Thinking of a solo trip to Chicago but wondering where to start? Known as the Windy City, Chicago is packed with vibrant attractions, cultural gems, and culinary delights. For solo female travelers, it’s not only a safe city but a truly enriching destination with plenty to explore. This comprehensive 4-day Chicago trip itinerary will guide you through sights, eats, and tips to make the most of your visit.
Day 1 in Chicago: A Day in Grant Park
Morning: Start Your Journey at Grant Park
Begin your adventure in the heart of Chicago at Grant Park. Spanning over 319 acres, this lush green space is a tranquil spot surrounded by iconic skyscrapers—a wonderful blend of nature and urban beauty. Stroll through the scenic paths, admire the expansive greenery, and take in the serene vibes.
Millennium Park
On the northwest side of Grant Park, you’ll find Millennium Park, home to the iconic Cloud Gate sculpture, lovingly known as "The Bean." No trip to Chicago is complete without a visit to this shiny masterpiece. Snap a selfie while catching your reflection on its mirror-like surface for a memory that’s uniquely Chicago.
Buckingham Fountain
Situated at the heart of Grant Park, Buckingham Fountain is an awe-inspiring centerpiece you won’t want to miss. Its grandeur and elegance make it a picture-perfect spot to pause and soak in the beauty of your surroundings.
Agora "Big Feet"
One of the most unique sections in Grant Park is Agora, also known as the "Big Feet." Located at the park’s southern edge, this striking installation features 106 towering sculptures of legs. Gifted by the Polish Ministry of Culture, it’s a must-see for anyone who appreciates bold street art—I know I do!
Museum Campus
Grant Park’s Museum Campus brings together some of Chicago’s most popular cultural institutions. Here, you can explore the Adler Planetarium, the Field Museum of Natural History, and the Shedd Aquarium. It’s a treasure trove for history buffs, science enthusiasts, and marine-life lovers alike.
Art Institute of Chicago
Nestled within Grant Park, the Art Institute of Chicago is a haven for art enthusiasts. Featuring an extraordinary collection of American art, this museum is also known as one of the nation’s top art schools. Whether you're an art lover or just curious, it’s absolutely worth the visit.
Navy Pier
One of my favorite places in Chicago is Navy Pier. Stretching out into Lake Michigan, this lively spot offers something for everyone. From the Ferris wheel to its shops, restaurants, and entertainment options, it’s an easy place to spend a few fun-packed hours without running out of things to do.
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Day 2 in Chicago: Explore Iconic Landmarks
Morning at Willis Tower
Start your second day at Willis Tower (formerly Sears Tower). With its towering antennas and Skydeck featuring “The Ledge,” it's one of Chicago’s most recognizable skyscrapers. If you’re brave enough, step out onto the glass box and look at the bustling streets from 103 stories up.
Chicago Theatre
Take a short walk to visit this historic venue built in the 1920s. Whether you catch a show or take a guided tour, the architecture and ambiance will leave you impressed.
The Magnificent Mile
It’s time for some retail therapy! This upscale shopping district boasts high-end stores, eateries, and charming boutiques. Regardless of whether you’re window shopping or splurging, this area is a shopper’s delight.
Chicago Riverwalk
This scenic, walkable stretch along the Chicago River is perfect for soaking in the city’s skyline and ambiance. Stop by cafes or grab a drink to unwind.
Architecture River Cruise
One of the highlights of any solo travel to Chicago, this cruise offers an educational and breathtaking way to explore Chicago’s architectural legacy. Marvel at the towering structures by day or see the skyline sparkle on an evening cruise.
Day 3 in Chicago: Parks, Views, and Sports
Morning at John Hancock Center (360 Chicago)
Kick off day three with another high-rise view. The 360 Chicago Observation Deck offers panoramic views of the city and Lake Michigan. Feeling bold? Try the thrilling TILT ride, which lets you lean out over the city for a heart-pounding experience.
Afternoon in Lincoln Park
Escape the urban bustle and make your way to Lincoln Park, Chicago’s largest public park. It’s a haven for nature enthusiasts with trails, open spaces, and a free zoo.
Evening Visit to Wrigley Field
End the day at Wrigley Field, home of the Chicago Cubs. If there’s no game during your visit, sign up for an insider tour of this historic ballpark.
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Day 4 in Chicago & Beyond
Morning at the Chicago Botanic Garden
The Chicago Botanic Garden is a true gem—a peaceful haven filled with an incredible variety of trees, plants, and stunning landscapes. While it’s located just outside the city, making the drive is absolutely worth it. Once you’re there, you’ll feel a world away from the hustle and bustle of urban life.
Pro tip: If you visit during the winter holiday season, don’t miss Lightscape. This immersive event transforms the garden with illuminated trails, captivating sound installations, and cozy spots to roast s’mores. With the larger setting of the Botanic Garden, it’s truly unmatched.
Afternoon in Milwaukee
After enjoying a few peaceful hours at the Chicago Botanic Garden, hop in the car and head to Milwaukee to explore the Mitchell Park Domes Horticulture Conservatory. These unique domes are like compact versions of botanical gardens, featuring a mix of exotic plants and fascinating displays. They aren’t huge, so you’ll only need around 1–2 hours to take it all in. This way, you’ll have plenty of time to drive back to Chicago for dinner or catch a flight home.
Must-Do Chicago Eats
No Chicago itinerary is complete without mentioning the city’s iconic food offerings. Here’s what you need to try:
Deep-Dish Pizza
Deep-dish pizza is a Chicago classic, and trying it is practically a rite of passage when visiting the city. The top spots to indulge are Lou Malnati’s, Giordano’s, and Pequod’s. Pick the one closest to your stay or try all three if you’re feeling adventurous. You really can’t go wrong with any of them!
Now, will you love deep-dish pizza? That depends on your personal taste. Having lived in NYC for years, I’m partial to New York-style pizza’s thin crust and grab-a-slice ease. Deep-dish, on the other hand, feels more like a pot pie. You eat it with a fork and knife instead of your hands, which takes away some of the charm for me. The taste is good, but the texture isn’t my favorite. That said, don’t just take my word for it! You might fall in love with it, and it’s a must-try when in Chicago.
Pot Pie Pizza
While deep-dish wasn’t my favorite, pot pie pizza was a whole different story! You’ll find this unique dish at Chicago Pizza and Oven Grinder Co. Unlike deep-dish, it fully embraces its name as a "pot pie." It’s an individual serving made from scratch with a savory tomato sauce, sausage, and mushrooms.
Here’s the fun part: when it’s served, it arrives upside down with the buttery crust on top. The server flips it over, revealing the cheesy, saucy goodness inside a bread bowl. It’s decadent, hearty, and absolutely delicious!
Chicago Hot Dog
Chicago-style hot dogs take the classic to a whole new level. Unlike NYC’s simple hot dog with just ketchup or mustard, Chicago’s version comes fully loaded. Nestled in a poppy seed bun, it’s topped with mustard, neon relish, chopped onions, fresh tomato slices, a dill pickle spear, and pickled sport peppers.
While I do prefer the simplicity of a NYC hot dog, this style offers a fun, flavor-packed experience. Be warned though, it can get messy to eat. Definitely try it at least once for a true taste of Chicago!
Stan’s Donuts
Stan’s Donuts is heaven for anyone with a sweet tooth. Their wide range of flavors makes it hard to pick just one, but you really can’t go wrong. I tried the Biscoff and banana donut, and it was an easy 10/10. Pair it with a coffee for the ultimate breakfast treat.
Brunch
Brunch is a must when traveling, and Chicago has plenty of options to satisfy. Yolk is a popular spot, though be prepared for a short wait—I waited 20 minutes with my friends, but it was well worth it. Other fan favorites include Batter & Berries and Wake ’n Bacon.
Dinner
For dinner, Chicago’s restaurant scene has something for every palate. Some of my recommendations include Girl & The Goat, Boka, Monteverde Restaurant & Pastificio, and The Purple Pig. For an unforgettable fine-dining experience, treat yourself to the innovative, three-Michelin-starred Alinea.
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What About the Accommodation in Chicago?
Mid-Budget Hotels
Chicago offers plenty of fantastic mid-budget hotels that balance comfort and style. Some excellent options include The Gwen – a Luxury Collection Hotel, Sofitel Chicago Magnificent Mile, and LondonHouse Chicago – Curio Collection by Hilton. Each of these hotels provides great amenities and convenient locations for exploring the city.
Luxury Hotels
If you're looking for a little more indulgence and have a larger budget, Chicago's luxury hotel options won't disappoint. Treat yourself to a stay at The Peninsula Chicago, The Langham, or Four Seasons Chicago, all situated in the heart of downtown with exceptional service and stunning accommodations.
Hostels
To be honest, hostels aren’t really my area of expertise. I’m in my 30s now, and comfort is a top priority for me, so I always prefer hotels over hostels. That said, hostels can be a great choice for younger travelers or those looking for a more social vibe—I’m just at a different stage in life where hotels are my go-to.
Airbnbs
I also tend to lean toward hotels instead of Airbnbs. While Airbnbs can provide a unique and sometimes budget-friendly option, I’ve found hotels to be more reliable. One time in Miami, my friends and I booked an Airbnb that looked fantastic in the pictures but turned out to be a total disappointment. We ended up switching to a hotel instead, and since then, I’ve been cautious about Airbnbs. That’s why, when in Chicago, I’d personally recommend sticking with the city’s excellent hotel options!
Practical Tips for Solo Travel in Chicago
- Safety as a Solo Female Traveler: Stick to popular areas such as downtown and always remain aware of your surroundings. Chicago’s main tourist hubs are generally safe.
- Getting Around: Use the Chicago L train for affordable public transport. Taxis, rideshares, and walking are great for shorter distances.
- Book in Advance: Reserve tickets for must-see attractions like Skydeck, 360 Chicago, and museum visits to avoid disappointment.
- Pocket-Friendly Pass: Grab a Chicago CityPASS to maximize savings and group admission for top attractions.
Why We Recommend Chicago for Solo Trips
Whether you’re spending one day in Chicago or an extended 4 nights in Chicago, the Windy City offers charm, history, and adventure in equal parts. With safe neighborhoods, welcoming locals, and endless discoveries, Chicago is a fantastic destination for solo female travelers. Plan your trip today, explore new horizons, and don’t forget—every corner of Chicago has a story to tell!
