36 hour curated itineraries for the modern traveler

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Weekend travel guide to Chicago, Illinois including the best hotel recommendations, restaurants, bars, museums, things to do, eat, see and explore. 





As the tale goes, in 1871 when Mrs. O’Leary’s cow kicked over a lantern in the family barn that burned down most of the city, city planners took the proverbial "bull by the horns”, and with Midwestern grit and determination, reconstruction began quickly.  Although a tragic event, The Great Chicago Fire was the beginning of the Chi-Town we know and love today:  a city second to none, blessed with groundbreaking, bold architecture, extraordinary museums and parks, excellent shopping, and an amazing restaurant, bar, and entertainment scene.  And that’s just the tip of the iceberg (just kidding. . . no icebergs on Lake Michigan).   In addition to the Windy City's historical treasures, our Guide spends a lot of time dining, “barring”, and hanging in the West Loop, which draws a young, creative crowd.  Bring your walking shoes; we’ll explore some of the coolest streets in town.  Along the way, you’ll experience Midwestern charm and hospitality and meet some of nicest people ANYWHERE in this city
that has it all!







Photo courtesy of Chicago Athletic Association

Photo courtesy of Chicago Athletic Association

CHICAGO ATHLETIC ASSOCIATION HOTEL. You might think this venerable 1890s Venetian Gothic building across from Millennium Park sits simply as a well-preserved landmark.  Head up to the lobby level of this former men’s athletic club turned hotel, and you’ll understand immediately why this special place has become a must-experience destination that fuses past and present.  Dark woods and soft lighting invite you to sink into tufted leather sofas and experience the elegance of a bygone era.  But don’t get too comfortable; the nearby Game Room beckons billiard and bocce enthusiasts (and cards or checkers, anyone?).  For an exceptional dining experience, head to Cindy’s rooftop restaurant and bar (our Guide takes you there), and enjoy spectacular views from the rooftop deck.  Shake Shack on the first floor can be delivered to your room.  Yes, heaven does exist.


SOHO HOUSE CHICAGO. This forty-something room hotel has three levels of club space, rooftop pool, four dining options, multiple bars (they will even bring the bar cart to your room), social events, spa, and workout classes in the stunning gymnasium that will make you feel like a local.  Even in the not-so-good weather months, the roof's fire pits make it the coziest place in town.  Its location in the West Loop has you within walking distance to the best restaurants in the city.


Photo courtesy of Ambassador Chicago 

Photo courtesy of Ambassador Chicago 

AMBASSADOR CHICAGO. This legendary Gold Coast hotel (recently known as Public Chicago)  juxtaposes traditional glam (over-sized furniture, white paneled walls, vaulted ceilings, and grand fire places) with sleek, modern lines, gilded accents, and a minimalist attitude (a la Ian Schrager).  The public spaces, restaurants, library, coffee shop, and guest rooms are simply stunning and spare no design detail.  Its Gold Coast location is appealing, tucked away from the more congested part of downtown in one of the most charming and desirable neighborhoods.






DRINK_ SAWADA COFFEE.  Hop over to the hip West Loop (unless you're staying at Soho,  since its right across the street).  The Military Matcha Latte, matcha with a shot of espresso and dash of cocoa powder, might just be our favorite caffeine drink of all time.  Also, it's one of the only places to grab donuts from DONUT VAULT (besides their actual store), which sell out immediately upon opening.  

EAT_ LITTLE GOAT.  If you want a more hearty breakfast after your coffee, or if donuts aren't your thing, head across the street to LITTLE GOAT.  Set up like an upscale diner, the food resembles just that.  They take a savory stance on your favorite dishes like "Elvis waffles," crispy chicken french toast,  and pork belly home fries. 

SEE_ ARCHITECTURE RIVER CRUISE.  To fully appreciate the beauty of Chicago (the river, architecture, history) take The Chicago Architecture Foundation river cruise.  It's a five-star tour and experience.  It gives you a unique perspective of the city in more ways than one, and merges the old with the new. (Reservations recommended).  


EAT_ 3 ARTS CLUB CAFE AT RESTORATION HARDWARE.  Inside the building that was home for decades to a women's art school, resides RESTORATION HARDWARE.  It doesn't look like a retail store; it's a humble, antiquated brick building in a residential neighborhood.  Brunch here is a must.  Add your name to the list as soon as you arrive, as the wait can easily be an hour.  Spend your wait time wandering through the perfectly designed spaces and floors that might make you wish the wait was longer.

WALK_ GOLD COAST (WELLS  STREET).  Walk down Wells Street in the GOLD COAST (just a few blocks from Restoration).  The quaint neighborhood has boutiques, bars, and restaurants.  It's a perfect place for a post-brunch stroll.  


EAT_ AU CHEVAL or THE GIRL AND THE GOAT.  If you want the best gourmet burger you'll ever have in your life, head to AU CHEVAL.  If you consider yourself a foodie but don't necessarily want to indulge in a burger, head to THE GIRL AND THE GOAT (across the street from Au Cheval).  We always say, you remember a good restaurant if you remember what you ate.  We first ate at THE GIRL AND THE GOAT six years ago shortly after it opened, and we still remember every single dish.  They pioneered the small plate movement, and the crowd and food is as on point as when it opened.  You could throw a dart at the menu, and wouldn't be disappointed.  

DRINK_ AVIARY.  Post dinner, head to AVIARY to witness  the crown jewel of craft cocktail bars where mixology and presentation are taken very seriously.   As you first step inside, it might feel like a stuffy three-star Michelin restaurant with the clean smooth décor, dim lighting, private round booths, and an abundance of well dressed servers.  Each cocktail is about $25, and it won't take more than five minutes to understand why.  Make sure you walk by the cage to view the  kitchen or "lab," as it will give you flashbacks of science class watching cocktailers use beakers, bags, machines, and the stovetop to create unique compositions and flavors, with over-the-top presentations. 






EAT_ 3 GREENS MARKET.  Don't let the name fool you.  This is not your typical market.  At first glance, you could be in an antique mart, as much of the furniture, decor, seating, and signage feels vintage.  There's a self-service bar area that rotates options throughout the day for BL&D. For breakfast, expect quiches, eggs, pastries, donuts, and a full service coffee bar.  

WALK_ CHICAGO LAKEFRONT TRAIL.  Start your walk (or rent a bike if you're feeling more adventurous) down the beautiful Lakefront trail (weather permitting).  Head south to end up at Millennium Park. 


SEE_THE ART INSTITUTE OF CHICAGO and MILLENNIUM PARK.  THE ART INSTITUTE OF CHICAGO has one of the most impressive permanent collections we've seen.  Not to miss: the photography galleries, contemporary wing, famous Nighthawks by  Edward Hopper and everyone's favorite, American Gothic by Grant Wood.  Afterwards, stroll through Millennium Park and see the famous Bean sculpture for an obligatory photo.

EAT_ CINDY'S ROOFTOP at THE CHICAGO ATHLETIC ASSOCIATION.  Head up to the rooftop of the Chicago Athletic Association to CINDY'S not only for the most incredible views of  Millennium Park and Lake Michigan, but for one of the best dining experiences in the city.  The food is fresh with a Mediterranean flare.  You'll want to stretch your lunch into a two-hour event.

HANG_ GAME ROOM AT THE CHICAGO ATHLETIC ASSOCIATION HOTEL.  If you aren't staying at the hotel, stop by the gorgeous lobby and then head to The Game Room, which pays tribute to the buildings roots of the old athletic club.  And if your calendar permits, stay for a drink and games.  They have bocce ball, shuffleboard, billiards and more that sets the vibe for an adult playground.


WALK_ MICHIGAN AVE and RUSH STREET.  We have taken you through many less notable streets, but there is no escaping MICHIGAN AVE.  As you walk North, on MICHIGAN AVE head one block West over to RUSH STREET.   We love the block of RUSH STREET from Pearson North as it is charming with some of the best shopping, restaurants, and luxury hotels in the city.

DRINK_ VIOLET HOUR.  For a pre-dinner adventure, head over to VIOLET HOUR in Wicker Park.  This prohibition-inspired cocktail lounge takes their cocktails and atmosphere seriously.  No cell phones, no reservations, no hats, no saving chairs, so you can be fully present and appreciate the experience. Also, take a walk around Wicker Park, as you'll experience a side of Chicago you haven't seen yet. 

EAT_ BLACKBIRD or AVEC.  If you're looking for a more formal experience, head to BLACKBIRD, where they describe the cuisine as "Midwestern" which we interpret to mean clean, classic, quality home grown ingredients made with integrity.  Their decor is award winning as well.  If you're craving a more relaxed shared plate wine bar atmosphere, walk around the corner to AVEC.  This Mediterranean small plates restaurant focuses heavily on quality ingredients as well as reasonably priced wine (win, win).