Chicago Summer Guide #2: Outdoor Markets, Festivals, and Entertainment


In our first Chicago Summer Guide, we covered some of the best places to dine outdoors this Summer.  Today, our second Chicago Summer guide is all about fun activities taking place all Summer long across the city. We're covering outdoor markets, music festivals, street festivals, outdoor theater productions, and we're introducing you to your new best friend for finding great free activities in the Chicago Parks! Make sure to check out our favorite activities below, and stay tuned for next week's third (and final) Chicago Summer Guide! For outfit details, scroll to the bottom of the post.


Farmer's Markets:

Nothing says summer like Farmer's Markets brimming with fresh produce and other local food goods.  Honestly maybe one of my favorite things to do in Summertime is to stroll through a Farmer's Market! There are a TON of neighborhood farmers markets in Chicago, and all of them are open at different dates and times, so definitely check out the full list HERE if you're planning a trip. In case you find yourself unsure how to prioritize which markets to check out- our absolute favorites are listed here:

Logan Square - This market spans a large portion of Logan boulevard- the selection is big and the environment is energetic.  This one is definitely my personal favorite of all the Farmers Markets in the City!

Lincoln Park - The Green City Market in Lincoln Park may actually be the largest outdoor Farmers Market in the city. Located at the south end of the park, this market occupies a lot of space and the environment is just as buzzing and energetic as Logan Square.  The selection is amazing and afterwards you can take your spoils and picnic along the Lake. This is a great one for tourists to visit while in town as there is free street parking nearby (if you're patient and willing to walk a couple of blocks) and is just a short trip from Mag mile and other downtown sights.

Daley Plaza (The Loop) -  Considering the downtown location, this farmers market is impressively large and a GREAT spot to do lunch on a Thursday if you work downtown. There are some pretty tasty baked goods and other food stands at this one, so definitely have a good look around beyond just the produce if you find yourself here!

Wicker Park - Although this neighborhood market is comparatively a bit smaller than Logan and LP, the Wicker Park farmers market is a really fun one to visit.  You'll still find a great selection, and after you peruse the market, you can head wherever you please in the always-bustling Wicker Park neighborhood.

Randolph Street Market (West Loop) - Ok, this one isn't really a farmers market, but it is decidedly a market as opposed to a street fest, so here it falls! Randolph Street Market is known for it's huge selection of vendors that set up each year for an impressive flea market that has a broad selection of all things antique, vintage, and re-purposed. The market will be open the last full weekend of each month during the Summer.

Street Festivals:

Each Summer, Chicago is home to plethora of street festivals. While each has its unique charms, you simply couldn't hit all of them (unless you never did anything else I suppose) so we're sharing the ones we've enjoyed most and would recommend heading to! For a full lineup of ALL the festivals check over HERE.

Andersonville Midsommarfest ($10 entry fee) Andersonville; June 8-10 - Celebrate midsommar the Swedish way! There's a variety of vendors selling all kinds of goods (jewelry, antiques, art), a good selection of food vendors, and an excellent music stage for live performances. I've perused the lineup to see that 16 Candles (Chicago's best known 80s cover band who I dearly love) will be playing one night!! Always a good time when 16 Candles comes on :)

West Fest: ($5 entry fee) West Town; June 6-8: This epic street festival on Chicago Ave is especially known for it's great live music lineup.  The Empty Bottle - a local dive bar and music venue- brings you two distinct stages. The main stages features indie, alternative, and rock bands while the second stage features house DJs.

Southport Art Festival: (no entry fee) Lakeview; July 14-15 - A great place to go and peruse local artwork of all kinds!

Wicker Park Fest: ($10 entry fee) Wicker Park; July 27-29 - LOADS of vendors flock to this amazing street festival/market. A great environment and a great place to pick up unique, one-of-a-kind goods.

Fiesta Del Sol:  (no entry fee) Pilsen; July 26-29 - Everything about this festival is FUN. This is a booze free event, but trust me, you won't miss it! The festival is a celebration of Mexican culture and is full of games, rides, entertainment, music, vendors etc.  This is a great festival for families with lots of activities that kids would love :)

Renegade Craft Fair: (no entry fee listed) Wicker Park; September 8-9 - I know it still a long ways off, but still technically during the Summer! This is probably our favorite of all the street festivals in Chicago. SO many artisans from near and far selling all kinds of decor, art, crafts, jewelry etc. Every year we find the most amazing things here!

Music Festivals AND Concerts:

Chicago Blues Festival (free admission) Millenium Park; June 8-10 - Once known as the "blues capital of the world" Chicago has a storied history with blues music.  It's no surprise then that this amazing festival is able to attract incredible blues musicians. You can bring in food, so make a date night of it by packing a picnic and sitting on the lawn!  Unfortunately, you can no longer BYOB to the Blues Festival but beverages are available for purchase nearby. 

Kendrick Lamar, SZA, and Schoolboy Q Concert (lawn seating starting at $44) Tinley Park, IL June 15 - Kendrick Lamar is on fire right now, and after SZA's amazing feature on "All the Stars" with Kendrick for the Black Panther album I'm sure we'll be seeing her name a whole lot more! This is technically outside the city, but worth a little trek!

Country Lakeshake Festival (one day tickets starting at $99, 3 day passes $150) Northerly Island; June 22-24 - Big names in country music and several up and coming country artists will be playing for 3 consecutive days at Northerly Island. 

Journey and Def Leppard Concert (tickets starting at $48) Wrigley Field; July 14 - A stellar lineup and a great concert venue with plenty to do post-show in the Wrigleyville neighborhood!

Windy City Smokeout ($40-45 single day ticket, $110 three day pass) River West/Fulton Market; July 13-15 - LOTS of good BBQ. LOTS of great country music artists. What is not to love? Your entry fee pays for your general admission ticket, but you'll still need to purchase BBQ. Still a great deal to see several BIG and up and coming names in country music!

Pitchfork:  (Single Day $75; 3 Day Pass $175) Union Park; July 20-22 - Pitchfork is Chicago's biggest indie and alternative music festival. You'll get to hear both emerging artists and established names like Fleet Foxes, War on Drugs, and Lauryn Hill.

Grant Park Music Festival (free admission -lawn seating) Millenium Park; June 13- August every Wed, Friday, and Saturday- This series features mostly classical and/or orchestral music. The perfect FREE date night. Pack a picnic and bring a bottle of wine along for this BYOB concert series! Check out the full schedule to see who is playing throughout the Summer.

Beyonce and Jay-Z (Tickets starting at $68) Soldier Field; August 10 & 11 - O. M. G.  Definitely the show of the Summer for Chicagoans!

Chicago Jazz Festival (free admission) Millenium Park; August 30-Sept 2 - Similar to the Blues Festival, the Jazz festival is free and and will allow you to bring your own food for a picnic dinner. Alcoholic beverages will be available for purchase.

Lollapalooza (1 day passes starting at $120) Millenium Park; August 2-5 - Probably one of Chicago's best known music festivals. With representation from Indie, Alternative, Pop, EDM, Rap, Hip Hop, Rock and Roll, Folk, and Country music there's a lot to love! plan ahead if you want to use restrooms (lines can be crazy!) and if there's a headliner you're dying to see up close, make sure to stake your ground during the PREVIOUS musician's show!

Outdoor Entertainment:

MY CHI PARKS: I won't be able to even scratch the surface on all the outdoor entertainment and activities available, but I will point you all in the right direction with the amazing My Chi Parks App!! Make sure to download this from the App store, and you'll be able to find everything from free yoga classes to movies in the park.  You can view activities on a map or chronologically. I find the map feature to be super helpful so I can see what's taking place in parks right near me!  

Shakespeare in the Park: For a great outdoor theater production, check out Shakespeare in the park to see when they'll be near you!


We hope you found some ideas for how to spend your Summer Days- stay tuned for our third and final Chicago Summer Guide coming next week!

With love from Chicago,

Daniel + Jennifer