48 Hours in Wintry Chicago
A winter getaway to a cold city? Yes, and here's how to maximize your fun.
Winter in the Midwest isn’t fun, but it doesn’t have to be that way. Milwaukeeans can find a quick, cosmopolitan respite from the day-to-day grind with a jaunt just 90 miles south to their favorite suburb, Chicago.
The Second City (though really the third-biggest U.S. city) has a lot to offer, even for regular visitors. When the weather outside is chilly, the city has a dizzying array of options for tourists ranging from galleries and museums to restaurants and bars.
This guide is in no way comprehensive, but gives you plenty to get out and experience on a cold weather weekend, and more than enough fun to keep you busy for 48 fast-paced hours.
How To Get There
There’s only one way a Milwaukeean should ever get to the Windy City, via the Amtrak Hiawatha Service. The 90-minute ride from downtown Milwaukee to the heart of Chicago eliminates the hassle and headaches of driving, the discomfort of riding the bus, and the absurdity of taking a 20-minute flight. Fares start at $22 each way, which is less than what someone will spend on tolls and parking in The Loop.
Where to Stay
Chicago, like Milwaukee, has seen a wave of new downtown hotels open in the past few years. One that stands out is the Conrad Chicago (101 E. Erie St.), which opened in early 2017. Owing to its history as the offices of advertising giant FCB, the hotel’s two-story lobby on the building’s top floors has a distinctly Mad Men-esque vibe with a mid-century design accented with modern touches.
The five-star, 289-room hotel has a variety of room types to suit every type of traveler, ranging from 1,557 square-foot presidential suites to 400 square-foot rooms with king-sized beds, 65-inch televisions and views of the iconic Magnificant Mile of Michigan Avenue.
Guests and visitors alike will enjoy 20th-floor restaurant Baptiste and Bottle, which serves up classic American dishes with a modern twist. I personally enjoyed the mac and cheese with jalapenos and the triple seared prime New York steak. The restaurant prides itself on its bourbon selection and pairs that with a variety of cocktails, including the Chocolate Whip (hot chocolate, brandy, bourbon and grand marnier) that is presented with a fiery display.
If you stop by in the warmer months, the rooftop restaurant and bar, Noyane, features great city views, a wide variety of sushi, and delicious drinks.
Members of the Hilton Honors rewards program can leverage their points to stay at the hotel.
What To Do
The Art Institute of Chicago
A variety of special exhibits consistently breathe new life into this large art museum. You’ll find a number of great works featured in your introductory art classes, including American Gothic by Grant Wood, and course the museum’s remarkable impressionist collection, including the Monet haystacks. Once you’re done at the art museum, head up N. Michigan Ave. to the Chicago Cultural Center, which has free admission and the largest Tiffany glass dome in the world.
If art isn’t your thing, head down to the Museum of Science and Industry.
You’ve never seen so many Italian products under one roof outside of Italy. Stop by, browse the two-floor store and enjoy a quick snack (43 E. Ohio St., River North).
Looking to do little shopping while you’re in town? There are countless shops on Michigan Ave., but my favorite local shop is Foursided. They have a variety of quirky tchotchkes and Chicago gifts. (2958 N. Clark St., Lincoln Park).
John Hancock Observatory (360 Chicago)
There is a bit of an arms race underway between Chicago’s two tallest observation decks. At 360 Chicago, you can “ride” in the tilt, which leans you out over the city, a 1,000 feet from the ground. It’s a unique experience, but make sure to go on a clear day (875 N. Michigan Ave., River North).
The Magic Parlour
I admittedly wasn’t sold when my wife pitched me this idea. A magic show, really? But I was pleasantly entertained. Led by magician and mentalist Dennis Watkins, the show features a series of twists and turns that keep you guessing, and entertained. Performed inside the Palmer House Hilton Hotel (17 E. Monroe St., The Loop).
If you haven’t been, you must go. If you have been, skip the tourists. For the uninitiated, this is the iconic park built atop a railyard that features Cloudgate (The Bean) and a variety of other engaging pieces of public art. A winter bonus is a skating ribbon in adjacent Maggie Daley Park (201 E. Randolph St., The Loop)
I have a nostalgic streak in me for vintage video games. Replay, a Lincoln Park bar, features a variety of vintage arcade games and pinball machines available at the right price… free. That’s right, all games are free to play and the beer isn’t too absurdly priced. It was a welcome indoor activity while it was freezing outside. So whether it’s The Simpsons or NBA Jam, grab a cold one and battle your friends (2833 N. Sheffield Ave., Lincoln Park).
Poised to be redeveloped in the coming years, the neo-Gothic skyscraper was originally home to the Chicago Tribune newspaper offices. While tours inside are only available on rare occasions, the facade along N. Michigan Ave. offers a global mini-experience: Embedded in the facade are fragments of buildings from around the world (435 N. Michigan Ave., River North).
Where To Eat
Be prepared to wait. But don’t fret, at the end of the line is one of the best burgers of your life. This small restaurant has been drawing rave reviews since it opened in 2012 (800 W. Randolph St., West Loop).
Looking for breakfast? Look no further than Firecakes Donuts. They’re my favorite Chicago donuts, and I’ve tried a number of them (68 W. Hubbard St., River North).
Green Street Smoked Meats
This unassuming barbecue joint is tucked away in the booming West Loop neighborhood. Portions are set up in sizes that are easy to share. Prices are affordable. You won’t leave hungry (112 N. Green St., West Loop).
Little Goat, a modern diner, is a spin-off of Stephanie Izard‘s award-winning Girl and the Goat Restaurant. It features a wide range of up-scale comfort foods (820 W. Randolph St., West Loop).
Revival Food Hall
Spending only 48 hours in Chicago doesn’t leave you with enough time to try every highly-rated restaurant. You can cut some corners by stopping at Revival Food Hall (125 S. Clark St., The Loop). The food hall, an emerging dining concept, features all local restaurants. There is barbeque from Smoque, fried chicken from The Budlong, delicious cookies from James Beard award winner Mindy Segal of Mindy’s HotChocolate, and tacos from Antique Taco Chiquito. There are plenty of healthy options as well, but do calories count on vacation?
This Rick Bayless restaurant (449 N. Clark St., River North) features a wide variety of tortas in a casual atmosphere. The “fully dressed” guacamole was perhaps the most unique I’ve ever had, if not the best. Don’t miss out on the churros.
Baptiste and Bottle
See our description above in Where to Stay.
Where To Drink
Billy Goat Tavern
A Chicago classic that you have to experience at least once. Stop on down (it’s underneath Michigan Ave.) for a cold Schlitz and a cheeseburger. The restaurant was made famous by Saturday Night Live (“Cheezborger, Cheezborger, Cheezborger, No Pepsi… Coke”). Don’t expect much in the way of frills and they won’t expect much of your cold hard cash (430 N. Michigan Ave., River North).
After leaving The Magic Parlour at the Palmer House Hotel, we were searching for a welcoming tavern to debate how we were fooled by the magician. We stumbled upon Miller’s Pub, hidden off of State St. in the heart of The Loop (134 S. Wabash Ave.). Inside you’ll find a mix of locals and tourists, a friendly staff and above-average beer selection. The later you’re there the better the people watching seems to be.
There is one thing Milwaukee will seemingly always have over Chicago, the downtown bar scene. There are plenty of bars in the heart of Chicago, but few of them are as accessible. An exception to the rule is Monk’s Pub, hidden by the ‘L tracks on Lake St (205 W. Lake St., The Loop). They boast a great beer selection, friendly staff and good bar food.
Will’s Northwoods Inn
If you happen to be in the city while the Green Bay Packers are playing, you’ll feel right at home at Will’s Northwoods Inn (3030 N. Racine Ave., Lakeview). The large bar is dedicated to the green and gold, a welcome respite in the home of the Bears. Game days feature the game blaring along with bratwurst, beer, free popcorn and most importantly, cheese curds.
How To Get Around
Chicago features a robust transit system. If the weather allows for it, walk as much as you can. If you’re in The Loop and freezing, check if you can use the underground Pedway System. Signage isn’t great, but if you have a map you can navigate the system.
The Chicago Transit Authority provides bus and ‘L service via one fare card. If you’re a regular visitor to the city, the card is a must-have. This is probably easiest way to get from Union Station into the heart of the city.
Chicago has a bike sharing system, Divvy, that offers unlimited three-hour daily rides for $15 or a single 30-minute trip for $3/hour. Milwaukeeans will find many more docks spread across the city than the Milwaukee system.
Uber, Lyft and a number of taxicabs are readily available in the heart of the city. They’ll get you door-to-door, but at rush hour things can be pretty congested.