Chicago Mini-Moon from Olivia Leigh Photographie

We can’t think of a better city than the windy city to kick off our Mini-Moon features in 2016!  So grab a pen and paper because we have your itinerary ready for your next trip to Chicago.


Words and photos by Olivia Leigh Photographie.

Olivia Leigh | Snippet & Ink


Having grown up in a small town an hour south of Chicago and having lived in the city for nearly ten years, I’m little biased in thinking that Chicago is a truly world class city. But with some of the country’s best art, music, theater, festivals and food, it’s hard hard to imagine anyone not finding something to love about the city. While the unpredictable weather can turn people off, if you choose a good time of year — or are simply optimistic and resilient — I’m certain you’ll fall in love with the city as much as I have.





With direct flights from most states in the country, Chicago is an ideal long weekend or mini-moon. Weather-wise, mid-August through mid-October is generally the best time to visit Chicago, with beautiful, temperate weather, and locals enjoying festivals throughout the city, drinking on patios, and biking along the lakefront. June is also wonderful, with lots of fun summer activities throughout town. The rest of the year is hit or miss, with December sometimes having 70 degree days, snow sometimes in April, and July either being rainy, pleasant or sweltering. In general, it’s best to just cross you fingers and hope for the best! While most people visit in just the summer or fall, if you live somewhere cold to begin with, I think Chicago can be a  great winter option, with many of the city’s great attractions — museums, theater, comedy, music, restaurants — being great indoor activities, and winter hotel rates being extremely affordable.


Most hotels in Chicago are centered on the Magnificent Mile, a stretch down Chicago’s famed Michigan Avenue, in the heart of the city’s downtown tourism and shopping district. With that said, Chicago is often called “a city of neighborhoods,” with each one having a unique personality, style of residents, and vibe. In my opinion, its a must to get out of downtown to experience some of the other areas of the city. To plan a trip, I recommend staying in a neighborhood that most appeals to your likes and style for a home base, and then using Divvy (the public bike system), the CTA (the “El” — train — or bus) to experience some of the other areas.


West Loop/Fulton Market

Olivia Leigh | Snippet & Ink(Au Cheval) 

STAY: Soho House Chicago — The largest outpost of the exclusive, artsy Soho House private club offer rooms to non-members, as well. Decorated in a luxurious, artistic, hipster vibe, the hotel itself has several wonderful restaurants, bars, a rooftop pool (one of the hottest spots in town in the summer), and a chic-artsy clientele.

EAT: Randolph Street is known as Chicago’s “Restaurant Row,” home to many of the city’s hottest restaurants, like Au Cheval and Girl & The Goat. Two blocks north, the rapidly changing Fulton Market has morphed from meatpacking warehouses into a street full of award-winning restaurants such as the The Publican and Moto. For something slightly off the main drag, check out two of the restaurants that started it all, with Mediterranean-inspired small plates at Avec and stunning, modern American cuisine at Blackbird (be sure to check out their insane $25 prix fixe deal at lunch).

DO: Pay a visit to The Aviary, a cocktail bar that operates more like a fine dining restaurant. Buy tickets (yes, tickets to a “bar”) online, and enjoy a cocktail tasting menu that provides a great intro to Chicago’s molecular gastronomy scene via fun, playful drinks. Afterward, check out a show at City Winery, which features intimate sets in a acoustically outstanding room.


Downtown/Mag Mile

Olivia Leigh | Snippet & Ink(Chicago Athletic Association Hotel)

STAY: Chicago Athletic Association Hotel — The recently opened hotel is a stunning renovation of the Chicago Athletic Association, with spaces and rooms full of period details and nods to the athletic history. Its central location across from Millennium Park makes it a great place to stay, but the hotel itself has become a hot spot for Chicagoans, as it houses the city’s hottest rooftop bar (Cindy’s); a fun bar with football, shuffleboard and bocce available to play (The Game Room); delicious retro-inspired cuisine in a Mad Men-like space (Cherry Circle Room); the newest bar from local cocktail celeb Paul McGee (Milk Room); and even a Shake Shack.

EAT: The Loop can have slip pickings for food that’s not overpriced or a tourist trap, but nearby River North has many great options. Check out Gilt Bar for delicious pastas, meats and cocktails in a sexy setting, Joe’s for a swanky throwback surf and turf meal, complete with waiters in tuxedos, or one of celeb chef, Rick Bayless’, famous Mexican spots (I prefer the lunch spot, Xoco, for tortas and churros).

DO: The Art Institute of Chicago was voted the best art museum in the world by Trip Advisor members, and its no surprise given its stunning collection that includes everything from one of the best collections of impressionist art in the world to modern photography. Crowds are small compared to comparable museums in NYC and LA, making for a relaxing and inspiring afternoon. Parts of Millennium Park can be known as a bit of a tourist trap with it’s famous “Bean” sculpture, but the park is a truly beautiful space in the city that plays host to myriad events throughout the year, from ice skating in the winter to almost daily free concerts or movies in the park come summer. Also be sure to stroll north to check out the recently revitalized Chicago Riverwalk, which makes for a gorgeous day or evening walk with some of the best views of the the architecture. To see even more, take the Chicago Architectural Boat Tour, the one must-do for any visitor to Chicago.


Lincoln Park/Gold Coast

Olivia Leigh | Snippet & Ink(Chicago Riverwalk)


STAY: Public Hotel — Four blocks south of Lincoln Park in the Gold Coast, Public’s all-white, simple and modern rooms make for a sexy, romantic stay.

EAT: If you want to make your mini-moon extra special, save your pennies and then book a table at , the best restaurant in Chicago and one of the top restaurants in the world. The price is extreme, but its worth coming to Chicago just to dine at this amazing restaurant, that is part entertainment, part art, and part mind-blowingly good food. For a something more relaxed, check out Midwestern-inspired fare at Perennial Virant, rustic Italian at Balena, and gorgeous pastries, tartines and salads at Floriole.

DO: No trip to Chicago would be complete without seeing theater or comedy, and Lincoln Park is a fabulous place to see both. The Second City is famous for starting the careers of many of the country’s most famous comedians (Billy Murray, Stephen Colbert, Tina Fey, Amy Poehler), and you can catch up-and-coming sketch comedy stars every night at one of their Lincoln Park theaters. For improv, visit iO (also home to many top comedians), and for more serious theater, head to the famous Steppenwolf Theater. If you’ve still got energy after theater, pay a visit to Kingston Mines for some of Chicago’s best live blues until 4 or 5 am every night of the week. After recovering in the morning, stroll around the actual Lincoln Park, a 1,200+ square foot public park with gorgeous views of the Chicago skyline and that houses gardens, a conservatory, the Nature and History museums, animal sanctuaries, a zoo, and a tranquil lily pond.


Logan Square

Olivia Leigh | Snippet & Ink(Mojito and Mimosa from Lula)

STAY: Longman & Eagle – This Michelin-starred restaurant is also home to an eight-room b&b, decorated in a minimalist, hipster vibe. Located just off the main square, its location can’t be beat, with the Blue Line train taking you downtown in just 20 minutes.

EAT: Logan is chock-full of trendy, tasty restaurants. A visit to Logan Square necessitates dining at: Lula, the first of the farm-to-table restaurants in the neighborhood and a great option for breakfast, lunch, dinner or drinks. If you’re visiting in the summer, there’s no more lively patio than the one at Parson’s Chicken & Fish, where patrons enjoy fried chicken and slushie negronis. You can also do a tour of world cuisines by visiting Table Donkey Stick (The Alps), Fat Rice (Macau), L’Patron (Mexico, with my favorite tacos in Chicago), and Osteria Langhe (the Piemonte region of Italy).

DO: Stroll down the main street of Milwaukee Avenue, and browse the gorgeous flowers and gifts at Fleur, fresh, unique juices at the most gorgeous juice shop you will ever see in your life at Owen & Alchemy, and enjoy a movie and a cocktail at the renovated retro-chic Logan Theater. Or, for a little activity, rent a Divvy bike for a day and cycle across town on the 606, Chicago’s version of the NYC High Line.


Chicago's Millenium Park(Chicago’s Millenium Park)


Clearly, there’s no shortage of amazing things to do in Chicago, and this list is just the tip of the iceberg. Beyond these four neighborhoods, a plethora of other amazing options abound throughout the city, from enjoying jazz at The Green Mill in Uptown to having a picnic on the lake at Promontory Point. Just book a flight, choose a neighborhood, and get ready to see where the city leads you!


This Mini Moon post was written and photographed by Olivia Leigh Photographie.

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