1829 followers

Follow

Follow

Follow

1/6

24 saved

38

12

Chicago Summer/Fall Activities 🌷🫧

Planning a trip to Chicago ? These are my 3 go to things to do in the city that never disappoint

🚤 Chicago River Architecture Tour

Get a whole new perspective on the city’s iconic buildings as you cruise down the river. The guides share fun facts and history, and it’s incredibly photogenic, especially golden hour tours

🌆 Skydeck Chicago

Stand 1,353 feet above the city on a glass ledge that juts out from the Willis Tower. It’s a bit nerve-wracking, but so worth it for the view and the Instagram pic 📸

🚌 Big Bus Chicago Hop-On Hop-Off Tour

The perfect way to explore the city without stressing about transportation. Sit back, listen to the guide’s stories, and hop off at landmarks like Millennium Park and Navy Pier whenever you’re ready to explore. Perfect for first-timers!

#chicagotourguide #chicagotravelguide #chicagoitinerary #chicagoguide #chicagodaytrip

2025/8/20 Edited to

Chicago offers an array of unique summer and fall activities that highlight its rich architectural heritage, vibrant culture, and scenic beauty. Among these, the Chicago River Architecture Cruise stands out as an immersive way to explore the city's most iconic buildings from the water, providing fascinating commentary and excellent photo opportunities, particularly during the golden hour. For enthusiasts of breathtaking views, Skydeck Chicago in the Willis Tower is a must-visit attraction. Standing at 1,353 feet above ground, the Skydeck features a glass ledge that extends outward, offering visitors an exhilarating perspective of the city skyline, Lake Michigan, and beyond. This experience combines thrill with perfect photo moments, making it highly popular among tourists and locals alike. Navigating Chicago’s extensive urban landscape is made effortless by the Big Bus Chicago Hop-On Hop-Off Tour. This sightseeing tour offers flexible exploration options, allowing travelers to easily visit landmarks such as Millennium Park, Navy Pier, and various historic districts without worrying about transportation logistics. Scenic city views and the refreshing lake breeze enhance the experience, while engaging guides enrich the tour with stories about Chicago’s history and culture. Additionally, Chicago’s summer and fall seasons provide favorable weather for outdoor activities and festivals. Visitors can enjoy lakefront paths, gardens, and seasonal events that celebrate local music, food, and art. Planning trips around these months ensures that travelers experience the city at its liveliest and most picturesque. Overall, combining these top activities crafts a comprehensive Chicago itinerary catering to diverse interests, enhancing the travel experience with culture, adventure, and convenience. Whether it’s your first visit or a return trip, these tours and experiences capture the essence of Chicago’s vibrant urban charm.

12 comments

Chicago looks so aesthetic. Adding this to my travel bucket list for sure.

See more(1)

Related posts

A vibrant street scene in Chicago with tall buildings and cars, featuring the text 'Chicago 2025 FREE MUSEUM DAYS' and a 'SELF PARK' sign, announcing upcoming free museum days in the city.

An intricate artwork resembling a map of Africa, adorned with small framed portraits and medallions. The text highlights 'The Art Institute of Chicago' and its free days: Monday, Thursday, and Friday from January 6 to March 1, 2025.

The interior of the Adler Planetarium, showcasing models of planets and interactive exhibits. The text indicates 'Alder Planetarium' offers free admission every Wednesday evening from 4 to 10 p.m.

Free Museum Days! 🏛️ | Chicago

Looking for something to do in city or visiting and want to check out our iconic museums? To kick off 2025 many Chicago Museums are offering free days! Now is time to explore the wonders of the city! #chicagoactivities #chicagotourguide #chicagoexplore #new #letsgrowtogether

817 likes

Chicago Activities I’d Do Again & Again & Again

There’s so many fun things to do in Chicago and tons of unique experiences that I wish I could do all over again! Here are my top 10 Chicago activities I do again in a heartbeat 💗 #thingstodoinchicago #chicagoactivities #chicagotravel #chicagoexplore #chicagorecommendations

385 likes

An aerial view of the Chicago River with boats and bridges, flanked by tall city buildings under a clear sky. Text overlay reads 'your chicago travel guide'.

A black cat with green eyes lies on the control panel of a vintage arcade game, which displays a space-themed game. Text overlay says 'visit the catcade'.

The exterior of a brick building with large windows displaying 'NO JUMPER CHICAGO' and a city skyline graphic. A sign with a lock and keys hangs outside. Text mentions pop-ups.

Underrated Chicago Activities ✨

One critique I hear from a lot of my friends is that there isn’t much to do in Chicago besides eat and drink. When I was regularly visiting Chicago, I was too broke to eat out and too young to drink, so I had to find other forms of entertainment and fun in the city. I also get bored of tours and si

28 likes

Two women enjoy a picnic on a checkered blanket with the Chicago skyline and Lake Michigan in the background, illustrating summer activities in Chicago and its suburbs.

A baseball stadium filled with fans, featuring a person on the field holding a 'W' flag, highlighting a baseball game activity with ticket information in the caption.

A vibrant beach scene with people and the Chicago skyline, listing free access Chicago beaches: Montrose, North Ave, Oak Street, and Fullerton Beach.

SUMMER ACTIVITIES IN ILLINOIS

fun things to do this summer so you’re not just sitting in that parking lot 🫣🌇 #chicagoactivities #illinois #summer #thingstodoinchicago Illinois TICKETS FOR CUBS GAME: https://www.mlb.com/cubs/tickets TICKETS FOR SOX GAME: https://www.mlb.com/whitesox/tickets/single-game-ticket

50 likes

A title image with "CHICAGO INTERACTIVE Museums +PRICES" in bold white and brown text, set against a blurred background of city buildings.

An interactive exhibit room at Color Factory Chicago, featuring a large ball pit filled with light green balls and geometric wall art. Text indicates the ticket price and Willis Tower location.

The Museum of Ice Cream features a pink-themed room designed like a pool, filled with pink and red sprinkles, where three people are playing. Text shows the ticket price and Tribune Tower location.

Chicago Interactive Art & Museums

1. Color Factory 🎨 Color Factory Chicago ☆ Take a journey through 14 immersive art exhibits as stunning as they are colorful. Fun for all ages, Color Factory Chicago is the place ☆ INCLUDES SWEET TREATS AND SNACKS 2. Museum of Ice Cream MUSEUM OF ICE CREAM ☆ 14 interactive installatio

367 likes

Chicago places every girl should visit

10 places every girl should visit when they’re in Chicago 💕 1. Altar Home - Chicago coffee shop & home decor shop 2. Selena Mural - Located in Pilsen 3. Fleur - Logan Square flower shop 4. Museum of Ice Cream - Interactive ice cream exhibit with unlimited ice cream 5. Laila Textiles - Fl

837 likes

First time guide to Chicago ✨

Here’s a guide on what to do for your very first time to Chicago! I made sure it hit all the iconic spots, so you can experience the best of the best ❤️ #chicagoguide #chicagorecommendations #chicagoactivities #thingstodoinchicago #chicagotravel

88 likes

Must visit locations in Chicago

Tom (Ping) Memorial Park One of Chicago’s most underrated spots! With its sweeping views of the city and peaceful riverside paths, it’s the perfect escape from the downtown buzz. Plus, it’s a great spot to bring some local eats from Chinatown nearby for a beautiful picnic! Tiffany Dome S

290 likes

Chicago Candy Shop in Chinatown 🍭

This sweet Chicago shop has hundreds of candies and sweet treats imported from Asia 🍭 Every time I come to Chicago Chinatown, I make sure to stop at Ichiban Candy and it’s ALWAYS packed with people! #chicagoactivities #chinatownchicago #chicagodesserts #chicagotravel #chicagoexplore

1240 likes

A nighttime view of tall city buildings with illuminated windows, featuring the text 'CHICAGO Winter Activities' and a 'SWIPE' arrow, indicating a guide to winter activities in Chicago.

A nighttime scene at Christkindlmarket Chicago, showing people gathered around festive market stalls adorned with lights and garlands, with a large building in the background.

A wide shot of Christkindlmarket Chicago at night, with multiple decorated stalls displaying goods and people browsing, highlighting that it's a free and cultural market.

Free winter activities in Chicago 🤍

Christkindlmarket Chicago This is me and my bfs 3rd time going and it’s our favorite thing to do we love walking around and seeing what all the stands have to sell! Every year we get hot chocolate which come with the option of coming in the holiday mugs this year they had 2, they had a nutcrack

173 likes

A night view of Wrigley Field's illuminated sign and scoreboard, showing a baseball game score. Overlay text lists three Chicago hidden gems: The Charnel House, Promontory Point, and The Magic Parlour, with descriptions.

A daytime street scene in Chicago with a tall building and a sign for "The Wieners Circle." Overlay text lists two hidden gems: North Pond, a Michelin Star restaurant, and The Violet Hour, a cocktail bar.

Actual Hidden Gems in Chicago ✨🏙️

1. The Charnel House - a small theater in Logan Square, really unique artsy performances here! 2. Promontory Point - Really beautiful spot in Hyde Park. Perfect views of the Lake and Skyline of the city! 3. The Magic Parlour - Hidden Magic show in the Palmer House hotel. Super small show an

424 likes

7 Things I'm Doing in Chicago This Summer

Summertime Chi is a whole vibe! From festivals and rooftop views to art, food, and enjoying movies in the park, here are 7 things I'm making time for. Whether you're a local or visiting, here are some of my fav ways to enjoy Chicago. Which one would you try first? #chicagofun #things

15 likes

My Favorite Quirky Activities in Chicago 🏙️

As a 25 year old teacher, here are a couple of my favorite quirky and unique activities to do in Chicago! 1. Concerts at Gallagher Way 💫 Throughout the end of summer and in fall, Gallagher Way hosts many concerts with lots of country artists (Hunter Hayes) and Indie artists (Misterwives). Co

129 likes

How to impress out of town guests in Chicago

Live in Chicago and got guests coming into the city soon? Or are you a Chicago tourist looking for fun Chicago activities? Here’s your ultimate guide of things to do in Chicago that will be sure to impress out-of-towners! #thingstodoinchicago #chicagoactivities #chicagofun #chicagotra

210 likes

Nickelodeon Pop-Up in Chicago, IL 📍

My daughter and I went to this very fun and nostalgic Nickelodeon Pop-Up. We enjoyed ourselves. Is this something you’d try? #chicago #nickelodeon #popup #familyfun #chicagoactivities Chicago

801 likes

A couple sits on a road with carved pumpkins on their heads, surrounded by pine trees. The image features text overlays "couple activities Fall Edition" and a "SWIPE" arrow, suggesting a list of fall activities.

A scenic dirt path winds through a forest with vibrant orange and yellow autumn foliage. Text overlays suggest outdoor fall activities like "visit a pumpkin patch," "go to a corn maze," "take cute pictures," and "go on a walk."

An indoor scene features fall decorations, including lit candles and a decorative pumpkin, placed on a windowsill with condensation. Text overlays list indoor fall activities such as "scary movie marathon," "carve pumpkins," and "bake cookies/treats."

couple activities for fall🎃🍂🖤

i’ve personally done a majority of these, and those i haven’t done are on this years bucket list! very very fun! and of course for all my singles out there; this is also perfect for the besties💕 plus most of these things are free and very simple, but nonetheless, adorable:) #fall #fall2023 #f

2499 likes

Steal My Chicago Itinerary ✨

Took a 5 day, 4 night trip to Chicago recently and I can’t get over how much I want to go back! 🥰🥹 the trip was a 10/10!! Can’t wait to return in the summer when it’s warmer 🙂‍↔️ #chicagotrip #chicagoitinerary #chicagovlog #chicagolifestyle #chicagovibes

705 likes

Fall Learning Activities For Toddlers 🍁🎃✏️

Follow for more ideas! 📓 #toddlerschool #falltoddlercrafts #schoolingwithtoddlers #fallwithatoddler #ideasforschool #preschoolactivity #preschool #activitiesforpreschoolers #toddlerlearningactivities #toddlerlearning

1873 likes

My favorite fall activities!🍁

Fall is by far my favorite season! As much as I love summer fall is just so much more comforting! #fallplaces #fallactivity #fallgetaway #fallpictureideas #fallactivities #falltime #fallsesthetic #falltimes #unfiltered #Lemon8Diary

300 likes

Chicago St. Patrick’s Day hits different🍀

The Chicago River is dyed green for St. Patrick's Day by the Chicago Plumbers union, which uses 2 boats to spray a vegetable-based powder that turns green when it comes into contact with water, so it’s completely safe for the wild life! The union first dyed the river in 1962, using 100 pound

111 likes

Fall Activities to do with friends! 🍁🎃🍂☕️

🍂Here are some of my favorite fall activities to do with my friends during the fall season! I tend to do all of these with either family or friends and it brings me so much joy! 🍂I personally love the fall season and it gets me into a better mood over all, especially since that means it’s almos

378 likes

Chicago places I’d rush back to ASAP

Here’s a list of 10 places I absolutely love in Chicago and always look forward to going back to ❤️ Add these to your Chicago bucket list! #chicagorecommendations #chicagoactivities #thingstodoinchicago #chicagofood #chicagocontentcreator

142 likes

CHICAGO SUMMER ACTIVITY IDEAS 🌞

Summer is so short in the Midwest so I always like to make myself a little bucketlist when summer starts so I can make sure I get to everything I want to this season. Here are some Chicago summer activities that I am adding to my list: 🧘🏻‍♀️ staying active with the free summer workouts at

14 likes

SUMMER IN THE CITY: CHICAGO EDITION ☀️🌊🚕

I love the city for many reasons, and these are some of my favorite places to go in Chicago! They are definitely worth seeing! - - - ⭐️Overall rating: /10/10 Chicago #chicagotrip #chicagoexplore #chicagolifestyle #navypier #beach #concert #funthingstodo #city #summer

268 likes

5 Fall Learning Activities 🎃🍁✏️

Follow for more ideas! 📓 #toddlerschool #schoolingwithtoddlers #ideasforschool #activitiesforpreschoolers #preschoolactivity #schoolworkideas #fallwithatoddler #preschool #preschoollife #activitiesfortoddlers

1500 likes

Must-Visit Places in Lakeview Chicago

Chicago neighborhood are so charming, and here are my favorite places in the neighborhood I called home for over 7 years ❤️ 1. Guthries Tavern 2. Lost Never Found 3. Murphy’s Bleachers 4. Wrigley Field 5. Reckless Records 6. Cuddle Bunny Yoga 7. Laugh Factory #chicagocontentcreator

85 likes

Chicago 🇺🇸 Winter FREE Outdoor Activities

Ice skating at the McCormick Tribune Ice Rink in Millennium Park is a fun activity to do in Chicago. Skating on the rink is FREE, skate rental is available for a small fee.⛸️⛸️ 📍 Location: The McCormick Tribune Ice Rink 🎟️ Admission: skating is FREE. Skate Rental $16-$20

16 likes

10 MUST-DO Fall Activities in NYC 🍂🗽

We’re almost a month away from the official start of fall, and I don't know about you, BUT I AM SO EXCITED! If I could choose the best place to see and experience fall, I would always say New York . The city becomes magical - the leaves changing, the colors of everything… it’s just PERFECT.

73 likes

Fall Activities 🍁

Here are some fun ideas you can try this fall 🍂 What’s your favorite thing to do during the fall? #fall #Activities #fun #ideas #spookyseason

165 likes

Fall self-care activities for your overall health🍁

Hello Dream Girls!🌸🥰 🍁 **Autumn Self-Care Bucket List** 🍁 Want to make this fall extra special and full of self-care? Here are some cozy and relaxing ideas to help you embrace the season: 1. **Buy Yourself Flowers** 💐 Brighten up your space and lift your spirits with a beautiful bouquet o

139 likes

Shop on N. Clark Street, Chicago IL🛍️

Ran over to North Clark street to see what they had! During my high school days I’d go pick up jewelry and little cute purses for the low😂. If you’re looking to start a cute accessory business for yourself or simply like cute throw on items, go scout the block 💕. Some store do require you to have

1516 likes

Simple Chicago Activities 🥰

Looking for something simple and easy to do in Chicago that doesn’t require a lot of planning? Hop in an uber and check out these Chicago activities 🥳 1. Vintage shopping at Lost Eras 2. Visit Garfield Park Conservatory 3. Explore the National Museum of Mexican Art 4. Tour the Richard Drieha

55 likes

Color Factory in Chicago, IL 📍

It’s always blast here. Have you been? Would you go? #chicagoactivities #family #chicago #familyfun #colorfactory Chicago

69 likes

Chicago October Activities 🎃🍁👻

Which spooky event are you going to attend??! Chicago #fallactivities #chicago #halloween #spookylifestyle #activityideas

10 likes

A woman in a red dress stands on a brick path, posing in front of the Buckingham Fountain with its water displays. The Chicago skyline rises majestically in the background under a clear blue sky, showcasing the fountain's prime location.

A scenic view of Grant Park with a curved body of water and green lawn. White tents are set up in the mid-ground, suggesting an event. The Chicago skyline is visible in the distance under a partly cloudy sky.

A close-up of the Buckingham Fountain, showcasing its multi-tiered structure with water spraying dynamically. A seagull perches on the edge of the fountain's basin, with green sculptures visible in the water and a clear blue sky above.

Chicago🇺🇸Places You Must See This Summer 👇

One of the activities I enjoy doing in the summer is to visit the Buckingham Fountain, the Grant Park’s centerpiece. Located right along the lake in the heart of the park, this majestic fountain is the one Grant Park attraction you shouldn’t miss. ⛲️Historical Significance – Built in 1927, it i

6 likes

Fall ActivitiesFor Toddlers

Follow for more! 🍂🍁🎃 #follow #fallwithatoddler #toddleractivityideas #fallactivityforkids #activitiesfortoddlers #toddlerfunactivities #fallkidsactivity #toddleractivityidea #toddleractivity #toddleractivityinspiration

588 likes

chicago summer days 💐🫧

Activities to-do: 🚶🏽‍♀️ walking downtown 🌊 go to the beach 💐 visit a farmers market 🥂 cook dinner with friends 🌅 sunset drive through the city • • #chicagotrip #chicagoactivities #chicagosummer #chicagovlog #Lemon8Diary

8 likes

A wooden bridge surrounded by trees with bright orange and yellow fall leaves, with the text "CUTE FALL Activities" overlaid.

A vast pumpkin patch filled with many orange, white, and green pumpkins, with a red barn and hay bales in the background, and the text "PUMPKIN PICKING" overlaid.

A cozy outdoor fire pit surrounded by stones and two wooden chairs, with string lights overhead and fall leaves on the ground, featuring the text "FIRE PIT".

Fall activities 🍁

Just some fun fall activities on my bucket list!! Comment some fall activities you have planned 🍂 #fallvibes🍂 #fall2024 #fallideas #bucktlist #fallactivities #fallactivity #fallsesthetic #fallactivityforkids #fallplaces #fallpictureideas

496 likes

Fall activities for kids!

Fall with toddlers means making cozy memories 🍂✨ From pumpkin patches & petting zoos to painting pumpkins, sensory bins, and even a fall library trip 📚🎃 Don’t forget the kid-friendly fall movies for those cozy nights in! 🍁 #fallwithatoddler #fallvibes🍂 #fallactivities #toddlerdevelopment

572 likes

Affordable things to do in Chicago ✨

Cloud Gate : Take a picture at the Bean, one of the most popular attractions in Chicago for the cool reflective sculpture MUSEUM OF ICE CREAM : one of my favorite museums ever! They have different rooms all filled with different photo props. You get an ice cream sample at every different them

187 likes

Art Thrift Store in Chicago 🎨

Who knew about this art thrift store in Chicago where they provide heavily discount, donated arts and crafts supplies to the public?! The WasteShed, located in Logan Square, is one of the coolest Chicago shops and they offer free art materials to teachers and schools ❤️ They do all this while s

110 likes

Free Chicago Outdoor Activities

Chicago summers are short and sweet. It’s some of the best months here but it only lasts 3 months so I take every chance I get in order to enjoy the outdoors. Here are some activity ideas that are completely FREE! 🎾 PLAY TENNIS ON THE LAKE Waveland Park Tennis Courts — there are tons of

195 likes

A woman enjoys high tea outdoors, holding a pink macaron. A tiered stand displays macarons and finger sandwiches, with iced coffee and champagne on a marble table, illustrating girly spring activities.

A woman in a white sweater and floral skirt gently pets a white horse adorned with blue flowers, resembling a unicorn, at a Renaissance Festival.

A woman in a pink floral dress sits in a rowboat on a lake in Central Park, with a stone bridge and city skyline in the background, enjoying a boat ride.

spring activities & spring outfit inspo 🌸🦢🌷

These are some of my favorite girly activities to do in the spring🌸 1. Go to the renaissance festival! Depending on where you live, these festivals can happen throughout the year! Here in Arizona the festival usually happens around February-April! There are so many fun activities to enjoy at thes

1990 likes

An aerial night view of the Chicago skyline with illuminated skyscrapers, featuring the overlay text "Fun things to do in Chicago With kids!".

A daytime view of "The Bean" (Cloud Gate sculpture) in Millennium Park, Chicago, surrounded by people and city buildings, with the text "VISIT THE BEAN".

The exterior of the John G. Shedd Aquarium building with a large, colorful fish sculpture made from recycled materials in the foreground, and the text "SHEDD AQUARIUM".

FUN THINGS TO DO IN CHICAGO WITH KIDS

After many trips to Chicago, these have been some of our favorite activities to do with our kids! All of these activities are within walking distance (or a very short Uber) from The Magnificent Mile area. 1. The Bean: A must visit if you are in Chicago! A fun place to take pictures and wander ar

29 likes

See more