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.  


Concours d'Elegance

When you marry a car enthusiast, you can expect to attend a lot of car shows. Luckily, Pebble Beach Concours d'Elegance is one of my favorites!

Consider this the Kentucky Derby of Car shows, there's even suggested attire– "a polished appearance, paired with the perfect hat!" 

Considered one of the world's most prestigious car shows, since 1950 Pebble Beach Auto Week has demonstrated a captivating combination of beauty and technology. Lathered in luxury, this is a week of parades, auctions, races, and viewings, with awards and debuts throughout. Awards range from Best of Class, Elegance, Specialty, and Class. Whether it's "sophisticated German technology, sleek Italian coachwork, or delightful minis," there's something for everyone. 

Set along one of America's most iconic coast lines, and nestled in one of our favorite little towns, this is not only a charming, but elegant weekend retreat. I will in no way pretend to be a car expert, but I can certainly appreciate the classics making this the perfect event for both of us to enjoy. 

To no surprise, for Paul, Pebble Beach Auto Week has become a yearly tradition, and I fully support it. In fact, just writing this gets me excited to head back sometime, however this year Paul will be spending the week with his dad, while I head to TX for a girls' weekend. 

This year's events take place August 15-20th. While most VIP tickets have sold out, you can still purchase general admission tickets here. If you're unable to attend, you can follow on the official Concours dElegance Instagram.


San Antonio Travel Guide

Travel - San Antonio Travel Guide
Travel - San Antonio Travel Guide

Top | Shorts - similar | Boots | Jewelry c/o | Aviators | Lipstick

The last thing I want to do is encourage cliches, but the last couple months have been insane! I know everyone and their mother says that, so don't get me wrong, I'm lucky and recognize I have no reason to complain. That said, after a two month marathon of wrapping up work projects, organizing our move, and prepping for our trip to Alaska, things are finally starting to wind down, and the stillness is intensely comforting.

Prior to our move, the hubs spent a month commuting between CA & TX, which meant our weekends were precious time to enjoy some our favorite destinations in TX.

If you haven't yet visited, don't underestimate TX as a getaway destination! San Antonio is one of our favorite cities to weekend, and I swear that riverwalk is magic in moonlight!

Moving forward Glitterary will feature more travel destinations with local tips to inspire and guide your adventures, and to get us started, below is a quick bucket list to San Antonio...


Scene: Riverwalk - at night! Don't get me wrong, you should definitely visit the riverwalk in daylight - it's much better for pictures, but there is something about the riverwalk at night that seduces you - it's magic, and once you experience it, you know :)

Instagram: The Alamo A National Historic Landmark, the Alamo is an old Spanish Mission built by Catholic missionaries in 1744. Most famous for the 1836 Battle of the Alamo (Independence of Texas from Mexico), "Remember the Alamo" became the cry of the Texans for the remainder of the war.

Foodie Moment: Zinc Bistor & Wine Bar Open late, this quaint bistro is nestled in a historic building more than a century old. The menu is simple bistro fare with an upscale southwestern flare. With an french emphasis on champagne, the bar menu is endless, and the specialty cocktails are divine! If you'll be dining in the courtyard, be sure to ask about the fine imported cigars ;)

Rest & Relax : Omni La Mansion del Rio Est. 1853 as a school, which later became St. Mary's College, and in 1966 was purchased by two former students to be remodeled as a luxury hotel, just in time for Hemisfair, San Antonio’s 1968 World Fair. Did I mention it's on the riverwalk?...

Explore: Pearl District Up and coming neighborhood surrounding Pearl brewery. Here, many historic buildings have been restored as restaurants and shops with a new trendy energy. Not a tourist destination, and not necessarily representative of San Antonio's history, rather a blend of the culture that's come to be. If you want to hang with the locals, enjoy the weekend farmer's market!

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Home Away from Home

Winter holidays create our favorite time of year, but they can also be the busiest time of year. In the middle of all the baking, turkey basting, decorating, and "Elf" quoting, sometimes all we want is quiet, sweet relaxation. Unfortunately, in the midst of holiday gift shopping and limited vacation time, a trip across country can be hard to come by, at least for a few more months.

In celebration of Thompson's grand opening, this month Steph and Paul (the hubs) were able to enjoy a little pre-holiday staycation– the calm before the storm. With its residential feel and inclusive ambiance, Thompson quickly proved to be a stylish retreat from the hustle and bustle, and the perfect home away from home.

Set in the heart of Chicago's Gold Coast, Thompson boasts breathtaking views of the city, and presents the perfect local for a stroll down Chicago's Magnificent Mile, or window shopping on Oak St. When the weather's unkind, Thompson's sophisticated and off-beat decor creates a warm and soft invitation to view Chicago's grandeur from the comfort of it's blue velvet chairs (thank you Tara Bernerd). We can only imagine sipping hot cocoa while watching the snow fall!

The evening of our stay we enjoy a fun little night cap soirée in one of Thompson's modern and trendy penthouse suites. After some wine and "pillow talk" with friends, the evening concluded with the sweetest turn down service we've seen since our honeymoon. Milk, cookies, and a monogramed bath robe courtesy of Monogrammed Bathrobes.

In the crazy calendar we keep, we were set to fly out for Texas early the following morning. While we already had travel arrangements, we'd be lying to say we didn't do a quick Google search for a Thompson Hotel in the area.

Truth is we've already recommended Thompson Chicago to our closest family and friends. Like most of our favorite things, Thompson Chicago is more than a product/service, it's the extension of a lifestyle brand dedicated to creating an experience in an understated yet sophisticated manner.

For more information about Thompson Hotels and locations, click here. // Thompson Hotels Manifesto. // Dining: Nico Osteria (December 2013)

This is a sponsored post, however, all opinions are our own. The integrity of this site is far more important to us than any compensation or brand partnership. – D&S