Curator’s statement
Chicago feels special to me because it effortlessly blends luxury, culture, and incredible food with a sense of warmth and ease. It’s a city where you can enjoy skyline views, stylish hotels, and beautiful architecture while still finding calm moments along the river and lakefront. I love Chicago because it’s perfect for designing trips that feel elevated but never overwhelming. Every visit feels intentional, stylish, and memorable, which is exactly how I believe travel should feel.
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Day 1: Arrival, Riverwalk & rooftop views
Day 1 in Chicago is about settling in and getting a feel for the city without rushing.
After checking into your hotel, I recommend starting with a walk along the Chicago Riverwalk, which is one of the most scenic ways to experience the city’s architecture and energy for the first time. It’s a calm but beautiful introduction to Chicago and perfect for photos or a casual drink by the water.
In the evening, head to Cindy’s Rooftop for cocktails and skyline views, which I love because it feels stylish yet relaxed. My tip is to go around sunset for the best views and to make reservations ahead of time to avoid long waits.
Day 2: Brunch, shopping & the Chicago skyline
Day 2 is perfect for leaning into Chicago’s chic side with great food and shopping.
Start your morning with brunch at The Hampton Social, which is one of my favorite spots because it feels bright, fun, and perfect for a girls trip.
After brunch, spend the afternoon shopping along Michigan Avenue and exploring the West Loop, where you’ll find a mix of luxury brands and trendy boutiques.
Later in the evening, I highly recommend the Chicago Architecture Boat Tour, especially at night, because seeing the skyline from the water feels magical and completely different from street-level views.
A note from Taylor Johnson
Book a later tour, bring a light jacket, and plan dinner afterward so the night feels effortless and unhurried.
Day 3: Culture, West Loop dining & a luxe night out
Me, heading to dinner
Day 3 is a great balance of culture and elevated dining.
Begin the day with coffee and a slow walk through downtown or along the Riverwalk, which is one of the best ways to enjoy Chicago at a relaxed pace.
I recommend visiting the Art Institute of Chicago, even if museums aren’t usually on your itinerary, because it offers both iconic artwork and beautiful spaces that feel inspiring and immersive.
In the evening, head to Bavette’s Steakhouse for dinner, which I love for its moody atmosphere and classic, upscale feel.
After dinner, explore the West Loop’s lounge scene, where you can choose between intimate cocktail bars or livelier spots depending on your group’s vibe.
A note from Taylor Johnson
Plan one evening specifically for dressing up and enjoying a more glamorous side of the city.
Need to know
Additional tips: Girls trips & couples notes
Chicago is one of those cities that works beautifully for both girls trips and couples trips because there’s so much variety in what you can do.
For girls trips, I always recommend planning at least one rooftop night, a brunch day, and some time for shopping or exploring different neighborhoods. Chicago makes it easy to feel dressed up and relaxed at the same time, which is perfect for group trips. For couples, the city feels romantic in a subtle way, river walks, skyline views, cozy restaurants, and intimate cocktail bars make it easy to create meaningful moments without overplanning.
One thing people don’t always realize about Chicago is how quickly popular spots book up. Restaurants, rooftops, and tours can fill up faster than expected, especially on weekends, so having reservations in advance makes the trip feel much smoother. Another thing I love about Chicago is that some of the best experiences aren’t always downtown. Areas like the West Loop and River North have some of the most stylish restaurants and hidden gems, and they’re worth exploring if you want a more local feel.
Chicago weather can be unpredictable, so packing layers is always a good idea, even when the forecast looks warm. I also encourage travelers to leave a little space in their schedule instead of planning every hour. Chicago is a city that’s best enjoyed when you allow yourself to wander a bit, discover new spots, and move at your own pace.
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Taylor Johnson
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