Chicago City Guide


Ok, today I'm letting you in on a few secrets... If you've visited us in Chicago, you'll likely remember all off this, & if you're heading our way soon, spoiler alert, this is likely our weekend agenda. After 8+ years of living in the heart of this city, we've learned a thing or two about giving a proper Chicago tour, and while there will always be a few tourist attractions we have to oblige to, we have our own spin on how to do those too ;)

Not gonna lie, I'm a little hesitant to share my secrets, use these wisely...


Friday Night:

John Hancock Building ... at Sunset

Here's the secret, skip the observatory & head up to the 96th floor for a cocktail at the Signature Lounge. This is two floors above the observatory & I'll be honest, the drinks are sub par, but you're paying for the view & that view wont let you down. Personally, I prefer getting a table on the south side at night, but the best view is from the women's bathroom– any true Chicagoan will agree, sorry boys. 

Big Star Tacos + Violet Hour

With this combo, you can't go wrong! Lauded as some of the best tacos in America, Big Star menu is brief, but this taco & margarita pairing you simply can't skip! Expect a long wait on weekends, particularly if the weather is nice, but there's always the to-go window, which you may want to return to after a few cocktails at the Violet Hour. Located directly across the street, these two share the same owner. GQ Magazine loves the Violet Hour, with numerous articles since it's opening in 2006. This is one of Chicago's original serious cocktail lounges, and the first time we visited back in 2010, we walked by it 5x before finding the door. Styled as a true speakeasy, there's no signage, just a graffitied wall with one outdoor lantern lit during business hours. Fast forward to 2018, and you'll find a line of fans out the door, but order the mixologists' latest creation and you'll gladly stand in line for another. 


Architecture Tour

There's a reason this activity draws tourists from around the world, Chicago is home to some of the world's best architects and their designs are masterfully displayed along our riverwalk. While a sunset cruise is uniquely captivating as you witness the city transform from daylight to city lights, in order to maximize your stay, I actually recommend a morning cruise. Grab some coffee and a quick bite, then head to Navy Pier or Michigan Avenue to catch your ride. Most tours last about 75minutes. You'll likely even encounter some Chicago natives out for a day of sightseeing. We recently spent a day with Entertainment Cruise for an architecture + lake tour– these views never disappoint! 

Walk Michigan Avenue to Gold Coast

Michigan Avenue's Magnificent Mile, is Chicago's pride and joy of luxurious retail. Enjoy a stroll from the River to Lake Michigan's Oak Street corner, and you'll experience world-class shopping on all sides. At the very least, get some steps in while enjoying the window displays, I photograph these windows almost daily on my way home from work. Some of my favorites include Saks, Neiman Marcus, Burberry, and Max Mara on the north end of Michigan Avenue. Here, you'll spot the iconic Drake Hotel and wander into Chicago's Historic Gold Coast. Take some time to explore this vibrant neighborhood rich in dining, shopping, and entertainment. Once you've had your fix of sightseeing, order an Uber & head to West Loop for a late lunch or dinner– it's called Restaurant Row for a reason..

West Loop Dining

These are our old stomping grounds, and for a brief couple years, this neighborhood was a hidden little pocket of Chicago. In fact, locals would recommend you not tell your friends about it... so good, we wanted to keep it all to ourselves. Fast forward to 2018 and this neighborhood is no longer "up and coming", it's the heart of Chicago's dining, showcasing some of the world's most awarded chefs and their latest (often limited run) menus. My personal recommendations include...

  • Au Cheval, a relaxed french corner of Restaurant Row serving what Bon Appetite Magazine declared the best burger in America. People wait hours for a seat here, and with good reason, as a passion for eggs bring unique spins to french classics. 
  • Hi Five– hands down the best ramen you'll ever have & we search for ramen everywhere we travel! This speakeasy styled ramen house only seats about 20 guests, so try to get on the list as early as possible! They open at 5pm and don't take reservations.
  • Girl & the Goat, Chef Stephanie Izard's own design & Chicago's pride & joy. Expect family style servings of bold flavor with global influence. Note, this is one of the toughest reservations in town, so book it the day you book that flight ;)
  • NEXT– I've actually never visited, but have heard wonders of these time-capsule styled menus! If you're a true foodie, you already know, this is one of Chef Grant Achatz's Alinea Group Restaurants, and as one of the most starred chefs in Michelin history, you can expect nothing short of a theatrical experience. Tickets sell seasonally– like a play– so keep an eye out for the next menu, and if you still need convincing, watch Chef's Table S2, E1.

Finally, for drinks, get to the Aviary, there's simply no need for other distractions. Yet another notch in Chef Grant Achatz's modernization of dining, this cocktail lounge will inspire and awe with it's show-stopping presentations of unusual & innovative cocktail servings. Caution this is not a bar, rather a kitchen of cocktail chefs, so expect a restaurant-like experience. 

The Second City

Here's the tricky one, there's never enough time in a Chicago weekend, but if you can squeeze in a show at the Second City comedy club, don't overthink it, just go! Whether this happens before dinner (geographically closer to Gold Coast), or you hop in an extra Uber that day, make the extra effort to laugh a little. This comedy club is home to such alumni as Tina Fey, Amy Poehler, Steven Colbert, Steve Carell, & Bill Murray. The current casts are always developing new shows, but frankly the improv bit at the end of the show is always my favorite. The Second City is is a staple of Chicago culture, so go ahead and laugh a little!


Brunch at Cindy's

Located in the Chicago Athletic Association Hotel, Cindy's Rooftop is a relatively new favorite, but views are hard to beat! Come Sunday, take it easy and book brunch at here. Not only will this yield seasonal menus worth celebrating, but the views of Millennium Park are Instagram gold!

Millennium Park

Pending on your flight plans, consider a walk around the park after brunch. Be sure to snap a shot by the Bean, then walk over to Buckingham Fountain, these are both Chicago "must-see" attractions. Cheesy as it might be, nobody's too cool for the Bean, & Buckingham Fountain is among the largest in the world.

Sears Tower / Art Museum

If you're lucky to catch a full Sunday in the city, step into the Art Institute just steps from Millennium Park, or head to Willis Tower, pronounced by Chicagoans as "SEARS Tower" ;) Unlike the views from John Hancock, which I recommended at night, I suggest you visit Willis by day– the best views are northbound & nothing beats the thrill of that Skydeck Ledge.