T A I L E Y O N

1105 followers

Follow

Follow

Follow

1/6

0 saved

10

Chicago trip✨🔥

#PhotoDump #ootd #mensfashion #foryou #mensstyle

2025/1/17 Edited to

Chicago is a vibrant city known for its stunning architecture, diverse culture, and delicious cuisine. Whether you’re wandering along the Magnificent Mile, enjoying deep-dish pizza, or exploring Millennium Park, there’s something for everyone. Don’t forget to bring your camera to capture the iconic skyline, particularly from vantage points like the Willis Tower Skydeck or the John Hancock Center. If you're interested in fashion, the Chicago shopping scene has unique boutiques as well as popular chains. The city is a hub for style, especially with events showcasing local designers. Additionally, navigate the neighborhoods for eclectic outfits that resonate with your personal style, incorporating the #ootd and #mensfashion topics. Enhance your experience by diving into local art scenes and communal spaces that reflect the city's creative spirit, making your Chicago trip not just a vacation, but an exploration of rich culture and community.

Related posts

If you’re visiting, here are some of my favorite spots in Chicago (or around). #chicagotravel #chicagotrip #chicagoexplore #Lemon8Diary #chicagoitinerary Bonchon Do-Rite Donuts & Chicken MUSEUM OF ICE CREAM Shedd Aquarium Ume Tea Fogo de Chão Brazilian Steakhouse Th

853 likes

A scenic view of the Chicago River flowing between tall city buildings under a clear sky, with a light blue banner overlay stating "3 Days in Chicago: Must-Visit Spots."

A boat cruises on the Chicago River with the city skyline in the background, overlaid with text detailing "Iconic Eats & Skyline Views" and a day's itinerary.

An aerial view of a city with numerous buildings extending towards a body of water, featuring an overlay with "Neighborhood Gems & Local Culture" and a day's itinerary.

3 Days in Chicago: Must-Visit Spots

3 days in Chicago = food, skyline views, and hidden gems. From deep dish to jazz bars, here’s how to make the most of a long weekend in the Windy City! What’s your must-do in Chicago? #ChicagoTravel #WindyCityAdventures #WeekendInChicago #TripUnlocked #Chicago

564 likes

A four-panel collage for Day 1. Top left: "DAY 1" text. Top right: People viewing art at the Art Institute of Chicago. Bottom left: The Chicago Riverwalk with city buildings. Bottom right: The Cloud Gate sculpture at Millennium Park at dusk.

Save for your Next trip to Chicago 📍🫶🏽

Day 1 Millennium Park Visit the iconic Cloud Gate home of “The Bean” and explore Crown Fountain and Lurie Garden. Highly recommend dressing warmly as it can be windy near the lake The Art Institute of Chicago One of the best museums I’ve been to, featuring works from Monet, Van Gogh an

994 likes

Chicago has been by far the coolest trip my boyfriend and I have been on! Everything is so beautiful, the sceneries, the architecture!!! Def recommend you try these places out, if you stay in downtown everything is super close by! We def want to go back in the summer ❤️‍🔥☀️ #travelwithme2024

16 likes

Chicago🇺🇸The PERFECT 3 Days Itinerary (Winter)

☃️Save this 3 Days Itinerary for a future trip to Chicago with the best places to visit in the winter season. ❄️🎄 Would you like to visit Chicago in 2025 ❓ Day 1️⃣ The Chicago Theatre : Admire the stunning architecture ($15–$20 for tours). Museum of Illusions Chicago : Interactive fun

310 likes

A wide shot of The Bean (Cloud Gate) in Millennium Park, Chicago, with people around it and city skyscrapers in the background. The image has a title overlay: 'Things to Do in Chicago MUST VISIT PLACES AND FUN FACTS!'.

A wide shot of The Bean (Cloud Gate) in Millennium Park, Chicago, with people around it and city skyscrapers in the background. The text identifies it as 'The Bean' in Millennium Park, a popular Chicago attraction.

A hand lifts a slice of deep-dish pizza from a pan, showing long strands of melted cheese stretching. The text identifies this as Giordano's, a deep-dish pizza restaurant.

Save this for your Chicago trip!

Thank you for visiting my post! 🥹 Feel feel free to drop your favorite places in Chicago in the comments! - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - I love Chicago so much! I hope I can visit in the wintertime when everything's so magical. What places would you

1234 likes

Chicago trip 📍🏙️

#chicagoskyline #chicagoexplore #chicagotrip #chicago #CITY Chicago

11 likes

An aerial view of Chicago's skyline featuring Millennium Park with Cloud Gate, skyscrapers, and Lake Michigan. The image is titled 'Chicago Girls Weekend Itinerary' with decorative hearts.

A festive interior of Gilt Bar, decorated with a lit Christmas tree and bottles on shelves, creating a cozy atmosphere. Text suggests visiting for 'outstanding pasta + cozy vibes'.

A stunning nighttime aerial view of Chicago's illuminated cityscape and skyscrapers. The text recommends visiting 360 CHICAGO for 'the best views of the city at sunset' for $35 per person.

Girls Weekend Itinerary 🌆 Chicago Edition

Chicago is such an underrated city! We just spent the perfect girls weekend here! Some of my top recommendations include: - Visiting Gilt Bar for amazing food, vibes and there’s a vintage photobooth in the basement! $5 per round of photos! - Get tickets to 360 CHICAGO ! This experience

292 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

709 likes

The best day trip Chicago itinerary ✨🤍

Chicago is such a diverse city with nature, harbor, skyline views, and so much more. The food is diverse, there are so many different areas to stay in, unique bars to go to that if you had only a day, save this post to make your day trip to Chicago unforgettable. 🥘 Kasama 🫘 Cloud Gate 🚞

741 likes

A woman sits on a boat on the Chicago River, surrounded by city skyscrapers, with the text 'Actual HIDDEN GEMS IN CHICAGO' overlaid. She holds a drink, looking towards the city.

A list of ten Chicago hidden gems, including The Music Box and Empty Bottle, is displayed over a background of the Chicago skyline and a boat full of people on the river.

An aerial view of the Chicago skyline with the green Chicago River, featuring the text 'Skip the Tourist Traps and try out a couple of my favorite hidden gems in my favorite city, my home: CHICAGO'.

Actual Hidden Gems In Chicago 💎 🏙️

Here is a list of my favorite places in my home, Chicago 💎🏙️. Most of these are off the beaten path or places most tourists or visitors do not go to while in the city! 1. The Music Box Music Box Theatre : An Old and vintage theater that plays old black and white films along with classics and

1843 likes

Weekend Trip to Chicago 🥰

It’s always a vibe in Chicago ❤️‍🔥 Overall: 9/10 Things to do - Take the Chicago Architecture River Tour, Chicago River - Go to Starbucks Reserve Roastery - Go to Marc Jacobs - Oak Street - Go to Cloud Gate #chicagotrip #chicagoitinerary #contentcreator #blackgirltr

353 likes

#chicago #style #photography #lemon8photography

13 likes

A night view of Chicago's Cloud Gate sculpture with city buildings in the background. The image features text 'Travel guide for. CHICAGO' and 'Swipe', indicating a guide for the city.

A list titled 'Random Stuff to do in Chicago', featuring various attractions and activities like shopping, museums, zoos, and entertainment venues.

A list titled 'bars & Clubs in Chicago', detailing various nightlife options including specific bars, clubs, and arcade bars, with some indicating crowd demographics.

You can never be bored in Chi-town! Chicago #chicagotrip #travel #explore #fyp #rockthepatch

341 likes

#Chicago 🇺🇸 4 Day Itinerary

Save this post for a future trip to Chicago, the Windy City. Day 1️⃣ Chicago Theatre, Millennium Park, Art Institute of Chicago, Buckingham Fountain (Grant Park) Day 2️⃣ Lincoln Park, Lincoln Park Conservatory, Lincoln Park Zoo. Day 3️⃣ Navy Pier, Skyline Boat Tour, Milton L. Olive Park,

325 likes

A young woman smiles on a bridge overlooking the Chicago River with city buildings in the background. The image includes text about spending a day in Chicago on a budget.

A collage showing the interior of a money museum, with exhibits like a large cube and a display of currency. A woman poses next to a sign for the museum.

A collage featuring a large reflective bean-shaped sculpture in a park. A woman poses with the sculpture, showing reflections of herself and the surroundings.

chicago trip 🚕🏙️

spent the day in chicago yesterday for under $50! we walked everywhere, minus one uber ride for $8, did a bunch of free museums and touristy things to make the most of the day in the cheapest way! overall i only spent $45 for food and one new clothing item from the mall! 🛍️ we also took the

15 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

428 likes

Top 3 Niche Travel Spots You Need To Check Out🔥

5 likes

Quick Chicago Trip 🌃

Spent a long weekend in Chicago for work this past month and had the best time 🖤 We were flown out as a thank-you for our work on the account, and after a few meetings, we squeezed in an architecture walking tour, a Blackhawks game, and bar-hopping (ending at Redhead Piano Bar, iykyk). I stayed

12 likes

Where are some places you visited in Chicago?

11 likes

My trip to chicago 🎀

We’re spending the weekend in Chicago. 🏁 First stop , Museum of Ice cream 🍦 Tomorrow is going to be so special. Me , my mom, my daughter and my niece 🎀 #chicago #musemoficecream #girlstrip #girlstravel #momanddaughter

696 likes

Chicago Gems: 📍Roscoe Village

Roscoe Village is a laid-back Chicago neighborhood with cozy coffee shops, low-key bars, and a vibe that feels like home. A great part of Chicago that feels less chaotic but plenty of things to do. I absolutely love this area when trying to find a spot that’s not too busy, but filled with people in

34 likes

A Trip Back Home: Chicago

My recent trip back home to Chicago was everything I hoped it would be and more. As soon as I landed at O'Hare Airport on my favorite airline, Delta, I felt an overwhelming sense of nostalgia and excitement. There’s something about that city skyline that feels like a warm hug. I decided to k

18 likes

Bookish Trip in Chicago 📚

A sister book trip to Chicago = the perfect combo. • We found the cutest bookish hotel, ate our way through the city, and of course, squeezed in a dreamy bookstore stop! • Hotel @Hotel Zachary • Food @happycamperbarco •Food @stansdonuts •Bookstore @UnabridgedBookstore #lemon8bookclub

181 likes

chicago girls trip!

📍 City/Country: Chicago 🌞 Day 1: Walked ALOT. found a good spot for instagram pics and walked down to the river walk to Taco Rio and had some delicious chicken loaded nachos. We also stopped at Mochinut and got boba, smoothies and DELICIOUS mochinut donuts. We went back to the hotel and rested f

37 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

188 likes

QUICK TRIP TO CHICAGO

First time in Chicago and I absolutely LOVED IT. First of all, with it being a massive city, I felt totally safe there. We got to see the Bean, and walked around Millennium Park. We saw all of the sports arenas for NFL, MLB, NBA/NHL. We had a Chicago deep dish pizza, of course. I can honest

10 likes

A street view of downtown Chicago featuring tall buildings, a "CANAL ST" sign, and traffic. Overlays read "Chicago Trip" and "TUESDAY," accompanied by small landscape photos.

Quick chicago trip ✨🌆

Chicago is one of my favorite places to visit for theatre, I did a show there back in high school 🤓 and just loved it. I can’t wait to go back 🤎🌃 #chicago #travel #blacktravel #blackgirllemon8 #blackgirl

15 likes

Things to do in Chicago

📍 Chicago 10/10 definitely recommend!! So much to do and see out there WNDR- interactive museum Ice Cream Museum-unlimited ice cream and they have a bar!! Navy Pier- get tickets for one of the boats and enjoy the scenery!! Water Taxi- The water taxi takes you to Chinatown! If you’re a foodi

188 likes

Two banners for the NASCAR Chicago Street Race hang from a lamppost against a blue sky, advertising the event on July 6-7 with event details and sponsor logos.

A street view from inside a car in Chicago, looking forward under the city's elevated train tracks, with buildings and other vehicles visible.

An ornate, antique-style clock with two faces and a decorative statue on top, mounted on a building in Chicago, with modern architecture in the background.

I love showing off my trips!!! This weekend, I'm in Chicago for the NASCAR street race, and it's said that this is their last time doing it. I absolutely love that this is my first experience with NASCAR, and we got VIP tickets!!!!! Is anyone else experiencing this, too?? These pictures

1 like

Chicago trip🫶

#Lemon8Scrapbook Destination List ✈️ City: Chicago 🌆 ✨ Pros: Food, drinks, city 👀 Cons: Cold 🥶 so cold 🗺️ Tips: if you like snow January is a perfect month for you if no I recommend going between July or August. The city is beautiful but parking is expensive so use the bus 😉 #chicagowin

11 likes

5 Free Things to Do in Chicago ✨

5 Free Things to Do in Chicago 1. Walk the Chicago Riverwalk Beautiful views, public art, and a lively vibe along the water. 2. Explore Lincoln Park Stroll through gardens, ponds, and even visit the free Lincoln Park Zoo. 3. Catch a Lake Michigan Sunrise or Sunset H

382 likes

Chicago Travel Guide: Fall Edition🍂🎃

📍 Riverwalk The riverwalk is so fun and a great way to see some fall colors!! 📍 Chicago Botanic Garden 📍 Jack's Pumpkin Pop-up is so much fun and a great way to visit a pumpkin patch without having to leave the city!!! There are so many opportunities for fun pics too! 📍 Starved

82 likes

An aerial view of the New York City skyline at sunset, featuring the Empire State Building prominently. Text overlay reads "DAY TRIP TO NYC Travel with me from chicago to NYC steal my itinerary."

An airplane wing is visible from a window, flying over a city with lights at dusk or dawn. Text overlay indicates "6:15 AM en route to nyc."

A view from an airplane window shows an airport runway, a body of water, and a distant city skyline. Text overlay states "8:45 AM touchdown!!! VELCOME TO NEW YORK."

Day Trip to NYC from Chicago!! ✈️🍎🗽 part 1

New York #traveltok #nyc #daytriptonyc #chicagotonyc #solotravel

24 likes

A woman stands on a Chicago sidewalk with buildings and trees in the background. Text overlays announce "MY FAVORITE (NON-TOURISTY) SPOTS IN CHICAGO" and "brat city," introducing a guide to local recommendations.

An outdoor patio at Avli Taverna in Lincoln Park, featuring vibrant purple bougainvillea, string lights, and white pergolas, suggesting a pleasant dining atmosphere for a "Girl Dinner."

A large variety of colorful sushi rolls are neatly arranged in a white box, resembling a pizza box, from Tanuki Sushi & Grill in Lakeview, highlighting the unique "Sushi in a Pizza Box" concept.

How to Be BRAT in Chicago (my fav spots) 🏙️

It’s officially my 3rd year in my favorite city of Chicago so here are a couple of my favorite little spots that don’t get enough attention. 1. The BEST Mediterranean dinner at Avli Taverna There are two locations for Avli (Lincoln Park and River North). Been to both but love the neighborhoo

297 likes

Weekend Trip From Chicago: Lake Geneva, WI

If you want to get out of the city this summer, take a weekend trip to Lake Geneva, WI! Though you'll be in a different state, Lake Geneva is just 1.5 hours from Chicago and it's the perfect place for a weekend getaway in nature. The Abbey Resort & Avani Spa Grand Geneva Resort

11 likes

must eat on your chicago trip

Chicago is such a lovely city to visit in the summer and these are what I would eat: 1. Lou Malnati’s ($15) - deep dish pizza is a classic in chicago. this is one of the famous spots for deep dish, others include Pizzeria Uno and Giordino Lou Malnati's Pizzeria 2. Mr Beef ($12) - the

28 likes

🌸Cute day trip near chicago🌸

Need some weekend plans? Here's a cute spring itinerary thats just one hour from Chicago Stop 1: coffee Coffee (and maybe breakfast) at Sparrow Coffee Naperville . It's bustling which means you know it's good. Stop: 2 spring trees! Just 10 minutes down the road is the ar

1 like

Chicago trip 🔥

#chicagotrip #chicagoexplore #chicagoland Harold Washington Library Center, Chicago Public Library

9 likes

A vibrant image showcasing the Chicago skyline and river under a bright sky, with text overlays reading "brat city" and "MY FAVORITE SPOTS IN CHICAGO," introducing a guide to favorite places.

A woman on a swing in a colorful polka-dotted room at Whim Chicago, an escape room experience. Text indicates tickets are $15 for 10 art installations/rooms.

A scenic view of North Pond restaurant by a calm body of water, surrounded by trees. Text highlights it as a hidden restaurant with specialized meals from Chef Cesar's garden, starting around $50.

brat city : some of my favorite spots in Chicago

Here are a couple of my favorite spots in the beautiful city of Chicago 🏙️ 1. Whim Chicago @ Stage 773 THIS experience is unlike anything else in Chicago! For $15- experience 10 different rooms that are created by Chicago artists! Some even have secret ways to escape to get to the next room

281 likes

Traveling is life. #travel #chicago #navypier

9 likes

My Chicago trip 📍

Have you ever been to Chicago? What’s been your favorite city to visit? #lemon8diarychallenge Chicago #chicagotrip #chicagoexplore #chicagoskyline #chicagoitinerary

22 likes

quick chicago trip

my Chicago weekend trip in a few pictures💗 #dayinmylife #dayinthelife #citygirl #city

10 likes

🌞 Day 1 #birthday #chicago #chicagotrip #chicagoexplore

6 likes

Had so much fun in 2 days in Chicago. Mom, model, content creator, coach- you can do it all at once! Start YOUR TRANSFORMATION! DM “MINDSET” asap for coaching #model #mom #lifestyle #contentcreator #shareyourthoughts #mindset #transformation #blogger #momsoflemon8 #trave

72 likes

A street-level view of Chicago's downtown architecture under a clear blue sky, featuring historic buildings with clocks and modern skyscrapers, with the title 'Things to do in Chicago' overlaid.

A woman sits on a glass ledge at the Sky Deck, overlooking a vast cityscape of Chicago from a high vantage point, showcasing the incredible views.

Inside the Art Institute of Chicago, a gallery features classical paintings and sculptures on display, with visitors admiring the art in a spacious room.

Add This to Your Chicago Daytime Itinerary ✨

8 Things to do in Chicago ✨ Weather it’s your first time visiting or returning, these are some of the places you definitely need to check out when coming to chicago! Chicago is by far one of my favorite cities to visit, there’s just so much to do and see here! Feel free to add more suggest

521 likes

Chicago #chicagotrip #foryoupage

2 likes

girls trip to chicago❄️✨

digital scrapbook memories from my trip to chicago🌃 #chicago #digitalscrapbook #wintertravel #chicity

45 likes

See more