Posted December 13, 2012 by Sam in Trips

Chicago for the Holidays

Macy's Window in Chicago
Macy's Window in Chicago

Whopperjaw took a very short, unexpected trip to the Windy City for the weekend. We’re pretty familiar with Chicago, usually visiting at least twice a year–once for Lollapalooza and once to take advantage of a too-good-to-pass-up fare on Southwest.  But, with a tight schedule, holiday festivities and a few newbies in tow, this was a little more tourist-y than our usual time spent catching a concert at Schubas Tavern, spending game day at Wrigley Field or indulging in a vegetarian brunch at The Chicago Diner.

We arrived in town late on Friday. We opted to stay at the Hotel Allegro. Located in the theater district, Hotel Allegro is a Kimpton with a very slightly worn hipster vibe (some carpets and wallpaper could stand to be replaced). We liked the location, the hospitality (there was a winter hot cocoa bar with toppings ranging from white chocolate shavings to chunks of Heath Bar) and the price. Others in our group picked another Kimpton: the charming and historic Burnham Hotel in the Reliance Building. Located in a National Historic Landmark, the cozy Burnham sits right in the heart of some great shopping and right across from the holiday windows of Macy’s (formerly Marshall Field’s). Check out our pics from this year’s festive decorations.

We kicked off our first full day with a Grayline Bus Tour. While we’ve experienced a pretty entertaining ethnic grocery tour with an animated guide who picked us up in her Volvo at a CTA train stop, but we’ve never done a 101 guided motorcoach trip. We went all in, paying for the four-hour Grand Tour (north and south sides) followed by the opportunity to see Chicago from 1,000 feet up in the John Hancock Observatory. Hotel pickups were available, but the tour officially left from another iconic Chicago lodging, the Palmer House. (If you don’t stay at this Hilton Property, at least be sure to visit the beautiful lobby.)

We pre-bought our spots and traded in our electronic passes for hard tickets in the back of the lower level of the hotel. Arrive plenty early because the ticket organizer also walks the groups from the lobby to the bus and is missing from her post for ten to 30 minutes at a time. Although the process for boarding and starting the tour was a bit of a mystery (involving multiple stubs and about 15 minutes more of our patience than it seemed it should), once we started the trip, things went well. The north side tour was markedly more exciting, taking us through downtown, along Lake Michigan and around Lincoln Park and The Gold Coast. Our driver narrated the drive with a emcee-like flair and knack for pointing out all Obama-related highlights from where our country’s leader gave a key speech to where he ordered takeout pizza. The guide really capitalized on his Presidential expertise in the south side tour which, while way more low key, did take us around the University of Chicago, past Frank Lloyd Wright’s Robie House and by the Obama home, which you can see fleetingly (we’re pretty sure we caught a glimpse of the right residence) in this photograph.

Bring a little somethin’-somethin’—at least a granola bar and a bottle of water—if you’re on the grand tour. It’s four hours with some very brief breaks, so you’re likely to need the sustenance along the way. All in all, we learned a lot about history, landmarks and home values our trip and it was a great geographical primer for our fellow travelers. The journey ended at the John Hancock Tower. It was a little foggy so our 360° view of the city didn’t enable us see “up to four states and over 80 miles,” but the 40-second elevator ride to the top still afforded us some great almost ethereal views of urban expanse below. See them here.

Lincoln Park ZooLights After the tour, we grabbed a bite to eat, stopped in a few shops along The Magnificent Mile and headed to see the ZooLights at Lincoln Park Zoo. (Your CTA pass can be used on the bus as well as the ‘L,” so don’t even think about driving—the parking lot was a mess–and skip the expense of a cab if you can.) This Zoo is beautiful draped in colorful, twinkling lights. Most exhibits are open and animals were out when were there. The best part? It’s always free.

Want more ideas for your next trip to Chicago? Read on.

A Few Places to Fuel Up

Hash House A Go Go – A favorite large-portion comfort food eatery, Whopperjaw has had a few ‘farm food” brunches at Hash House a Go Gos in Nevada. This is the first of its kind in Chicago and it was just as satisfying.

The Berghoff Restaurant Founded by a German immigrant, the Chicago restaurant has a long and storied history. Grab a bite to eat and wash it down with a Berghoff brew.

XOCO – This Rick Bayless contemporary Mexican quick-service cafe serves up some very tasty tortas that pair amazingly well with Mexican hot chocolate and churros.

Piece Brewery & Pizzeria – We know Chicago is known for its deep dish pizzas, but that’s no reason to pass up a chance to indulge in a little New Haven-style thin crust ‘za and some microbrews.

Haymarket Pub & Brewery – We don’t remember much about the food, but the spacious brewery  had a number of beers on tap and features “more than 10 house brewed varieties with space to offer other craft beer selections .”



Sam is live-music -loving vegetarian communications professional with an entertainment, travel and tourism background. A restless soul, Sam believes in getting out there and doing things because you only go around once but knows she could benefit from a little more sleep. Give her a reason to see a movie, catch a concert or explore a new destination at [email protected].