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Chicago Weekend

Join Us for an Unforgettable Women’s Weekend in Chicago!

Ladies, it’s time to pack your bags and escape to the vibrant city of Chicago, IL for a weekend filled with fun, relaxation, and unforgettable memories! Friday June 13 - Sunday June 15, 2025

Stay in luxury and comfort at the Hilton Suites on the Magnificent Mile, just steps from world-class shopping, renowned restaurants, and breathtaking views of Lake Michigan.

cindygaffney@travelmation.net

Cindy Gaffney

Trip Information

Trip Information

Friday June 13 - Sunday June 15, 2025

I’m so excited to host this incredible women’s weekend in Chicago—my hometown! As a local, I can’t wait to share the best of this amazing city with you, from its iconic landmarks and world-class shopping to its incredible food and hidden gems.

We have a block of rooms reserved at the Hilton Suites on the Magnificent Mile.

Located in the heart of Chicago's city center, Hilton Chicago/Magnificent Mile Suites offers exceptional accommodations within walking distance to major attractions.  Amenities include an indoor pool, fitness center, lounge and restaurant on site. 

This is an all-suite hotel and each room also has a pull out sofa.

Our group rates are: 

$279 for a King Bed One Bedroom Suite

$304 for a Two Double Bed One Bedroom Suite 

*Rates are quoted before occupancy tax of 17.39%

I will provide you with a booking link to reserve your room at these discounted rates.

Jun 13 ·
Friday

Arrival and Check In - Hilton Suites on the Magnificent Mile

Arrive anytime on Friday June 13. 

Hotel check in begins at 3:00 p.m.

Meet and Greet
Activity ⸱ Fri, Jun 13 at 5:00pm

Join the group for a meet and greet in the hotel lounge! 

Group Dinner
Activity ⸱ Fri, Jun 13 at 6:30pm
Location
TBD

Join the group for an optional dinner at a nearby location to be announced closer to the trip.

Note: Meal price is not included in the room rate. 

Jun 14 ·
Saturday - Optional Activities

Michigan Avenue Walking Tour – From the Hilton Chicago Magnificent Mile to the Starbucks Reserve Roastery
Activity ⸱ Sat, Jun 14 at 9:30am

Step out of the Hilton Chicago Magnificent Mile Suites and onto one of the most famous streets in the world—Michigan Avenue—for a walking tour filled with history, architecture, and a special coffee experience!

Starting at the northern end of the Magnificent Mile, we’ll stroll south along Michigan Avenue, taking in the breathtaking skyline and discovering the rich history behind Chicago’s most iconic buildings. Along the way, we’ll pass legendary landmarks like:

  • The John Hancock Center – One of the tallest buildings in the city, offering incredible views of the skyline and Lake Michigan.
  • The Historic Water Tower & Pumping Station – One of the few buildings to survive the Great Chicago Fire of 1871, now a symbol of the city's resilience.
  • Tribune Tower – A neo-Gothic skyscraper adorned with stones from historic sites around the world.
  • The Wrigley Building – A dazzling white terra-cotta masterpiece that has been a Michigan Avenue staple since the 1920s.

Midway through our journey, we’ll arrive at the Starbucks Reserve Roastery, the largest Starbucks in the world and a coffee lover’s dream. Take a break from walking to explore this five-story coffee palace, where you can:
☕ Enjoy a handcrafted specialty coffee or tea
🥐 Indulge in freshly baked Italian-inspired pastries
🔥 Watch master roasters at work, creating exclusive small-batch blends
🍸 Sip on a unique coffee-infused cocktail at the Arriviamo Bar

Experience Chicago’s Breathtaking Skyline on an Architecture River Cruise
Activity ⸱ Sat, Jun 14 at 12:00pm
Duration
90 minutes

Sit back, relax, and take in some of Chicago’s most iconic views on this architectural river cruise—a must-do experience in the Windy City! Glide along the Chicago River as your expert guide shares fascinating stories and insider details about the city’s renowned skyline. Along the way, marvel at architectural masterpieces like the Wrigley Building, Tribune Tower, and the John Hancock Building, all from a unique waterfront perspective.

This tour covers multiple branches of the Chicago River, offering an unbeatable way to explore the city in a time-saving and scenic fashion. Whether you're a first-time visitor or just short on time, this cruise provides stunning photo opportunities and a deeper appreciation for Chicago’s world-famous architecture—all without the crowds of street-level sightseeing.

I will secure tickets with the exact time once we know how many are interested in this. Tickets are typically $49 per person. 

Andersonville Midsommarfest
Activity ⸱ Sat, Jun 14 at 5:00pm

We will head North of Downtown Chicago to visit Andersonville Midsommarfest: A Celebration of Music, Culture, and Community

One of Chicago’s oldest and most beloved street festivals, Andersonville Midsommarfest transforms Clark Street into a lively hub of music, dance, and community spirit every second weekend in June. Rooted in the Swedish Midsommar tradition, this vibrant festival welcomes the summer season with a dynamic mix of live performances, delicious food, and an eclectic street fair featuring local artisans, businesses, and non-profits.

More than just a street festival, Midsommarfest is a cherished tradition that embodies the heart of the Andersonville community. The event is known for its inclusive and welcoming atmosphere, proudly celebrating diversity, LGBTQIA2+ pride, and the power of connection. Whether you're here to dance to live music, explore unique vendors, or simply soak in the energy of the crowd, Midsommarfest is the perfect way to kick off summer in Chicago!

We can opt to partake of local street fare from the various vendors or find a restaurant to sit down for dinner. There will be plenty of live music and fun! 

Jun 15 ·
Sunday

Departure

Depart anytime. 

Hotel check out is 11:00 a.m. 

I am happy to coordinate additional activities for those not departing until later in the day. 

Optional Group Breakfast

Join the group for an optional group breakfast prior to departure.