‘Tis the season for the BEST TIME IN CHICAGO summer. My favorite. There is so much to do around Chicago and honestly a lot of things have been booking up early in advance. Ever since COVID, reservations seem to be a must. That’s one of the reasons I wanted to get this out to you ASAP! There are event dates on here, but always confirm with their website or socials too.

The ABC’s of Chicago Summer

A: 

• Aperol spritz on a patio in Andersonville
• Architecture Boat Tour
• Argyle Night Market (7/24)
• Astronomer in the Parks

B:

• Belmont-Sheffield Music Fest (5/22-24)
• Broadway in your Backyard
• Bud Billiken Parade (8/8)
• Burger Fest in Roscoe Village (7/17-19)

C:

• Casa Cactus Cafe for a Cafe de Olla 
• Chicago Cultural Center
• Chicago Jazz Festival (9/3-6)
• Chinatown Summer Fair (7/25-26)

D:

• Dock at Montrose Beach
• Drag brunch at Kit Kat Club or Walnut Room
• Drinks on a rooftop
• Drive-in movie night

E:

• Edgewater Music Fest (8/28-30)
• Edison Park Fest (8/28-30)
• El Grito Chicago (9/12-13)
• Elston Electric

F:

• 57th Street Art Fair (6/7)
• Family movie night in the parks
• Fireworks at Navy Pier
• Flavors of Albany Park (6/24)

G:

• Garfield Park Conservatory Children’s Garden
• Gene’s Sausage Rooftop in Lincoln Square
• Glenwood Avenue Arts Fest (8/14-16)
• Griffin Museum of Science + Industry

H:

• Happy Hour at RPM Seafood
• Hyde Park Jazz Festival (9/26-27)
• Holy Grounds Cafe in Pilsen
• Hot girl walks on the Lakefront Trail

I:

• Ice Cream Crawl in Logan Square
  • Pretty Cool Ice Cream
  • Miko’s Italian Ice
  • Logan Vegan
  • Jeni’s
• Improv Show at The iO
• Indie Bookstore Crawl in Beverly
  • Bookies
  • Honey & Hue
  • Undercover Books
• Italian dinner at Mart Anthonys

J:

• Jazzin’ at the Shedd
• Jefferson Park Farmer’s Market
• John’s Food and Wine for Happy Hour (5/24)
• Join a neighborhood cleanup

K:

• Karaoke night with the girls at Lincoln Karaoke
• Kayak Glow in the Dark tour
• Kids eat free at Community Tavern Tuesday – Thursday & Sunday
• Korean BBQ Night

L:

• Lickity Split Frozen Custard & Sweets
• Lincoln Park Greek Fest (6/5-7)
• Logan Square Arts Festival (June 26-28)
• Lunch at The Lakefront Restaurant 

M:

• Mario’s Italian Lemonade
• Mayfestiversary (5/23-24)
• Millennium Park Summer Film Series
• Minecraft Experience 5/26 (Use code CHICAGOGOODLIFE10 for 10% off tickets – book through this link here)

N:

• Night Market at Water Tower Place on Thursday Nights
• North Park Nature Center
• Northalsted Market Days (8/7-9)
• Northerly Island Picnic

O:

• Obama Presidential Center
• Old Town Art Fair (6/13-14)
• Original Rainbow Cone in Beverly 
• Outdoor Movie at the Park

P:

• Palmisano Park
• Pokémon Fossil Museum at the Field
• Portage Park Public Pool
• Pride Parade (6/28)

Q:

• “Quit work early” summer date
• Queso + margarita patio night
• Quiet bookstore browsing at Quimby’s Bookstore
• Quiet luxury tea service at Peninsula

R:

• Rent a boat
• Ribfest Chicago
• River lunch date at Taco Rio (8/24)
• Rooftop Cinema 6/24)

S:

• Salt Shed Market (5/31)
• Sandwiches at Panes Bread Cafe (7/25)
• Southport Art Fest (7/11-12)
• Square Roots (7/10-12)

T:

• Tacos at Pacos Tacos
• Taste of Polonia (9/4-7) (8/25)
• Thrifting in Avondale
• Tuesdays on the Terrace

U:

• U-pick berry farm day trip
• Ultimate Self-Care Day using Resort Pass
• Unplugged spa day at AIRE Ancient Baths (12/25)
• Urban winery visit at Vin 312 or Bronzeville Winery

V:

• Veuve Clicquot Courtyard at the Waldorf Astoria (5/26)
• Vietnamese food crawl on Argyle
• Vinyl record store browsing
• Volunteer at a food pantry

W:

• Waterfront Cafe in Edgewater
• White Sox game
• Wicker Park Fest (7/24-26)
• Windy City Smokeout (7/8-12) (7/25)

X:

• eXchange books, toys, or clothing locally
• XOXO girls’ brunch and gossip session
• eXplore a new-to-you neighborhood
• X-tra long beach day

Y:

• Yap session on the beach
• Yard games at Park and Field
• Yoga by the lake

Z:

• Zero plans Chicago summer wandering
• Zero Waste small business shopping
• Zoo date at Lincoln Park Zoo
• Zoom around on Divvy bikes (6/24)

For more Chicago summer fun and guides, like our huge roundup of farmers markets, follow me on Instagram and TikTok!