Chicago Fall Bucket List 2019

September 16, 2019

Summer time in Chicago is best, however, fall is another really great time to get out and explore the city. I always tell people from out of town that September and early October are also great times to visit. Why? Because there is so much to do and flights and hotels are usually much cheaper! So I’ve put together a list a fall bucket list of fun things to do around town either with your friends, family or solo!


32nd Lincoln Square Ravenswood Apple Fest- This fest for the adults AND kids with live music, food and alcohol to purchase including fresh apple pie from Bang Bang, hot apple cider, or even a whole bushel of apples. It is Saturday, October 5th & Sunday, October 6th 2019. 9am-6pm. We will be there!

TIP: $5 suggested donation that goes to the Lincoln Square Chamber of Commerce.

Chicago Park District’s Pumpkin Patch– We found out about these pumpkin patches at the park district from a friend and went to Horner Park last year. We had so MUCH FUN! Petting zoo, face painting, pumpkins available for purchase, etc. It is free, but certain activities require purchasing tickets. But there was even more FREE activities inside the building like coloring, jumpy house, balloons, etc. There are several ones across the city on different dates, definitely worth going for a few hours with the family. This was us last year when I pregnant with Mila!

TIP: Tickets sales stop at a certain time, so check the CPD website before going.

County Line Orchard- Located in Hobart, Indiana, about 40 miles outside Chicago, it’s my go-to for apple picking. In fact, when I was a teacher, I would bring the students every fall. There’s a tractor ride, small petting zoo, big sitting area with food available to purchase. Not to mention the cider donuts are so good….fall is the best time for cider anything!

TIP: Some of the best cider and cider donuts!

Goebbert’s Pumpkin Patch– Located in Pingree, Illinois, about an hour outside of the city. This is a massive pumpkin patch, but so much more. Petting zoo, tractor rides, haunted house, straw maze, and so much more. We took Noah here for the past two years, but HIGHLY recommend going on a weekday, because it does get really crowded. We go early and make an entire day out of it, there’s a ton to do for kids of all ages!

TIP: Buy tickets in advance! The longest line we waited in was for tickets. You can do it directly through their website.

Goebbert's pumpkin patch is a great place to take the family this fall in the Chicagoland area. Add it to your Chicago Bucket List!


SkyYoga– At 360 Chicago, located at the top Hancock Building, there will be a yoga class on Sunday’s now beginning September 29th. I took the kids to watch the Air and Water Show last month and the views are amazing! This would be so fun with a group of friends before heading out for brunch for the day. Plus, those views are quite ‘grammable 🙂

It is from 9-10am and tickets are $18. It includes access to the observation deck,

TIP: Pre Registration is required for the event, so sign up before it sells out!

Bacon and Beer Classic- Located at Soldier Field, it’s the 5th annual Bacon and Beer Classic with 100+ craft beers from the best local breweries, unlimited original bacon-inspired dishes from local restaurants, games, giveaways, and music. Plus, you’re on Soldier Field, how cool is that? It would be fun to get some friends together and do some day drinking!

I did something similar with the Chicago Beer Classic and had SO much fun. Plus you get some great photos for the gram. 🙂

TIP: There are always discount codes floating around Instagram, be on the lookout for it!

Jack’s Pumpkin Pop-Up- This past summer, I went to Neon Lights, which is run by the same agency and was super impressed. Although I didn’t go last year to this pumpkin pop up, I will definitely be going this year with the family. It’s not your traditional pumpkin patch, but fun to take pictures and enjoy some fall fun in the city. It opens October 4th and open for only a month. We will definitely be going for the media preview night, I will be sharing on stories!

TIP: Kids are allowed before 7pm and children 4 years and under get in for free. 

The Urban Glamping Package- This is currently available at The Gwen Hotel, which is located right downtown. I wish I would have learned about this earlier in the season because this is seriously the ultimate girls night.

The package offers guests a night under the stars in a tent on the 1,000 square-foot suite’s private terrace on the 16th floor. It includes:

  • A s’mores turndown service
  • Access to the two-bedroom, two-bathroom Grand Lux Suite
  • Round-trip airport transportation
  • Access to the hotel’s Elite Ambassador Service, reserved for The Gwen VIP guests

I mean how cool is that?! Only available for a few weeks longer! Such a good bachelorette idea too.

TIP: Reservations can be made by calling the hotel at 312-645-1500.

Glamping at the Gwen Hotel is a perfect girls night activity on your Chicago Bucket List this fall!
Photo Courtesy of The Gwen

Date Night

Pier Pumpkin Nights at Navy Pier– For the first time ever, Navy Pier is having a FREE pumpkin patch with fall themed cocktails (available for purchase), jack o’ lanterns and more. It would be fun for the family, but I think it would make an even better date night.

We will be going for the media preview night, I will be sharing on stories to give you a sneak peek.

UPDATE: We went last night and it was lots of fun! There are 5 pumpkin “exhibits” along the pier, with the best one right underneath the ferris wheel (perfect for pictures). Several of the restaurants like Harry Carry’s, Tiny Tavern, Riva’s and a few more have some fall themed drinks and food. The best by far with Tiny Tavern with a spike cider and bread pudding.

Here are some things I would recommend:

  • We went on a Monday and the pier was empty! Great time to go, but the ferris wheel and most restaurants/shops close at 8pm.
  • I haven’t been on the Ferris Wheel in YEARS. It was so much fun! Plus the views!
  • If you have more time and go on a weekend, we use Spot Hero and always park in the same spot for less than $16 dollars. The parking garage address is 509 N. Preshtigo Ct.
  • If you are going for a date night, hit up the Shore Club for some drinks after! The views are incredible. Kids are NOT allowed, so enjoy it without the little ones.
  • If you want to make an entire day, we absolutely loved the Fireboat Tours on Lake Michigan and the Chicago River. The boat departs about 5-10 minutes away from the pier. They are running until mid- November and I saved a highlight of our experience on my Instagram page.


TIP: Check in at the Energy Pavilion in the Polk Bros. Park for a map of the pumpkins!

Open House Chicago– I originally found this out through my blogger friend, Alex from Sassy Confetti and now it is on our bucket list this fall. On October 19th and 20th, you can get behind-the-scenes access to more than 350 buildings across Chicago. It is hosted by The Chicago Architecture Center and would make a great date day!

You can explore the hidden gems and architectural treasures of Chicago’s diverse neighborhoods—all for FREE. We have our eye on the University of Chicago this year!

TIP– Sign up for their e-news to get update on all their locations.

The Blackstone hotel in Chicago has beautiful architecture and available to tour during Open House Chicago
Photo Courtesy of Blackstone Hotel

Outdoor Curling Cabin and Rink at The Gwen– Located on the fifth floor of The Gwen hotel starting November 1st, the outdoor terrace is transformed into an iceless Curling Rink and new Curling Cabin experience. I think this would be the best date night! There will be a lounge in the cabin’s living room area, with electric fireplace, faux furs, twinkly lights and a holiday soundtrack help set the scene.

The Curling Cabin can accommodate up to 15 guests and features an Alpine-inspired menu along with from winter cocktails. Admission for The Gwen Curling Rink is $25 per person, which includes a choice of one cocktail and 30 minutes of curling play time.

TIP: Reservations for the Curling Rink and Cabin are available via OpenTable

Curling and Cabins at The Gwen Hotel in Chicago. Great late fall/early winter activity on my bucket list.
Photo Courtesy of The Gwen

Midwest Travel

If you are thinking about taking a road trip around the midwest, here are some great towns with beautiful fall foliage. I’ve been to all these and can say they are great for couples and families!

So that’s it! Here are 10 things that we will try to do this fall. Although, there are so much more, I will add to this list as I hear of some more events happening around town.

Any of your favorites? Let me know!

Until next time,


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