I never visit Chicago without stopping by the Fashion Outlets of Chicago, because they have some of the absolute best deals you can find on authentic, luxury designer clothing, shoes, accessories, and more. The mall has stores like Burberry, Prada, Moncler, Gucci, Pandora Jewelry, Tory Burch, Jimmy Choo, Theory, and other stores like Vineyard Vines, J.Crew, Banana Republic & more. Sometimes outlets have direct to outlet pieces they produce at lower quality and for a lower price, but this is not one of those outlet locations, everything here is the real deal straight from the brand. Here’s which stores I visited on my most recent trip to the Fashion Outlets of Chicago, and what I bought.
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My Chicago Guide, created in partnership with Choose Chicago, will share the most interesting things to do, the best luxury accomodations, and the best places to eat in the Windy City. I love visiting Chicago, and it’s always been a special place for me and my husband, because we have so many happy memories here together. I can’t wait to share the many, many reasons we love Chicago!
Dock your boat at (or walk/drive to) Pizzeria Portofino in downtown Chicago along the Chicago River and step inside the Italian Riviera. With an extensive menu of delightful Italian dishes, refreshing Mediterranean cocktails and mocktails, seafood brought in fresh daily, and an interior that will make you feel like you’re on vacation, Pizzeria Portofino is another fantastic addition to Chicago’s phenomenal pizza scene.
Chicago is one of my favorite cities in the United States. They have nearly 100 museums, 23 Michelin Star restaurants (read What Are Michelin Star Restaurants?if you’re not sure what these are), a dozen 5-star hotels, tons of fantastic events, festivals, musical performances, and pop-ups around the city, world-class luxury shopping, and so much more. We’ve visited more than a dozen times in the last couple of years, and we always find something new to love in the Windy City, which is why I wanted to share my favorite things to do in this Chicago itinerary. I hope this helps you plan the perfect luxurious weekend getaway to Chicago, whether it’s for a mini-honeymoon, family vacation, an anniversary trip, or to simply explore somewhere new!
Summer House Santa Monica is a breezy, light-filled, California-inspired dining spot in the Gold Coast neighborhood of Chicago. We had the best brunch there on our last day in the Windy City, and it was a fantastic experience. Here’s why we loved this gorgeous, culinary destination that’s perfectly laid back, completely Instagrammable, and very allergy-friendly.
The Art Institute of Chicago has some of the most famous works of art in the world, like American Gothic, one of Vincent van Gogh’s earliest self-portraits, A Sunday Afternoon on the Island of La Grande Jatte, Nighthawks, The Old Guitarist, Waterlillies by my very favorite artist Claude Monet, and so many others. Along with ancient coins, marble statues from Ancient Greece, and thousands of other incredible works of art, the Art Institute of Chicago is one of the world’s best art museums, and something that can’t be missed on a visit to Chicago.
Somerset restaurant inside Viceroy Chicago hotel is one of the best brunch spots in the city, with plenty of options from Japanese inspired to classic American fare, all set inside of a luxurious Art Deco style eatery. Read why this delightful restaurant has captured the heart of Chicago, and beyond, and you’ll see why it’s always booked solid! Pro-tip: Make your reservations as soon as you know you’ll be visiting, so you don’t miss out!
The Viceroy Chicago is one of Chicago’s most luxurious 5-star properties. Set in a 120 year old building in the historic, easily walkable Gold Coast district, this 1920s Art Deco style hotel is completely unique from anywhere else we’ve ever stayed. Every aspect of our stay was absolutely sublime, and their attached restaurant, Somerset, was the perfect spot for brunch prior to heading out to explore the city. Here’s what we loved the most about Viceroy Chicago hotel.
After thoroughly enjoying my very first experience with Ralph Lauren’s restaurants in Tokyo, at Ralph’s Café, which is attached to the luxurious Tokyo flagship store, I knew I wanted to seek out other fantastic dining opportunities by Ralph Lauren. The RL Ralph Lauren Restaurant in Chicago is attached to the largest Ralph Lauren store in the world, which is the Michigan Ave. flagship. Famed for their luxurious and beautifully appointed surroundings, the RL Ralph Lauren Restaurant in Chicago was a beautiful way for fans of the brand to enjoy an extension of the Ralph Lauren lifetsyle, and enjoy great food.
The Fairmont Chicago Millennium Park is one of Chicago’s most elegant and luxurious hotels, and arguably has the best location in all of the Windy City. From the hotel, which is surrounded by 400 acres of wooded park land, is an oasis within the busy city. The Fairmont Chicago Millennium Park also has an incredible view of the Chicago Skyline, Lake Michigan, and the surrounding parks, making it a great spot to enjoy the city from within and without a guest’s room. From our room, we could see beautiful Lake Michigan, the Shedd Aquarium, several marinas, and gorgeous views of the city.
On our most recent visit to Chicago, we went to the Fashion Outlets of Chicago, which are very near the Chicago O’Hare airport. Every store in the mall, including high-end brands like Gucci, Prada, Jimmy Choo, Burberry, Moncler, Theory, and more offer deeply discounted goods, up to 85% off.