Our blessed Chicago summer has finally arrived and we all have one goal: Make the most of it! Don your sunglasses and head out the door to enjoy Chicago’s best summer experiences. Because Chicago is so vast and I still have plenty of places I want to try, my list of things to do in Chicago this summer is broken down into two parts – “What I Love” – my own recommendations – and “What I Want to Try” – the places I’ve been dying to go. If you’ve experienced any of the things I want to try, please comment below and let me know how they are!
Al Fresco Dining
\\ What I Love \\
- The Southern (1840 W. North) – This outdoor, partly-shaded patio gets sweeter every time I go. Refreshing seasonal cocktails are paired with a rotating southern menu, allowing you to try something new each time. When weather permits, the second story opens up with breezy cabanas for hosting your best group of friends. My favorite experiences have included Johnny Cakes, hushpuppies and even an all-you-can-eat crawfish boil.
- Oak Street Beach Bistro (1001 N. Lake Shore Drive) – While most know about Castaways, Oak Street Beach Bistro is a tamer version at the next beach over. Don’t worry if your feet are covered in sand, stop in for a beer and some fish tacos while you people-watch the afternoon away.
- Derby (1224 W. Webster) – Also featuring southern fare and drinks, Derby is fun year-round. When it’s a sunny Saturday in the middle of the summer, Derby is my first choice when I’m looking for outside seating – I’ve been lucky enough to get a seat each time! While the brunch menu isn’t that large, their main menu has an extensive list of choices, all of which you can top off with a Mint Julep, Beermosa or Cool as a Cucumber.
\\ What I Want to Try \\
- RM Champagne Salon (116 N. Green) – Paying homage to one of my favorite drinks, RM Champagne Salon has a courtyard strung with party lights (gorgeous in the pictures). The restaurant opens up at 5 p.m. each night and 11 a.m. on Sundays for brunch. I can see myself lounging under the sparkling lights, ordering a cheese plate while sipping a glass of champagne…
- Elle on the River (330 N. Wabash) – Situated on the patio outside the Langham Hotel and restaurant Travelle, this sweet new spot is serving up Mediterranean tacos, craft sodas (with the option to add your liquor of choice), and summer-flavored punch bowls titled “Better than a Bradford,” “Elle a Noir” and “Down by the River.” Don’t forget the lovely view of the city over the river.
Rooftop Party Hopping
\\ What I Love \\
- ZED451 (739 N. Clark) – While ZED451’s rooftop is only two floors high, it still offers great city views of the surrounding buildings. You’ll enter through the restaurant’s first floor bar, climbing a set of stairs to get to the top. With a number of seating options – long benches, two-seater high-tops and mini cabanas for groups – you can sit down and order a bite off the restaurant’s lighter Cravings menu. This is a great spot for a special event or a night out with friends.
- J. Parker (1816 N. Clark) – The drinks may be expensive, but the view makes up for it. Take the special elevator up to the top of Hotel Lincoln and step out to incredible visibility of Lincoln Park and the lake. The view encompasses some of Chicago’s best natural beauty and reinforces your love for this great city. Expect a hip see-and-be-seen crowd, and don’t expect to get a seat during peak hours.
\\ What I Want to Try \\
- I|O Urban Roofscape (127 W. Huron) – Swanky hotel The Godfrey boasts an indoor/outdoor rooftop space serving up food and drinks to its fabulous visitors. Open from breakfast/brunch through late night, the restaurant/bar sits under a retractable roof that allows for year-round entertaining – and they even take reservations! My apartment window overlooks the hotel, leaving me wanting to go every day. One of these days I will make it happen!
- 52Eighty Rooftop Lounge (166 E. Superior) – Several of my fellow Chicago bloggers made me jealous with their recent pictures from Mile North Hotel’s new rooftop, 52Eighty. Twenty-eight stories up, this brand-new space looks like it’s going to be one of the summer’s hottest rooftops!
- Little Goat Rooftop (820 W. Randolph) – My Mom and I stumbled across this little gem while waiting to be seated in Little Goat’s main dining room. This cozy space offers cushioned benches, an outdoor bar, and even a few manicured plants and flowers to enhance the atmosphere. Perched on top of the main restaurant, this rooftop offers a great view in the middle of the West Loop. Since it is adjacent to the dining room that can be rented for private events, the rooftop is only open for very specific hours – please check their website for more details.
Fresh Air Fitness
\\ What I Love \\
- Running the lakefront trail – In my Chicago Marathon training days, I conquered approximately 10 miles (out and back to get in a total of 20!) of that well-worn trail. While the stretch between Fullerton and Oak Street is especially popular due to the beaches, this congested area is not the only scenic part of the route. Heading north between Montrose and Foster you’ll take in expansive fields, nearly empty beaches, and plenty of peaceful spots to camp out for the afternoon. Heading south, you’ll pass by beauties such as the Buckingham Fountain, incredible skyline views by the museum campus, and ultimately more sandy shores looking back up on the loop.
- The Color Run – Read about my experience at The Color Run and enter to win 2 tickets here.
\\ What I Want to Try \\
- Yoga at Lincoln Park Zoo’s Nature Boardwalk – Held under the unique wooden sculpture modeled after a turtle shell, weekly yoga classes bring your workouts back to nature. In addition to the picturesque view of the city skyline, you’ll be surrounded by wildlife living in the boardwalk’s ecosystem. Curious? You can even try it out for free – on Saturday, May 31 from 9 – 10 a.m. and Sunday, June 1 from 10 – 11 a.m.
- Stand-up Paddleboarding – If you haven’t seen pictures of this unique sport, it’s a cross between surfing and kayaking – you’ll stand up on a board and paddle around in the lake. Chicago SUP offers rentals, lessons and even crazy classes such as SUP-Yo (yoga on the board) and SUP-Fit (cross training on the board). Who wants to sign up with me??
Low-Cost Culture & Events
\\ What I Love \\
- Navy Pier Fireworks – Seeing a spectacle in the sky is not just for 4th of July anymore – in Chicago, you can be dazzled with fireworks every Wednesday at 9:30 p.m. and every Saturday at 10:15 p.m. While you can go directly to Navy Pier to view the fireworks shows, I would recommend finding a rooftop to watch them from, or go out on a fireworks cruise on a boat or kayak.
- Movies in the Park – Movies in the Park is entering its 14th season, bringing communities together to view classic and modern movies under the stars – for free! Bring your blanket, chairs and picnic to enjoy a balmy evening with friends. I had the pleasure of seeing my favorite movie, Ferris Bueller’s Day Off, at the Chicago History Museum last year. Favorites this summer include:
- July 5: Gravity at Jonquil Playlot (1001 W. Wrightwood)
- July 9: Ferris Bueller’s Day Off at Chicago History Museum (1601 N. Clark)
- July 17: The Sandlot at Wicker Park (1425 N. Damen)
- August 8: The Goonies at Wrightwood Park (2534 N. Greenview)
- August 12: The Blind Side at Montgomery Ward Park (630 N. Kingsbury)
- August 23: Wizard of Oz at Oz Park (2021 N. Burling)
- Arlington Racetrack – Bring your floppy hats, your sundresses and your bowties to spend a day in the sunshine at Arlington’s beautiful horse racing track. Unlike some of the other horse racing experiences you may have had, you can actually see all of the horses at this track. Even though this location is in the suburbs, it’s easy to take the Metra from Clybourn station and you can even drink on the train. With tickets typically only $12, you’ll get to see the horses race every 20 minutes and grab some food/drinks or place a bet before the next one. The track’s biggest race, the Arlington Million, will be a big party on Saturday, August 16.
- Farmer’s Markets – There’s nothing like finding fresh inspiration for your dinner from the bountiful produce, meats, cheeses and more flowing from local farmers at Chicago’s many Farmer’s Markets. While my favorite remains the Green City Market in Lincoln Park, many neighborhoods host their own markets on various days of the week, including lunch hours in the Loop. Visit the link above to find one near you.
\\ What I Want to Try \\
- Jazzin’ at the Shedd – I still haven’t made it to this weekly (every Wednesday 5 – 10 p.m. from June 25 – September 3) summer event, but not for lack of trying! I bought tickets/Groupons the past two years but had conflicts both times. This year I am determined to enjoy the concerts featuring rotating artists outside the Shedd Aquarium. Attendees can choose from various food and beverage options for purchase. Bonus points for fireworks in the background and extended hours on select museum exhibits.
- Free Concerts at Millennium Park – The gorgeous Jay Pritzker Pavilion hosts free concerts throughout the summer, another great spot to bring a blanket and set up a picnic. There are several sets of concerts – Loops and Variations, which features new music mixed with electronica on Thursdays at 6:30 p.m., and Downtown Sound, which features varied genres of artists every Monday at 6:30 p.m.
Festivals, Concerts and Tours
\\ What I Love \\
- Chicago Pride Parade – This has got to be one of the city’s most fun one-day events. While the Pride Fest takes on a full week of festivities, the parade on June 29 guarantees color, spirit and a whole lot else! Warning: there might be sights you can’t un-see. But don’t let that stop you – the costumes, floats and performances make this a huge street party running for blocks and blocks in Boystown.
- Chicago Food Planet Tour (Bucktown/Wicker Park) – In addition to getting your fill of Chicago-based delicacies, you’ll be treated to a neighborhood history walking tour. I had the opportunity to learn about the “Beer Baron Mansions,” the painted lady houses, and the history of the park (Wicker Park) itself. This tour also provided my only “official” tutorial on the history, components and principles of the Chicago-style hot dog.
- Taste of Lincoln Avenue – One of Chicago’s most popular street festivals, Taste of Lincoln Avenue attracts a gathering so large you might end up crowd-surfing. To avoid the congestion, attend at off peak hours, catch one of the local cover bands (such as my favorite 80s cover band, 16 Candles), and sample the flavors of nearby restaurants you’ve never tried. This year’s festival is scheduled for July 26 – 27.
\\ What I Want to Try \\
- Do-Division Street Fest – Held this upcoming weekend, May 30 – June 1, West Town’s street festival hosts concerts, a sidewalk sale of artisan vendors, local food options and even a fashion festival (runway show!). Centered on the unique businesses and shops that make up the area, this festival gives true neighborhood flair and welcome to visitors from all over.
- Chicago Blues Fest – I feel like I’ve never fully taken advantage of Chicago’s history of blues music. From June 13 – 15, we can experience numerous blues and honorary acts in Grant Park for free. Headliners include Billy Boy Arnold, Bettye LaVette, Dr. John and more.
Follow The Chicago Lifestyle’s summer adventures around town on Twitter and Instagram.
Which of these have you tried? What tips would you give us for the places we haven’t been? Please comment below!