Guide to Summer in Chicago

It’s officially the first day of summer! Because winters are long and brutal, Chicagoans go all out from squeezing in patios wherever there’s space to extra long beach days. Even if it’s 100 degrees and humid, you’ll see patios and rooftops packed. And while you’ll find me hibernating for a better part of the warm season, it’s fun to get into a summer dress and enjoy an ice cold glass of rose. Whether you’re a local or visiting for a few days these next few months, we’ve got your guide to summer in Chicago from where to eat to how to escape the heat when it becomes too much. Grab your sandals and let’s start the celebration!

WHERE TO EAT
Breakfast at the Allis
Start the day in style at the Allis in Soho House. One of my favorite places in Chicago, the Allis has a unique, welcoming environment with design elements that scream to be shared on Instagram. Choose from house made baked goods, cold pressed juices, and delightful egg selections. The French Toast with berries and vanilla creme anglaise are delightful. The Baked Eggs in arrabbiata sauce are a unique choice with tons of flavor or build your own omelet. I’ve had almost the entire breakfast menu at the Allis and I haven’t been disappointed yet.

Lunch at City Winery on the Riverwalk
The riverwalk has recently gone through a makeover in the last couple of years. Previously a place that locals and visitors avoided, the City of Chicago has put a lot of money into cleaning it up and making it a place for people to enjoy. There are plenty of areas to sit back and relax, landscaping has been added and there are a sprinkling of restaurants and grab-and-go food joints. One of the restaurants in particular that I love to enjoy after a long day is City Winery on the Riverwalk. City Winery is a pretty popular establishment with a few locations scattered across the country. They’re known for wine, of course, and also live music performances. City Winery at the Riverwalk is a casual spot with a fantastic wine selection and delicious shared plates. They’re a great option for lunch because it tends to get crowded later in the day and the shared plates make munching easier when it’s warm outside. If you happen to be coming in the cooler months, they have heated domes so you can still enjoy the gorgeous views even if it’s below freezing.

Afternoon Tea at LondonHouse
Get out of the heat with afternoon tea at Bridges in LondonHouse. Their menu features sweet and savory bites, a variety of teas, and lovely wine selection for those looking to embrace the “rose all day” mentality. For a complete experience, order the LondonHouse Tea for a $50 flat fee per person. It comes with all their sweet and savory treats in a beautiful tiered presentation and your choice of tea. Sip a cup of Earl Grey or glass of Whispering Angel while enjoying unbeatable views of the Chicago River in a comfortable, sophisticated environment. It’s a lovely way to spend an afternoon.

Dinner at Shore Club
Possibly the hottest new spot to hit the scene this year, Shore Club takes beach casual and merges it with sophistication. Located on North Avenue Beach, Shore Club has gorgeous views of the lake and a variety of seating and dining options. Enjoy a romantic dinner for two in the restaurant or get the night started with the girls in one of the cabanas. Their menu is inspired by Mediterranean cuisine and has something for everyone. This is the #1 spot on my summer bucket list and I hope to see you there as well!

Dessert at Smallcakes Cupcakery & Creamery
The hottest dessert craze in Chicago at the moment, Smallcakes offers homemade cupcakes and ice cream to anyone with a sweet tooth. Their Limited Edition Mason Jars with Smallcakes SMASH has taken over social media and for good reason too. Cupcake meets ice cream in a mason jar filled over the brim with all kinds of goodness. You choose a cupcake and two scoops of ice cream. They stuff a mason jar. Try one of their regular cupcake flavors like the Chocoholic or Cookies n Cream. They also feature monthly flavors with a different one for each day of the week. It’s the ultimate summer treat.

WHERE TO GET OUT OF THE HEAT
Browse Impressionist Art at the Art Institute of Chicago
Illinois residents, save a buck at the Art Institute of Chicago on Thursday nights after 5pm with free entry! Browse the well-renowned modern wing, see ancient artifacts, or walk through the 2nd largest collection of Impressionist art in the world. Outside of the D’Orsay in Paris, a museum strictly for Impressionism, the Art Institute has the largest collection with pieces from Monet, Manet, Degas, Renoir, and more. I can get lost in the paintings from this era. Make sure to check out upcoming events at the Art Institute as well. They have them regularly and might provide a nice activity for your visit.

Experience TV History at SNL: The Experience
Last fall, the Museum of Broadcast Communications launched SNL: The Experience, something Chicago is very proud of. Second City has given Chicago a name in the world of comedy. Many of the comedians that have performed and worked at Second City have also made a name for themselves on SNL like Tina Fey, John Belushi, Steve Carell, Bill Murray, and Stephen Colbert. The exhibit takes you through the entire SNL experience from the first meetings of the week to what happens after the show. They also have recreations of famous sets like Wayne’s World and Weekend Update, plus a replica of Studio 8H.

See Chicago From 94 Floors Up
360 Chicago has one of the best, if not the best, views of Chicago. With a 360 degree view of the city 1000 feet up, there’s nothing quite as ethereal like seeing the lake extend out for miles during sunset. Lucky for you summertime visitors, the 360 Chi Series is all summer long and features special events and activities throughout the week. Enjoy yoga in the mornings on Saturdays, Sunday Funday for families or my favorite, happy hour on Thursdays! If you have the guts you can also try Tilt which has you leaning over the city. It’s the craziest thrill seeking adventure that I’ll ever do.

THINGS TO DO
Hit the Beach!
From the South Side to North Shore, Chicago is full of beaches along the lake. It isn’t summer in Chicago if you don’t visit at least one of them. My personal favorite is Oak Street Beach tucked away near Navy Pier. It’s smaller and not as well known so it doesn’t get as crowded as the likes of North Avenue Beach. Of course, North Avenue is one of the places to be if you’re heading to the lake and I encourage the experience at least once. Montrose Beach is another great option farther north of the city close to the Uptown neighborhood. And if you’re willing to go even further, Rogers Park (the last neighborhood in Chicago before hitting Evanston) has beautiful parks along with the beaches up there. The beaches on the south side have unbeatable views of the skyline, FYI. For a complete guide to beaches in Chicago, I suggest checking out this recent article from Thrillist.

Enjoy one of the MANY Festivals.
With summer being such a short season in Chicago, we’ve learned how to pack in all the good stuff and that is including festivals. From May through September, it’s a safe bet to expect several festivals every single weekend throughout the city. Windy City Smokeout coming up in a few short weeks is one of my personal favorites. Barbecue joints from around the country come and serve their favorite dishes like BBQ Pulled Pork, Ribs, Fried Chicken and more. And what’s barbecue without a little country music?! A few bands and artists I’ve seen perform at Smokeout include Maren Morris, Dan + Shay, Chris Young, Big & Rich, Billy Currington, and Kacey Musgraves. A few other festivals I’d recommend are Logan Square Food Truck Social (because, food trucks, duh!), Northalsted Market Days, and Chicago Gourmet. RedEye Chicago has a complete guide to Chicago festivals and Choose Chicago breaks down the biggest ones by month in case you need help shuffling through the mess.

Take a Ride on the Water.
The best part about Chicago being located on a lake is that the lake tours are one-of-a-kind and spectacular. Shoreline Sightseeing has really affordable boat tours. Take an architectural tour that goes along the Chicago river and into Lake Michigan or just take a Classic Lake Tour. While it doesn’t have all the history of the architectural tour, it does share a few facts and you’ll be on the lake the entire time instead of the river. They’re also shorter which is nice if you have kids or a short attention span. Tour times are available all day long but if you’d love a great sight, Chicago at sunset from Lake Michigan is unbeatable. Check your weather app and get in line early to make sure you grab a spot.

Watch a Movie in Millennium Park
Tuesdays through August, see a free movie in Millennium Park. Get there early to grab one of the seats in front or take a picnic basket filled with snacks and a blanket to kick back on the green. It’s a local favorite. You’ll find lots of couples enjoying a date night and groups of friends having wine and a dinner they pulled together on their way over from the office. If you’re visiting Chicago on your own, there are plenty of people who enjoy the free movies in the park on their own as well so you’ll be in good company. A few of the movies playing this summer are WALL-E, Coco, Slumdog Millionaire, and Get Out.