Text Us at (770) 232-6483
Text Us at (770) 232-6483
June 24-28, 2027 | 4 Nights | Thu – Mon
A curated escape for women ready for lakefront skylines, bold architecture, world-class dining, and a sisterhood that makes a big city feel personal.
Leave the routine behind for a Chicago weekend that is bold, bright, and built for celebrating.
The Windy City shows off all summer. The skyline mirrored in The Bean at Millennium Park, a breezy walk along Lake Michigan, dinners that range from celebrated chefs to the Black-owned brunch spots of historic Bronzeville, and Great Migration roots that shaped American blues, gospel, and so much of who we are.
This is the weekend you stop saving for someday. Chicago is big enough to match your energy and warm enough to feel like a homecoming, all at once.
City Energy in the Heart of Chicago’s Loop
Bold, contemporary, and positioned at the center of Chicago’s Theatre District, theWit offers a vibrant home base for experiencing the city. With skyline views, a celebrated year-round rooftop, inviting dining spaces, and walkable access to the Riverwalk, Millennium Park, and downtown attractions, this stay places guests close to Chicago’s culture, entertainment, and unmistakable energy.
Hotel Amenities:
Yes. Many guests come solo. This experience is designed to feel welcoming whether you arrive alone or with friends.
No. Flights are not included. This is a land-only package.
Two Options
Yes. The weekend is designed with a balance of curated Travel Divas moments and personal time. You will have an entire day to explore on your own, along with recommendations.
Dress in polished city-chic attire with comfortable daytime outfits and elevated evening looks. A style guide will be shared before departure. You will also receive a Travel Divas Store gift card to purchase the official destination T-shirt, and your trip host will let you know when to wear it.
Yes. Payment options are available when booking 120 days or more before departure. You have a choice to pay monthly or bi-weekly. Autopay is available and highly recommended.
Choose the weekend that feels bold and bright, the celebration you keep telling yourself you will get to one day.
A beautiful stay in the heart of Chicago’s Loop. A curated Travel Divas experience. A circle of women ready to make it unforgettable.
Questions? Text us at (770) 232-6483
This experience may include walking, standing, hotel entryways, city sidewalks, stairs, ramps, elevators, restaurants, event venues, and transportation areas that vary in accessibility.
Travelers requiring mobility assistance, medical accommodations, dietary considerations, or special support are encouraged to notify Travel Divas in advance so we can share requests with the appropriate suppliers where possible.
While accessibility and accommodation requests may be submitted, they cannot be guaranteed. Guests are responsible for determining whether this experience is suitable for their individual mobility, health, and comfort needs.
Missing a trip is disappointing. Losing the money you paid for it can feel even worse. Travel insurance is strongly recommended to help protect your investment.
You may purchase travel insurance on your own through providers such as:
Due to contractual obligations with our suppliers, monthly or bi-weekly payments are required unless your reservation is paid in full. Auto pay is highly encouraged to help keep your reservation current and avoid missed payments.
Automatic billing is complimentary and allows your remaining balance to be divided into scheduled payments after your initial deposit.
Payment dates and amounts will be outlined on your invoice at the time of booking.