72 Hours of Summer in Chicago: A Guide to Where to Eat, Stay, and Play Outdoors

“In the midst of winter, I found there was, within me, an invincible summer.” – Albert Camus

Forget endless summer, Chicagoians embody the words of Camus in their pursuit of the invincible summer. Leave it to a city that battens down the hatches for the bitter winter months to know how to reemerge with an unbeatable determination to make the most out of their summer season.

Post-pandemic, the microvacation is a way for eager travelers to make up for lost time and 72 hours in a city can be high impact when planned correctly. Sure, there’s plenty of travel guides for the Windy City, but we’re bringing you our list for maximizing a quick weekend getaway with just three days to explore the illusive Chicago summer. Given its fleeting nature, we jam packed our schedule with some tried-and-true, must visit destinations, as well as some stops that are off the beaten path. Think of this as a food-centric itinerary with a side of sightseeing.

Day 1

Dog Days of Summer | Take the early flight and touch down at O’Hare in time to head straight for a city staple, the Chicago Dog. Beat the crowds and check this dish off your bucket list early, we popped into Portillo’s for a dog and frosty mug of beer. It was the perfect way to kick-off our trip and provided sustenance for the day ahead.

Photo Op in the Park | Walk-off your lunch by heading over to Millennium Park, where the main attraction is Cloud Gate, a sculpture by Sir Anish Kapoor, affectionately known as “The Bean.” The installation really shines bright this time of year with reflections of the summer sun and blue sky in its curvaceous mirrored exterior.

The G.O.A.T. | When you turn wary in the heat, treat yourself to a cold beer or cocktail in the no-frills hideout, Billy Goat Tavern. Located in a tunnel underneath bustling Michigan Avenue, this relaxed spot is a great place to take a pause and be a part of celebrity history. Made famous on SNL in the 70’s, enjoy learning about their iconic pop culture status via a collection of photographs and articles that adorn their walls, spanning the tavern’s several decades in business. Look for the sign above the stairs by The Wrigley Building to sneak down to one of the greatest underground bars of all time.

London Calling | Take a break from sightseeing and check into the chic London House hotel, the best spot for expansive river views and rooftop drinks. Their location is ideally situated around much of the city’s entertainment district and is in walking distance to the shops on Michigan Avenue. Their LH Rooftop Bar was recently ranked #2 on the list of best rooftop bars in the country, so of course, we had to stop by for a visit. Enjoy the 1920’s architecture of the rooftop space with a cocktail and be sure to catch the sunset overlooking the Chicago River. Hotel guests are given priority access to the rooftop, which is a favorite of locals all summer long.

A Vacation Inside a Vacation | After a day of traveling and sightseeing, you’re likely to be exhausted- what better way to refuel than with carbs? Head over to Eataly where their aperitivo bites and spritz bar will temporarily transport you to summer in Capri by way of Chicago. We found their seasonal burrata menu to be delizioso!

Day 2

Rolling on the River | One of the best ways to take in the storied significance of Chicago’s skyline is through an architecture river cruise tour. We opted for the cruise hosted by the Chicago Architecture Center to support a local nonprofit organization and were extremely impressed by our knowledgeable docent. Enjoy anecdotes for numerous architectural marvels and a sea breeze from the comfort of the rooftop deck with a bloody mary in hand.

Let’s Dish | No visit to Chicago is complete without a slice or two of deep-dish pizza. We opted for Lou Malnati’s, who happens to have a location conveniently situated within steps of the cruise’s docking point. After all that sightseeing, the cheesy, gooey little slice of heaven was a feast for the eyes, and stomach.

Riverwalk Respite | An eventful morning and an even fuller belly later, we decided to leisurely approach the afternoon by posting up at one of the city’s many lounge areas on the waterfront. Our favorite was City Winery; with a casual walk-up window and menu chalk full of summer beverages, it was the ultimate place to relax next to the water and people watch. Next time, we’ll be renting a boat and floating up to the winery, where you can dock right at the winery’s steps and grab a bottle of rosé for the voyage.

Feeling Salty | If you’re not already familiar, let us introduce you to Hogsalt: a prolific hospitality group whose portfolio includes some of the best restaurants in Chicago. With a limited amount of time, it was a challenge deciding which location to patron, but landed on Bavette’s Bar & Boeuf for a classic Chicago steak night. Everything from the décor to the food and hospitality was exceptional. The environment was cozy, sexy, and reminiscent of a bustling late-night scene at a French bistro. Pro Tip: Be sure to request a side of their house made steak salt blend- definitely worth hogging.

Day 3

Unfinished Business | With only 72 hours in a city, it’s likely that you’ll head back home with some unfinished business; don’t let that be missing one of Chicago’s incredible museums. This trip, we opted for the Museum of Contemporary Art Chicago to see their current Unfinished Business exhibition, showcasing artists whose work is never fully complete or is always evolving (Including one of our favorites, Alexander Calder). With so many impressive cultural institutions, be sure to set aside some time to visit at least one- plus, being in the AC doesn’t hurt, either. Pro Tip: The contemporary museum has a summer rooftop series with live music on their terrace every Tuesday. Get your tickets early!

Sun’s Out Bun’s Out | Soaking in the beauty of Chicago’s many museums will likely work up an appetite. Popping in for a burger at Au Cheval is a wise, and satisfying, use of your clock. Their burgers are quite well-known and absolutely worth the wait. If you’re pressed for time, stop by their Small Cheval outpost in Aster Hall. The elegant food hall is an art deco dream, and the satellite location certainly does their signature burger justice.

Ralph Lauren’s Residence | If you’re lucky enough to find yourself in a city that boasts one of Ralph Lauren’s restaurants, then you simply must stop by for a classic cocktail, or two. We reserved the coveted library nook table for afternoon drinks and oysters, which did not disappoint. The restaurant is so magnificently curated with interiors honoring the design legend’s impeccable point of view that we felt as though we were being hosted in Ralph’s house for happy hour- he makes a killer martini.

Fast and Furious | You’ve been going full speed for the last couple of days, and you want your last night’s dinner to take you across the finish line. Enter RPM Seafood: a posh riverfront location with delectable dishes. Relish the views and summer air one last time as you dine on a menu of refined seafood, steak, and handmade pastas. We found a hidden gem on their wine list from one of our trips to Sonoma a few years back and enjoyed a wonderful al fresco meal that ended our trip on a high note. Fun fact: the Chef has his own oyster producer and we treated ourselves to a half dozen of his signature shells.

Christmas in July: Planning Ahead for Holiday Events

This Season, Consider Planning Ahead for Holiday Events – You’ll Be Glad You Did

Guest Post By Claire Kelly

Photo Courtesy Of Cassie LaMere Events

Christmas came in June this year for my mother and me as we strolled through Dallas’ colossal Market Hall Center, literally rubbing elbows with the crowds of buyers, designers, and tastemakers making the twice-yearly pilgrimage to the Big D to scope the latest luxury products and assess trends.

Always a fun and inspiring trip, this year’s jaunt had us noticing a tendency within ourselves that seemed to also apply more broadly. We were consistently drawn to vendors showcasing holiday items – glittering showrooms decked with colorful displays of holiday-themed dinnerware, linens, wreaths and garlands, tree ornaments, and countless other types of regalia – and we weren’t alone. These shops were noticeably more crowded than ones with less season-specific offerings.

One reason for this trend seems obvious: our preoccupation with all things holiday could be owed, at least in part, to the global requirement of this past year to simplify – to trim the guest list rather than the tree. Whatever the reason, the message ringing through the halls in Dallas was clear: the 2021 holiday season is sure to be one to remember. Going all-out is definitely in.

And while this tone shift brings with it a welcome dose of optimism, it's easy for even the most seasoned event planner or host to become overwhelmed by the thought of the highly anticipated return of holiday entertaining after a long hiatus from the social status quo.

With this season getting us *cautiously* excited about the possibility of no holds barred soirées, we want to make sure you're prepared for an especially elegant - and extroverted - time. To that end, here are a few tips to help you make the most of the weeks and months ahead so that when November and December do arrive, you can relax and cherish meaningful moments with family and friends. After all, that's what the holiday season is all about.

Solidify your venue plans

If your event – be it a corporate Christmas party, family holiday gathering, annual holiday dinner, or other festivity – requires a venue that you must reserve, make sure those plans are locked in now. With countless would-have-been 2020 events taking place in the second half of this year, venue space continues to be extremely limited.

Understanding this reality will not only help you whittle down your list of potential venues, but also encourage you to consider lesser-known or outside-the-box spaces – places that are likely to have a lot to offer in terms of uniqueness and bang-for-the-buck but may not have been top picks initially. If you do have your heart set on a certain location, see if the venue includes multiple spaces and inquire about reserving a different area within the same setting (a hotel’s rooftop bar rather than its ballroom, for example).

Hop on the micro-event bandwagon...or don’t

2020 reminded us that intimate gatherings can be just as stylish as more grandiose affairs, which means the sky’s the limit in planning right now. The micro-event trend is still in full swing as people realize that small-scale events come with a lot of perks, but large-scale celebrations are also having a moment.

The thing to remember then is to socialize in whatever way is best for you. If you’re excited by the prospect of an ultra-lavish affair, embrace that. Or, if you prefer something smaller, blow your closest family and friends away by prioritizing quality over quantity- you’ll be able to spend twice as much per guest by cutting your list in half. So, whether you’re throwing a petit fête, or the event of the decade, do it up in (your own) style.

Embrace alternatives

If the past year has taught us anything, it’s the value of being flexible and not sweating the small stuff. Successful event planning is as much about creativity as it is about logistics, so avoid the temptation to try to make festivities look exactly like they did before 2020 and think about ways to incorporate new traditions.

Restaurants booked up every weekend in December? Why not host a company Christmas party brunch or happy hour on a weekday rather than a Saturday night dinner? Agonizing over not being able to order your Thanksgiving meal from the catering company you’ve used for years? Consider trying a completely new food genre rather than attempting to recreate the same menu through another service.

Focusing on creating a warm, gracious setting – instead of focusing on what didn’t work out – will ensure that friends, family, or whoever you’re hosting walks away having had a truly meaningful – and fun – experience.

Think about gift-giving now

Selecting truly unique, thoughtful gifts – especially for people beyond your circle of closest friends and family - can be one of the most daunting aspects of holiday prep, which is why getting shopping done well before the holiday season kicks off can reduce stress significantly and leave you freer to actually enjoy the rounds of events on the horizon. But how does one get inspired to shop without the festive atmosphere of retail holiday hustle and bustle?

If you're responsible for finding gifts for multiple employees, colleagues, or clients, it can be helpful to remember that many vendors now offer bespoke, personalized gift options online. Many companies - including Cassie LaMere Events - design, source, and execute custom gifts, curated gift boxes, or experiential deliveries for those looking to send specialized gifts.

Opting for services like these not only frees up your to-do list, but ensures that your gifts are creative and something recipients will actually want to use. They can even promote shopping local, as specialty gifting companies often make a point of collaborating with makers, artisans, or boutiques to create gifts that are highly customized or original. Avoid last-minute gifting blunders that don't make an impact; it's obvious to the recipient who took the time to select a thoughtful gift and those who grabbed something expected due to time constraints.

So know that you’re not alone – there are plenty of creative, convenient options for expressing appreciation for the people in your life. Just be sure to put your orders in extra early this year, as shipping delays are impacting the availability of goods worldwide.

Pro tip: Don’t forget the host! Keep a stash of simple-yet-stylish goodies on-hand so you have hostess gifts ready to go for last-minute events and invites. You can build your stash by looking at everyday outings as opportunities for inspiration; finally trying that trendy new restaurant? Remember the foodies in your life and see about picking up a run of gift cards. Headed out-of-town? Jaunts to new destinations are perfect opportunities to pick up smaller presents or unique stocking stuffers.

Identify your priorities ahead of time...and stick to them

Perhaps the most significant lesson 2020 gave us is the value of slowing down and truly cherishing the moment. But remembering this wisdom amid the holiday whirlwind is challenging to say the least, which is why it’s crucial to take some time to reflect on your own social priorities – whether you’re a host or a guest – well before the invitations start rolling in.

Consider saying “yes” to fewer invites this season so that you have mental and emotional energy for the gatherings that are most important. Leaving space in your calendar for restorative downtime helps ensure that when you do go to a social event, you can do so with an authentic, gracious attitude. And remember, there’s no urgency to “make up for lost time” – 2021 is just one of many festive years to come.

Styling: What to Wear to Summer Weddings and Events

You’re ready to RSVP “YES” and we’re here to help with styling tips to ensure you’re the best dressed guest.

Summer weddings and events are the much-needed occasions we’ve all been longing to dress up for and it's time to live it up! We’re going beyond decoding the dress code to share our tips for selecting the perfect event ensemble. Our tried-and-true styling secrets have been honed after many years in the field and when it comes to being the best dressed guest, we know a thing or two about what it takes.

From party attire that makes for picturesque photos, to why the art of dressing well requires research- these are our secrets for enjoying upcoming soirées in style.

Opt for a Block Heel | You've likely lost your stamina for the incline of your favorite stilettos after a year of athleisure, sneakers, and slippers. Couple that with all of your pent up dance party energy and we can guarantee you're not going to want your shoes to come between you and your favorite song on the dance floor. By making sure your attire works with a chunkier block heel, you’ll be able to carry yourself with confidence, instead of being that guest whose feet clearly hurt (Been there) and keeps you prepared for any unexpected foes of fanciful heels at the event venue such as a dewy lawn or cobblestone path. Dance the night away, darling!

Research the Venue | One of the best ways to make a statement at any event is to dress in tones that are complementary to the environment. Take the time to look up images of the venue and past events at the space to get an idea of the existing color tones, textures, and surroundings. Not only will you have a collection of visuals to help inform your look, you’ll also glean insight into whether other environmental details will play a factor- such as planning for sunnies at the ceremony before the sun goes down, or a light jacket draped over your shoulders in the evening for an al fresco dinner under the stars. Once you understand the vibe of the location, you’ll be better equipped to select an ensemble that will feel harmonious within the space, which makes for picture-perfect images.

Never Underestimate the Power of the Accessory | If sustainability or budget are your focus, consider repurposing a staple dress or jumpsuit as your attire and freshen up the look with accessible accessories. A pair of clavicle duster earrings, an updated petite minauderie, or patterned pumps can pack a punch, making a look feel brand new for the occasion. Accents like jewelry or purses are a great way to incorporate of-the-moment stylish trends that will help that key wardrobe workhorse item appear au courant.

Consider the Itinerary | As event designers, we know first-hand how an ensemble can make or break a guest’s experience. A key to selecting the right outfit for an occasion lies in breaking down the itinerary. If the ceremony is in a garden overlooking a vista, you’re probably going to want to opt for a breathable fabric. If the hosts are foodies and are treating guests to a multi-course seated dinner with wine pairings (Lucky you!), you’ll enjoy the experience more if you select an outfit with softer draping, as opposed to sitting for hours with a tight waistband or corseted boning. If the bohemian bride prefers low to the ground lounges and tables, then you’ll want to ensure there’s some length to your ethereal gown, instead of a hot mini cocktail dress number that doesn't allow you to sit comfortably on trendy party poufs.

Images Courtesy Of: 1 | Loeffler Randall x BHLDN 2 | Monique Lhuillier x Moda Operandi 3 | Cult Gaia x Neiman Marcus 4 | Atmosphere x Over the Moon