If you’re planning a girls’ weekend full of good vibes, great food, and even better company, Chicago checks every box. The city is overflowing with fun things to do, fabulous restaurants that cater to every appetite, exciting nightlife options, and gorgeous hotels and accommodations. If you’ve read any of my previous posts, you know I have a strong affinity for my hometown, and writing these posts is always a blast for me. Not only did I share my personal recommendations, but I also enlisted the help of my fellow Chicago girlfriends to gather their suggestions. This post has everything you need for an unforgettable girls’ weekend in Chicago, written and vetted by a local Chicago gal.
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Know Before You Go
I’ve compiled some helpful pieces of basic information to help you kick off the planning process for your girls’ weekend in Chicago:
- If you’re flying into Chicago, you’ll arrive at O’Hare or Midway airport, depending on what airline you select. You can easily grab a cab or Uber from either airport to get downtown. Alternatively, you can take the CTA into the city if you want to avoid peak traffic times (and trust me, you do).
- Once you’re downtown, getting around is fairly easy! Uber and Lyft rideshares are readily available all around the city. The CTA is also straightforward to navigate, allowing you to get anywhere in the city. You certainly could drive, but I wouldn’t recommend it, as parking can be a pain and expensive, depending on where you stay.
- While you can have a good time in Chicago regardless of the season, the winters can be a bit oppressive if you’re not accustomed to the cold (and I mean bitterly cold). The sweet spot to avoid the uncomfortably cold months is traveling to Chicago between April and September, with an honorable shoutout to the summer months, as Summertime Chi is a vibe.
- Like with any major metropolitan city, things book up quickly. It’s recommended to book your reservations in advance to ensure you don’t miss out on anything you want to do or see. This applies to hotels, activities, and especially restaurants!
- Chicago can get a bad rap for being considered an unsafe city in the US. However, I lived downtown for nearly a decade and always felt safe while I was there. When visiting Chicago, follow the same safety rules as you would in other parts of the world: watch your belongings, travel in pairs at night, and stick to the central neighborhoods in the city.
Where To Stay
Once you’ve decided to plan a girls’ weekend in Chicago, it’s time to book your accommodation. You might need a single hotel room or a large Airbnb, depending on the size of your group. Below are my top recommended places to stay:
The Hoxton: Located in the West Loop, this hotel offers chic accommodations in addition to being home to a fantastic bar and restaurant to kick off your evening on the town.
The Langham: This ultra-luxe hotel, situated along the Chicago River, would be the perfect spot for a girls’ weekend in Chicago. Especially if you’re looking to incorporate an elite spa day into your itinerary.
LondonHouse: Another glamorous Chicago hotel near the river is LondonHouse. Come for the views, stay for the comfortable and stunning rooms, and the proximity to everything the city has to offer.
The Gwen: Located on the Magnificent Mile, this Art Deco gem is a stunning hotel that practically screams girls’ weekend.
Daytime Activities
Now that you have your accommodation booked, it’s time to start brainstorming how you want to spend your time on your girls’ weekend in Chicago. There are numerous great ways to spend the daytime hours, ranging from low-key spa days to exciting sporting events.
Bike Along the Lakefront
The lakefront is an iconic sight to see when visiting Chicago. Unlike most lakefronts you’ll witness across the country, our lakefront offers an incredible view of the Chicago skyline and some of the city’s most famous buildings. A fun way to explore the lakefront is by renting a couple of Divvy bikes and riding down the trail and exploring the various stops along the way.
Hit the Spa
A girls’ weekend is the perfect time to book a spa appointment and soak up some much-needed relaxation. Aire Ancient Baths is my top recommendation for a unique spa experience. There are six different baths, ranging from hot baths to cold plunges, salt baths, and two saunas. If you’re looking for a more traditional spa experience, you can’t beat Allyu Spa in River North for massages. The Cowshed in the West Loop is the place to be for an exceptional mani-pedi appointment with your girls.
Do a Little (or a Lot) of Shopping
If you’re looking to pick up a few new things while visiting Chicago, you’re in luck. It shouldn’t come as a surprise that Chicago offers a wealth of great shopping options. The most famous shopping area in the city is the Magnificent Mile, which is home to high-end shops such as Nordstrom, Dior, Saint Laurent, and Tiffany & Co. Aside from the Mag Mile, excellent shopping options are also available in Lincoln Park and on Southport Avenue in Lakeview. If you’re looking for some local businesses to explore, check out Alice and Wonder, Art Effect, Lost Girls Vintage, or one of the countless record shops in Wicker Park.
Take an Architecture Boat Tour
One of the best ways to take in the city’s amazing architecture is by booking a river boat tour. I’m a Chicago native, and I’ve done several tours throughout my time living in the city, and I’m never disappointed. Most tours include a bar, and some offer a meal if you’d like to make it a more formal event. Architecture boat tours are the perfect way to spend a few hours in the daytime with your girls.
Wander in the Lincoln Park Zoo
Another fun daytime activity is strolling through the Lincoln Park Zoo. When you usually think of fun girls’ weekend activities, the zoo doesn’t naturally come to mind. However, the Lincoln Park Zoo in Chicago is free and has some gorgeous views of the city. It’s located in Lincoln Park (obviously) and once you’re done at the zoo, you can explore the neighborhood, hit the shops, or grab a bite to eat.
Grab a Beer at a Chicago Cubs Game
A classic Chicago experience is attending a Cubs baseball game in Wrigleyville. If the girls you’re spending the weekend with enjoy sports, or simply enjoy an ice-cold beer and a hot dog on a warm summer day, then definitely consider grabbing some tickets. After the game, take a walk around Wrigleyville and check out the various bars and eateries in the neighborhood.
Witness the Iconic Millennium Park & The Bean
If this is your first trip to Chicago and you’re looking to see the most famous sights, then look no further than Millennium Park. This well-known urban oasis features lush greenery, artwork, a concert pavilion, and free events, in addition to being home to the iconic Bean structure, a fixture in Chicago. However, if you’ve visited Chicago and seen these sights before, I would consider skipping this and exploring other, less touristy areas of the city.
Sip Vino at a Wine Tasting
While Illinois isn’t known for having lush vineyards overflowing with wine, we do have a few places where you can enjoy a lovely wine tasting experience. City Winery in the West Loop is a fantastic place to take a wine tasting tour and experience live music all under one roof. A few additional standout locations to check out include J9 Wine Bar, Pops for Champagne, The Oakville Grill & Cellar, and Acanto.
Enjoy Tea Time with the Girls
If you’re craving a little elegance with your girls’ weekend, Chicago has a few standout spots for tea service. My top picks are The Drake Hotel and LondonHouse. The Drake delivers classic grandeur in one of the city’s most iconic buildings, while LondonHouse offers a more modern take on tradition, with skyline views and a sophisticated vibe to match.
Sweat It Out in a Workout Class
Like any major city, Chicago offers a variety of fun workout classes to partake in. While this might not be everyone’s favorite activity to do on a girls’ trip, it’s certainly a productive way to kick off your day. If you’re hoping to squeeze in a sweat session during your girls’ weekend, check out SALT and Studio Three. Both offer high-energy classes in beautifully designed, boutique-style spaces that make working out feel like a treat.
Create Your New Favorite Dish in a Cooking Class
If you and your friends are foodies, Chicago is truly the perfect place for a girls’ weekend. Not only do we have excellent restaurants, but we also have fantastic cooking classes available. What’s better than learning how to cook your new favorite dish with your girlfriends? If this sounds up your alley, check out classes at Chopping Block or Eataly, both of which are fun and enjoyable places to learn how to cook.
Stroll Along the Chicago Riverwalk
The Chicago Riverwalk has undergone a remarkable transformation in the past decade. What was once a vacant area along the Chicago River near downtown has turned into a bustling walking path with plenty to do. There are several places to grab a bite to eat, sip a drink, or hop onto a boat or kayak. In the evenings during the summer, you can witness the spectacular Art on The Mart, a display of digital art on the famous Merchandise Mart building.
Have a Beach Day
Craving a little lakeside relaxation? A beach day is the perfect way to slow things down during your girls’ weekend in Chicago. The city’s lakefront is dotted with free public beaches where you can soak up the sun, take a dip, or just lounge with an iced coffee in hand. Some of the most popular spots include Ohio Street Beach, Montrose Beach, and Oak Street Beach. Each offering its own vibe and stunning skyline views.
Craft a Signature Candle
Nothing says cozy girls’ night in Chicago like a handmade candle you made during a fun afternoon in the city. Candle making is a nice, low-key daytime activity where you can blend scents and create your own custom candle. Don’t worry, there are professionals there to guide you through the process. I recommend booking a mid-morning appointment at Aura Candle Bar and then grabbing lunch on Southport while you wait for your candle to cool before bringing it home.
If you need a comprehensive packing list for all your travel needs, I’ve got you covered! I created the ultimate packing list for your upcoming adventures, including carry-on essentials, toiletries, clothing, and location-specific items.
Where To Eat
Now that you have your daytime activities booked, you’re ready to plan out your meals! If you’ve read any of my previous Chicago guides, you know that this city is overflowing with incredible restaurants in every cuisine imaginable. The restaurants below are curated to fit the vibe for a fun girls’ weekend in Chicago:
Coffee & Cafés
Sawada Coffee
Sawade Coffee is the perfect place to kickstart your girls’ weekend in Chicago if you’re staying in the West Loop neighborhood. The coffee shop boasts a cool ambiance, featuring wooden panels, string lights, and unique artwork. Not to mention that the coffee and pastries they serve are delicious. Pick up an order of military coffees before exploring the neighborhood or make your way out to other areas of the city.
Ipsento 606
Wicker Park and Bucktown are home to many amazing coffee shops, but one of the standouts is Ipsento 606. They’re known for their handcrafted coffee drinks, incredible pastries, and the overall atmosphere of the space. From the exposed brick walls to the industrial finishes, this is another excellent option to grab a coffee with your girls.
Good Ambler
Good Ambler feels like a polished urban hideaway where warm wood tones and soft lighting invite cozy conversations over perfectly brewed lattes. Their pastry case dazzles with a variety of treats, from buttery croissants to elegant macarons and house-made chocolates. With its convenient location in the Fulton Market neighborhood, it’s another easily accessible place to start your day.
Cafe Deko
Stepping into Café Deko feels like entering a 1930s Art Deco daydream in the heart of Lincoln Park, where globe lamps, patterned wallpaper, and plush, earth-toned furnishings transport you into a bygone era, complemented by a modern espresso bar. To no surprise, the coffee and pastries are as elegant as the interior space they’re served in. The entire vibe is perfect for a girl’s weekend in Chicago.
Hexe Coffee Co.
Hexe Coffee Co. is an industrial-chic haven where blackened steel, oak casks, gothic art, and burlap sacks frame a striking roastery and café in Roscoe Village. Their divine house‑roasted and barrel‑aged brews, from their bourbon-barrel Boneshaker to smoky Campfire and floral Lavender Honey lattes, are matched only by creative pastries and light bites from an on‑staff baker.
Brunch & Lunch
Summer House Santa Monica
Summer House is easily one of the most stunning brunch spots throughout the city, making it the perfect place to sip mimosas on your girls’ weekend in Chicago. This bright and airy restaurant serves a lengthy menu of brunch and lunch dish favorites, refreshing cocktails to pair with your meal, and mouth-watering seasonal specials. The combination of Instagram-worthy interiors and great food makes it one of my top recommendations for a girls’ weekend brunch in Chicago.
3 Arts Cafe
The 3 Arts Café, situated within the Restoration Hardware gallery, is a pure aesthetic indulgence. An airy, light-filled space where chandeliers sparkle above velvet banquettes, and a relaxing water fountain hums around you as you sip rosé. It’s the kind of spot that feels made for long, leisurely brunches with your best girls, surrounded by curated beauty and avocado toast that’s almost too pretty to eat. Come for the Instagrammable setting, stay for the luxurious pause in the middle of your bustling weekend.
Etta
Etta is a well-known Italian hot spot located in the Bucktown neighborhood that should be at the top of your list for both brunch and dinner. However, for the sake of this girls’ weekend in Chicago post, I’ll be focusing on brunch. You can’t help but fall in love with the warm and bright dining space on the inside, and the covered outdoor patio on the second floor. An order from the breads and pastries menu is an absolute must, in addition to one of their savory main dishes or pizzas. Top it off with a mimosa, bloody mary, or the “etta” rita, and you’re in for a great time.
Dove’s Luncheonette
Dove’s Luncheonette brings retro diner charm with a soulful twist, serving up Southern-meets-Mexican comfort food in the heart of Wicker Park. With turquoise booths, spinning vinyl, and cocktails before noon, it’s the perfect spot for a laid-back brunch that feels both nostalgic and bold. Don’t skip the chicken-fried chicken; it’s the kind of indulgence a girls’ weekend practically demands.
The Whale
This Logan Square restaurant is a colorful, trendy place to grab brunch with your girls while exploring Chicago. As you walk into The Whale, you’re greeted by cool red and blue leather booths, ornate lighting, and an expansive bar along the back of the space. The brunch menu features American breakfast classics with unique twists. However, the real star of the show is the liquid brunch menu, which highlights the classic brunch cocktails they serve, as well as brunch towers. These towers are served on the weekends, and you can choose from 100-165 ounces of mimosas, sangria, or bellinis. Perfect for a girls’ brunch if you’re looking to day drink on a beautiful Chicago day!
Beatrix
A classic Chicago brunch and lunch spot is Beatrix in Fulton Market, River North, or Streeterville. All three locations are situated in ideal neighborhoods within the city, making any option a preferred starting point for your day. The spaces are warm and modern, and the expansive brunch menu serves up something for everyone’s specific taste buds. In addition to great coffee and cocktails, they also offer refreshing, freshly squeezed juices that really complement any breakfast order.
Spending a weekend exploring Chicago? Check out my ultimate Chicago neighborhood guide for West Loop & Fulton Market, Wicker Park & Bucktown, or my ultimate Girl’s Weekend in Chicago guide!
Dinner
Girl & The Goat
If you Google “best dinner in Chicago,” Girl & The Goat will likely show up in about 95% of your search results. Since its opening in 2010, it has consistently held a reputation as one of the best restaurants throughout the city. I’m here to say that I agree with that statement, which is why it would be a great dinner spot with your girlfriends for a weekend in Chicago. This new American restaurant has an extremely cool atmosphere as you enter through the door. In addition to the great vibes, the menu is tapas style, making it perfect for a group of girls looking to sample a variety of mouth-watering dishes. Trust me, you will not leave disappointed.
Aba
I could probably write a blog post/love letter dedicated to my love for the food at Aba. I can’t help but feature it in my blog posts since it’s one of those restaurants that checks a lot of boxes for me. What can I say, I adore the beautiful interior of the restaurant in addition to the amazing Mediterranean menu. This winning combination is the reason why it would be a great dinner spot for a girls’ weekend in Chicago. Aba is another tapas restaurant, and therefore ideal for a larger group, allowing you to sample more items from the menu. As I mentioned, the interior is gorgeous and very Instagram-friendly, making it an excellent location for a group photo.
Monteverde Restaurant & Pastificio
If you and your girls enjoy amazing Italian food (who doesn’t?) and warm, inviting spaces, then I highly recommend trying to snag a reservation at Monteverde. The experience at Montaverde from start to finish is nothing short of incredible. The cocktails and wine list are both extensive, featuring a wide range of tasty choices. The menu is a fusion of Italian food and tapas-style dining, allowing you to order a variety of dishes to sample. End your night with a dessert and you’ll leave with a smile on your face.
Piccolo Sogno
There is nothing more magical than a dinner on the string-lit patio at Piccolo Sogno during the summer months in Chicago. The impeccable vibes are only matched by the insanely delicious Italian food that you can expect when dining in this River West hot spot. An order of the Piccolo ravioli is a must, in addition to their pizzas, pastas, or other main courses. You can’t go wrong with anything on the menu, so be prepared to leave full.
Maple & Ash
If you’re in the mood to go all out, Maple & Ash is the move. Picture dramatic chandeliers, luxe leather booths, and a “I don’t give a f*@k” tasting menu that brings the party right to your table. The menu features seafood favorites, wood-fired steaks and chops, and mouth-watering side dishes, including mac and cheese, Brussels sprouts, and various potato dishes. It’s bold, indulgent, and made for celebrations (and Instagram stories).
Pizza Portofino
Tucked along the riverfront, Pizza Portofino brings laid-back coastal Italian vibes to the heart of downtown with Aperol spritzes, airy waterfront seating, and wood-fired pizzas that hit just right after a day of exploring. It’s casual-chic and perfect for sharing plates and taking in the sunset views with your girls.
Cabra
High above the West Loop in the Hoxton Hotel, Cabra is a rooftop Peruvian-inspired spot from Top Chef winner Stephanie Izard (i.e., the creative genius behind Girl & The Goat). Come for the shareable ceviches and bright flavors, stay for the skyline views and a pisco sour (or two). The breezy, colorful space is ideal for a girls’ night that feels both relaxed and elevated.
Looking for a relaxing and dimly lit place to grab a bite to eat in Chicago? If so, check out my 16 Must-Try Cozy Restaurants in Chicago blog post!
Nightcaps & Nightlife
When the sun sets in Chicago, the city becomes electric with a new, exciting energy surging through it. Naturally, it’s the time of day when most folks are looking for a nightcap or maybe somewhere to dance the night away with their girls. I’ve compiled my favorite spots for cocktails and late-night fun for your girls’ weekend in Chicago.
Cocktail Spots
The Aviary
The Aviary is more than a standard cocktail bar; it’s an immersive, artful experience, where drinks arrive in glass orbs, smoking vessels, or suspended ice spheres, and every sip feels like magic.
Cindy’s
Perched above Millennium Park, Cindy’s rooftop pairs skyline views with seasonal cocktails and the kind of golden-hour glow that turns a girls’ night out into a main character moment.
The Office
This speakeasy tucked beneath The Aviary feels like an intimate, vintage den where bespoke cocktails, rare spirits, and candlelit conversation reign supreme.
The Dawson
With string lights, fireplaces, and one of the dreamiest patios in Chicago, The Dawson nails that laid-back chic vibe, perfect for cocktails that stretch into dinner and dessert.
Recess
Playful and unapologetically over-the-top, Recess serves up boozy slushies, patio games, and a cheeky good time in a giant shipping container. It’s the perfect spot, ideal for letting loose with your friends.
Cira
Tucked inside The Hoxton, Cira brings Mediterranean flair and modern glam to its cocktail menu, with chic interiors that make it just as great for a girls’ toast as it is for a pre-dinner moment.
Pops for Champagne
Classic, bubbly, and endlessly fun, Pops is a River North staple where champagne towers, live jazz, and flutes on flutes set the mood for a sparkly start (or end) to your night.
High Low
This low-key gem in the West Town offers craft cocktails with zero pretense and just enough mood lighting to make it feel like your stylish best friend’s living room.
The Robey Rooftop (Up Room)
With panoramic views of the city and a swanky-but-chill vibe, The Robey’s rooftop lounge is the kind of place where sunset cocktails stretch well into late-night excitement.
Looking to grab a craft beer with your canine companion? Check out my 15 dog-friendly breweries in Chicago post!
Late Night Spots
Because sometimes, you just need to end the night dancing with your girls.
Goodnight John Boy
This groovy 70s-themed dance bar brings disco balls, retro cocktails, and just the right amount of nostalgia to fuel your glitter-filled night on the dance floor.
Beauty Bar
Equal parts kitsch and cool, Beauty Bar serves martinis with a side of manicures, all under glittering lights and vintage salon dryers, because self-care and dancing aren’t mutually exclusive.
Disco/Celeste
Located in a multi-level house of glam, Celeste’s rooftop garden bar and downstairs Disco club deliver moody cocktails, sparkly vibes, and late-night energy that hits just right.
Final Thoughts
By now, you should be feeling excited about your upcoming girls’ weekend in Chicago. With its blend of vibrant culture, delectable cuisine, and endless opportunities for adventure, the Windy City promises an unforgettable experience for you and your friends. Whether you’re indulging in a spa day, enjoying scenic views along the lakefront, or exploring the trendy neighborhoods for shopping and dining, there’s something for everyone to enjoy. So grab your best gals, start planning, and get ready to create amazing memories during your girls’ weekend in Chicago!
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