I suppose most people, when deciding their winter-break plans, don't think: "I would like to go somewhere cold." But the summer of 2025 was so hot that it seemed like cooler climes might be a good way to end the year. As so often happens, our best-laid travel plans were mislaid the minute we landed in Chicago -- temperatures were well above freezing. Without the holiday lights twinkling on some trees by the Chicago River (top left), one could have thought it was any old degree. After taking the train from the airport to downtown, it was so mild that we abandoned the "L" to walk around. It was Christmas Day, so the pickins were slim, but you can always count on an Irish pub -- in our case, the bustling diner-like Dublin's Bar and Grill (top right) -- and a drinking institution that lets you throw peanut shells on the ground -- for us, the dimly lit dive bar The Lodge (bottom).
During our pre-trip research we determined that more establishments would open after dinner, so we grabbed some take-out from EaThai, a clean, bright beacon during the darkness of winter. After eating and settling into our AirBnB, we descended back into the gloom, attracted to the illuminance at Small Bar (top left). We were among only a few patrons on hand right at opening time, so we got spots at the bar (top right). Eventually, others filled the stools beside us, some ordering Albany boilermakers -- Hamm's with a bourbon shot -- to sip while they played cribbage, even though it seems backgammon would have been a better match for the graphics on the old-school later (bottom). By the time we left, it was standing room only in the aptly named tavern, and our seats were snagged as soon as we stood up.
The next day, it was the distance, not the forecast, that put us back on public transportation. Google Maps does no justice to the scale of The Second City. After a bus ride, we strolled through the Lincoln Park Zoo, where surprisingly quite a few animals were out to eye (top left) or ignore us (top right). We did the tourist thing and had deep-dish pizza at Lou Malnati's for lunch (middle left). Then afterward, we stopped for a flight at Maplewood Brewery as we made our way home to rest up for one of the main reasons we had come to town. Bucktown Pub was the ideal spot to rub elbows with some locals (middle right) before we walked around the corner to see the Waco Brothers. And, feeling like my childhood basement except with string lights instead of stucco ceilings, The Hideout was the perfect venue to witness the infectious energy of such an audience-engaging band (bottom).
After the frenzy of a live show and the bustle of a big city, we were ready for some laid-back leisure in Milwaukee. We fueled up for our train trek at Lou Mitchell's, a long-standing and Bears-supporting eatery that is often cited as the eastern end of Route 66 (top left). Unfortunately, when we got to Union Station, despite the holiday decorations (top right), our spirits fell when we learned the schedules online weren't accurate, so we had some time to kill before the next departure. Luckily, the clement weather made it comfortable to wander to nearby sights. Along the lakeshore (middle left) and at the Millennium Park skating trail (middle right), the Windy City seemed more like the Foggy City. When we took a selfie at "The Bean" (bottom left), the reflection of the sky revealed a possible reason why the artist named his sculpture Cloud Gate (bottom right).
When we eventually detrained, we were ready for some of Milwaukee's Best -- well, not that beer, but a beer -- so we headed directly to Wizard Works Brewing Company, where we had the first of many pints of the night. After taking in some food and football at Hooligan's, we set out to find authentic drinking establishments. We deliberately strayed from historic Brady Street -- which was settled by Polish and Italian immigrants, but is now dominated by college kids from Marquette University -- and struck gold with entertaining imbibers at Scaffidi's Hideout and friendly bartenders at Wolski's Tavern. In fact, the next morning, we ran into a publican from the night before at Milwaukee Public Market (left), where we had an initial breakfast before picking up a secondary brunch at 3rd Street Market Hall (right).
As we schlemieled and schlimazeled past the Milwaukee River, we didn't see Laverne or Shirley, nor did we gaze upon the The Bronze Fonz, but we did see some signs of frigidity in the form of frozen ice (top). We didn't have time to linger because we were on our way to a blue-ribbon affair at the Historic Pabst Brewery (middle). The factory is no longer producing beer, so the company tour is more about the origins of the brand and the evolution of the buildings. It consists mostly of drinking while listening to a history lecture at Best Place, an event center that was once the brewery's administrative core (bottom left). But you do get to see some other parts of the factory, including the owner's office and the cellar, where employees would receive medical attention after drinking-on-the-job accidents (bottom right).
There are just so many quaint bars in the city (and okay, we were slightly buzzed, too), so we did a condensed pub crawl on the way back to our AirBnB, stopping by Y-Not II Tavern, Regano's Roman Coin, and Jack's American Pub. After this unusual dose of day drinking, we needed a nap, but we rallied in the evening to bowl a few frames at Landmark Lanes, where just a few days earlier Hugh Jackman did surprise karaoke to celebrate the release of the movie Song Sung Blue. It wasn't a late night, though, because we had to get up early to head back south for our flight home. Flakes were falling as we took a rideshare to catch our train, and as it chugged into the city, we saw patches of white on the ground. Then on our way to Portillo's for one last local treat, a Chicago hot dog, we had to penguin-walk through some slick spots. But still, the closest we got to our desired frozen sojourn was when our plane pierced through snow clouds to reach cruising altitude.
