How to Spend a Girls’ Weekend in Chicago in the Summer: Choose Your Personality
So you’re planning a girls weekend in Chicago but not sure where to start? There is SO much to do in Chicago - I struggle when people come in town because I want to fit everything into such a short period of time and it’s just impossible. Chicago has so many different neighborhoods to choose from and each one has its own vibe.
For the summer, I put together little Chicago itineraries that are perfect for each kind of girl that speaks to you.
Whether you are hosting a friend in town, visiting for the first time, going on a girls’ trip or bachelorette party, or even a repeat Chicago customer, you will definitely be able to find something in here that is unique and fun that fits your mood. Instead of a generic list of things to do in Chicago, I’m breaking down the city based on personality type.
Want everything planned for you?
My downloadable Chicago Summer Guide includes:
The best neighborhoods to stay in based on your travel style
Must-do summer activities and local experiences
My favorite outdoor dining spots and rooftops
The best cocktail bars, patios, coffee shops, and pizza in the city
Curated itineraries based on your personality
FIRST TIME VISITOR GIRL
If it’s your first time in Chicago, there are just some things you absolutely can’t miss out on. They are classic experiences and I wouldn’t skip out on them. I mean, the architecture boat tour is popular for a reason and I have done it several times (it never disappoints). And yes, if you’ve never had deep dish, you have to at least try it.
Spend your Friday shopping around Michigan Ave before hopping on a boat for the architecture tour. Grab a drink at Tiny Tapp after then head to dive into deep dish pizza.
On Saturday, grab brunch at Avec, walk it off around Millennium Park and then grab a drink at LondonHouse rooftop.
One of my all-time favorite tours is the Ghost & Gangsters Tour. It’s a walking tour that goes through the history of Al Capone, crimes, and even a serial killer. Use my code AMBER5 to get $5 off your first purchase.
Must Do Experiences:
Grab a drink at Tiny Tapp along the Riverwalk
See the bean and explore Millennium Park
Eat deep dish at Giordano’s or Lou Malnati’s
Go bar hopping in River North
Where to Stay:here’s a list of all the hotels I would recommend for your first time visiting Chicago.
THE CAMERA ROLL GIRLY
Your itinerary typically revolves around how to get the perfect photos for your Instagram dump. I can relate.
Luckily, Chicago has endless aesthetic opportunities and I know all the good spots.
Start your weekend shopping in the Gold Coast or just walking around taking photos, I mean, admiring all the nice houses. Then grab some cocktails and dinner at Lux Bar, Gibson’s, or sit outside at the Bellevue. End the night with some live music at Zebra Lounge
On Saturday, spend the day on a boat in the Playpen. Then head to NAIA for dinner on the river, it has literally the perfect views for Golden Hour.
Most Picture Perfect Spots:
North Ave Beach
Sunset on the Chicago Riverwalk
Playpen
JUST HERE FOR THE VIBES GIRL
This is for the girl who is down for whatever is going on this weekend. Someone who just wants good weather, great cocktails, and a weekend where the vibes are high.
Start your weekend with dinner at Ada Street before catching a concert at Salt Shed. If you’re still riding the high from the concert, bar hop throughout West Town where there’s a mix of cocktail bars and dive bars.
Saturday is all about brunch so start at Somerset, do a beach day at Oak Street Beach. For an easy dinner, head over to the Radicle where you order nostalgic dishes that remind you of your childhood at Chili’s but have an elevated modern taste. End the night at some dive bars in either Logan Square or Wicker Park.
Best Spots:
THE ACTIVE SPORTY GIRL
If your ideal vacation is movement and/or sports, I have the plan for you.
Start your weekend kayaking on the Chicago River - do it before the weekenders take over the river. Then grab dinner at Robert’s Pizza which is not only incredible pizza but the views are amazing.
On Saturday, walk, run, or bike along the Lakefront Trail. Grab a coffee on the way back and even wander through Lincoln Park’s Farmers Market.
At night, or even later in the day, cheer on the Cubs or the White Sox at a baseball game. It’s always such a fun way to experience Chicago - not to mention the Chicago hot dogs are a staple!!
Active Ideas:
Divvy bike everywhere
Beach volleyball at North Ave or Oak Street
Pickleball at Big City Pickle in West Loop
Find a fun yoga event
Hit golf balls at the Diversey Driving Range
THE “I’VE ALREADY BEEN TO CHICAGO” GIRL
So you’re a repeat customer? We love to hear it! Skip all the touristy stuff because you’ve probably already done it. And now you can experience Chicago like a local.
Spend your weekend boutique shopping in Lincoln Park, stop at Abrah for brunch or post-shopping cocktails. Grab a pizza and head to the lake for a picnic and people watching.
Rent an electric boat at sunset to float down the river with your girls!
For dinner, you’re going to go to one of my favorite restaurants: Maxwell’s Trading. Before you grab drinks at Bar Bambi.
Other Hidden Gems You’ll Love:
Garfield Park Conservatory
Check out a street festival (they’re free!)
THE ARTSY GIRL
This is for my girls who want to explore the artsy side of Chicago. So if you’d rather spend the day vintage shopping, catching a show vs. being in River North, this is the itinerary for you.
Spend Friday browsing vintage stores in Wicker Park all up and down Milwaukee St. Grab dinner at Mirra and then venture out in Logan Square.
Be sure to check out one of Chicago’s street fests that are free, full of tents with great gifts, and local food stands. At night, grab tickets to Drunk Shakespeare for a unique and fun comedy experience.
Dont Miss:
Vintage House
Randolph Street Market
THE NEIGHBORHOOD GIRL
Yes, the skyline is gorgeous and picture-perfect. But my favorite thing about Chicago is all the different neighborhoods and culture we have here. I know downtown is what draws everyone in but the different neighborhoods are also worth exploring.
Friday, you’re going to take the water taxi to Chinatown to eat at MingHin. Then you’re going to grab some cocktails at Nine Bar before hitting up the karaoke mics.
On Saturday, you’ll thrift your way through Andersonville stopping at any restaurants that catch your eye along the way. Head to Pilsen for dinner at Cerdito Muerto and drinks at the Alderman.
Favorite Neighborhoods:
Andersonville
Pilsen
Logan Square
West Town
Ravenswood
THE BACHELORETTE PARTY PLANNER
Now, what most of you probably came here for. As someone who has planned sooo many bachelorettes, many in Chicago, this is exactly what I would do.
Check into a hotel in River North or West Loop before you’re going to dinner at Lyra.
Recovery brunch at Pizzeria Portofino before hopping on a boat to party in the Playpen.
Finish the night at Trivoli Tavern to get your pictures in. Then end up at the club like Celeste or Kashmir. Or just bar hop in West Loop and see where the wind takes you!
Best Hotels for Groups:
The Hoxton
Emily Hotel
The Godfrey
The Gwen
Where to Stay in Chicago
River North: if you want nightlife and walkability
West Loop: if you’re visiting for the food and going out scene
Lincoln Park: if you want a quieter, more residential feel and want to be near the lake
Wicker Park: if you love feeling like a local
Here’s a list of hotels around the city that I put together
What to Pack for a Chicago Weekend
READY TO PLAN YOUR CHICAGO GIRLS’ TRIP?
Which kind of girl are you? Go to my Instagram post and leave a comment here.
And if you want it all packaged up in a pretty bow, don’t forget to grab my Chicago Summer Guide for even more hidden gems, rooftop bars, restaurants, and itineraries.
