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Five Star Hotels in Chicago

Curated by
Katie McAvoy
Chicago might not be the first place you think of for a luxury getaway. As a local, I may be a bit biased, but if you love great food and fabulous five-star luxury hotels, you need to get here. Did I mention that it’s an easy flight from just about anywhere in the US? Yes, winters can be cold, but with these hotels you don’t need to go anywhere but down to the spa. There are so many amazing five star hotels in Chicago that it was a challenge to pick my top 5, but here they are! Weekend away, planned.

Fun Christmas in Chicago

Curated by
Erica Christie
There’s something magical about Christmastime in Chicago. Not even the Grinch could resist feeling festive amidst the twinkling lights, ice skating, Christmas markets, and beautifully decorated hotels and restaurants. A Christmastime trip to Chicago will leave you feeling like a kid again!

Three–Day Group Trip in Chicago

Curated by
Alicia Anderson
Chicago – the Second City, the Windy City, City by the Lake, My Kind of Town. Whatever Chicago is to you, for me it is home! I recently had the pleasure to book a three-day corporate group for some clients in my home city, and no matter the season, Chicago has a lot to offer to groups of all sizes. Reach out to me for help booking your group trip to Chicago!

Time to be Pampered: Chicago's Best Luxury Hotels

Curated by
Katie Larsen
Chicago is a city full of culture, incredible food, shopping and entertainment. It also is home to some of the most luxurious hotels in the world. I’ve been lucky enough to spend time in what I would consider the top tier luxury hotels in Chicago and am ready to spill details on all of the best kept rooms and suites, spas, amenities and secrets with others to enjoy as well.

Elope in Chicago

Curated by
Alexandra Vigilante Chamberlin
Eloping in Chicago offers couples a perfect blend of romance, charm, and convenience. In this easy to reach metropolis with stunning backdrops ranging from the iconic skyline to picturesque parks, couples can intimately exchange vows amidst the city's beauty. Traditional weddings can be expensive, stressful affairs while eloping allows couples to embrace spontaneity, be authentic to their values, and still treat themselves to luxury. Chicago's vibrant culinary scene, rich cultural offering, and architectural wonders ensure an unforgettable and personalized elopement experience for every couple.

Chicago: Lollapalooza Weekend

Curated by
Meghan Irle
Chicago is a magical city, especially in the summertime. Attending Lollapalooza is a whole other beast. People travel from all over the world to attend the acclaimed festival which is located in Grant Park, AKA, the heart of the downtown. It is crucial that you plan your trip accordingly so you can get the best of the city while enjoying the art and culture of the festival.

A Rain or Shine Guide to the Windy City: Chicago, Illinois

Curated by
Jordan Schack
Visit Chicago this July and you'll get why some people say that a summer in Chicago is the best season in the world (it is). The city that I call home goes toe to toe with the best in the world, blending international flair with local charm, Michelin star restaurants with dive bars slinging hand made tamales. Chicago has forged its unique identity, filled with Midwestern charm, a food scene second to none and world-class attractions. Come for the deep dish, fall in love with the architecture, but don't you dare put ketchup on your hotdog.

Checking Into: Chicago

Curated by
Payton Brown
Chicago is a large metropolis located in the Mid-West of the United States that hosts a vast opportunity to learn about history or immerse yourself with art. Chicago developed into the expansive city that we know today and is popular for its walkability and convenient transit options to tour is town. You can spend time on the river walks surrounded by aesthetically designed skyscrapers, tour the streets and view wonderfully crafted artistry, or connect with locals over delicious deep-dish pizza.

A Perfect Day as a Chicago Local: Exploring Wicker Park & Bucktown

Curated by
MaryAlexa Divver
Wicker Park, Bucktown and Logan Square are some of Chicago's most vibrant neighborhoods, offering a mix of history, culture and creativity. Whether you're drawn to the eclectic boutiques, artistic vibes or the diverse culinary scene, this area is perfect for a day of exploration. From cozy breakfast spots to trendy dinner destinations, and everything in between, these neighborhoods provide a perfect snapshot of Chicago’s unique charm and energy.

Experience City Travel Like a Local: Chicago, Illinois

Curated by
Courtney Johnson
Chicago is my favorite city. I loved to visit so much that I spent years trying to move here, and now I've lived here for six years! Each area of the city has a unique vibrant culture and feel, but the city is easier to explore than New York or LA because it's smaller and still very accessible. Chicago has everything you could want — incredible food, unique attractions and a gorgeous shoreline.
Suggested Fora Advisors
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Katie McAvoy
Destination daydreamer and family CEO (chauffeur, entertainment concierge and organizer) for three boys and a dog. I love Chicago, live music, books, pasta, nature and feelings of discovery.

Erica Christie
I am a meticulous researcher with a massive case of wanderlust. Let's work together to craft an authentic and fun adventure that feels perfectly personalized to you!

Katie Larsen
Travel-obsessed detailed planner who is always wanderlust. Adventure seeker who wants to stop worrying about the small things and enjoy the journey.

Alicia Anderson
Scuba diver. Airline miles collector. Planner of all things, when I'm not planning travel I'm also a wedding and event planner!

Courtney Carter
A curious traveler who isn't afraid of solo travel. Turndown service + ocean views = paradise to me!

Morgan Dowling
The go to "planning" friend with a passion for unique, luxury destinations and detailed research and itineraries.

MaryAlexa Divver
Beach, mountains, food and shopping – in no particular order. Lover of all things adventure, sun, snow and new experiences. Currently calling Brooklyn home.

Courtney Johnson
A Chicago-based adventurer who lives to plan her next trip to a new destination to experience the food and culture (but mostly the food).

Jonna Robertson
Chicago-based travel advisor fueled by curiosity and compassion. Ask me about the UK, Alaska, expeditions, "cool-cations" and ethical wildlife encounters.

Meghan Irle
Chicago advisor who thrives on the logistics of planning seamless getaways. Boutique hotels are my love language, and I curate stays that balance adventure, relaxation and the perfect touch of luxury. When I’m not mapping out dream itineraries, you’ll find me with a book in hand, chasing new experiences or dancing the night away.

Amanda Schneider
As a passionate travel advisor, I specialize in crafting personalized, unforgettable journeys with exclusive perks, upgrades, and VIP experiences!

Kari Bradbury
When I'm not planning unforgettable getaways, you’ll find me enjoying food, family, and friendship or discovering new destinations. I believe in the magic of shared experiences, laughter, and a touch of spontaneity to make every journey special.