chicago events

Jack’s Pumpkin Pop-Up 2024

October 21, 2024

Fall (spooky season) is hands down my favorite time of year, and my favorite seasonal pop-up is back! This month, I enjoyed attending media night at Jack’s Pumpkin Pop-Up. I attend the Chicago event every year and each time look forward to what it offers – 2 acres of photo ops, carnival games, a large corn maze, axe throwing, and more. This year the pop-up will be open to the public until November 3. Read below for information about the aesthetic backgrounds, add-ons, and things to know before going!

Things to Do at Jack’s Pumpkin Pop-Up

Jack’s Pumpkin Pop-Up is the perfect Fall outing for friends, dates, and families. General admission includes the photo ops and the corn maze. The following items can be purchased in person or as add-ons:

Food and beverage (varies)
Pumpkin picking ($6-$9)
Carnival games ($20)
Axe throwing ($10 for 3 throws)
Fortune tellers (varies)
Gem mining ($12 for 5lb bag)

Add-ons can be selected when purchasing tickets online. Packages combining add-ons are also available. View my favorite 2024 photo backdrops next!

Photo Ops at Jack’s Pumpkin Pop-Up

The best thing about Jack’s Pumpkin Pop-Up is the great photo backdrops. There are so many! Each year they keep some of the same ones – like the pumpkin house and ‘How tall are you?’ measuring stick – and add new backgrounds relating to current trends – like ‘End of Begining’ song lyrics and Beetlejuice’s coffin. Throughout this blog post are my favorite backdrops from our 2024 visit.

Food & Games

Jack’s Pumpkin Pop-Up offers food and beverage options. Every year we get a cold apple cider and a cider donut! Multiple bars are set up throughout the grounds that serve beer, hard ciders, hard liquor, and specialty cocktails. Food for purchase includes cheeseburgers, nachos, BBQ chicken sandwiches, hot dogs, jumbo pretzels, and more. Pricing ranges between $4-$12 per item. A Mexican food truck is also available for tacos, burritos, elotes, and quesadillas ($5-$14 per item). Rotating food trucks occur on select weekend nights.

Near the food, you can find a row of carnival games. Carnival-style tickets are required to play and can be purchased as an add-on when reserving tickets. Games include Balloon Bust, Break A Plate, Down A Clown, and more. My sister won a stuffed animal last year!

Things to Know Before You Go

Tickets

Tickets start at $30 for adults, $28 for ages 5-11, and free for ages 4 and under when accompanied by a paid adult ticket. Add-ons are available as additional purchases.
The time slot you select when reserving tickets is your entry window. You can arrive anytime during your entry window and stay as long as you want once you’re in.
Walk-ups are accepted on a first come, first serve basis. Tickets may be already sold out.
All ticket sales are final and can not be refunded, but they can be rescheduled.
Tickets and packages can be bought online.

Location

Jack’s Pumpkin Pop-Up is 100% outside and full of straw, hay, and corn.
Strollers, wagons, and wheelchairs are allowed (FYI the ground is unpaved and uneven).
Re-entry to the pop-up is not allowed after entry.
Animals are not allowed except for certified service animals.
Jack’s Pumpkin Pop-Up is located at 1265 West Le Moyne Street, Chicago, IL 60642.

Other Info

Jack’s Pumpkin Pop-Up is 100% cashless and only accepts credit cards or Apple Pay.
Port-a-potties are available as bathrooms.
Axe throwing is 18+. Alcohol drinks are 21+.
More information can be found on Jack Pumpkin Pop-Up’s FAQ page.

Did you visit Jack’s Pumpkin Pop-Up this year? Leave your thoughts in the comments!

Lulus Besties That Brunch Chicago

June 7, 2024

Lulus Besties That Brunch Chicago

Kicking off the summer with Lulus Besties That Brunch! LuLus.com, a popular online fashion store, recently announced its “Friends for Life” out-of-home campaign in four major cities. The campaign celebrates women’s friendships and focuses on women supporting other women through the milestones in their lives. As someone who has bought many dresses from Lulus for past sorority and blogger events, I was excited to attend the Besties That Brunch out-of-home event held at Venteux Cafe & Oyster Bar inside Pendry Chicago, a boutique hotel downtown. It is sure to be the first of many Chicago events I attend this summer season.

Sips & Bites

Despite the event name, there was no sit-down brunch meal. Instead, waiters scarcely passed out light bites on small trays holding only 6-8 pieces at a time. We were so hungry and kept missing out when the bites were quickly snagged! Finally, we tried two: melted gruyere cheese and quail egg on mini toast, and egg salad with caviar on a potato chip. Both were delicious! There was also an included bar serving mimosas and different pre-decided cocktails.

The Swag

Lulus is known for their fashionable clothing and accessories. Attendees of Besties That Brunch Chicago were offered gift bags containing sunglasses and one of three different clutch bags: gold, white, and mauve pink. I chose the gold! Each clutch was embellished with beads or rhinestones.

Snap a Pic

Dresses from Lulus and a photo backdrop were set up in a room off of the cafe. The outfits were styled with accessories and shoes, and a professional photographer took both digital and Polaroid pictures with fun bestie props. Pictured above is our Polaroid! I loved that we got to take it home as a souvenir.

Flowers From Semillas Chicago

My favorite part about the event was the flower bouquet station in the cafe. Semillas, a plant studio located in the Chicago Pilson neighborhood, provided a wonderful variety of flowers arranged in small bouquets for event guests. I loved how mine turned out!

Lulus Besties That Brunch Chicago was a fun, fresh way to kick off summer events. It was well organized and had just enough things to do to keep you stimulated and engaged. Before leaving we got our flower bouquets, complimentary cafe coffee, and more pics. I’d love to see Lulus do more events in Chicago in the future!

Which Chicago events are you planning to attend this summer? Let me know in the comments!

Things to Do in Chicago: Winter 2023

November 16, 2023

Let’s hear those sleigh bells ringing! The holiday season is here, which means there are a lot of great events to check out in Chicago. My favorites from past years have included festive pop-ups such as Jack Frost Winter Fest Pop-Up and local markets like Christkindlmarket. Below you will find a list of recommended things to do in Chicago this winter!

Jack Frost Winter Fest Pop-Up

Date: November 30, 2023 – December 31, 2023
Location: Fulton Market
Cost: Admission $18-$34 + Selected Activities
View my 2022 Jack Frost Winter Fest Pop-Up review here!

ZooLights at Lincoln Park Zoo

Date: November 17, 2023 – January 7, 2024
Location: Lincoln Park Zoo
Cost: Mondays are free, other dates $7-$10 admission, possible drinks available for purchase

Christkindlmarket Chicago

Date: November 17, 2023 – December 31, 2023 (locations vary)
Location: Daley Plaza (Loop) & Gallagher Way (Wrigleyville)
Cost: Free admission, Food/Drink/Shop items available for purchase
View a recap of my past experience at Christkindlmarket here!

Santa Baby Christmas Bar

Date: November 17, 2023 – December. 31, 2023
Location: Bamboo Club in Wrigleyville
Cost: $5 cover charge on certain dates, Food & drink available for purchase

Pink Wonderland Pop-Up Bar

Date: December 2, 2023 – December. 30, 2023
Location: 324 W Chicago Ave
Cost: $25-$40 admission

Ice Skating at Maggie Daley Park

Date: November 17, 2023 – March 10, 2024
Location: Maggie Daley Park
Cost: $16-$22 admission, Locker rentals $3-$5, Skate aids $10

Jack’s Pumpkin Pop-Up 2023

October 7, 2023

Chicago’s Largest Halloween Festival

Something wicked this way comes! My favorite annual Chicago pop-up event is back. Jack’s Pumpkin Pop-Up, Chicago’s largest Halloween festival, is 2 acres of festive photo ops, carnival games, a corn maze, cocktail bars, axe throwing, food, and pumpkins for sale. It’s open all October and is perfect for feeling all the fall vibes. I have greatly enjoyed this annual pop-up (view pictures from my 2022 and 2021 recaps). Read below for this year’s experience!

Jack’s Pumpkin Pop-Up Photo Ops

My favorite part about Jack’s Pumpkin Pop-Up, and the reason we’re eager to go back each year, is all the great photo ops! The unique fall and Halloween backdrops are the perfect urban opportunity to get into the spooky spirit. Each year they have oldie-but-goodie photo ops (like the pumpkin house) as well as new ones (like the window from the TV show Wednesday). The window,

Jack’s Pumpkin Pop-Up Food & Drink

Jack’s Pumpkin Pop-Up offers multiple cocktail bars and food for purchase. There is a taco truck, sweets from Eiffel Waffle, and other food – including apple cider donuts, cheeseburgers, hot dogs, elote, BBQ chicken sandwiches, and jumbo pretzels. The bars offer both alcohol and nonalcoholic options. We tried the apple cider (cold) and loved it! Make sure to bring a credit card as they do not accept cash. Beer, liquor, and ciders range between $9-$14.

Specialty Cocktails

Jack’s Potion of the Day – Specialty cocktail of the day
Jack’s Midnight Moonshine – Batched in-house with a hint of cranberry & peach
Fall in Love – Whipped vodka, cardamom & cranberry

Jack’s Pumpkin Pop-Up Tickets

Jack’s Pumpkin Pop-Up will be open to the public now through October 31, 2022. Tickets start at $22, and $20 for kids 5-11 years old. Add-ons include drink tickets, orange pumpkins, apple cider donuts, carnival games, axe throwing, and gemstone mining. Tickets are offered for time slots throughout the day and evening and can be reserved online in advance. Have a fun, spooky time!

Taste of Chicago Grant Park

September 15, 2023

Chicago’s Annual Food Festival

One of Chicago’s most anticipated festivals each year is Taste of Chicago. While usually occurring in June or July, this year’s event was in September due to Grant Park’s backed-up summer entertainment schedule. After checking out Printer’s Row Lit Fest nearby, we did a short walk to the food festival and enjoyed delicious options. Read below to see what we tasted!

Taste of Chicago Food

Taste of Chicago Offerings

Taste of Chicago consisted of 35 food vendor booths and 17 food trucks. There was also a wine garden, cocktail lounge & garden, beer hall, Goose Island rail car, main stage, SummerDance stage, and a Lifeway Foods family village area. All around the nice view of Buckingham Fountain!

What We Ate

Sapori Trattoria – Pesto Gnocchi ($10) and Nonna’s Meatball ($5)
Tacotlán – Beef Quesabirria ($5)
Gaby’s Funnel Cakes – Deep Fried Oreos ($5)

Everything we tried was delicious! It was affordable and had perfect portion sizes for sharing.

I’m happy to report that the event was stress-free and more organized this year. In the past, Taste of Chicago had lengthy security lines at the entrance and you had to buy food tickets to get items from the booths. It caused extensive wait times and disorganized ordering. Now, there are more entrances, security lines are much shorter, and tickets are no longer required (can pay with credit cards or cash).

Have you been to Taste of Chicago? What was your favorite food there? Let me know in the comments!

Things to Do in Chicago: Fall 2023

August 14, 2023

Who’s ready for spooky season? I definitely am! I absolutely love Fall time in the city. From festive pop-ups to pumpkin-flavored treats to Halloween, there’s nothing better than the cozy aesthetic that comes with it. Looking forward to scheduling plans? Make sure to add the ones listed below to your calendar! This post will be updated as events arise.

Jack’s Pumpkin Pop-Up

Date: September 21 – November 3, 2023
Location: Goose Island (1465 N. Elston Ave.)
Cost: $22 for GA, food/drink & extras available for purchase
View my 2022 Jack’s Pumpkin Pop-Up recap post (this is my favorite fall event!)

Harry Potter Magic at Play

Date: Now – September 4, 2023
Location: Water Tower Place (835 Michigan Ave.)
Cost: $42.50 per ticket, treats & souvenirs available for purchase
View my Harry Potter Magic at Play recap post

Rooftop Cinema Club

Date: Now – September 4, 2023
Location: The Emily Hotel (311 N Morgan St.)
Cost: $22.50+ per ticket

Chef BBQ at Green City Market

Date: September 7, 2023
Location: Lincoln Park (1817 N Clark St)
Cost: $159 for GA, $289 for VIP
View my 2022 Chef BBQ recap post

Taste of Chicago

Date: September 8-10, 2023
Location: Polk Brothers Park (600 E Grand Ave)
Cost: Free admission, food available for purchase

Oktoberfest at the Zoo

Date: September 16, 2023
Location: Lincoln Park Zoo
Cost: $15 admission (early bird price), food & drink available for purchase

Chicago Gourmet

Date: September 21-24, 2023
- Sep 21: Tacos & Tequilas ($110)
- Sep 22: Hamburger Hop ($130)
- Sep 23: Grand Cru ($255)
- Sep 24: Prost! In the Park ($99)
Location: Harris Theater Rooftop (205 E. Randolph St.)
Cost: $99-$255 + tax
View my 2019 Chicago Gourmet recap post

Green City Market

Date: Now – November 2023
Location: Lincoln Park, West Loop, Avondale
Cost: Free admission, vendors selling items for a cost

The Exhibit House

Date: Indefinitely
Location: Water Tower Place (835 Michigan Ave.)
Cost: $30 per ticket
View my The Exhibit House recap post

ZooLights

Date: November 17, 2023 – January 7, 2024
Location: Lincoln Park Zoo
Cost: TBD

Things to Do All Fall

LeakyCon: A Magical World Fandom Convention

August 14, 2023

The Perfect Convention for Harry Potter Fans

This year was my first time attending LeakyCon, a fandom convention celebrating magical worlds such as the Wizarding World and Lord of the Rings. Sticking to my love for all things Harry Potter, I wore my best Slytherin wear and enjoyed the fun cosplay from others at the event. The convention featured sessions, a marketplace, and – the best part – photo and autograph opportunities with magical world celebrities. WE MET TOM FELTON. Keep reading for more information about this annual event!

The LeakyCon Convention

I attended LeakyCon under a media pass, but single general admission tickets were around $90 after tax. While the convention provides an impressive lineup of sessions and speakers at LeakyCon, the add-ons are truly once-in-a-lifetime moments. As a long-life Harry Potter fan (even my 9th birthday party was Harry Potter themed!), I was beyond ecstatic to meet and get a picture with none other than Draco Malfoy himself, Tom Felton. He was so nice! Other magical celebrities in attendance included Elijah Wood, Sean Astin, and Miranda Otto.

Experience Add-On Costs

Add-ons included autographs, selfie photos, professional photos in front of the LeakyCon backdrop, and content creation opportunities with Harry Potter-themed content creators. Prices ranged a bit, but we paid $147.50 for one professional photo with Tom Felton and were able to have both of us in the picture (you can have 2 people/per photo ticket). Photo extras were exact cash or Venmo only. Extra printed photos were $15 each, a digital version was $10 each, and protective slipcases were $5 each. Worth it!

LeakyCon Marketplace

The marketplace selection at LeakyCon Chicago was awesome. There were so many great shops showcasing unique items to buy and take home. While most were Harry Potter themed, there were a few that had selective Lord of the Rings, The Hobbit, Stranger Things, and Disney-inspired items. I was excited to finally find and buy a Sirius Black wand. Many shops took both cards and cash for payment. Pictured are some of the (linked) shops I enjoyed!

My Slytherin Outfit

(These are affiliate links and help make the blog what it is! Thank you!)

Slytherin Nightgown (Longer in person. I had it hemmed.) | Deathly Hollows Necklace | White Sneakers

Upcoming Events

LeakyCon events are held in a variety of cities each year! Make sure to follow their social media and website for location announcements. Have you attended a LeakyCon? What’s your favorite magical world?

Fleurs de Villes VOYAGE at The 900 Shops

May 7, 2023

Fleurs de Villes at the 900 Shops

Each year the 900 Shops on Michigan Avenue hosts a Fleurs de Villes event in anticipation for spring. This year’s theme, VOYAGE, featured floral displays of iconic destinations around the world. I was able to attend opening night to enjoy six floors containing displays, light drinks from Inspirio Tequila, and a night of dressing up! Keep reading below to view my favorite floral creations.

My Favorite Fleurs de Villes VOYAGE Displays

Upcoming Summer Events in Chicago

The Fleurs de Villes VOYAGE event was fleeting, but luckily there are many upcoming summer events in Chicago to look forward to. From festivals to pop-ups to concerts, you certainly won’t be bored. Out of all the events, I’m most looking forward to Millennium Park summer workouts, the new Malibu Barbie Cafe pop-up, Pride in the Park, Stan’s Donut 5k, and Chef BBQ presented by Green City Market. I’ve already checked out Harry Potter Magic at Play and The Exhibit House – highly recommend both. Which events are you planning to do this summer?

Things to Do in Chicago: Summer 2023

April 16, 2023

Summer in Chicago is the best time of year. Whether you’re a local or just visiting for a weekend, there’s always something to do to enjoy the city (and nice weather). Plenty to keep your calendar full! Read below for things to do in Chicago this summer, May through September! This post will be updated as events are announced.

May 2023 Events

Green City Market

Date: May – November 2023
Location: Lincoln Park, West Loop, Avondale
Cost: Free admission, vendors selling items for a cost

Pixar Putt

Date: May – September 2023
Location: Polk Bros Park outside Navy Pier (600 E. Grand Ave.)
Cost: $22-$33 per ticket
View my 2022 Pixar Putt Chicago recap post

Harry Potter Magic at Play

Date: May – September 4, 2023
Location: Water Tower Place (835 Michigan Ave.)
Cost: $42.50 per ticket, treats & souvenirs available for purchase
View my Harry Potter Magic at Play recap post

Sueños Music Festival

Date: May 27-28, 2023
Location: Grant Park
Cost: $179+ per ticket, view lineup

Millennium Park Summer Workouts

Date: May 27 – September 2, 2023
- 8–8:45am Pilates (no classes 7/1)
- 9–9:45am Yoga (no classes 7/1)
- 10–10:45am Cardio Kickboxing (no classes on 6/10, 7/1, 9/2)
- 11–11:45am Zumba® (no classes on 6/10, 7/1, 9/2)
Location: Great Lawn in Millennium Park (201 E. Randolph St.)
Cost: Free admission

The Exhibit House

Date: Indefinitely
Location: Water Tower Place (835 Michigan Ave.)
Cost: $30 per ticket
View my The Exhibit House recap post

June 2023 Events

Malibu Barbie Cafe Chicago

Date: June 7 – September 15, 2023
Location: TBA, Downtown Chicago
Cost: $35 for kids, $49 for adults (each ticket includes reserved seating, entree & side item)

Heatwave Music Festival

Date: June 10-11, 2023
Location: Huntington Bank Pavilion at Northerly Island
Cost: $99+ per ticket, food & drink available for purchase

Grant Park Music Festival

Date: June 14 – August 19, 2023
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free seating, first come first serve

Millennium Park Summer Music Series

Date: Mondays & Thursdays, June 22 – August 21, 2023 – 6:30-9pm (Gates open at 5pm)
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free admission

Pride in the Park Chicago

Date: June 23-24, 2023
Location: Grant Park
Cost: $75+ per ticket, food & drink available for purchase
View my 2022 Pride in the Park Chicago recap post

Joffrey Ballet’s “Joffrey for All Celebration”

Date: June 25, 2023 – 5:30pm
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free public performance

Chicago Symphony Orchestra’s “Concert for Chicago”

Date: June 27, 2023 – 6:30pm
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free public performance

July 2023 Events

NASCAR Chicago Street Race Weekend

Date: July 1-2, 2023
Location: Grant Park (337 E Randolph St.)
Cost: $269+ per ticket

Millennium Park Summer Film Series

Date: Tuesdays, July 11 – August 29, 2023 – 6:30pm (Gates open at 5pm)
Location: Jay Pritzker Pavilion in Millennium Park (201 E. Randolph St.)
Cost: Free admission

Windy City Smokeout

Date: July 13-16, 2023
Location: United Center parking lot
Cost: $55+ per ticket, food & drink available for purchase
View my 2022 Windy City Smokeout recap post

Chicago SummerDance

Date: July 15 – September 10, 2023
Location: Grant Park & Millennium Park
Cost: Free admission

Sad Summer Festival

Date: July 21, 2023
Location: Huntington Bank Pavilion at Northerly Island
Cost: $49.50+ per ticket, food & drink available for purchase

Pitchfork Music Festival

Date: July 21-23, 2023
Location: Union Park (1501 W Randolph St.)
Cost: $109+ per ticket, food & drink available for purchase

August 2023 Events

Lollapalooza

Date: August 3-6, 2023
Location: Grant Park
Cost: $125+ per ticket, food & drink available for purchase

Stan’s Donut 5k

Date: August 19, 2023
Location: Solider Field
Cost: $40 per registration
View my 2022 Stan’s Donut 5k recap post

Chicago Air and Water Show

Date: August 19-20, 2023
Location: North Ave Beach & along the Lakefront
Cost: Free admission, reserved viewing at certain businesses for a cost

September 2023 Events

Chef BBQ at Green City Market

Date: September 7, 2023
Location: Lincoln Park (1817 N Clark St)
Cost: TBD, tickets required
View my 2022 Chef BBQ recap post

Taste of Chicago

Date: September 8-10, 2023
Location: Polk Brothers Park (600 E Grand Ave)
Cost: Free admission, food available for purchase

Chicago Gourmet

Date: September 21-24, 2023
- Sep 21: Tacos & Tequilas
- Sep 22: Hamburger Hop
- Sep 23: Grand Cru
- Sep 24: Prost! In the Park
Location: Harris Theater Rooftop (205 E. Randolph St.)
Cost: TBD, tickets required
View my 2019 Chicago Gourmet recap post

Things to Do All Summer

Chicago Attractions

Chicago Museums

The Exhibit House Chicago

April 12, 2023

The Exhibit House in Downtown Chicago

Chicago’s latest experience, The Exhibit House, is located at the Water Tower Place in the Gold Coast neighborhood. The location consists of three large, themed exhibits (shown below) to take photos in; Secret Garden, The Mood Room, and Disco Dreamland. It is now open to the public and will feature different exhibits in the future. There are a lot of fun spots to create content! Keep reading below to see my favorite pictures and to learn things to know before you go.

Secret Garden

My favorite exhibit out of the experience’s three featured rooms was the Secret Garden room. In addition to the beautiful floral displays, the mini rooms within the Secret Garden were very aesthetically pleasing. My favorite mini rooms were Rose Room and a little nook when you walk in that had a “Let’s Share Secrets” neon sign. Other mini rooms included Desert Daze, Butterfly Forest, Mushy Madness, and Living Luminescence.

The Mood Room

The Mood Room was all about interaction. Each mini section featured a different emotion, color, and way to get you involved. My favorites in The Mood Room was Peaceful (light blue), Fear (green) where you can throw away a written fear, Passion (hot pink) where you can put a bead in the passion tube that resonates with you, and Sensitive (coral pink) where you can take an affirmation card to keep. Other sections included Trust (dark blue), Mysterious (purple), Sadness (cobalt blue), Cautious (yellow), Playful (orange), and Anger (red).

Disco Dreamland

The Disco Dreamland exhibit was a lot of fun. It’s the first room you walk into in the experience and is decked out floor to ceiling with disco decor. You can take pictures in front of The Exhibit House sign, the sparkly walls, and even use a 360 rotator to take a fun video. Lots of opportunities for content!

Thing to Know Before You Go

Tickets cost $30 each for all ages
Admission is for a one hour (60 minute) session
Coat & bag check is available for $3 cash or credit
The Exhibit House is located on the 4th floor of the Water Tower Place
There are no bathrooms in The Exhibit Place (public located on 3rd floor)
There are no refunds on tickets, but you can exchange for a different time
No outside food or beverage is allowed. Kites Ice popsicles are available for purchase on site.
$1 from every ticket will be donated to Lurie Children’s Hospital of Chicago
You can reach out to info@exhibit-house.com for more information and private events