Let us introduce you to Chicago, the vibrant and bustling city in the beautiful state of Illinois. Known as the "Windy City," Chicago is a cultural hub filled with diverse neighborhoods, iconic architecture, and a rich history. Whether you're strolling along the picturesque Lake Michigan shoreline, exploring the magnificent downtown skyscrapers, or indulging in its famous deep-dish pizza, Chicago has something for everyone. With its world-class museums, thriving music and theater scene, and passionate sports culture, you'll never run out of things to do and see in this dynamic metropolis. So, get ready to immerse yourself in the lively atmosphere of Chicago and discover all that it has to offer!
We’ve curated a short-list of moderately priced boutique hotels perfect for your next girls’ weekend.
Note: some of the boutique hotels we recommend have a nightly amenities fee for some awesome extras included in your stay. Be sure to read about what’s included to take full advantage!
Hotel EMC2 in Chicago is a captivating destination that fuses art, science, and luxury. Located in the vibrant Streeterville neighborhood, this boutique hotel offers a unique and immersive experience. The rooms are beautifully designed, featuring artistic touches and modern amenities. With its central location, guests have easy access to renowned attractions like Navy Pier and the Magnificent Mile. Indulge in delectable cuisine at the on-site restaurant, and unwind with a creative cocktail at the stylish bar.
Arlo Hotel in Chicago is a captivating urban retreat that exudes contemporary style and sophistication. Located in the heart of the city, this hotel offers sleek and modern rooms, coupled with exceptional service. With its prime location, guests have easy access to Chicago's iconic landmarks, trendy neighborhoods, and renowned dining and entertainment options. Whether you're admiring the breathtaking city views from the rooftop terrace or indulging in exquisite cuisine at the on-site restaurant, Arlo Hotel promises an unforgettable experience in the Windy City.
A chic and sophisticated choice for a girls weekend, The Gwen is a luxury retreat on Michigan Avenue in the heart of downtown Chicago. Its standout feature is the outdoor rooftop patio at Upstairs at The Gwen, where you can sip cocktails while overlooking the skyline. For a super unique experience, the Gwen offers the city’s first urban glamping experience on the private terrace of the Gwen Lux Suite. The hotel also offers fun, girls weekend–friendly packages and experiences (like bubbly, Girl Dinner, and themed activities) making it perfect for celebrating with friends!
Located in Chicago’s trendy Fulton Market district, The Hoxton Chicago is a stylish, design-forward hotel with a fun, social vibe. The rooms feature mid-century furnishings, floor-to-ceiling industrial windows, and cozy modern touches, while the lobby feels lively and welcoming with communal spaces and chic decor. You’ll love the rooftop pool and Cabra rooftop restaurant for cocktails and skyline views, plus the on-site bars and brunch spots that make it easy to stay in and celebrate. Surrounded by top restaurants, boutiques, and nightlife, it’s the perfect home base for a trendy, Instagram-worthy girls getaway.
We’re not gonna lie, trying to recommend a great place to eat in a large metropolitan area is like trying to hit a moving target. Where you stay and the activities you have planned often dictate where you will end up eating.
Most often when planning our weekends away, we put in a little time looking for nearby places that match our taste. Rather than give you a long list of places that might not be right for you, we’re giving you our favorite local search links to help you get started.
If you and the girls want a Chicago moment that feels both iconic and totally chill, the Riverwalk is the place to be. Stretching 1.25 miles along the south bank of the Chicago River, this award‑winning, pedestrian‑friendly path runs from Lake Michigan all the way to Lake Street, and it’s packed with views, vibes, and plenty of cute stops along the way.
As you wander, you’ll discover cozy little coves, breezy cafés, wineries, bars, public art, museums, and endless people‑watching. Sip fine wines on a sunny patio, grab tropical cocktails under a tiki hut, or sample local ciders in a spacious beer garden, all with sparkling river views and towering architecture around you.
And honestly, you can’t do the Riverwalk without getting out on the water. From May through October, take your pick of sightseeing cruises, architecture tours, or river excursions that show off Chicago from its most stunning angle.
The Riverwalk is also an open‑air gallery, filled with permanent and rotating pieces from top contemporary artists, everything from sculptures to bold murals. The crown jewel is Art on theMART, the world’s largest digital art projection, lighting up more than 2.5 acres of theMART’s river‑facing façade. Catch the free show every night from April through December, it’s magical.
Millennium Park is an absolute must on any Chicago girls’ trip. It’s the city’s lakefront playground packed with iconic spots, gorgeous views, and tons of things to do. Right in the heart of downtown, this massive park has everything: interactive fountains, peaceful gardens, public art, free events, skating rinks, rock climbing, and wide‑open green spaces perfect for lounging.
And of course… you have to visit Cloud Gate (aka The Bean). It’s one of Chicago’s most famous landmarks and the ultimate photo opp. Unveiled in 2005, this was artist Anish Kapoor’s first outdoor public sculpture in the U.S., and one of the biggest of its kind in the world. Snap a pic while you and the skyline sparkle in its mirrored surface.
Just steps away is the Jay Pritzker Pavilion, Frank Gehry’s soaring, sculptural masterpiece. Stainless‑steel ribbons stretch 120 feet into the air, wrapping the bandshell in dramatic curves. With its state‑of‑the‑art sound system (seriously, it feels like an indoor concert), it’s an incredible place to catch one of Millennium Park’s many free events. Bring a picnic blanket and claim a spot on the Great Lawn for the perfect girls’ night out.
Nearby, Crown Fountain adds a playful touch — especially on warm days — with its two towering screens and shallow reflecting pool. And don’t miss the McCormick Tribune Plaza & Ice Rink. In the summer, it transforms into a beautiful outdoor dining and cocktail spot overlooking Michigan Avenue. In the winter, it becomes a charming ice rink framed by The Bean and the city skyline. The best part? Skating is always free, and you can rent skates on-site.
If you’re looking for the ultimate “we’re really in Chicago!” moment on your girls’ trip, Navy Pier is the place to be. It’s the city’s go‑to destination for events, attractions, dining, culture, lake views, and nonstop energy, basically, fun lives very large here.
The event calendar is stacked all year long. There are free fireworks displays, live music and theater, cultural festivals, and plenty of lake cruises that show off the city from its best angle. If your group loves a good meal with a view, Navy Pier’s brunch, lunch, and dinner cruises pair great food with stunning skyline and lakefront scenery, perfect for celebrating or just treating yourselves.
And of course, you have to ride the Centennial Wheel, one of Chicago’s most iconic attractions. The views of the skyline and Lake Michigan from up top are unbelievable, it’s the kind of moment your camera roll will thank you for.
Don’t miss Navy Pier’s award‑winning, free fireworks shows (several times a year), which light up the lake and make the whole skyline sparkle. It’s the perfect way to end a night out with your girls.
If your girls’ trip needs a night full of big laughs, The Second City is calling your name. This legendary improv theater is where countless comedy icons got their start, and it still brings the heat with some of the funniest performers you’ll ever see on stage. Founded in 1959, The Second City is the longest‑running improv theater in Chicago, and one of the most influential comedy institutions in the world.
Whether you’re catching a sketch show, an improv set, or a late‑night performance that has everyone crying laughing, The Second City delivers that perfect, unforgettable “girls’ night out” energy.
The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip!
Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8.
Take in the Chicago skyline from a vantage point most travelers miss on this brunch cruise. Gaze up at the Willis Tower, the Old Chicago Post Office, the Tribune Tower, and much more as you drift along the Chicago River while listening to light commentary and enjoying a curated menu of brunch favorites.
Most people have to decide between a boozy Sunday and a river cruise. During this special boat ride in Chicago, you get the best of both worlds. Enjoy a range of mimosas and other brunch drinks for purchase as you cruise down the Chicago River. Enjoy front-row seats as you pass by iconic skyscrapers and other downtown landmarks, with staff available to answer your questions.
Take your Chicago experience to new heights with a ride on the iconic Navy Pier Centennial Wheel. Step into a climate-controlled gondola and enjoy sweeping views of the city skyline, Lake Michigan, and Navy Pier from 200 feet above the water. This attraction is perfect for visitors of all ages looking to add a fun and memorable highlight to their day in downtown Chicago. Admire the scenery as you complete multiple rotations, and enjoy easy access to restaurants, shops, and lakeside entertainment right on Navy Pier.
The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. Public tours are available Thursday – Monday. The museum is closed Tuesday and Wednesday. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
Discover a side of the Windy City that many visitors overlook and immerse yourself in its vibrant street art scene on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city’s ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city’s hippest neighborhoods.
The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there’s no waiting to get inside, as the tour includes a skip-the-line ticket.
Lincoln Park is one of Chicago’s premier shopping neighborhoods, blending national brands with chic independent boutiques in a lively, walkable setting. Along Clark Street and Diversey, you’ll find a vibrant retail corridor buzzing with shoppers popping in and out of bustling storefronts, so much so that it’s one of the most‑traveled pedestrian areas in the entire city. Just steps from the lakefront, Clark Street offers more than 100 restaurants, cafés, boutiques, and neighborhood gems, making it an easy place to spend the whole day. Whether you’re hunting for fashion, home décor, gifts, or a cozy spot for brunch or a nightcap, Lincoln Park delivers an authentic Chicago experience that feels stylish, energetic, and perfect for a girls’ day out.
The Magnificent Mile is Chicago’s ultimate shopping playground. With more than 430 retailers and three vertical shopping centers there are endless possibilities for every style and mood. Whether you’re chasing the latest designer drops, hunting for cozy home favorites, or mixing high‑end splurges with budget‑friendly finds, this iconic stretch delivers it all. It’s a vibrant, walkable avenue where fashion, food, and city energy come together, making it the perfect place to shop, explore, and soak up that unmistakable Chicago energy.
A buzzy, artistic area just three miles from downtown, Wicker Park is one of Chicago’s trendiest neighborhoods. Centered around the lively Damen–Milwaukee–North intersection, it’s packed with indie boutiques, galleries, cafés, and some of the city’s best people‑watching. Milwaukee Avenue is the neighborhood’s main artery, lined with eclectic boutiques, vintage shops, and fashion‑forward finds that make browsing feel like a treasure hunt. Getting here is easy with the Blue Line. Its walkable streets, vibrant nightlife, and endless mix of shopping and dining draw locals and visitors alike for a day that feels effortlessly cool and distinctly Chicago.
For those of you looking for a fun night out on your girls’ getaway, we’ve got your back. Whether it’s dancing the night away or girl talk over delicious cocktails, we’ve got options. We’ll help you find the right fit with our favorite local search links below.
Are you a travel blogger who lives in this destination? Write for us!
We are accepting Girlfriend Weekend Itineraries for this destination. Find out more here.
