48 Hours in Chicago

By James Reddicliffe

Friday- Flying these days is an adventure, and flying to Chicago in February is no different. Scheduled to leave at 8:30 a.m. on Friday, February 9, our flight was maybe the only one to leave LaGuardia for O’Hare that day. Thank goodness it did, because what ensued was one of the great eating and drinking weekends of all time.

Me and my wife Maeve landed in Chicago around 1:30 p.m. Chicago Time and hopped on the L to Logan Square, where we trudged across the street, dodging puddles and snow drifts as we went, to Longman & Eagle. Fortunately the walk was only 100 feet and we arrived just in time to catch the tail end of lunch service. We were joined by my sister, Rebecca, and her boyfriend, Martin, which meant that sampling many dishes and drinks was on the menu.

Longman & Eagle is a restaurant, whiskey bar and boutique hotel rolled into one and on the food and drink front it excels. If you’re in the mood for beer, which I often am, choose from one of the many local options like Pipeworks’ Ninja vs. Unicorn, Hopewell’s  Thank Me Later, or Metropolitan Brewing’s Generator Dopplebock. If you aren’t looking for something local, peruse their extensive bottle list for other domestic favorites. Of course, being in Chicago you can’t go wrong with an iconic Old Style, which paired nicely with the roasted cauliflower.

In the spirit of honesty, I had whiskey--Pappy Van Winkle 15-year, to be exact. It was a delicious complement to the wild boar sloppy joe but I think you could drink it with Salisbury steak from your middle school cafeteria and be pleased. I’m not a whiskey buff, but the list at Longman is extensive, well-curated and features tons of affordable options in addition to the rare, special occasion whiskeys for those with the funds. Get on the tasting flights for around $25 and sample four if you are newer to these classic spirits like I am.

 That's the motto as they say. 

That's the motto as they say. 

Once you’ve digested lunch, aided by some Revolution Brewing Denali Hero at the apartment, head to Small Bar for outstanding beer, great bar food and a laid back atmosphere. Tucked into the first floor of a corner apartment building, Small Bar is easy to miss if you don’t know what you’re looking for. The dark wood paneling and unassuming décor belie the quality of the beer selection and excellent eats. We feasted on pulled pork nachos and succulent wings while washing them down with selections from Marz (Chug Life), Pipeworks (Close Encounters), and Maplewood’s outstanding Charlatan IPA. This is the kind of place where you become a regular without putting too much thought into it. We ended our night full and content, working off our wings and beer by walking seven minutes back to my sister’s apartment. They say you burn more calories in the cold, right?

Saturday- After a good night’s sleep and some strong, local coffee at the home base, the boys headed out in search of breakfast. We were able to forage some delicious local pastries from an Asian/ Portuguese fusion restaurant and bakery called Fat Rice. The selection was as varied as it was unique and we ended up with an egg tart, a taro morning bun and a passionfruit malasada, the equivalent of small, cream-filled donut. Do not miss any of these sweet options! The taro morning bun was flaky and crisp with just a hint of the taro for a well-rounded earthiness and the malasada was delightfully sweet and tart.  

On the more savory side the char sui pineapple bun was gobbled up in seconds and left our group chanting for more. The only thing people thought they would skip the next time was the Chicago-style hot dog bun. It wasn’t bad, but go for the real thing if that’s what you’re craving.

 A poor photo of a beautiful taproom. Metropolitan Brewing, Chicago. 

A poor photo of a beautiful taproom. Metropolitan Brewing, Chicago. 

Next, load up the car with your furry friend and head to Metropolitan Brewing, beautifully situated on the Chicago River and one of the city’s original craft breweries; it was  founded in 2009 and this location is new. We navigated our way through a maze-like construction site to get the gorgeous top room, with floor-to-ceiling windows overlooking the water. We grabbed a section of one of the large communal tables and got to work ordering from the lager-only selection of German-inspired beers. The Heliostat Pilsner and Copper Lager paired beautifully with the tacos al pastor and chips and guac that we brought along with us. To top it off, don’t miss the Nitro-Jitterator, a version of the dopplebock blended with coffee. Roasty and just a little sweet, it was a great way to cap off lunch.

Can you tell that we did some eating and drinking this trip? Right, we get it, but we leave the sightseeing to other folks. After a quick regroup at the apartment, we decided to get tropical before dinner. Lost Lake is Logan Square’s hippest bar and their tiki drinks have people waiting in line even in February. At our table two people had the namesake cocktail featuring rum, Campari, passionfruit, lime and pineapple. It was as delicious as it was beautiful and the ceramic mugs are a kitschy blast from the past. They feature tiki heads, parrots and pineapples and make the experience even more fun. Did I mention I love Hawaiian shirts? Well of course all the waiters were wearing them. Other drinks not to miss are the banana daiquiri, which comes with a banana peel shaped like a dolphin, or any of the drinks for sharing. You really can’t go wrong here.

Next up was a true treat. As a wedding gift, my wonderful sister and her equally wonderful boyfriend, who is also our smoked beer expert, took us Roister. Roister is a restaurant owned by Grant Achatz and helmed by Andrew Brochu and the reputation is well-earned. We started the meal with an effervescent bottle of sparkling wine that paired beautifully with the aged cheddar rillettes and the mushroom toasts. Honestly, though, the food was fantastic and the wine was delicious, and you could have ordered any of them independently and been smitten. Wine and cheese is always good. With the Yukon fries peppered with bonito flakes and the buttered pasta with clams, we indulged in Three Floyd’s Alpha Kind and Pipeworks Ninja Vs. Unicorn. At this point our eyes started to roll into the back of our heads and we didn’t think we could get much happier until the dark and stormy pork butt arrived and we just about died and went to heaven. For dessert, don’t miss the cookies and milk, which is a dressed up version of your childhood dreams.

Deciding we hadn’t had enough of each other’s company and could handle more libations, we headed around the corner to Prairie School for some high-end cocktails. The price is steep and there may be a wait but the cocktails from expert Jim Meehan are fantastic. I had a Shamrock Shake that was outstanding, and started making airplane sounds with my lips. It is safe to say the fun, and the booze, went to our heads. I’d like to say we headed home and went straight to sleep but the truth is that once back in the apartment we sampled a little homemade brandy. When in Chicago, right?