13 Kickass End-of-Summer Outings in Chicago, Organized by Drake Lyrics

“My summer diet is just rosé and calamari.”

End of summer Chicago Outings
Squeeze in one last rooftop dinner while you can
Instagram/@drinkoffshore
By Claire Young / August 8, 2019 9:53 am

It’s hard to believe, but it’s already August, and for Chicagoans, that means there isn’t much summer left.

So plan your final warm-weather weekends and check off your most coveted summer to-dos before the weather turns. And if you’re fresh out of ideas, we put together a guide to the last remaining essential outings around the city … and then we organized them by Drake lyrics.

Why Drake? Because Champagne Papi’s lyrics have always had a certain catchy, endlessly repeatable and applicable sheen that’s ideal for captioning your assorted thirst traps, selfies and Hot Girl Summer posts. Consider:

  • No new friends
  • Too blessed to be humble
  • Mixing vodka and emotions
  • Started from the bottom now we’re here

Combine that with the fact that Drake just released Care Package, a new collection of odds and ends released between 2010 and 2016, and the timing couldn’t be better. So check out these summer hot spots and hashtag accordingly. It’s God’s Plan. 

Chicago end of summer outings
(Slim’s Chicago)

Sinatra lifestyle, I’m just bein’ frank with ya

Drake Track: 5am in Toronto

Outing: Consider Chicago History Museum’s Hot Dog Fest this weekend as an alternative, or end cap, for Northalsted Market Days. A suggested $5 donation gets you into the family-geared festival, then use food and drink tickets to sample over 15 hot dog vendors. Buy discounted tickets online in advance. Check out the Hot Dog History lessons on the Speakers’ Stage.

Details: Website, August 9 to 11, 11 a.m. to 9 p.m.

Location: Lincoln Park at Stockton & LaSalle

Chicago End of Summer Outings
(Chicago Electric Boat Company)

Spendin’ all my days on the east side. Forgettin’ who I was on the other side.”


Drake Track: Days in the East

Outing: Rent a boat, take in the river before it freezes over, and head to the open water of Lake Michigan. During the day, post-up at the famous Play Pen, and in the evening, watch the sunset behind the skyline and set skyscraper windows alight. For an eco-friendly ride, rent from Chicago Electric Boat Company

Details: Website, $150-$225 per hour depending on the vessel.

Location: Lake Michigan

Chicago end of summer outings
(Instagram/@cabrachicago)

My summer diet is just rosé and calamari


Drake Track: 4PM in Calabasas

Outing: Stephanie Izard’s Cabra, located on the top floor of the The Hoxton, Chicago hotel, is the perfect summer dinner spot. The top floor restaurant/bar/pool converts into a massive open air patio and guests can enjoy delicious seafood and a summer sunset. Reservations can be made online.

Details: Website

Location: West Loop

Chicago Summer Outings
(Instagram/@chicagosymphony)

This shit sound like what being rich feel like


Drake Track: My Side

Outing: Pack the candle sticks and take the Metra UPN to catch the Chicago Symphony Orchestra at Ravinia. Outside food is encouraged and picnic game is strong up north. Treat your someone special to blankets, pillows, a charcuterie board and take in some culture in the summer evening air. 

Details: Website, Friday 8/9, Saturday 8/17 and Sunday 8/18

Location: Ravinia in Highland Park

end of summer outings chicago
(Instagram/@shoreclubchi)

We move the operation to Cali soon as the snow drop


Drake Track: Jodeci Freestyle

Outing: Hit the beach in style at Shore Club. In its second full season, this spot rents beach cabanas and serves food at their outdoor patio and restaurant. Daybeds start at $50 and large cabanas (which can fit up to 30 guests) run $200 for four hour slots. Keep an eye out for their sponsored events if a whiskey tasting at the beach sounds like summer. 

Details: Website

Location: North Avenue Beach

End of Summer Outings Chicago
(Chicago’s Finest Tours)

I swear, you don’t know this city anymore


Drake Track: Club Paradise

Outing: It’s been said there are two seasons in Chicago: winter and construction. If you haven’t hit the pavement lately, there’s probably something new around the corner. Take advantage of the weather and join a walking tour. The Riverwalk or Devon Avenue are great places to get lost wandering. If you’d prefer to float, the architectural boat tour can’t be beat.

Details: Riverwalk Walking Tour, Devon Avenue Spice of Life Tour, Wendella Architecture Tour

Chicago End of Summer Outings
(Jonathan Daniel/Getty Images)

I’m on my King James shit, I’m tryna win here again


Drake Track: 5AM in Toronto

Outing: Can the Cubs finish the regular season first in the NL? October is right around the corner, so sneak in a game at the friendly confines before it turns into post-season frenzy. There are about 20 home games left. If the Cubs pull out a W, consider this alternate Drake lyric: Coming live from the motherfuckin’ North Side. (Trust Issues)

Details: Website

Location: Wrigley Field

Chicago Best Summer Outings
(Instagram/@monnieburkes)

“I don’t have to work in the morning so I always stay for one more


Drake Track: Free Spirit

Outing: The patio at Monnie Burke’s in Pilsen is the summer draw, but the food will keep you satisfied. A relatively new joint, their outdoor area has seats for 200. Sunday, August 18 the joint is hosting a Tiki Party and pig roast dinner. 

Details: Website

Location: Pilsen

Chicago End of Summer Outings
(Twitter/@chiwatertaxi)

These days keep going by too fast, so give me anything to make shit go slow


Drake Track: Free Spirit

Outing: Take the Chicago Water Taxi to Chinatown. Tickets are $6 one-way or $10 for an all-day, unlimited use pass. Once in Chinatown, grab dim sum atTriple Crown and rolled ice cream from Legend Tasty House. FYI food and non-alcoholic beverages are allowed on the water taxis, so pack some snacks for the slow boat to Chinatown. 

Details: Website, pickup locations are along the river

Location: Downtown 

Chicago end of summer outings
(Instagram/@wndrmuseum)

Either I’m gettin’ bigger or you’re just gettin’ smaller or it’s both


Drake Track: Jodeci Freestyle

Outing: Can’t do a post about captioning photos without name-checking the cit’s favorite Instagram trap: WNDR museum’s summer run ends September 2. While they will open up runs for upcoming months, there’s no time like the present.

Details: Website

Location: West Loop

chicago end of summer outings
(Instagram/@drinkoffshore)

Crazy how you gotta wait until it’s dark out to see who really with you


Drake Track: How Bout Now

Outing: Rooftop dinner and drinks are required reading. Any rooftop will do, but worth mentioning is Offshore. Yes, you’ll have to go to Navy Pier, but these are your final summer outings! Drink with unmatched skyline and lake views on the 20,000-square-foot terrace. Live music, fire pits and tons of seating might distract you from the solid food and drink menu. Relive your youth with a bagged cocktail called Secure the Bag; the mix of Malibu passionfruit, lime, orange and grenadine is the perfect salute to summer. 

Details: Website, Air and Water Show tickets are still available.  

Location: Navy Pier

chicago end of summer outings
(Instagram/@neonsummerchicago)

Certain shit is just too wild to reconcile


Drake Track: 4PM in Calabasas

Outing: Outdoor go karts, mini golf, axe throwing, food trucks. Neon Summer is the latest pop-up from the folks behind Jack’s Pumpkin Nights and Frosty’s Christmas Bar. There’s three bars and when the sun goes down, the neon comes up. Prices range from $8 to $55 depending on package

Details: Website, open until September 8

Location: Goose Island

Chicago end of summer outings
(Bud Billiken Parade)

And all I care about is my city, man, I can’t say it enough


Drake Track: Free Spirit

Outing: The Bud Billiken Parade, in its 90th year, is America’s largest and oldest African-American parade. Join hundreds of thousands of attendees (or watch with one million on ABC7) to send Chicago’s youth back to school with marching bands, parade floats and drill teams. The two-mile route ends with a giant picnic in Washington Park. 

Details: Website, The parade steps off at 10 a.m. on Saturday, August 10

Location: Bronzeville to Washington Park