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Pop Ups

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!

Filed Under: Chicago, Chicago Events, Lifestyle Tagged With: chicago, chicago events, halloween, jacks' pumpkin pop up, Pop Ups

Jack’s Pumpkin Pop-Up 2021

September 28, 2021

My favorite seasonal pop-up is back! Jack’s Pumpkin Pop-Up features Insta-worthy photo opps and a corn maze, as well as food & drink, carnival-style games, axe throwing and pumpkins for an additional cost. This year I attended with my sister, and we got to enjoy some of those add-ons. Read below to learn more about our experience!

Jack’s Pumpkin Pop-Up Photo Opps

This 2-arce pop-up is open now through October 31, 2021 in Goose Island. The best part about the event, in my opinion, are the photo opps. They have so many! Some are fall themed, while others deal more with pop culture. My favorite spots were the pumpkin house featured at the entrance of the pop-up (shown above), the fortune teller’s crystal ball, a black and white angel mural, a pink #freebritney cage, and Winafred’s spell book from Hocus Pocus. There were also some odes to Jack Skeleton, autumn, coffins, and more.

Jack’s Pumpkin Pop-Up Food & Drink

Aside from your usual water and soda, food and alcohol are offered at this pop-up. We ordered a cheeseburger and hot dog. My sister was pleasantly surprised to see that the cheeseburger came on a pretzel bun! The hot dog was pretty good, too. Also on the menu were walking tacos, grilled corn on the cob, elote, hot pretzels, nachos & cheese, Cheetos with cheese, and apple cider donuts. The donuts were delicious! Full bars are offered for those 21+ and up.

My Fall-Inspired Outfit

Although I’m not a fan of colder weather, I do love fall clothing. I was extremely excited to have the chance to wear my latest purchase, featured in my pictures taken at Jack’s Pumpkin Pop-Up. I’ve linked the items here for your viewing!

  • Go Your Own Way Black Fringe Sweater
  • Beautiful Sound Cream A-Line Suede Skirt
  • Similar black heeled boots: Option 1, Option 2, Option 3

Tickets to Jack’s Pumpkin Pop-Up

Jack’s Pumpkin Pop-Up will be open to the public now through October 31, 2021. General admission costs $25, and $23 for kids 5-11 years old. Add-ons include drink tickets, medium pumpkins, apple cider donuts, carnival games, axe throwing, and Smashing Pumpkin alcohol shots. Tickets are offered for timeslots throughout the day and evening.

Filed Under: Chicago, Lifestyle, Seasonal Tagged With: chicago, chicago event, jacks' pumpkin pop up, Pop Ups

29 Rooms vs. Happy Place: The Sensory Pop-Up Trend

July 30, 2018

If you’ve been on social media lately, you have probably noticed sensory pop-up events springing up like daisies in all of the major metropolitan cities. From the Ice Cream Museum to Happy Place to 29 Rooms to Wndr Museum, each one creates its own unique experience. 

29 Rooms

I’ve got 29 problems but a room ain’t one.

Refinery29’s pop up event, 29 Rooms, graced the Windy City this weekend for one quick extravaganza. As expected, the photo ops were so on point that even Chance the Rapper & stars from Orange is the New Black made an appearance one of the days. Featuring local artists’ work, each room was its own unique sensory experience. From shredding your negative thoughts in a paper shredder to laying down in a giant womb, the event did not fall short on giving a very feminine-focused, posh setting.

The ‘rooms’ were more like photo backdrops, only a handful were actually in a room setting. Nevertheless, all of them were still very intriguing. Due to there being lines waiting for photos, we didn’t get to all of the 29 exhibits. We did, however, prioritize which ones we did want to see – which I highly recommend to get the most out of your time. The tickets are broken out into three-hour segments, and you’ll need the whole time to walk through.

What I Liked

  • The exhibits I liked the best consisted of a huge rainbow arch, paper shredding room, silent disco and floral ceiling. I wish I took pictures of the name of each exhibit to know the official names, but it honestly did not cross my mind at the time. Within the paper shredding room, each participant wrote down something they wanted to shred, before taking it to a hand-turned paper shredder and throwing the remains in a pile. This was probably my favorite ‘experience’ of the night.
  • The event had a very sophisticated feel to it – a lot of celebrities, influencers and bloggers made their appearances through out the weekend. Many dressed up (including myself) to get the perfect shot in front of the trendy, future-forward rooms.

What I Would Change

  • There was no water to be found within the event – not even a simple cup of tap. After 3 hours of waiting in line and posing for the camera, we were all parched. Apparently you can bring water, however we assumed there would be some there. There was also no alcohol (yes, we wondered) or food. After-picture beverages and light snacks would have been nice to have available after getting done with all of the exhibits, especially for the night slot.
  • Mastercard holders received a special ‘skip-the-line’ key at the event to have their group bypass the wait at an exhibit of their choosing. This was something not advertised well beforehand and something that I wish was offered as a VIP ticket perk instead.








Happy Place

Compared to 29 Rooms, Happy Place – another highly anticipated pop up – had a much more youthful atmosphere. Open to both children and adults, participants started their time at Happy Place with a cartoon video – explaining the Do’s (take lots of pictures and be happy) and Dont’s (climbing on structures and using selfie sticks) of the layout. From there you are taken through a variety of different rooms, mostly empty expect for one main prop. The whole walk through took about an hour and the lines were scarce except for the jumping-into-a-pot-of-gold room. Happy Place is here in Chicago until August 6!

What I Liked

  • The Pot of Gold room was defiantly the highlight of the event, and my favorite aside from the confetti dome. While the line was longer than others for this exhibit, it was defiantly worth it. Workers of the event took stand-still and jumping photos for each group.
  • All of the rooms, and the atmosphere, defiantly brought a smile to my face. It was hard not to be happy while taking pictures with the fun backgrounds!
  • At the end of the walkthrough was offered food and a lemonade stand. I’m talking unicorn mac-n-cheese, rainbow grilled cheese and unicorn cotton candy. We didn’t buy any of these items, but the fact that they offered it was a nice touch.

What I Would Change

  • The event was almost too-quick to walk through, especially if you skipped some rooms – which we did due to some rooms being amazing and some not worth the photo at all.
  • While I could see this being a fun event for families, it would have been nice to have Adult-Only time slots for you to choose from to avoid .

(scroll all the way down for my opinion on which of the two pop ups was worth it)










Which of the pop ups was better? Honestly, it’s a hard choice. I liked Happy Place’s light and airy atmosphere compared to the more serious 29 Rooms vibes, however the photo ops at 29 Rooms were higher quality and more abundant. Since both cost around $30 for a general admission, without any VIP option, I’d say that 29 Rooms gave you more for your money’s worth. I think the fact that it was only offered for a weekend, compared to a whole month, also made it more sought-out. Due to these reasons, I would choose going to 29 Rooms again if I had to pick just one.

Been to any pop up events lately? Which ones are your favorite?

xo



Filed Under: Chicago, Lifestyle Tagged With: 29 rooms, chicago, Happy Place, Pop Ups

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About Alyssa

Alyssa is a lifestyle writer living in downtown Chicago. Her blog, Sweating Champagne, focuses on local events & festivals, mental health awareness, travel guides, and style. She loves urban living, personality quizzes (ISTP!), reading fantasy novels, listening to music, and hanging out her two cats.

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