Guide to an Epic Girls Weekend Trip to Chicago
Guide to an Epic 3-Day Girls Getaway to Chicago
As the third largest city in the United States, Chicago is an unbeatable destination for a girls weekend in the Midwest. Situated along the gorgeous Lake Michigan shores, Chicago, Illinois is well known for striking architectural buildings, its mouth watering deep dish pizza, plus an array of shows and museums to explore. So gather your gal pals and head to the Windy City for a much needed getaway. Whether you’re planning a bachelorette party or a mom’s weekend trip, there is plenty of entertainment and attractions to enjoy. With an incredible food scene, lively festivals, music venues and views of Lake Michigan, Chicago isn’t lacking for fun things to do downtown.
Chicago River
Chicago’s Arichetectural Boat Tour
Ideal Trip Time: 3-5 days
In my opinion, an ideal amount of time to visit is between 3-5 days to experience the best of Chicago. With endless cultural and thrilling attractions to chose from it can be a bit taxing to narrow down all the options, especially if you’re only visiting for a quick week or weekend vacation. That’s where I can help. Living only 3 hours away, I’ve visited this city a handful of times, most recently on a girls weekend trip. Let me help make your trip planning easier as I share my top recommendations for unmissable things to do in Chicago, plus suggestions for where to stay and where to dine when visiting downtown.
Chicago
3-Day Chicago Itinerary
DAY 1 Visit Field Museum on drive in/ Check into Hotel/ Water Tower place/ Get sky high view from Chicago 360 or Signature Lounge for Drinks & Appetizers/ Relax at Hot Tub or Hotel Pool
DAY 2 Starbucks Roastery/ Shop at Magnificent Mile/ Walk to Navy Pier / Take Architectural Boat Tour/ Off Shore Rooftop for drinks & food
DAY 3 Walk to Millennium Park (The Bean, Maggie Daily Park)/ Walk to Art Institute/ Lou Malanatis for Pizza/ Chicago Theater for Show or Wills Tower Skydeck
Drive to Hyde Park and grab sandwiches at Cafe 53/ Drive or Uber short distance to Science and Industry Museum
*If you have additional days, I would highly recommend adding the zoo, a baseball game, to your itinerary.
Map of Chicago Attractions & Hotels
When traveling, I find it immensely helpful to get the big picture of the city and how it’s laid out. Using Wanderlog, I created a map with my favorite attractions, restaurants and hotels in Chicago. Hopefully this will aid you in planning out your daily itinerary to maximize the best use of our time and where to walk or drive.
Getting There
Chicago is only a 3 hour drive for me from Michigan, so I have driven several times, but it’s not ideal due to the difficulty with parking and extreme prices. Choosing a hotel that has parking is highly advisable and then walk or uber places. Luckily, Chicago is easily explored on foot. Pack good walking shoes and get your fitness tracker charged because you’ll be logging some miles as you take in the sites and sounds of the Windy City. On this specific trip, my friends and I took the Amtrack train, which we found entertaining, cost effective and fast.
Airport Fly into O'Hare (ORD), a sprawling international airport, or Midway (MDW), which offers more convenient access to the city but with far fewer choices of flights? O'Hare is located northwest of the city, Midway to the southwest.
Train Chicago’s iconic & beautiful Union Station offers both Amtrak and Metra, the commuter rail service, for visitors. I was pleasantly surprised how simple the commute on a train ended up being and would definitely recommend it.
Driving Try to book a hotel with free parking and then plan to uber or walk to places.
Tips for Planning Your Visit
Most of the museums, zoos and cultural attractions close at 5:00 pm, leaving your evenings as a great time to enjoy dinner. We found the Skydeck and Water Tower Plaza were open later till 7 or 8 pm, depending on the day.
Where to Stay in Chicago For Easy Walkability
Choosing where to stay in Chicago is important. By being centrally located to the key attractions you can reduce your travel time, miles of walking and fees on Uber or taxi rides. As far as my personal recommendation, the best location to stay is North of the River and South of Water Tower Place, for the best walkability. No matter your budget, Bookings.com is a great resource, showing tons of affordable and splurge-worthy options in downtown Chicago. Here are three great options for hotels in downtown Chicago.
Hampton Inn and Suites Chicago is an ideal location
Hampton Inn and Suites Chicago Downtown Located on West Illinois, they offer a spacious suite with a sofa bed and kitchenette area. It included an impressive FREE breakfast spread, plus a 95 degree pool so you can relax in the evenings ( it felt like a hot tub) or get your workout on in the fitness center. Valet parking is available for a fee, if you don’t want the hassle of self parking, which can be a headache in Chicago
Hilton Garden Inn Chicago Downtown/ Magnificent Mile
If you love to shop, Hilton Garden Inn is only two blocks from the Magnificent Mile mile, plus it’s close by to Navy Pier and "The Bean". With all the amenities you will appreciate the free WIFI, indoor pool, fitness center, and the Weber Grill Restaurant on site.
Embassy Suites by Hilton Chicago Downtown River North With a great downtown Chicago location, the hotel offers a pool and continental breakfast.
Unmissable Attractions in Chicago for a Girls Weekend Getaway
Explore Green Space
Millennium Park
Do yourself a favor and put Millennium Park at the top of our list when exploring Chicago, especially on a lovely day with clear blue skies. Here are a few notable highlights items to see.
The Bean Arguably the most iconic statue in Chicago is Cloud Gate, or more commonly known as “The Bean”. Surrounded by towering buildings in the center of Chicago, the reflective silver sculpture is a perfect place to get a selfie picture in its gleaming surface. Located at the entrance to Millennium Park, it’s definitely one of the top things to do in Chicago, especially on a warm day.
Crown Fountain This massive 50 foot tall video boards with water spouts, represents the diverse cultures and faces of Chicago residents.
BP Pedestrian Bridge Next take a stroll across the shiny serpentine stainless-steel panels of the Frank Gehry’s winding BP Pedestrian Bridge. With its wide expanse, its a ideal time to get a panoramic view of the city as you walk along the snakelike panels over the expressway and leading to Maggie Daley Park. During your stay check to see if their is a musical event at the outdoor Jay Pritzker Pavilion.
Maggie Daley Park
Maggie Daley Park Bridge
For those both young and old at heart, enjoy the outdoor beauty at Maggie Daley Park. This stately, eye-catching suspension bridge stretches across the middle of outdoor play area, which draws those child-like individuals.
Maggie Daley Park is a beautiful place to visit in all seasons. On cold days, an ice skating path winds through the park for a winter adventure. While in the summer, soak in the sun as you enjoy biking, running or rollerblading along the path. You’ll also find a rock wall for climbing or compete with one another on a putt putt golf course. Welcome in spring, as you enjoy nature’s first signs with flowering spring bulbs, delicate magnolia trees juxtaposed against towering skyscrapers.
Grant Park
Another outdoor space worth the visit is Grant Park. Grab a picture at the impressive Buckingham Fountain. Additionally, gaze at the boats in the harbor, on beautiful Lake Michigan. Lots of lively festivals occur in Chicago from Taste of Chicago in July to Lollapalooza music festival in August, or Ice Sculptures in the winter. On the eastern edge of Grand Park, stretches a 1.5-mile, easily rent a bike and view Buckingham Fountain and the Museum Campus.
Sky Views of Chicago
Skydeck in Willis Tower - Chicago
Experience the city of Chicago from new heights. 360 CHICAGO in the John Hancock and the Skydeck in the Willis Tower give you a two options for lovely views of the city.
Skydeck in the Willis Tower
Journey up Willis Tower to see Chicago from the Skydeck. Feeling gutsy, walk out on the Ledge, into a clear, glass box to glimpse the city streets below while snapping an unforgettable picture. Skydeck: Admission $32-44 Adult (prices change based on date and time.)
360 Tilt
Another similar option is 360 Tilt, located close to Navy Pier. If your accommodations are North of the River, it’s a great spot to see the city. Try the tilt experience, as you hold on tightly to handles, while tilting at a angle suspended above the ground. Take in the thrilling 1,030 feet drop below. Admission: $30 Adult
Signature Lounge and Restaurant John Hancock
Signature Lounge and Restaurant John Hancock
Want a similar experience, grab drinks and dinner at the Signature Lounge and Restaurant at the top of the John Hancock building. During our stay, my friends and I enjoyed delicious, although pricey, drinks at night. The view is spectacular as the city is dazzling with lights. Even the women’s bathroom is an experience. Nowhere else can you enjoy a floor to ceiling glass view from the women’s bathroom. The restaurant is expensive so we grabbed drinks while there and enjoyed the views. If you’re trying to save money, consider going for lunch or visiting the lounge for a pre-dinner drink or appetizer.
Popular Attractions
Navy Pier
One of the most popular spots in Chicago is Navy Pier. Providing gorgeous views and a ton of fun. Ride all the attractions including the Centennial Wheel ($15/$18), swings or take trip on the Tall Ship Windy or Architectural Boat Tour that follows the Chicago River.
Architectural Boat Tour in Chicago
We opted for The City Architectural Tour , which was perfection as skies were clear and the cool breeze felt delightful on your face. Knowledgeable guides shared the unique architecture and history of Chicago. Being on the water in early September was a highlight during the trip.
At night Navy Pier is illuminated by the interactive fountain at Polk Brothers Park, which consists of jetted water streams that are programmed in assorted patterns. Head inside Navy Pier for a bit, for some shopping and to check out one of the newest attractions Fly.
Another great option is grabbing drinks and play yard games on the top of the Off Shore Rooftop Restaurant, while you enjoy a sky high view of the marina.
Off Shore Rooftop Restaurant
Wrigley’s Field
Take me out to the ball field, take me out to the game…. When in Chicago catch a game at the famous Wrigley’s Field to watch the Chicago Cubs.
Explore the Arts & Learn at a Museum
Chicago isn’t lacking for history, science and art museums. Depending on your interests, whether art, history or science, here are three of the best museums to visit.
Science and Industry Museum
Discover and learn about space, view the incredible 40-foot swirling tornado, tour a mine shaft or learn about the inventions in a James Bond Movie. Easily spend the day exploring and learning at this massive museum. Plan for ample time to see all the interesting exhibits. This is one of my all time favorite museums, even though I’ve visited twice, I’m still awestruck each time I go and discover something else. Admission Adult – $25.95
Field Museum
As you walk through the doors, you’re immediately struck by the immense size of titanosaur, the largest dinosaur hanging suspended above your head. View the largest T. rex skeleton in the world, glittery jewels, unique rocks and even meteorites. Dive into history through interactive exhibit including ancient Egypt, the Pacific Islands and China. The Mammal exhibits feels like your walking through a zoo featuring hundreds of taxidermized lions, giraffes, and birds.
Art Institute of Chicago
The Art Institute of Chicago is home to a collection of art that spans centuries and the globe, its one of the best art museums in the entire US. This one is on my list for the next time I visit.
Spend the day at the Field Museum in Chicago
Animal Experiences in Chicago
Get up and close with animals in Chicago, which two different zoos to choose from, plus a butterfly garden and aquarium. Want to save money, Lincoln Park Zoo is entirely free.
Mammal Exhibit at Field Museum
Very few attractions have free admission in Chicago, but the Lincoln Park Zoo is one of them. Enjoy free entry as you see wild animals from playful penguins and fierce lions to active monkeys.
Brookfield Zoo
On the outer edge of Chicago, is the impressive Brookfield Zoo. With a lovely 216-acre nature park, and phenomenal exhibits including an underwater polar bear enclosure and an expansive primate exhibit.
Admission is $24.95 adults
Shopping Galore
Is it truly a girls trip without shopping? There is no lacking in opportunities to shop, shop, shop!
Magnificent Mile
The most well known area for shopping is obviously the Magnificent Mile which features a plethora of shopping spots. Stop in at Gucci, Bloomingdale's, and Nordstrom, plus over 450 retail stores and boutiques, you could easily spend the whole day in this one mile stretch.
Water Tower Place
Water Tower Place glass elevator
From the towering glass elevator to the kid-friendly shops designed with your children’s favorite toys, Water Tower Place is an unmissable stop when visiting Chicago. Home of both the LEGO store and popular American Girl, make a stop at Water Tower Place if you want to bring home a fun momentum of your time in Chicago.
Restaurants
Without a doubt , Chicago is home to a robust food scene. From fine dining to jaw dropping views and sweet treats, the foodie in you isn’t lacking for options.
Starbucks Roastery
At your core if you have a coffee obsession, head to the Starbucks three-story Starbucks Reserve Roastery, featuring an chic interior with a one-of-a-kind store.
Starbucks Roastery
Located in Hyde Park, this is a great stop when visiting the nearby Science and Industry Museum. Featuring scrumptious oven baked sandwiches overflowing with meats, cheeses and unique sauce blends all on a Dutch crunch bread, its a winner in my book. I can vouch for the Chicken Pesto, Sumac and Honey Barbecue Chicken, all of them were delicious.
Lou Malnati’s Deep Dish Pizza in Chicago
A must when visiting Chicago is to indulge in Chicago style deep dish pizza. My top pick- Lou Malnati’s, is one of Chicago’s oldest pizza place, and in our personal opinion the best. This local restaurant features fresh cheeses and toppings- but the chef’s kiss is the sauce bursting with unique blend of flavor from basil, garlic and Roma tomatoes.
Experience quick Chicago street food at Portillo’s. This massive warehouse style restaurant in River North has a wide array of the food - Italian beef, Chicago hotdogs, & spaghetti. A great place to try Chicago classics, on a budget. FUN FACT A Chicago Style hotdog includes mustard, relish, celery salt, freshly chopped onions, sliced tomatoes, a kosher pickle, and peppers stacked onto a warm poppy seed bun.
Rosebud Restaurant
Enjoy fine dining with Italian cuisines. With generous portions and wide selections of drinks this was one of my favorite dinners of the trip.
Prepare to for a hefty price tag, but if you want sugar high concoctions, then this place has loads and loads of sugary drinks. In my personal opinion it was a bit overrated and I’d skip it.
JoJo’s Shake Shop
JoJo’s Shake Shop
Featuring the luxury milkshakes, with several locations throughout Chicago, these epic shakes, although pricey, included sugary fixings like cookies, cotton candy, and marshmallows etc. Both the Unicorn and Girl Scout were huge and full of delicious ice cream! I’d definitely advise splitting these massive shakes.
Experience the Fine Arts
Broadway Muscial
Get dressed up and enjoy the fine arts of theater. View a show like the Blue Man Group at Brier Street Theater or a Broadway musical show. On a previous trip, I was mesmerized by the captivating performance of Wicked. The performers are top notched, trust me you won’t be disappointed.
Try Something New & Get Active
Some of my very best times with my friends is when we decided to step outside of our comfort zones and try something new. These are the easiest times to create some unforgettable memories together.
Dancing at Disco (River North)
Located in River North, this 70’s era dance club with disco balls and colorful LED lights is a fun time. Why not get dressed up and get out on the town in your best 70’s attire.
Take a class at Air Fit, either Intro to AIR or Foundation, both are aerial fitness classes that are great for beginners and all ability levels for a group of women.
How to Save Money in Chicago
If you’re not a resident of Illinois, many fees at museums are more expensive. After scouring websites for discounts and trying to figure out if it was worth purchasing a Chicago City Pass or GO Chicago cards. Here’s my personal opinion. If you’re planning to pack in multiple expensive attractions, it will save you money and time in lines. Some of the more expensive entry fees for attractions are Shed’s, SkyDeck, and the Science and Industry Museum.
The Chicago CityPASS costs $110 for an adult. This reduces your ticket fees to around $20 per attraction, which is a decent discount and will save you money, if you plan on visiting three of the higher priced attractions or museums.
Adult – $139
Chicago C3 CityPASS: Included attractions
Shedd Aquarium, Skydeck Chicago, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Shoreline Sightseeing Architecture River Tour, Centennial Ferris Wheel at Navy Pier, Field Museum and the Adler Planetarium
Closing Thoughts
Hopefully this has inspired you to start planning your weekend getaway to Chicago with the ladies! Briming with attractions, cultural events, museums, history, festivals, outdoor parks and shows, there is a host of activities to satisfy the entire group. Don’t forget to follow Discovering Anew on Facebook for more vacation destinations and camping guides. If you found this content helpful, pin and save for later.
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