A girls weekend in Chicago can do wonders for your friendships, your mental health and, less importantly, your Instagram. There’s fun to be had all over the city: in scenic, lakefront bike rides, at funny improv comedy shows, dancing at bars, sipping trendy rooftop cocktails and much, much more.
You’ll come to love Chicago in a whole new way when you don’t have to visit children’s museums and eat at restaurants serving chicken tenders.
As a lifelong Chicagoan, here are some activities I recommend to have the best time with your besties:
Chicago Architecture Center River Tour
Before you say, “I don’t care about architecture,” let me assure you that the Chicago Architecture Center’s River Cruise boat tour is the best and most scenic tour in Chicago. Do they talk about architectural styles? Yes. But it is also a delightful, informative, 90-minute tour on a slow-moving boat that winds through the downtown skyscrapers on the Chicago River. You’ll learn some Chicago history and have unique views of some of Chicago’s most famous buildings.
I strongly recommend buying tickets in advance, as nice-weather weekends sell out quickly. There’s an option to include a tour of the architecture museum, and while it’s a cool museum, it’s better suited to actual architecture fans. Groupon usually has a discounted ticket offer.
This is important: the tour goes rain or shine and the tickets are nonrefundable. But if it’s raining, you’ll need to put on rain gear and sit outside. Sitting in the boat’s indoor area will prevent you from seeing anything! Pack the rain poncho.
Dare to step over the edge of skyscrapers
Downtown Chicago has two skyscraper observation decks with panoramic views of the city: Willis Tower and 875 N. Michigan (aka “the John Hancock building”).
The views are worth the trip, but to make it more memorable, try one of their daredevil features. You can walk out onto an all-glass Ledge at Willis Tower’s Skydeck, 103-stories above the sidewalk. It’s hard not to squeal when you take that first step! At 875 N. Michigan, there’s 360 Chicago’s TILT, my personal favorite. At TILT, you step into a glass box, hold on to the handles, and then you’re slowly tilted over Michigan Avenue, facing 1,000 feet straight down. Aaaaah!
Read More: Fun Things to Do in Naperville, a Chicago Suburb Worth a Visit
Sip afternoon tea
This British tradition is a thing in Chicago. Several hotels offer this decadent, delicious late afternoon activity. The afternoon tea at the Drake Hotel’s Palm Court is the fanciest and most famous. You’ll want to dress up a bit for this glamorous room with a live harpist playing. You’ll feel like fancy ladies as you sip flavored tea from china cups (pinkies up!) and eat bite-sized crustless sandwiches and gorgeous little gourmet desserts. The Langham Hotel, the Peninsula Hotel and LondonHouse Chicago are among the other hotels with excellent afternoon teas.
Read More: 12 Secret Spots and Hidden Gems in Chicago
Cheers on a rooftop bar
On nice weather days, Chicago’s rooftop bars are a quintessential Chicago activity. Happy hour is the best time to go, before the see-and-be-seen crowd shows up. Expect high prices but beautiful views, fun vibes and great Chicago photos.
Three of my favorites are LondonHouse Hotel’s LH Rooftop, located downtown on Michigan Avenue; The Up Room in The Robey Hotel, in the trendy Wicker Park neighborhood; at Utopian Tailgate in Old Town.
Located right next to the Blue Line “L” train, The Up Room winds around the building’s roof, with all sorts of fun little nooks to sit in while you soak in the skyline views. There’s also a tiny swimming pool if you need to dip your toes in. LH offers gorgeous views of the Chicago River and the iconic “corncob” Marina Towers and Trump International Hotel & Tower. Utopian Tailgate is a casual vibe, with colorful decor, bar food, lots of games and some swinging seats.
Bike the lakefront
Chicago borders Lake Michigan, and the lakefront area is one of the city’s most beautiful places. A 22-mile walking and bike path goes up and down the shoreline. Rent bikes (either from Divvy or one of the bike rental shops) and cruise up and down the lake.
Good places to stop: Lincoln Park Zoo (free admission), Buckingham Fountain and North Avenue Beach. Optional: wear a bathing suit under your bike shorts and pop in the water at Oak Street Beach. Or, pack a volleyball and grab a net at North or Foster avenue beaches.
You can’t ride bikes on Navy Pier, but it’s a nice stop along the path for some of the best city skyline views. Buy one of Chicago’s famous Rainbow Cones (a multi-flavor ice cream cone with flavors like pistachio and cherry), and indulge in some of the touristy activities, like ride on the Ferris wheel or take a boat tour.
Get tix for theater and improv
Chicago rivals New York when it comes to theater, so nighttime should include a show. I always love The Second City comedy club, a landmark Chicago theater where literally dozens of celebrities – from Tina Fey to Chris Farley – got their start doing improv. iO Theater in the Lincoln Park neighborhood is another good option.
Downtown theaters will host Broadway shows like “Hamilton” and “Wicked,” but there are many excellent smaller theaters doing outstanding work, like the Steppenwolf and Goodman theatres.
Not sure what you want to see, or are making last-minute plans? Check out the discounted tickets available at HotTix.org.
Go shopping
The place where you’ll have the most density of stores is on the north end of Michigan Avenue, aka “The Magnificent Mile.” To avoid the crowds along Michigan Ave., you can find more unique items (and good restaurants!) neighborhood spots like Milwaukee Avenue in Wicker Park; Wentworth Avenue in Chinatown; Lincoln Avenue in Lincoln Square; and Clark Street in far north Andersonville, where handmade artwork, toys, accessories and more is sold in the small boutiques and in the Andersonville Galleria.
Check out Chinatown
Yummy restaurants, bubble teas, dim sum, foot massages and shopping for cheap tchotkes — Chinatown is a fun day out. A good way to get there in the summer and fall is the Chicago Water Taxi, which drops you off at Ping Tom Memorial Park (you can also rent kayaks at this park!).
The Chinatown Square has zodiac statues, so you can find the year you were born and read what your sign says about you – always good for a few laughs (and surprisingly accurate!).
A visit to Chinatown is better during the day, as the neighborhood can be a little sketchy at night. If night is your only option, take an Uber rather than the Red Line L train.
Eat Chicago’s famous foods: deep dish pizza, Italian beef, hot dogs and Garret’s popcorn
The hit series “The Bear” reminded the world that Chicago’s delicacies extend beyond deep dish pizza. Italian beef sandwiches (or “beefs” as locals call them) are everywhere in Chicago, including “The Bear”-inspired Mr. Beef. But the popular hot dog and beef chain, Portillo’s, is also a solid choice.
For a healthier meal, or something more geared toward foodies, have brunch or meals at cafes. 3 Arts Club Cafe is a lovely spot in atrium in a Restoration Hardware furniture shop, where you’re encouraged to shop and sit on the cool furniture afterward. Giant is a tiny Logan Square restaurant with tremendously good food. Frances Deli and Brunchery in Lincoln Park is adorable, and tacos and carnitas in Pilsen, including Carnitas Uruapan (featured on Netflix’s “Taco Chronicles”). Chicago’s trendiest restaurants are in the West Loop neighborhood. One of my favorites is Girl & the Goat, the first restaurant opened by Top Chef winner Stephanie Izard.
When it’s time for “dranks“
One of my favorite memes says, “Are we having drinks tonight, or are we having dranks? Let me know so I can dress appropriately.” There are literally hundreds of cool bars for trendy cocktails, craft beer and spirits or good wine. On girls weekends, though, we’re usually in bachelorette party mode, looking to drink, dance and sing-along to the music. Howl at the Moon piano bar and downstairs at The Hangge-Uppe in River North will not disappoint. Beauty Bar, decorated like a 60s beauty shop, is a fun but small dance bar playing 80s and 90s tunes on the weekends. Bonus: you can also get a manicure there!
Take photos at the Cloud Gate (aka “The Bean”)
Gotta go for the photo op at this mirrored art piece in downtown Chicago, and you can walk over and see the Crown Fountain, the Pritzker Pavilion and the iconic Art Institute of Chicago lions. Across the street is Shake Shack, for cheap order-at-the-counter burgers and shakes. Or go upscale at Cindy’s Rooftop overlooking Millennium Park and the lake (if you can get a reservation). You can play bocce ball in the back room of the Chicago Athletic Association – all less than a block from the Bean.
A weekend getaway girls trip to the Windy City should be added to your friends’ bucket list!
Leave a Reply