12 Hours in Chicago

February 10, 2015

In honor of the launch of our newest bag, THE PEAK, we’re sending out our favorite women, all incredible, strong, beautiful and extremely well traveled, to locations across the globe to bring you tips and tricks for 12 hours spent visiting some of the world’s most interesting cities.

To begin, right here in the USA…


by Leah Young


8am: After an early morning flight, I’d head straight to my favorite boutique “home away from home,” theHotel Allegroon West Randolph Street right in the heart of Chicago’s theater district. I discovered this hotel 2 years ago and have been staying there ever since. The location is extremely central and their rates are surprisingly inexpensive. What sets the Allegro apart is their unique touches: Happy Hour every day in the lobby from5pm-6pmcomplete with homemade Sangria and appetizers and a yoga mat waiting for me upon arrival (I won’t claim to actually use it). In the summer, I check out one of their free beach cruisers to make getting around the city a bit easier.

9am: After checking in, I’d head East towards Millennium Park and grab a big cup of dark roastIntelligentsia Coffeeat one of the brands original outposts. Although you can find Intelligentsia everywhere now, I still enjoy going to one of their original spots in Chicago. Their coffee is always perfect.


10am: After coffee, I’d stroll intoMillennium Park.My first stop is always“The Bean”(also referred to as “Cloud Gate”), apublic sculpture designed by Indian-born British artistAnish Kapoorandrumored to be inspired by Liquid Mercury. The sculpture’s surface reflects and distorts the city’s skyline which can be really entertaining. I love taking pictures and depending on the weather and cloud reflections, your photos are almost never the same! No trip to the park is complete without a visit toLurie Gardens– a 2.5 acre oasis near the Southern end of Millennium Park. The plants and flowers here in the spring and summer are breathtaking.

11pm: I’m getting hungry so I’ll head North to Clarke Street and across the river to a newly discovered spot,XOCO, a casual and reasonably priced Rick Bayless gem. I stumbled upon XOCO on my last visit because my favorite Bayless spot, Frontera Grill wasn’t open yet – and boy am I glad I did! XOCO is known for their Mexican soups (caldos) and sandwiches (tortas). My recommendations: XOCO margarita and fully loaded guacamole to start, Carnitas or Shortrib Caldos (soup) and the churros with Mexican chocolate dipping sauce for dessert.

12pm: I love being a tourist in new cities but I try to do a ton of research beforehand so that I don’t necessarily LOOK like one. One of my favorite tourist activities are the boat tours along the Chicago River and Lake Michigan. It’s a great way to learn about the city in a relaxed atmosphere.Shoreline Toursis my favorite guide company but there are many depending on what experience you’re looking for. For those who want a spectacular view of the skyline from Lake Michigan, try the 30 minute door-to-doorSkylineTour. In the summer, the evening cruise comes with a front row view of the Navy Pier fireworks display. For those wanting to learn about the city’s history and architecture, the 2 hourArchitecture Tourcan’t be beat.


2pm: After the boat tour, I’ll stop byFrontera Grill(now that it’s open) and grab aTopolo Margarita. I literally never leave Chicago without having one (or two). Don’t bother trying to get a table at the restaurant. Just snag a seat at the bar and make friends with the friendly bartenders. I am no lightweight but 1 of these gets me loopy. Two – and I need a cab to drive me the .5 miles back to the Allegro Hotel. Their food is amazing but not cheap. I always prefer to spend my $20 on a few of the Topolo’s and leave feeling happy (and most definitely buzzed).

6pm: There are a LOT of amazing restaurants in Chicago but I was recently impressed byRPM Italian.I must admit, I didn’t want to like it but I was so blown away. The vibe has a very Miami, Vegas feel but for as swanky as it is, the prices are reasonable. Be willing to take an early or late reservation just to get a table….it’s so worth it. My first stop would be their bustling bar for a cold (and surprisingly large) glass ofhouse Prosecco. Once my table was ready, I’d start the ordering:Brussel Sprout Salad, Prosciutto Grissini, Truffled Garlic Bread (MIND BLOWING) and Imported Burrata. I cannot recommendMama DiPandi’s Buccatinimore. It is so simple but so impeccably done. Add themeatballs, add the meatballs, ADD THE MEATBALLS. The Buccatini rivals (and in my opinion, beats) Scarpetta’s famous Spaghetti Pomodoro.

7pm: After dinner, I’d grab my blanket and head back to Millennium park to catch a live show atJay Pritzker Pavilion.Anyone can watch as theGrant Park Orchestraand Chorus (along with guests artists) rehearse upcoming performances. Rehearsals take place Thursday-Friday all season long. The Pavilion itself is a sight to be seen so even if there isn’t a live concert/rehearsal going on – stop by to see the architecture. On your way home, pop byCrown Fountainat the edge of Millennium Park.The fountain consists of two 50-foot glass block towers at each end of a shallow reflecting pool that project video images from a broad social spectrum of Chicago citizens. The best time to go is at night where you can really enjoy this public art installation in all its glory.


8pm: After the concert, I’d head to my favorite back alley bar,Three Dots and a Dashlocated right off North Clark Street (look for the tiki torches and blue neon lights). There’s always a huge line but it’s so worth it.Three Dots is a cocktail focused tiki lounge that is unlike anything I’ve ever seen. The menu features a craft approach to both classic and modern tiki cocktails with fresh juices and syrups made in house along with an insane selections of rums (150 to be exact). My favorites:thePainkiller No. 3made from rum, coconut liqueur, passion fruit purée, pineapple juice, and a hint of cream or theBunny’s Banana Daiquiri, a frozen mélange of rums, coconut liqueur, banana, lime, and nutmeg.