As a professional traveler who hosts group trips several times a year, I can say Chicago has everything you need for a weekend to remember. The city offers a stunning skyline, world-class wellness spots and luxury shopping, but it's also really manageable. Chicago is easily accessible via direct flights from dozens of cities, highly walkable and supported by a reliable public transportation system. It’s a culturally packed destination that proves you don’t have to choose between a fun night out and a meaningful travel experience.
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When's The Best Time To Visit?
Reflected, Chicago, Skyline, Lake Michigan, Illinois, AmericaGetty
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The Classic Chicago Experience
The Bean, The Cloud Gate Sculpture in Millennium Park, Chicago, Illinois, USAGetty
From the intricately arranged flower shows to public installations, Chicago is an artsy city. Although it’s officially named “Cloud Gate,” The Bean is a popular tourist attraction and the world’s largest permanent outdoor art installation. Even while shopping at The Fashion Outlets of Chicago, there are beautiful murals on the walls and ceilings to admire, as well as rotating exhibits throughout each level from local and global artists.
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Views and Souvenirs
875 North Michigan Avenue, built as and still commonly referred to as the John Hancock Center, is a 100-story, supertall skyscraper located in Chicago, Illinois.Getty
After you’ve spent time shopping on the Magnificent Mile, commemorate your girls' trip with permanent bracelets. It's not only a fun and easy bonding activity but a long-lasting souvenir that won’t take up space or add any clutter. During one of my recent trips to Chicago, my friends and I visited Alexandra Marks Jewelry to get bracelets and anklets. We were greeted with wine and a relatively large selection of chains and charms, so we were really able to get something that represented us, our trip, and our friendship.
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Relaxation and Wellness
Cropped shot of an unrecognizable male chauffeur opening a car doorIf your crowd isn’t especially keen on spending an entire day at the spa (or if time doesn’t allow), places like NOW Massage are ideal for a quick moment of peace and relaxation. There are three massage types to choose from, with add-ons like deep tissue, cupping, and hot stones, with appointments starting at just 25 minutes. That still leaves plenty of time to explore the city.
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Where to Eat and Stay
Chicago Pizza on a wooden tableRonny Maye
You may be in the Midwest, but you can never go wrong with a delicious Southern-style meal. For that, you’d want to head over to Luella’s Southern Kitchen for their boudin biscuit sandwich or creole catfish. What’s a girl's trip without brunch? Head over to The Dearborn, where you can get some great New Orleans-inspired dishes like beignets or cajun shrimp and grits. Or, give the fried perch Benedict a try. But, foodies may really enjoy trying the classic fish and chips, known for beating Chef Bobby Flay on his cooking show!
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