Chicago: Skyline Dreams & Summertime Diva Energy

Divas in the City 2026 Summer Series:

Skyline Dreams & Summertime Diva Energy

Chicago, IL | July 9–13, 2026

Bold Beats & Southern Diva Heat

When the summer sun hits Chicago, the whole city glows—and so will you.

It’s time to trade your everyday for sky-high vibes, deep-dish indulgence, and streets humming with rhythm, style, and soul. This July, Travel Divas is bringing the glam to the Windy City for a weekend of joy, connection, and culture made just for you.

We’re posted up at theWit Chicago, a sleek downtown stay where modern meets magnetic. From lakefront views to rooftop lounges where you can toast to your brilliance, every moment of this trip is laced with legacy, elegance, and real Black woman joy. We’ll stroll through historic neighborhoods, support Black-owned gems, and get a taste of the rich, proud pulse that powers the city.

✓ This is a celebration of culture, connection & confidence.
✓ Summertime Chi, the Diva way.
✓ Get into this glow-up.

This isn’t just a vacation—it’s an invitation to reconnect with yourself and your squad while soaking in the magic of Summertime Chi.

THIS IS TRAVEL, THE DIVA WAY.

Stay at theWit, where bold design meets prime downtown energy
Connect with dynamic, joy-forward women during our signature meet & greet
Explore the city’s rich Black history and cultural landmarks
Snap pics under skyline sunsets and city lights
Indulge in food, fun, and moments that pour right back into you

WHAT TO

EXPECT

LAND ONLY PACKAGE

INCLUDES:

Testimonials

I usually travel solo. I tried group travel once b4 liked it but not how was ran. I tried with the Travel Divas and loved it. Everything was wonderful. It was well beyond my expectations. I am looking for another trip for 2027.

Antoinette G.

I like Travel Divas because it provides me with opportunity to be a part of a Sistahood and travel to other parts of the world. Experiencing different cultures while learning their history.

Angela H.

My experience was full of culture, activities and Laughter!! I had Amazing Hostesses, great Food and long days!!! I love the Traveldivas because they make sure you are taking care of from the time you book till the time you say your good byes 🥰 Always a great time!!!

Monique W.

It was a very good success, all was planned well with expertise and dedication in what you do I enjoyed the moments big time

Ronald W.

I've been to 2 trips with these ladies and I'm ready to go to 20 more. Of you're looking to just plug and play, these ladies are EXPERTS. 10 out of 5.

Fritz S.

My trip was phenomenal. Accommodations were top notch, itinerary was packed full of fun, was well fed everyday, met some wonderful people. Looking forward to many many more trips with the Divas

Tj T.

ACCOMMODATION

DETAILS

Located in the heart of the Loop, theWit Chicago is your bold, boutique launchpad for experiencing the city’s best. Think sleek rooms, dramatic city views, and rooftop nights you won’t forget. This isn’t just where you sleep—it’s where your Chicago story begins.

Room & Resort Amenities:

King or Double Queen Beds with Plush Linens
Floor-to-Ceiling Windows with City Views
Flat-Screen HDTV & Free WiFi
Spa-Inspired Bathrooms with Luxe Toiletries
24-Hour Room Service
Rooftop Lounge & Award-Winning Dining
Onsite Spa, Fitness Center & Concierge
Steps from the Riverwalk, Millennium Park & More

Reserve Your Trip Now

Reserve Your

Trip Now

LAND ONLY PACKAGE WITH NO FLIGHTS

SINGLE:
$2999
per person

DOUBLE:
$1999
per person

ADDITIONAL

INFORMATION

WHAT’S NOT INCLUDED:

Flights or transportation to/from Chicago, IL
Airport transfers or rideshare/taxi services
Meals and beverages (unless otherwise noted)
Gratuities (suggested: $5–$10 per day)
Travel Insurance (highly recommended)
Items of a personal nature
Optional excursions, nightlife, or entertainment not listed in package

TRAVEL INSURANCE:

Missing a vacation is bad enough. Losing the money you paid for your vacation is even worse. Trip insurance is therefore recommended. You can purchase travel insurance on your own.
Travel Guard
TravelEx

AUTOMATIC BILLING PLAN:

You can enroll in our automatic billing and relax knowing that your future payments will be made automatically. When you book, we’ll calculate an evenly divided automatic billing plan for you, and you will know in advance the day of every month that your payment will be processed. Your initial deposit is due at the time of booking, and your future payments will be charged according to the schedule you see on your invoice. Automatic billing is available at no charge.

TRAVEL NOTES:

Roommate Matching is available. Select “Roommate Requested” on your reservation form if you’d like to be paired. Matches will be made 45 days before departure once 75% of your package is paid.
Final itinerary, event details, and helpful travel tips will be emailed 30–60 days prior to travel.
A credit card is required at hotel check-in to cover incidentals.
All pricing is based on current rates and availability. In the event of changes or updates from suppliers, your invoice will reflect any necessary adjustments.

TERMS & POLICIES:

All payments are non-refundable and non-transferable.
You may pay in full at booking or select a monthly payment plan.
Payment plans include automatic billing, which can be opted out of by emailing: info@thetraveldivas.com.
Travel documents and final instructions will be emailed once full payment is received.
It is each guest’s responsibility to update us with any email address changes to ensure timely delivery of travel info.
Any name or occupancy changes should be directed to the Travel Divas Team. Failure to do so results in a $250 Name Change Fee + any vendor fees.
Late payment of $250 per person is required after the final payment date on your invoice.
A reinstatement fee of $250 per person is required in addition to your past due balance in order to reinstate your booking anytime after cancellation.
Men are welcome on this trip when traveling and rooming with a woman in your party.

IMPORTANT LINKS

Terms and Conditions | FAQs of Automatic Billing Option | Travel Divas Private Member’s Only Group

Skyline Dreams & Summertime Diva Energy

THIS IS TRAVEL, THE DIVA WAY.

WHAT TO

EXPECT

Walking & Adventure Level:

Native Language:

Travel Style:

In Destination Airport Transfers:

Cuisine:

Leisure Downtime: