First Timer’s Guide to Chicago in the Winter
Excerpts from an article that originally appeared in Locale Magazine.
The Windy City certainly has earned its reputation as being cold. However, if your plans take you to Chicago, that doesn’t mean that you have to stay inside! From outdoor activities to great food, to live music, there’s no reason to stay inside (although the great bars in the city certainly make a strong argument). So, trade in your flip-flops for boots and your tank top for a sweater and head to the Midwest for some fun.
OUTDOOR SPORTS
Winter can be a brutal business in Chicago, but that doesn’t seem to be stopping anyone from being outside! Chicagoans can be seen outside all times of the year, day and night, regardless of the wind, cold, or snow. Here are just a few ways you can embrace the cold while still having fun!
Ice Rinks in the Chicago Park District
337 E Randolph St
Chicago, IL 60601
312.742.3918
www.chicagoparkdistrict.com/parks/maggie-daley-park
There are eight outdoor rinks run by the city that are free to skate on (skate rental is available and the cost varies by location). The newest addition this year is the Maggie Daley Ice Skating Ribbon, which is the city’s most popular rink this year. The Ribbon is set between the lake and the city making for breathtaking views of the skyline while on the ice. Unlike other rectangular shaped rinks, this is a quarter mile loop with gentle slopes that is an innovative design. Get to the rink as soon as it opens and avoid weekends whenever possible as the rink gets crowded quickly, and the ice conditions deteriorate. If the crowds and/or the rental line is too daunting from the Ribbon, the ice rink in Millennium Park is within easy walking distance and often considerably less crowded.
Snowshoeing on Northerly Island
1400 S Linn White Dr
Chicago, IL 60605
312.745.2910
www.chicagoparkdistrict.com/parks/Northerly-Island
When the snow covers the ground, it’s a great opportunity to go out snowshoeing. Snowshoeing is extremely easy and requires no previous experience; all that is needed is at least three inches of snow cover. The fee to rent snowshoes is just $5 at the park, so it makes a cheap activity and is certainly not something commonly available in Southern California. Should you not want to venture to Northerly Island, the REI in Lincoln Park also rents snowshoes ($29-$35 per day). You can rent the shoes and take off to one of the city’s many parks. A great place to snowshoe is the Lincoln Park Zoo where you can see how the animals handle the snowy weather. Admission to the zoo is free and is open 365 days a year.
ARTS & MUSIC
From improv to blues to jazz, clubs are numerous in Chicago so there is always somewhere to go when the sun sets. With many clubs having sets that begin at 2am or 3am in the morning, night owls will never be bored.
Second City
1616 N Wells St
Chicago, IL 60614
312.337.3992
www.secondcity.com/locations/chicago
This famous comedy theater that dates from 1959 has turned out more famous stars than nearly anywhere else: Tina Fey, Steve Carell, Mike Myers, and John Belushi just to name a few. Always original, always funny, you never know what you are really going to see when you show up. A Chicago classic and not to be missed, Second City troupes perform at various clubs around the city in addition to their main stage on North Wells. All the shows are improvisational, so even the actors don’t know what’s really going to happen each night.
The Green Mill
4802 N Broadway Ave
Chicago, IL 60640
773.878.5552
If you want to hear jazz, at virtually any time of the day or night, this is the place to go. Steeped in history, this club dates back to the early 1900s. During Prohibition, a network of tunnels under the club was used by gangsters for all sorts of illegal business. In fact, you can still sit in Al Capone’s booth where he and his henchmen were able to see both entrances to the club from this vantage point. History aside, the jazz played at the Green Mill runs the gambit from traditional to bebop to improvisational so you can never be sure exactly what you are going to hear on any given night. This is a place for serious jazz aficionados though, not a place to sit and talk (you may actually get shushed should you try to have a conversation while the music is on). That doesn’t matter though, as you’ll want to give your full attention to your cocktail and the music.
Kingston Mines
2548 North Halsted
Chicago, IL 60614
773.477.4646
If blues is more your style, head over to Kingston Mines where the unique split room layout of the club allows for one band to set up while the other is on stage. When one group’s set is done, everyone picks up their drinks and walks over to the other side of the club where the next band is ready to play. This two-stage format has been in operation since 1968 and is open every night until at least 4am. You can get both food and drink at this club although given the size of the crowds on some nights, you don’t want to be eating a full dinner here while people are streaming past. This is a great place to watch not just the musicians but other patrons as well; seeing others, you won’t be able to help but get swept up into the music yourself.
EATING
Pizza, pizza, and more pizza, that is what most people think of the Chicago food scene. While some great pizza can be found here, there is so much more going on that is worth checking out. Come hungry!
Elizabeth Restaurant
4835 N Western Ave, Unit D
Chicago, IL 60625
773.681.0651
This Michelin two-star restaurant is not for the budget conscious or unadventurous eater. If you have any interest in local foods prepared in ways that can only be described as dazzling, then this needs to be a destination for you while in town. The idea behind Elizabeth is to offer only food from their garden, the woods, local farmers, fishers, and hunters. The menu varies and is entirely dependent on the season. Currently on the menu is bear from local hunters, fried mushroom (the mushrooms having been foraged by the kitchen staff themselves), and Great Lakes salmon (vegetarians can also be accommodated). What you can be sure of is that the experience will be an education in native North American foods, and every course will have you amazed in both the presentation and taste. Even better, there is an open kitchen so you can see each course artfully being prepared. It is highly recommended that you do not eat before dining here as you will be served anywhere from 12 to 20 small courses depending on the menu. As the restaurant seats very few, reservations must be made and pre-paid in advance, but every penny is well worth it.
Eataly
43 East Ohio St
Chicago, IL
312.521.8700
Eataly is a creation of Mario Batali, who has done his best to relocate part of Italy to downtown Chicago. This two-story grocery store/espresso bar/cooking school/restaurant has literally everything you could want when it comes to Italian cuisine. The best cappuccino this side of the Atlantic can be found here. Gelato with milk from Italian cows is handmade in the store. Pasta is rolled on-site. Cheese is made daily. Freshly baked bread is always available. Basically, everything they serve in any of their micro-restaurants on the second floor is made in the store, from scratch. The micro-restaurants all specialize in different types of food. In the mood for fish? Try La Pesce & Le Verdure. Want meat? Eat at La Carne. Want pasta? Stop by La Pasta. The store even has a Nutella counter where Nutella is spread on all manner of foods. You can spend hours in this store, but even if you just stop by for a coffee or a gelato, it will be well worth it.
Pequod’s Pizza
2207 North Clybourn Ave
Chicago, IL 60614
773.327.1512
There is no shortage of pizza places in Chicago, and every Chicagoan will be happy to tell you their personal favorite (they will also want to share the places that they think are horrible). My personal favorite is Pequod’s. With only one location in the city, the lines for this pizza place are often out the door, and the wait can easily be 2 hours. I have waited the 2 hours and I can honestly say it was worth it. What makes this pizza joint unique is that they bake their pies until the crusts become caramelized. As a result, the restaurant has a cult following among locals. Chicago style pizza takes around 40 minutes to cook, so when you put in your name, it would behoove you to order your pizza at the same time. That way, when there is finally a table available, your pizza is ready and delivered to you right away. This is also a great place for lunch as they have the best lunch special around: a PBR and a personal pan pizza for $5. If you can beat that, let me know.
TO DRINK
Chicagoans like beer. There is no getting around this fact. What this means is that at every bar and restaurant in the city, you will be able to choose from dozens of micro-brews produced locally. Cheers!
Guthrie’s Tavern
1300 W Addison St
Chicago, IL 60613
773.477.2900
If you like to drink and you like board games, then this is the place for you. Located near Wrigley Field, this bar encourages its customers to pass hours here playing from one of dozens of games they keep the bar stocked with. The range of games available is wide: Sorry, Cards Against Humanity, Scrabble, etc., so no matter what kind of game your group likes to play, they probably have something you can all agree on here. You can order food from restaurants nearby and eat it here as Guthrie’s only serves drinks—lots on tap, reasonable prices and tons of fun!
Hopleaf
5148 North Clark St
Chicago, IL 60640
773.334.9851
This popular beer bar is known for its wide variety of Belgian beers on tap. But really, any kind of beer that your heart may desire can be found on draft here. The draft beer menu goes on for pages as does the bottled beer selections. If you can’t find a beer you like here, then you clearly don’t like beer. You can have a beer at the bar while you wait for a table (reservations are not accepted, and the restaurant is often busy) and then try something different with dinner. Food here is hearty with Winter Vegetable Gratin and Risotto currently on the menu in addition to classic Belgian items such as Pomme Frites (with garlic aioli) and Mussels. This is a great place to hide out when the weather gets cold and warm up with some good food and drink.
Emporium Arcade Bar
Wicker Park
1366 North Milwaukee Ave
773.697.7922
Logan Square
2363 North Milwaukee Ave
773.360.8774
If classic video games is your thing, then this is the place to hang out. You can play all manner of arcade games here: Frogger, Tron, Pac-Man, plus a variety of pinball machines, all while drinking. They have a good beer selection and a huge whiskey list (over 50 different kinds). There’s no food, but as with many bars in Chicago, you can bring your own food in. Better yet, all the games are just 25 cents to play!