Chicago's Ultimate 2021 Summer Bucket List
Chicago's Ultimate 2021 Summer Bucket List

Chicago's Ultimate 2021 Summer Bucket List

Because there’s nothing like summertime Chi! ☀️ Check out 21 of the latest in-season gems. Presented by White Claw.

Published May 19, 2021

Summer is special in a lot of cities, but nothing quite tops a Chicago summer. Come May, the Windy City transitions from its iconic frigid winter to a cauldron of summertime bliss. Rooftops and street festivals galore, with the best nights beginning along the riverwalk. Summer might have slipped away from us in 2020, but we've teamed up with White Claw to ensure that Chicagoans don’t miss another summer again. So crack open a chilled seltzer and prepare to have the chillest summer Chiacgo has ever seen.

This year we’ve rounded up 20 of the best things to do around Chicago--the ultimate summer bucket list. Plus, be sure to bookmark this guide as we’ll be continuing to update it with new events, experiences and discounts (!!!) all. summer. long.

Mini Golf at Maggie Daley Park

Credit: City Mini Golf

Bring your friends and your best swing (a mask, too!) for an afternoon of mini-golf with iconic skyline views. This 18-hole minute golf course features Picasso and Chicago-inspired obstacles for a unique twist on a classic summer game. After your game wraps, be sure to head over to the Maggie Daly Park picnic groves for a summertime snack. Our recommended picnic box of choice: White Claws, sliced watermelon, cheese & charcuterie 🤌🏼 *Chef's kiss*

When: Monday – Thursday: 11:00 am – 8:00 pm
Friday & Saturday: 10:00 am – 9:00 pm
Sunday: 10:00 am – 8:00 pm
Daily opening is dependent on the weather. Last golfers accepted 45 minutes before closing. 
Where: 337 E Randolph St, Chicago, IL 60601 

Attend a Cubs or Sox Game

Credit: @Cubs

Grab a Chicago-style beer and a group of friends. There's no better way to spend a beautiful, socially distant day than at Wrigley. Pro Tip: Hit Clark Street afterward for a celebratory sip with over 40 bars to choose from). 

When: Check here for the Cubs schedule
Where: 1060 W Addison St, Chicago, IL 60613

Kayaking On The River or Lakefront

Credit: Urban Kayaks Chicago

Summer is calling! Grab a kayak and explore the city by water. You’ll get a front-row (pun intended) view of Chicago’s best architecture. Pro tip: Date night? Book the sunset tour for a bit of romantic Chi-town magic.

When: Dates and times vary
Where: Riverfront: 435 E. Chicago Riverwalk Chicago, Il 60601 | Lakefront: 110 N. Lakeshore Dr Chicago, Il 60601

Day Trip To Starved Rock State Park

Credit: Ryan Heuer via Unsplash

Escape the city hustle and head just 90 minutes southwest to Starved Rock State Park. With a beautiful waterfall and canyon-like hikes, you'll feel one with nature right in your own backyard. 

When: 6:30 a.m. - Sunset, Daily
Where: 2678 E 875th Rd, Oglesby, IL 61348

See a Movies At ChiTown Drive-In

Missing the good ol’ ‘dinner and movie’ summer nights? Lucky for us, they’re making an epic comeback in a totally vintage way. Catch film classics like Grease from the comfort of your car at the drive-in theaters. Here, social distancing and safety measures at the forefront of the fun. 

When: Varies. Follow @ChicagoBucketList for weekly movie schedule updates.
Where: 2343 S Throop St, Chicago, IL 60608

Celebrate Pride 

Credit: Mercedes Mehling via Unsplash

Take to the streets of Chicago with Pride! This year's Pride In The Park will be returning June 26th & 27th marking one of the city's first major live events to return. Set in the iconic Grant Park, headlining artists include: Tiesto, Chaka Khan, Gryffin and more! Note: Pride Fest set in the Northalsted Neighborhood is currently TBD with potential Fall dates. 

When: June 26 - June 27, 2021
Where: Grant Park

Bike The 606 Trail

Grab your wheels and hit The 606 – a 2.7-mile elevated railroad that was re-constructed into a biking and running trail. With art installation and landscape design along the way, The 606 is an urban oasis and a unique way to explore while exercising. 

When: 6:00 AM to 11:00 PM, Daily 
Where: 1805 N Ridgeway Ave, Chicago, IL 60647

Picnic and Concert at Ravinia Festival

Credit: Ravinia Festival

The Ravinia Festival is reopening this summer! *Cue the good vibes* Take the metra train out of the city to Highland Park for a concert at Ravinia. Bring along a few friends, a picnic basket, and enjoy the music. Pro tip: Show your concert ticket for a free ride on the Metra.

When: Varies
Where: 1418 Ravinia Park Rd, Highland Park, IL 60035

See a Comedy Show at Laugh Factory 

Credit: Michel Grolet via Unsplash

Ready for laughs and libations this summer? Come for the comedy, stay for the vibes!  Laugh Factory offers the best stand-up comedy in Chicago and has reopened safely and socially distanced. Featuring today's biggest names, these local comedians will deliver something for every taste and style of comedy!

When: Monday - Friday & Sunday, 11 AM - 11 PM, Friday, 11 AM - 12 AM
Where: 3175 N Broadway, Chicago, IL 60657  

Visit Your Local Farmers Market 

Credit: Gary Butterfield via Unsplash

Summer was made for trips to the farmer’s market. Get some sun, fresh food, and locally-made favorites at one of Chicago’s 20+ markets. Pro tip: Check out the iconic Maxwell Street Market starting June 6th!

When: Varies, Maxwell Street Market: Every 1st and 3rd Sunday of the month, 9 AM - 3 PM
Where: Varies, Maxwell Street Market: 800 S Desplaines St, Chicago, IL 60607


See The Fireworks At Navy Pier 

Credit: Navy Pier Chicago

Nothing says summer quite like hanging by the lakefront with fireworks for a view. Grab your friends and head to Navy Pier for a magical evening beneath the Chicago stars.

When: Every Saturday at 9:00 PM
Where: 600 E Grand Ave, Chicago, IL 60611 

Drink Wine at City Winery Riverwalk

Credit: City Winery Chicago

Rosé the day away at City Winery! Enjoy a glass (or three, no judgement) with scenic views of the Chicago River. The winery’s alfresco dining makes it easy to sip while staying socially distant.  

When: Monday-Friday 1 PM - 9 PM, Saturday-Sunday 11 AM - 9 PM
Where: 11 W. Riverwalk South, Chicago, IL 60601 

Original Rainbow Cone

Credit: Original Rainbow Cone

Summertime Chi wouldn’t be the same without scoops from Original Rainbow Cone. Chicago's favorite treat, the rainbow cone gained popularity for multi-layered ice cream to represent the colors of the rainbow - and the result is delicious.  

When: Varies by location 
Where: Chicago-Beverly: 9233 S Western Avenue, Chicago, Illinois 60643 | Lombard: 498 E Roosevelt Road, Lombard, IL 60148 | Navy Pier: 600 E Grand Avenue Chicago, IL 60611 

Cruise Lake Michigan On Tall Ship Windy 

Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. 

When: Varies, May- September 
Where: Navy Pier – Tall Ship Windy 600 E Grand Ave Chicago IL 60611

Rent a Boat and Tailgate on the Playpen

No matter the occasion, celebrating on a boat is sure to be a good time. Bring your own booze and cruise Lake Michigan for the ultimate day party.  Best part? A Beer Pong & Flip Cup Table and Bluetooth speaker come along for the ride, too!

When: May through November
Where: Located just North of the Chicago Yacht Club, 400 East Monroe Street, Chicago, IL 60603

Dine at your Favorite Patio 

Credit: Happy Camper Chicago

There’s no party like a patio party. Pull up a seat at Happy Camper for creative slices and cocktails. This boozy playground for adults makes for the perfect afternoon out.  

When: Varies by location 
Where: Old Town: 1209 N Wells St Chicago, IL 60610 | Wrigleyville: 3458 N Clark St, Chicago, IL 60657

Plan A Luxury Picnic At The Park

Credit: Picnics In The Chi

Why have a regular picnic when you can do it in luxury? Celebrate at home or in the park with a perfectly curated picnic experience.

When: Custom date and time 
Where: Your house or desired location

Have An Outdoor Movie Night

Movie night is better beneath the stars! Round up your friends for a specially-curated outdoor movie night. Whether in your backyard or a hotel room, this experience will be a night to remember. 

When: Custom date and time 
Where: Your house or desired location

Beachside Drinks At Shore Club

There aren't too many cities in the US where you can sit beachside and feel like you're in the Bahamas – while gazing out at 100-story skyscrapers. For the best of both worlds, check out one of our favorite seasonal spots: Shore Club. You can dine, sip tropical drinks, and even book cabanas all right on the sand. Get ready to set your Out of Office because Shore Club will instantly transport you to island time. 

When: Opens Saturday, May 22
Where: North Avenue Beach

Drinks with a view at LondonHouse's Rooftop

Credit: LondonHouse Rooftop

Overlooking the Chicago River, LondonHouse has some of the best views in the city. Enjoy sweeping skyline views while taking back a mimosa. 

When: 11 AM - Midnight, Daily
Where: 85 E Wacker Dr, Chicago, IL 60601

Explore the Immersive Van Gogh Exhibit

Can you imagine being bathed in full-room projections of the animated, jaw dropping works of the legendary Vincent Van Gogh? Travel through the artist’s sunny landscapes and twilight scenes, be up close and personal with his vividly detailed portraits and still lives, all while maintaining their 6-foot sanitized distance within the impressive venue.

When: Extended through November 2021 
Where: 3418 W Armitage Ave, Chicago, IL 6064 

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