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Here's your plan for a spooky 2-hour ghost tour cruising Chicago's lake and river with BYOB. Watch the video 👇

Experience an unforgettable spooky season adventure on the water with this 120-minute Ghost Tour with Chicago Boat Company. Get $10 off with code GHOST2025!

Spooky Ghost Tour on Party Barge 👻 🎃 ⛴️

Book a 120-minute BYOB spooky ghost tour with Chicago Boat Company for chilling Chicago stories and haunting lake views. Reserve your spot for an unforgettable Halloween adventure!

Ghost Boat Tour

💻 How to book
• Reserve directly through Chicago Boat Company to secure your date and time

🤑Discount Code
• Use my code to receive $10 off a Ghost Tour cruise of your own: GHOST2025 (Valid 9/23 - 11/2)

Book your spot

Enjoy a spooky 120-minute BYOB ghost tour with Chicago Boat Company. Dress warmly for the wind and arrive early for an unforgettable haunted cruise experience.

Boat Ghost Tour

🌯🥤 BYOB
🥶🧥 Dress for the windy weather
⏰⛴️ Arrive 10-15 minutes early
📸😀 Capture the moments and have fun!

Must-knows 🧐 

Kick off spooky season in Chicago on a ghost tour that floats.

It's a 120 minute guided ghost tour on a pontoon boat,

You get to see such beautiful views of Chicago,

or the Great Chicago Fire of 1871 that wiped out nearly the whole city,

your heartwarming holiday story you'd expect.

The guides keep you hooked with haunting details and eerie visuals.

And an October night in Chicago already looks straight out of a ghost story.

This experience is BYOB so you can pack whatever you want for the ride.

I highly recommend bringing something pumpkin spiced.

The river even got a little wild on the way back,

which I'm pretty sure it was a ghost that was rocking the boat.

If you're looking for classic Halloween chills with a Chicago twist,

Here's your plan for a dog-friendly hike at Palos Park Woods near Chicago with coffee and beer stops. Watch the video 👇

Head just outside the city for a dog friendly hike! 

Stunning Hike 30min from Chicago

Enjoy a beautiful hike at Palos Park Woods-North, just 30 minutes from Chicago. Dog-friendly trails range from 1 to 15 miles, plus nearby coffee and brewery options.

Hiking Trail

✅ Before you go
• get coffee at Ashby house before  

💪 Pro tips
• stop by emperial brewing after for beers and a pizza spot nearby!


Go for a hike 

I've been looking for hiking trails near Chicago and

so I recently checked out Palos Park Woods.

You can do anything from 1 mile to I think like 15 miles.

It's just absolutely stunning and dog friendly.

I'll drop the all trails link in the notes.

we stopped at this coffee shop and then after our hike,

we went to this brewery and grabbed some beers.

so I'll be making sure to check that out next time.

Here's your plan for a solo night with dinner at Grant Park Bistro and a Chicago Symphony show. Watch the video 👇

You can never go wrong with dinner and a show 🤗 On Michigan Ave., you can enjoy an early dinner at Grant Park Bistro before walking down to the Chicago Symphony Orchestra to enjoy one of their concert performances. 

Solo Date Night on Michigan Ave 

Enjoy creative American dining and a warm ambiance at Grant Park Bistro, perfect for an early dinner or happy hour on Michigan Ave.

Dinner Dining

✅ Before you go
• Their happy hour is from 4-6pm from Sundays-Thursdays if you want to eat well and save some money. 
💪 Pro tips
• They also have daily specials that can sometimes be an even better deal than what you find on their happy hour menu. 😉 

Grant Park Bistro

Enjoy a world-class concert at the Chicago Symphony Orchestra, with opportunities for last-minute ticket deals and beautiful city views in the heart of downtown Chicago.

Orchestra Concert

✅ Before you go
• Aim to arrive 15-20 minutes before your concert starts so you can have time to get through the line and find your seat before the show starts. 
💪 Pro tips
• You can join their mailing list or even one of their community networks to get access to discounts, ticket offers, and exclusive events: https://cso.org/concerts-tickets/tickets-subscriptions/
• Also, some shows offer tickets 50% off if you purchase tickets the day of, so you can even save some money if you want to be spontaneous. 

Chicago Symphony Orchestra 

Need a solo date or even a regular date idea?

Start with dinner at Grant Park Bistro on Michigan Ave.

and they also have daily specials and a happy

hour from Sundays through Thursdays from 4 to 6pm. 

and offer an inviting atmosphere for you to come in,

and once you see this flag blowing in the breeze,

The Chicago Symphony Orchestra has plenty of

performances that you can come and attend.

They also have great aerial views of the city.

I highly recommend grabbing dinner and enjoying a show at the Chicago

Symphony Orchestra the next time you're looking for a date idea.

Here's your plan for exploring Lincoln Park Conservatory and relaxing with coffee at Cafe Deko. Watch the video 👇

Explore the beautiful Lincoln Park Conservatory then grab a coffee at an art deco themed cafe! 

Conservatory 🪷 + Cafe 🍵

Visit the Lincoln Park Conservatory to explore lush gardens and rotating botanical exhibits. Free entry—just make sure to reserve your time slot online!

Explore Conservatory

✅ Before you go
- Totally free!! Just make sure to book a time slot before hand. https://www.lincolnparkconservancy.org/conservatory-reservations/

💪 Pro tips
- Open Wed- Sun. 
- Also check out the free zoo right next store! 

1. Lincoln Park Conservatory 🪷

Relax with a chai or coffee at Cafe Deko, a dreamy 1930s-inspired cafe with plush seating and vintage decor. Perfect for unwinding after your garden stroll.

Coffee at Cafe

✅ Before you go
- Dreamy, 1930s Art Deco/Victorian-inspired with chandeliers, floral details, and plush furniture. 

💪 Pro tips
- There’s 2 locations so make sure to go to the Lincoln Park one! 

2. Cafe Deko ☕️

This is the perfect inexpensive spring or summer day plan

you're going to go near the Lincoln Park Zoo

They have different rotating exhibits all spring and summer and winter,

You could honestly spend a few hours in here because there

is so much to see and it is all so beautiful.

but you have to reserve them ahead of time online for a specific time slot.

we walked through Lincoln Park and saw some beautiful greenery outside

We ordered a chai and sat in the sunlight

for the rest of this beautiful Saturday afternoon.

Here's your plan for enjoying a peaceful park walk and exploring diverse art on Second Fridays. Watch the video 👇

If you’re downtown and looking for a way to get some fresh air, you can take a walk through Maggie Daley Plaza. It’s a nice place to enjoy nature in the middle of the concrete jungle. Also, if it happens to be the 2nd Fridays of the month, you can visit the Fine Arts Building a few blocks away for Second Fridays where they open the building for you to see and hear from different artists for free! 

Nature & the Arts in the Loop

Enjoy a peaceful walk or outdoor activities like rock climbing and mini golf at Maggie Daley Park, a nature oasis in Chicago's downtown Loop.

Park Walk

💪 Pro tips
• There are additional paid activities that are opening back up for the spring/summer like rock climbing and mini golf if you want to plan ahead! 


Maggie Daley Park

Explore three floors of artist studios, performances, and music at Second Fridays in the Fine Arts Building, happening monthly in downtown Chicago. Free entry, creativity everywhere!

Art open studios

✅ Before you go
• You can RSVP ahead of time on their website, https://www.fineartsbuilding.com/events/second-fridays/  but it’s not required if you want to attend spontaneously. 
💪 Pro tips
• There are a wide range of artists here, so I’d recommend showing up closer to 5pm so you can have the full 4 hours to browse around and see (or hear) what you find! 


Second Fridays 

Apart from the hustle and bustle of downtown,

Taking a walk through the Maggie Daley Park is one way.

this park offers a great moment of tranquility.

It's not as big as Millennium Park or Grant Park,

but it allows you an opportunity to take in

the fresh air with a little less foot traffic.

If you find yourself downtown on the 2nd Friday of the month,

you can just take another 10 minute walk down Michigan Ave,

or through Grant Park and find the Fine Arts Building.

Here, you'll find their monthly event called Second Fridays,

where you have the opportunity to explore all 10 floors of

the history and art that lives in the Fine Arts building.

There is so much creativity and artistry that you can find at Second Fridays.

You'll find visual artists of every medium,

there is also a bookstore within the building that

you can buy books from up until 7 o'clock.

You never know what you'll find at Second Fridays. 

I stumbled upon a full stage play read while I was there.

So, I highly recommend making plans for the next Second Fridays at the Fine Arts building.