Last month, my sister and I took our first girls’ trip to Chicago. I had always wanted to visit and experience everything this vibrant city offers, and it exceeded my expectations. As a native New Yorker, I felt drawn to the iconic tourist attractions like Cloud Gate and the incredible food scene—and I explored exactly that.
Below, you’ll find a curated weekend guide to Chicago—perfect for a two- or three-day trip. You’ll have just enough time to explore the city, eat delicious food (yes, I’m talking about deep-dish pizza), and unwind if you’re in the mood to relax.
Where to Stay in Chicago
Hyatt Regency Chicago
I stayed at the Hyatt Regency Chicago, a beautiful hotel just steps away from The Loop, Millennium Park, The Art Institute of Chicago, and other must-see sights. The hotel offers a variety of rooms and suites, including some with breathtaking views of the Chicago River.
Guests can enjoy a 24-hour fitness center, three on-site restaurants, a mini-mart for grab-and-go snacks, and a package pickup area. When I didn’t feel like leaving the hotel, I grabbed a bite at American Craft Kitchen & Bar—don’t miss the vegan cauliflower risotto or the kale and quinoa salad.
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Virgin Hotels Chicago
If you love theater, consider booking a room at the Virgin Hotels Chicago, located just steps from the iconic Chicago Theatre. The hotel features stylish, modern rooms and luxury amenities in the heart of downtown. It’s also pet-friendly and offers spacious rooms—many with gorgeous city views.
Before heading out for the night, I relaxed with drinks at Cerise, the hotel’s rooftop lounge. The next morning, I treated myself to breakfast at Miss Ricky’s—the savory Miss Ricky’s Pancake (filled with cheese and topped with berry jam, syrup, and butter) was unforgettable.
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What to Do in Chicago
Cloud Gate
I couldn’t leave Chicago without visiting Cloud Gate, better known as “The Bean.” Located in Millennium Park, this reflective sculpture attracts crowds snapping selfies and kids running around, but it’s absolutely worth seeing in person.
Walt Disney Birthplace
As a Disney fan, I couldn’t pass up the chance to visit Walt Disney’s childhood home on Tripp Avenue. I joined a guided tour (offered once a month), which took us through each room while we learned about the family’s early days, the home’s restoration, and its historical significance. For any Disney enthusiast, this experience is a rare treat you can only experience in Chicago.
The Skydeck
I headed to The Skydeck at Willis Tower to take in a 110-story-high view of the city. It’s a great indoor activity with plenty of photo ops and historical tidbits about Chicago’s architecture, food, and neighborhoods. I also picked up a fun souvenir at the gift shop before heading out.
To make the most of my visit, I bought the CITY PASS, which gave me access to 5 attractions—including The Skydeck.
River & Architecture River Cruise
One of the best ways to experience Chicago’s skyline is from the water. I hopped on a 75-minute architecture cruise along the Chicago River, which showcased the city’s stunning buildings and provided rich commentary from our guide. It was the perfect way to capture photos and enjoy a different view of the city.
AIRE Ancient Baths
If you’re looking for somewhere to rest and relax in Chicago, then you’ll want to visit the AIRE Ancient Baths. Inside you’ll find thermal baths of varying temperatures that you can sit in and decompress. It’s a great way to take the edge off after perhaps a day of stressful travel or if you’re looking to have a more relaxing day in Chicago.
Where to Eat And Drink in Chicago
FireLake Grill House
Located inside the Radisson Blu hotel, FireLake quickly became one of my favorite dining spots. The menu features locally sourced, sustainable dishes. I recommend the two-pound mega pretzel, rotisserie chicken flatbread, pan-roasted salmon, or the prime filet.
If you’re in town on the weekend, treat yourself to their afternoon tea service with scones, finger sandwiches, and pastries.
Cindy’s
Cindy’s at the Chicago Athletic Association lives up to the social media hype. I snagged a rooftop table with an unbeatable view of Millennium Park and Cloud Gate. I ordered the grilled chicken Caesar salad and the pecan chocolate cake—both were absolutely delicious.
SheBuysTravel Tip: Make a reservation in advance to guarantee a spot indoors or on the patio.
Margie’s Candies
If you have a sweet tooth, then you’ll want to venture over to Margie’s Candies during your weekend in Chicago. This family owned and operated establishment serves up some of the best ice cream sundaes and traditional soda foundation favorites (sandwiches, melts, appetizers, etc.) The turtle sundae is a must-try for those fans of caramel and nuts plus you can’t forget the hot fudge that is unlike anything you’ve ever had before — trust me.
Giordano’s
A trip to Chicago isn’t complete without trying some deep dish pizza. Giordano’s has several locations throughout Chicago and the downtown area so you’ll stumble across one as you’re exploring. Not sure what to order? You can’t go wrong with the Chicago classic or the fresh spinach. The restaurant tends to get busy quickly so I’d recommend going as soon as they open — plus the deep dish takes around 45 minutes to prepare so you’ll be spending quite a bit of time at the restaurant.
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