Girls weekend Trip to Chicago

Chicago
2024/6/11 Edited to

... Read moreChicago is absolutely perfect for a girls' weekend getaway, and my recent trip definitely proved it! If you're planning your own adventure with your besties, let me share a few more tips and insights to help you make the most of your time in the Windy City. First off, let's talk about the Chicago Riverwalk. It’s truly a gem, and spending time there was one of the highlights. We started our day with some delicious food and wine at City Winery at the Riverwalk, which offers amazing views and a super relaxed vibe. It’s ideal for catching up, enjoying a good meal, and people-watching. You can easily spend a couple of hours just soaking in the atmosphere. For an even more active experience on the water, consider renting kayaks! It’s a unique way to see the city's architecture and get some exercise, especially if you're looking for something a bit different than just walking. Speaking of unique experiences, the Chicago Water Taxi was a surprisingly neat way to get around! Not only is it practical for hopping between attractions, but it also offers fantastic views of the skyline from the water. Definitely budget some time for this, as it's more scenic than a regular taxi or public transport. We loved cruising along the river, feeling the breeze, and seeing the city from a new perspective. For a dose of relaxation and pampering, Leaf Spa Chicago was a lovely treat. After all the walking and exploring, a spa visit is a great way to unwind and recharge. It’s perfect for a girls' trip, allowing everyone to de-stress and feel refreshed before heading out for dinner or another activity. We felt totally rejuvenated and ready for more fun! Now, about the MUSEUM OF ICE CREAM... I have to agree, it felt a little overpriced for what it was. While it’s fun for photos, if you're on a budget or prefer more substantive experiences, you might consider skipping it or looking for other unique photo ops around the city. Chicago has so many vibrant murals and iconic spots that are free to enjoy anyway! Beyond these specific spots, when planning your Chicago girls' trip, remember to think about transportation. The 'L' train system is fantastic for getting around, but comfortable walking shoes are a must because you'll want to explore on foot a lot. Also, be sure to pack layers – Chicago weather can be unpredictable! For busy days of sightseeing, having some travel snacks on hand (like the ones from Southwest Airlines, if you flew in with them!) can be a lifesaver to keep your energy up between meals. Don't forget to explore the diverse food scene – from iconic deep-dish pizza to trendy brunch spots and vibrant rooftop bars, there’s something for every palate. A Chicago girls' weekend is truly an unforgettable experience; just tailor it to your group's interests for maximum fun!

12 comments

loviden's images
loviden

Great photos! Chicago looks amazing, I'd love to go there.

Captain Lemon8's images
Captain Lemon8

Welcome! So excited to see more from you in the future💛

Related posts

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
Trip Unlocked

Trip Unlocked

556 likes

Chicago Weekend Getaway
Weekend trip idea from Chicago ✨ Pro-tip: Frankenmuth is only 5 hours from Chicago and 1.5 from Detroit ! Tag your road trip buddies (🎥: alabamasavannah via TikTok) #chicago #chicagobucketlist #roadtrip
CHI Bucket List

CHI Bucket List

672 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
Sam Richard

Sam Richard

289 likes

A low-angle view of modern skyscrapers in Chicago under a blue sky, with the text overlay "Chicago 3 Day Itinerary" in white and black outline. The Lemon8 logo and username are in the bottom left corner.
A street view of Chicago with tall buildings, cars, and traffic lights. Text overlay reads "WHERE TO STAY" with arrows pointing to "Park Hyatt Chicago," "The Langham," and "The Gwen." The Lemon8 logo is in the bottom left.
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
GetawayGuide

GetawayGuide

979 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
Erie Valentine💞👑

Erie Valentine💞👑

344 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
Aria 𖹭

Aria 𖹭

1194 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
MomOf3

MomOf3

692 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 🚞
Grace Kim

Grace Kim

721 likes

GIRLS WEEKEND 🫶 CHICAGO NIGHTLIFE EDITION 🌃
Chicago girls weekend! 🌆 Bars to visit and nightlife to explore: - Gilt Bar (vintage photo-booth in basement) - London House Rooftop (amazing city views) - Cindy’s Rooftop (millennium park view) - Starbucks Reserve (largest Starbucks in the world) ✨ Tips: Purchase an unlimited 72 hour
Sam Richard

Sam Richard

145 likes

girls trip to chicago❄️✨
digital scrapbook memories from my trip to chicago🌃 #chicago #digitalscrapbook #wintertravel #chicity
Alexa

Alexa

45 likes

Chicago trip 🥰
#chicagotrip #chicago #chicagoskyline #chicagoexplore #chicagoweekend Skydeck Chicago
Edder Villaseñor

Edder Villaseñor

18 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
daniellesavich

daniellesavich

13 likes

CHICAGO
Chicago let me go back 😍 life time Texan, first time visiting Chicago! I want to go back I miss it! So much to do, to see. #chicagotrip #chicago #chicagoweekend #traveling #takemeback Top 3 Niche Travel Spots You Need To Check Out🔥
PansyB’s many Books 📚

PansyB’s many Books 📚

6 likes

Chicago trip 🌸
Travel isn’t just a trip , it’s my therapy , my reset , my joy ❤️ #travel #solotravel #chicago #embracevulnerability #girlssupportinggirls
TheRealNiyahD🩷

TheRealNiyahD🩷

16 likes

Things to do in Chicago other than a bar ✨
Here are a couple of my top activities I do in Chicago! 1. Flyover - This is such a unique experience located at Navy Pier ! It is SO much like the Soarin ride at Disney world where you sit in a “hang glider” and feel as if you are soaring through Chicago! $15 for a ticket and it’s SO wor
Millie Britt

Millie Britt

232 likes

✨Chicago ✨
#chicago #chicagoweekend #chicagotrip #chicago
Chikiss

Chikiss

7 likes

Downtown Chicago
Weekend trip in Chicago Chicago ⭐️ Rating: food 9/10 People10/10 #downtown #chicagotrip #summer #trip #weekend #weekendactivities #lemon8diarychallenge
Marie_Riot

Marie_Riot

9 likes

CHICAGO
Happiest place in the world Photo 4: Layla & Ringos Photo 5: Taste of Chicago Photo 6: Benchmark Purse Sprits Photo 8: Goddess & the Baker Photo 9: Taste of Chicago Photo 10: The Bean! #chicagotravel #chicagotravelguide #chicagotrip #chicagoinfluencer #chicagoweekend
em

em

30 likes

All things Chicago!
Location: Chicago ✨ Pros: walk everywhere ! See all the sights ✨Outfit Details: Dress warm if going in the winter it is chilly 🥶 👍Why I like it: I’m not normally a big city girl , but traveling here for a weekend Trip and walking to see all the things is amazing the architecture is incredible
Lainey Kessler

Lainey Kessler

8 likes

Things to do in Chicago - April 2026
#lemon8dairy #chicagoitinerary #chicagoexplore #chicagotravel #chicagotrip What you up to this weekend?! 🤩
CHI Christian Entertainment

CHI Christian Entertainment

2 likes

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, es
GetawayGuide

GetawayGuide

21 likes

Chicago ✨
#chicago #boba #weekendtrip #nofilterneeded
Tiar3

Tiar3

14 likes

quick chicago trip
my Chicago weekend trip in a few pictures💗 #dayinmylife #dayinthelife #citygirl #city
jenna clair

jenna clair

10 likes

Chicago Nights #iTravel
This one weekend where me and the girls flew to Chicago for a few days & nights…..travel will always be top tier to me
Shaun Jones

Shaun Jones

24 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
Baggagegirls

Baggagegirls

10 likes

I’m ready for a weekend trip to Chicago ‼️
Chicago #chicagoweekend #chicagotrip #chicagoexplore #vacation #roadtripideas
🎀 A•A•R•I•E 🎀

🎀 A•A•R•I•E 🎀

3 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
mak

mak

37 likes

CHICAGO DAY 2
72 hours in chicago - honey bear cafe -millennium park -dinner cruise booked through city cruise #chicagoweekend #chicagotrip #chicagoeats
tionabreyon

tionabreyon

11 likes

Chicago Bachelorette Trip
We've rounded up our best tips to help you plan a Bachelorette Trip in Chicago! Check out where to stay, where to eat, and what to do in the Windy City for a Bachelorette weekend with your girls Chicago Marriott Downtown Magnificent Mile The Hampton Social - River North The Signatur
Baggagegirls

Baggagegirls

12 likes

Chicago Trip
Take the trip! This was back during St Patrick’s Day! #travel #chicagotrip #friends #weekendtrip #greenriver
Natasha Webster

Natasha Webster

15 likes

Chicago Night Out
Recently I spent the weekend in Chicago and I had the absolute best time. I only wish that I had more time to go out and see everything the city has to offer. This isn’t my first time in Chicago, but I always have a new experience every time I come to the city. We stayed at the 21c Museum Hote
Savannah Turner

Savannah Turner

67 likes

Cheap weekend trips from Chicago in May✈️
How to find a cheap weekend getaway from Chicago on Google Flights✈️ 1. Go on Google Flights and the “Explore” tab 2. Write in your departure airport 3. Choose “anywhere” in the “where to?” box 4. Choose “flexible dates” and click your travel month and “weekend” in the calendar box
Iisa Hero

Iisa Hero

19 likes

Day trip from chicago
#chicagobean #chicagopizza #chicagotrip #3dayweekend 📍Location:Chicago Overall rating: 8/10:
nancys

nancys

4 likes

Weekend in Chicago
10/10 #chicago #thechi #downtown #tao #taochicago
christinaciara

christinaciara

112 likes

Reliving Moments of Chicago in December
I planned a weekend getaway for my friends and I last year to Chicago and wanted to share some of my favorite moments. The way that I love downtown Chicago so much is unreal! Keep Moments: - Stayed at the Intercontinental Hotel on Magnificent Mile. In my opinion, it is the absolute best locat
IsabelleB

IsabelleB

21 likes

Chicago Journal
My journal pages from my quick trip to Chicago last week! #chicagotrip #junkjournaling
Mattie

Mattie

3 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
Symantha

Symantha

80 likes

Chicago Girls Trip Vlog ✨
Chicago #lemon8tainment #lemon8travel #lemon8challenge #lemon8partner
alexuhmoreno

alexuhmoreno

4 likes

Chicago girls night activity ✨
360 CHICAGO was one of my favorite things we did when in Chicago ! It’s only $35 per person to enter and there is no time limit! We grabbed drinks at their bar CloudBar at 360 CHICAGO and enjoyed the sunset over the city! There’s lots of seating and amazing views! If you arrive just bef
Sam Richard

Sam Richard

4 likes

Weekend trip :)
#trip #lemon8challenge #chicagotrip #chicagobean 📍 City/Country: Chicago, Illinois Restaurant : Harry Caray’s tavern on the pier The bean: 30 minute walk from the pier ⭐️ Rating: 10/10
Karla

Karla

10 likes

Chicago🫶
#lemon8diarychallenge #chicago #chicagoskyline #thebean #chicagoexplore #chicagotrip #Lemon8Diary #gothtarget #fun #chicagoweekend
🍃Mel 🐌

🍃Mel 🐌

16 likes

Chicago
Exile in Bookville Recap Summer Trip: Spent three hours in Chicago and somehow it was exactly what I needed. Saw the Bean, wandered through Exile and completely fell in love with it (can confirm there were tears) and just took in the city. No real plans, just vibes. Sometimes you don’t need a
8Chi8

8Chi8

8 likes

See more