak’s Hiawatha Service to Union Station. (Even better is a weekend jaunt, which is why I’ve bent the rules here a little and included a hotel suggestion, too.)
Grab a backpack with your phone charger, toothbrush and a change of clothes – for when you decide a day isn’t enough – and hop aboard the train to Chicago.
What to do & see
Chicago Fireboat Tours
111 N. Lake Shore Dr., (312) 919-3367
Climb aboard the 1937 Engine 41, aka the Fred A. Busse Fireboat, and explore the Lake Michigan shore and the Chicago River on this roughly 90-minute tour. You’ll get up close to a lighthouse, see amazing skyline views, experience the lock that connects the river and the lake, learn about the history of Chicago, maybe drink a good local beer and have a great time. Photographs and memorabilia on the walls explain the history of Engine 41. There are historical tours and sunset cruises, too.
Chicago Deep Dish Pizza Tour
Finger Licking Foodie Tours
This self-guided tour gets you a sausage and cheese pie at three of the pioneering Windy City deep dish pizzerie: Uno (the originator), Gino’s (known for its graffiti-laden walls) and Lou Malnati’s (celebrating 50 years in 2021). A web link provides a description of each place – including audio so you can listen while you travel to your next stop. And, thankfully, you can easily walk between them or you’d never make it out alive: Three deep dish pizzas is a lot of deep dish pizzas!
You get to skip the lines of eager, waiting diners, and the restaurants know you’re coming so your pie is ready when you get there and you don’t have to wait 45 minutes for each one to cook! Best of all, you get to see three Chicago dining landmarks so you can compare and contrast.
Art Institute of Chicago
111 S. Michigan Ave., (312) 443-3600
The Art Institute, guarded by its iconic giant stone lions, is anything but a secret, but it is one of the world’s great art museums and despite many, many visits, I never get tired of exploring – revisiting familiar favorites and doing deep dives into collections I haven’t visited in a long time.
Chicago Architecture Center
111 E. Wacker Dr., (312) 922-8687
The center is worth a visit for its displays and great bookstore and gift shop, but while you’re there, sign up for a walking tour of the city or for an architectural boat tour. There are great programs of all kinds and CAC also organizes the annual Open House Chicago every October.
Macy's on State Street
111 N. State St., (312) 781-1000
With the holidays upon us, the Macy's on State Street is a must-see. Built as Marshall Field's, there's an incredible Tiffany glass dome inside, plus holiday decor galore, including classic show windows facing State Street. A little holiday cheer in the Walnut Room is the stuff of memories for families. Here's a history of the building.
Where to eat
Breakfast: Do-Rite Donuts
Great chicken sandwiches for lunch, dinner or snack and top-notch coffee for a buck, but you’re really here for the donuts and more specifically for the chocolate old fashioned which is, to me, without equal anywhere in the world. I’ve never had a donut as crisp and crunchy on the outside and as soft on the inside with such a heavenly chocolate coating. You’re welcome. You're on vacation, so a donut breakfast is OK, but try not to let yourself convince yourself that this is a good option for all three meals today.
224 N. Michigan Ave., (312) 777-9003
Located inside Pendry Hotel in the landmark Carbon and Carbide Building, Venteaux – whose Chef Donald Young is the city's youngest Michelin-starred chef – combines French traditions with great seafood. The vibe is upscale casual, but it’s a hotel restaurant, so everyone is always welcome. The service is friendly and efficient and, best of all, the food is – not surprisingly – delicious. There’s a raw bar, so you can’t go wrong with oysters, and I can vouch for how perfectly the halibut is cooked. Don’t miss the Eggs 5 Ways, with a dollop of caviar, or the lobster pasta (pictured above) with a touch of spice. But even simple classics like the burger and the French onion soup are ace.
Dinner: The Dawson
730 W. Grand Ave., (312) 243-8955
Located on the site of the Dawson Fireplace Mantle and Grate Company, The Dawson is on the western edge of downtown, an easy walk, quick Uber or one-stop CTA El ride from the Loop. Opened by the folks behind The Gage, it’s a lively restaurant and bar with a modern industrial look, plus great craft cocktails. The Wisconsin cheese curds are sinfully good, as were the perfectly seared Hudson Bay scallops with esquites (pictured above). A wood-fired grill is always adding aroma ambience, and a changing selection of dishes is cooked on its fragrant heat. The menu is seasonal and changes often, so the choices I had might not be the same as the ones you’ll be offered, but I’m guessing whatever’s on the menu will be great.
Where to get a beer
Crushed by Giants
600 N. Michigan Ave., 2nd Floor, (312) 702-7963
Chicago has more breweries than any other U.S. city these days (roughly 200), so there are countless places to drink a brew made on-site, but as I noted last year when I visited on its opening day, Crushed by Giants is the first proper brewery in the heart of downtown Chicago.
Launched by the DryHop family of breweries – DryHop, Corridor and Roebuck – the venue, located upstairs in the AMC Theatres complex, has a full on-site brewery, taproom and kitchen and makes a a variety of great craft beers in all styles. Note that although the address is 600 N. Michigan Ave., you’ll find it more easily on the northeast corner of Ohio and Rush.
Not far from downtown you’ll find a cluster of breweries in the Brewing District, which is easily reached by the CTA Green and Pink Lines. There are also a few in the South Loop, too, like Motor Row and Moody Tongue. On the north side are countless fine breweries, including Dovetail, Maplewood and Half Acre, to name but a few.
Make a weekend of it
230 N. Michigan Ave., (312) 777-9000
Because you’ve decided one day isn’t enough, check out Pendry. As I wrote here, in the 1928-29 Burnham Brothers-designed Art Deco Champagne bottle of a building called the Carbon and Carbide Building. The green and gold terra cotta exterior is unique and the lobby is a stunner, with brass elevator doors and Art Deco accents everywhere. The rooms are up-to-date, with classic finishes and views up Michigan Avenue and out west along the Chicago River. Just steps from attractions like Millennium and Grant Parks, State Street shopping, the Art Institute and the Chicago Architecture Center, too. Fun fact: the top of the building is covered in real 24-karat gold (1/5000th of an inch thick).
Best place for a selfie
Cloud Gate, by Sir Anish Kapoor
201 E. Randolph St.
Since 2006, Sir Anish Kapoor’s mirrored stainless steel “Bean” has been THE Chicago selfie site thanks to its cool carnival funhouse mirror effect and its Chicago skyline backdrop. So, while it’s pretty hackneyed, have you really even been to Chicago if you haven’t done a photo there?
However, if you’re looking for something equally striking and a tad less overdone, head 30 seconds east and snap your selfie in front of the Jay Pritzker Pavilion. You’ll get architect Frank Gehry’s shambolic masterwork and part of the Chicago skyline, including the Prudential Tower, in the background.
Born in Brooklyn, N.Y., where he lived until he was 17, Bobby received his BA-Mass Communications from UWM in 1989 and has lived in Walker's Point, Bay View, Enderis Park, South Milwaukee and on the East Side.
He has published three non-fiction books in Italy – including one about an event in Milwaukee history, which was published in the U.S. in autumn 2010. Four more books, all about Milwaukee, have been published by The History Press.
With his most recent band, The Yell Leaders, Bobby released four LPs and had a songs featured in episodes of TV's "Party of Five" and "Dawson's Creek," and films in Japan, South America and the U.S. The Yell Leaders were named the best unsigned band in their region by VH-1 as part of its Rock Across America 1998 Tour. Most recently, the band contributed tracks to a UK vinyl/CD tribute to the Redskins and collaborated on a track with Italian novelist Enrico Remmert.
He's produced three installments of the "OMCD" series of local music compilations for OnMilwaukee.com and in 2007 produced a CD of Italian music and poetry.
In 2005, he was awarded the City of Asti's (Italy) Journalism Prize for his work focusing on that area. He has also won awards from the Milwaukee Press Club.
He can be heard weekly on 88Nine Radio Milwaukee talking about his "Urban Spelunking" series of stories.