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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.