The Ultimate Chicago Bachelorette Itinerary
What better way to celebrate finding the love of your life than bonding with your best friends in one of the most famous cities in the country? Get ready to paint the town pink and celebrate love, laughter, and unforgettable memories with the ultimate Chicago bachelorette itinerary! Ladies, it's time to grab your squad, put on your sassiest heels, and embark on a whirlwind adventure through the Windy City like never before.
Whether you're a local bride-to-be or you're bringing the bridal party from afar, Chicago has everything you need to create the bachelorette bash of your dreams.
Chicago has a little something for everyone, whether you’re looking to relax at a spa, relish the amazing food and drinks, soak in the sun by the river, or discover museums and music venues. We've curated a guide that's all about embracing the glam, the giggles, and the girl power. Let's dive headfirst into a weekend of fabulous fun that'll have you saying, "I do" to the best Chicago send-off ever!
You’re welcome to refer to this itinerary for some of the best things to do in Chicago for your bachelorette party. Feel free to switch some things out or move the timeframe around!
Thursday
Welcome to Chicago!
If you want to stay in a boho-chic paradise, book an Airbnb like this 3-level home in Wicker Park!
Not only is this space located within walking distance of a hip neighborhood, but the street itself is nice and quiet, allowing you to come back and unwind.
Evening
Taste of Chicago
Once you’ve organized yourselves a bit, get ready to fuel up and kickstart your weekend! The Perch Kitchen & Tap is a hip bar and grill with an abundant cocktail menu. Featuring a wood-fired grill, The Perch offers quite possibly the best rotisserie chicken you’ll ever taste (lightly seasoned with their signature spice blend).
Make sure to also order their prickly pear margarita or if beer is your thing, they house-brew their own craft beers.
Walk Off Dinner
And head back to your place, perhaps stopping at Jeni’s Splendid Ice Creams, made from local ingredients!
Unwind and get a good night's sleep (you’ll thank me at yoga tomorrow morning!)
Friday
Morning
Detox to Retox
The Balanced Bachelorette! Your instructor arrives at your Airbnb for an hour-long customized private yoga session, complete with a Mimosa Bar and a playlist of the bride's favorite tunes. You’ll be refreshed and recharged to take on the town.
Afternoon
Explore Wicker Park
Known for its “hipster” vibe, Wicker Park is your go-to spot for thrifting and browsing unique boutiques.
Leisurely Brunch
A popular neighborhood brunch spot, Bongo Room, offers luscious options to fill your empty bellies. If you’re feeling indulgent, taste one bite of the lobster roll benedict (toasted New England-style buttery rolls topped with house-made lobster roll filling, two poached eggs, and topped with green goddess hollandaise sauce served with house potatoes) and you won’t be able to turn back.
Recharge
Relax on your private outdoor patio, sip a local beer or wine, and maybe have a fun photo shoot! Sometimes when you have an activity-packed weekend, you forget to capture any of the moments!
Evening
Dinner Downtown
Top of the list on Trip Advisor’s go-to restaurants, The Dearborn is located in the heart of Chicago’s Loop. Settle into their spacious, welcoming dining room and enjoy Chef Aaron Cuschieri’s Midwest-focused cooking.
Their sweet chili prawns are a popular share plate, featuring jumbo head-on prawns, foie gras fat, housemade 4-chili sauce, toasted garlic, and sopping bread
They also offer a list of seasonal cocktails; right now, the Desert Flower is a must (mezcal unión, casa mexico tequila blanco, prickly pear, ginger, d.o.m. benedictine, agave, lime, black lava sea salt rim - rocks).
Laugh It Off
Only a .4 mile walk (less than 10 minutes) from the Dearborn lies Chicago Comedy Club!
Saturday
Morning
Early Bird Gets the Brunch
Enjoy your first real meal of the day at Cracked on Milwaukee, whose slogan is, “Lovers of all things eggs, cheese, and bacon, Cracked has you covered.” Their morning bender breakfast sandwich is a simple, yet satisfying option (Cheddar cheese, hash browns, a fried egg, and cream cheese on a French roll).
Afternoon
Get On The Water
Weather permitting - Island Party Boat opens seasonally in April and brings the tropics to Chicago! They offer ticketed Chicago river cruises
Or…
Rent a private power, sail, or Polynesian-themed boat with your group. Some boats offer water slides, full tiki bars, and premium sound systems!
Head Back To Your House
Change out of your (possibly wet) clothing and into something fresh and fun. You can also skip this part and bring dinner clothes with you (or just go out as you are!)
Evening
Dinner With A View
Built on the iconic Chicago River with stunning views of downtown, River Roast is a dynamic social house and gathering place. With an American spin on British food, you must try the whole roasted fish (Branzino, Salsa Verde, Tomatoes & Herbs).
Featuring 2 bars and riverfront views, you won’t tire of this place
Shots Shots Shots!
Brando’s Speakeasy is quite possibly the best lounge and karaoke bar in Chicago! Pick your favorite 90’s tune, grab a mic and a shot of tequila, and hit the stage!
Sunday
Morning
Re-Fuel With A Classic
Açaí bowls! After running around town all weekend, you’ll probably want something quick, appetizing, and nourishing at this point. Head to Deep Purple for a health-conscious smoothie or bowl! With many locations throughout the city, pick the one closest to you!
Embrace Your Sophistication
At the Art Institute of Chicago, home to approximately 300,000 works of art. Visiting the second-largest art museum in the country is sure to inspire you in one corner or another.
Afternoon
Lunch It Up
Hit locals spot Chiya Chai Cafe (located in the Loop) for one of the most delicious chai’s in town AND Nepalese and Indian specialties. Samosas, momos, curry bowls, savory pies, and more are sure to satisfy your midday cravings.
Evening
Kick Back
Prep dinner at home (or takeout!) and enjoy a relaxing final evening at your Airbnb. This is a perfect time to share photos and bond with your group once more before saying goodbye (until the wedding day, that is!).
The Neighborhoods
Chicago has 77 distinct communities that represent a distinctive collection of cultures, people, and experiences. We chose a handful for you, but this city can be endlessly explored!
Wicker Park
Known for its “hipster vibe,” Wicker Park offers vintage stores, record shops, and underground music venues nestled next to bustling nightlife, dining, and entertainment venues.
For the best breakfast/lunch in the neighborhood, opt for Dove’s Luncheonette. Set to the sounds of 1960s and 70s Chicago soul and blues, this restaurant will inspire you to want to wear your bell bottoms.
If you’re a fan of Creole cuisines like gumbo, po’boys, and etouffee, stop in for dinner at Ina Mae Tavern. Their fried shrimp Po Boy is a favorite (served on French bread and dressed with lettuce, tomato, and pickles).
Vegan/vegetarian? Or open to trying some veggie-forward cooking? Bloom Plant-Based Kitchen is your answer!
Garfield Park
The area’s namesake park opened in 1874 and remains a sprawling urban oasis.
Garfield Park Conservatory is the neighborhood’s crown jewel, where you’ll find abundant displays of exotic plants from all over the world.
Taste a classic Chicago hotdog at the Original Maxwell Street!
Inspiration Kitchens is run by a nonprofit to support the homeless who want to begin their careers in the kitchen. Try their tasty brisket hash for brunch and support a good cause!
Edgewater
This town may seem fully laid back, but it’s brimming with a plethora of activities, including sandy beaches, flavorsome international eateries, and storefront theaters.
Edgewater got its name for being, well, on the edge of the water! (Lake Michigan). Check out Waterfront Cafe, a seasonal outdoor cafe on Lake Michigan with snack-shack eats & weekend live music.
Delicious homemade Mexican food? This is what you’ll find at Flaco’s Tacos! The street corn chicken burrito is a fan favorite.
Sicilian street food more your jam? Sfera prepares the most delicious fried Risotto balls filled with Sicilian Beef Ragu, Saffron Risotto, and Mozzarella. Served with Sfera Marinara!
The Loop
This vibrant area, comprised mostly of high rises, hosts the iconic “Cloud Gate” sculpture. Grant Park features the large, rococo-style Buckingham Fountain and the renowned Art Institute of Chicago.
Experience the finest of Chicago dining at Hoyt's American Tavern with sweeping views of the acclaimed Chicago River.
Time Out lists Tony’s Rooftop Bar as one of the best rooftop bars in Chicago! Located in the west loop, this cozy all-season rooftop bar is adorned with vintage Time Out London covers, string lights, and beautiful wood beams that stretch the length of the room.
Inspired by the styles of France, Morocco, and Italy, Beatnik on the River feels like a sanctuary decorated with more than 600 living plants and antique furniture. The tuna ceviche is the perfect starter for the table (Nikkei Style, Leche De Tigre, Daikon, and Nori).
Other Bachelorette Activities in Chicago:
Spa Day
An afternoon of self-care at the spa! For a more unique experience, indulge in Aire Ancient Baths, located in a 1902 restored factory and one of two locations in the US (the rest are in cities such as Seville, Barcelona, and London).
They have nine different bathing experiences including six thermal baths, an indoor/outdoor pool with a waterfall, and two steam rooms with aromatherapy.
And, massages! Offered with several rituals including warm Amethyst crystals and rich sandalwood oils.
Kayak
Beginning in May of each year, Urban Kayaks offers single and tandem kayaks to explore the city via the river.
Wine Tasting
At the Hubbard Inn! Choose your favorite from the dozen wines you’ll get to taste at your own private table. Buy a bottle (or 3) and unwind (or unWINE)!
Transportation
The main transpiration in Chicago is the Chicago Transit Authority, which operates the city’s eight 'L' train lines and 129 bus routes
“Riding the Loop”- To go around the whole Loop, board a Pink Line train at Randolph and take that to Quincy. At Quincy, change to an Orange Line train and ride the loop back round to where you started
All the train lines meet downtown to form a loop (hence the name “the loop”), and it's simple to access different parts of the city
Like all major cities in the US, Lyft and Uber are a phone tap away.
If you have extra time, you can also get around certain areas on foot, which is a wonderful way to explore and exercise at the same time!
Weather
Spring
Temperatures in April typically range in the 50s°F, while May can reach up to around 70°F.
Flowers will begin to paint this city with every color imaginable!
You can start to bring out your flowy dresses, but make sure to also pack a jacket and boots! (And am umbrella fit occasional rainfall)
Summer
This city is bustling! Make sure to check out any festivals or special events that pique your interest, for the summer is when it all comes out.
Temperatures average around 78°F – 92°F, so be sure to rock your frilliest skirts and chicest halter tops.
Fall
Though the temperature begins to cool, moving from the 70’s to mid-40s closer to December, Chicago is still buzzing.
Catch an NHL game with the Blackhawks if you have a sporty group!
September into October will request a sweater, whereas, in November and December, you might opt for long pants, a scarf, and a cozy hat.
Winter
Temps have officially reached the 30’s!
BUT Winter brings picturesque snow, holiday traditions, and beautiful lights everywhere.
Christkindlmarket is a Christmas market held annually at Daley Plaza in Chicago.
Make sure to bring your gloves and cute wool hat!
