Jeramey Jannene
Urban Guide

48 Hours in Wintry Chicago

A winter getaway to a cold city? Yes, and here's how to maximize your fun.

By - Mar 9th, 2018 12:11 pm
Chicago in the Winter. Photos by Jeramey Jannene.

Chicago in the Winter. Photos by Jeramey Jannene.

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).

Millennium Park

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).

Tribune Tower

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

Au Chavel

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).

Firecakes Donuts

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

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).

Miller’s Pub

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.

Monk’s Pub

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.

5 thoughts on “Urban Guide: 48 Hours in Wintry Chicago”

  1. GRNDPAKWH says:

    I grew up in Chicago and once worked at then the tallest building in the world, The Prudential Building, which is now a shadow of a Starbucks and overlooks Millennium Park. We will do at least one weekend in Chicago every winter. Our budget does not allow a loop hotel so we take advantage of the O’Hare hotel specials then utilize the CTA from Mannheim road downtown in under thirty minutes.We also have access from that same CTA station to all the great neighborhoods in Chicago. I highly suggest the Garfield Conservatory which is free, with a donation. Hop on and off the “L” for great ethnic foods.
    Like Milwaukee,Chicago is a safe city to visit.The violence you hear about is all concentrated in a very small area.

  2. MidnightSon says:

    I might add that Miller’s Pub is also a great place for dinner. Old-style menu for steaks, chops, Italian, burgers, etc. Very good food, above average portions, and reasonable prices. (My favorite is two 10 ounce pork chops with potato and salad…and bread basket…for just $19.25. Just add a couple manhattans! (Or old fashioneds.).

    It’s gets busy, so reservations help. Made only by phone.

  3. TransitRider says:


    Unless I’m missing something, Chicago’s Prudential Building (601 feet tall) was never the world’s (or even America’s) tallest. New York has over a dozen buildings that are both taller and older.

  4. Ron Hockersmith says:

    I want the Amtrak to Chicago to work, but as soon as you aren’t traveling alone, it doesn’t add up. You can drive a car and park it in Chicago overnight for less than the $88 it will cost you to take the Amtrak roundtrip for two. Since many of my favorite places in Chicago aren’t in the loop, you have to add in additional costs to get to Logan square or wicker Park or Pilsen. Spothero with a little advanced planning can get you secure overnight parking for half the cost of hotel parking.

  5. Gregg Mulry says:

    To each his or her own, I guess. Yes, with careful planning, two people might be able to get to and from Chicago with a bit less expense with a car than on the train. However, driving means you do it, the traffic can be horrendous, parking garages are no fun, and finding further parking wherever you choose to go in the city isn’t either. In addition to wear and tear on me, there is some on my car as well. For me, the train, a Ventra card (no cash needed for the L, buses and Metra), plus Lyft and Uber are far less hassle for getting there and getting around. Hotel specials are available from time to time in the Loop and Michigan Ave areas, so check. Right before Christmas for example several are listed under $100 a night. And there you can walk to a plethora of things.

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