Things to Do

Kick-off Summer in Chicago

Kick-off summer this year Chicago style with these fun events scheduled in May.

The city of Chicago is ready to embrace summer and is beginning to gear up with the most lively outdoor events. Throw away the lockdown blues with a variety of attractions in Chi-town from world-class museums to Instagram-worthy buildings and pamper yourself this summer with these exciting events. 

Riverwalk Beer and Cocktail fest.

Date: Saturday, May 1

Island Party hut will be set up beach-style with private seating by the Chicago Riverwalk. Indulge in food, 12 delicious beer and cocktail tastings, and freebies worth up to $200. Win a free ticket by spreading the word, but hurry, because seats are limited.


Cocktail fest, Source: Event Brite

Price: $30-$180

Island Party Hut 
(Between Lake Shore Drive 
and Columbus on the Riverwalk),
355 Chicago Riverwalk
Chicago, IL 60601,
United States

Book your tickets

Wine Fest on the River

Date: Saturday, May 8, famous for hosting Chicago’s best liquor-tasting events, is here with one more. Take in the views of the Chicago river, sway to the beats of good music, indulge in delicious food, wine, and cocktails  As your glass empties, it is refilled with a better-tasting wine than the last one. 

This is a socially distanced event with limited tables available. Book your tickets and get a chance to win early bird prizes from Skyline Cruises.


Wine Fest on the River, Source: Event Brite

Price: $30-$210

Rivers Restaurant
30 South Wacker Drive
Chicago, IL 60606
United States

Book your tickets

Mother's Day High Tea Experience at Thorn Restaurant & Lounge

Date: Sunday, May 9

Bringing mothers the closest-ever experience of a perfectly curated English High Tea, with everything that The Queen would include in hers, the Thorn Restaurant and Lounge has gotten it just right. The high tea begins with the Blooming Flower Green Tea and includes a vast selection of tea sandwiches and desserts like macarons; apple turnover; an Early Grey strawberry tart and a Petite Opera Chocolate sponge Cake. Top it off with their MOMosas, Rosemosas, and the perfect melodies played by Dina Bach for a Mother’s Day experience moms truly deserve.


Mother's Day High Tea Experience at Thorn Restaurant & Lounge, Source: Patch

Price: $60

Thorn Restaurant & Lounge, 
5200 Pearl Street, 
Rosemont, IL, 60018

Book your tickets

Chicago Wine Fest- Spring Edition

Date: Saturday, May 15

Craft Hospitality presents the Official Chicago Wine Fest! Enjoy live entertainment along with especially curated wines from several wineries. VIP and General Admission tickets are available With the VIP admission offering an extra hour of tasting and mingling before the rest of the crowd arrives. This event is just what’s needed to bring in the summer.

Chicago_Wine_Fest- Spring_Edition

Chicago Wine Fest- Spring Edition, Source: Eventbrite

Price: $30-$60

Lincoln Park Zoo
Regenstein Small Mammal 
Reptile House and Foreman Pavilion
2121 N Stockton Dr
Chicago, IL 60614
United States

Book your tickets

Back to The Office Pop-up

Date: Sunday, May 16

This is THE OFFICE comes to life with the Arcade bar turning their space into the sitcom show. The experience is complete with Office-themed cocktails and food. Throw off your favorite Michael Scott quotes as you sip on his signature Scotch and Splenda. Snack on hot pretzels that put a Stanley-like smile on your face. The ticket includes a $20 credit for beverages.


Back to The Office Pop-up, Source: Timeout 

Price: $20

2833 N Sheffield Ave

Book your tickets

Chocolate and Wine Lovers Extravaganza 

Date: Tuesday, May 18

Ever thought about how Charlie felt the moment he walked into Willy Wonka’s factory? Bordering that experience is what Chocolate and Wine lovers Extravaganza has in store for you. Watch the Plumbers Union Hall turn into chocolate, wine, and spirit heaven as 50+ vendors delight their palate with varietals and blends of exceptional taste and quality. Top artisans will showcase their creations; you may sample these sumptuous treats and pick up some to take home. 


Chocolate and Wine Lovers Extravaganza, Source: All Events

Location: Chicago, Illinois, United States

Book your tickets

Mimosa Fest

Date: May 22-23

Mimosas are summer in a glass and The Party Hut has an event for you to live it up. The Mimosa Fest brings to you a safe and socially distanced cocktail tasting session with privately placed tables and 12 majestically crafted mimosas, Palomas, and screwdrivers for your taste buds to relish. With the tiki-style decor giving you the perfect beach vibes, taste your way through the cocktails being served. A limited number of tables are available for booking, make sure you don’t miss out on yours!


Mimosa fest, Source: Eventbrite

Price: $25

Lincoln Park Zoo
Regenstein Small Mammal 
Reptile House and Foreman Pavilion
2121 N Stockton Dr
Chicago, IL 60614
United States

Book your tickets

Chicago Virtual Speed Dating

Date: Saturday, May 29

Single, ready to mingle? Virtual Speed Dating is a great opportunity for singles to find that someone special. In these times when we are still wary of meeting strangers, this is a safe and socially distanced way to meet new people. Settle in from the comfort of your own home and get ready to talk privately with a new person every 7-8 minutes with the host at bay to assist with any questions. Don’t miss this opportunity to meet someone new in your city today! 


Chicago Virtual Speed Dating, Source: Eventbrite

Price: $28.75 - $30.75


Book your tickets


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