Chicago Girls Trip Itineraries

Chicago Girls Trip Itineraries

Why vacation with your girl friends?

Planning a vacation with your girlfriends can be an incredibly rewarding and enriching experience for several reasons:

1. Bonding: Vacationing with friends allows you to strengthen your bonds and create lasting memories together. Shared experiences, adventures, and laughter can deepen friendships and create a stronger sense of camaraderie.

2. Support System: Your girlfriends can provide valuable emotional support and companionship during your travels. Whether you're exploring new destinations, navigating unfamiliar situations, or simply relaxing on the beach, having your friends by your side can make the experience more enjoyable and stress-free.

3. Shared Interests: Planning a vacation with friends gives you the opportunity to pursue shared interests and activities. Whether you're foodies looking to indulge in culinary delights, adventure seekers craving outdoor thrills, or culture enthusiasts eager to explore museums and landmarks, traveling with friends allows you to tailor your itinerary to suit everyone's interests.

4. Empowerment: Traveling with girlfriends can be empowering and confidence-building. Exploring new destinations, trying new experiences, and navigating unfamiliar environments together can boost self-esteem and foster a sense of independence.

5. Fun and Laughter: Vacations with friends are often filled with fun, laughter, and spontaneous adventures. Whether you're sharing inside jokes, trying new activities, or simply enjoying each other's company, traveling with friends can bring joy and laughter into your life.

6. Shared Expenses: Splitting the cost of accommodations, transportation, and activities with friends can make travel more affordable and budget-friendly. Sharing expenses allows you to enjoy luxurious experiences and accommodations that might be out of reach on your own.

7. Different Perspectives: Traveling with friends can provide fresh perspectives and insights as you explore new destinations together. Sharing travel experiences with friends from different backgrounds and life experiences can enrich your own understanding of the world and broaden your horizons.

8. Memorable Experiences: From epic adventures to quiet moments of reflection, vacationing with friends can create unforgettable experiences that you'll cherish for years to come. Whether it's watching a sunset on the beach, hiking to a breathtaking vista, or simply sharing a meal together, the memories you create with your girlfriends will last a lifetime.

Chicago Girls Trip Itineraries

How to plan a girls trip:

Planning a girls' trip can be exciting and rewarding. Here's a step-by-step guide to help you plan a memorable getaway with your girlfriends:

1. Choose Your Destination: Discuss potential destinations with your girlfriends and decide on a location that appeals to everyone's interests and budget. Consider factors such as travel time, activities available, weather, and any special events happening at the destination during your planned dates.

2. Set a Date: Coordinate schedules and choose dates that work for everyone. Consider factors such as work schedules, family commitments, and any other prior engagements. Aim for a timeframe that allows everyone to relax and enjoy the trip without feeling rushed.

3. Create a Budget: Determine a budget for the trip, taking into account expenses such as transportation, accommodations, meals, activities, and souvenirs. Discuss budget expectations with your friends to ensure everyone is comfortable with the proposed expenses.

4. Book Accommodations: Research and book accommodations that suit your group's preferences and budget. Whether you prefer a luxury hotel, a cozy vacation rental, or a budget-friendly hostel, make reservations well in advance to secure the best options.

5. Plan Activities: Brainstorm activities and attractions you'd like to experience during your trip. Consider everyone's interests and preferences, whether it's exploring cultural landmarks, trying local cuisine, shopping, or enjoying outdoor adventures. Create a rough itinerary with flexibility for spontaneous activities.

6. Arrange Transportation: Determine the most convenient and cost-effective transportation options for reaching your destination and getting around once you're there. Whether you're flying, driving, or taking public transportation, make arrangements in advance to ensure a smooth journey.

7. Pack Wisely: Encourage your friends to pack light and efficiently, considering the climate and activities planned for the trip. Create a packing list to ensure everyone brings essential items such as clothing, toiletries, medications, and any necessary travel documents.

8. Stay Organized: Keep all trip-related information, including reservations, itineraries, and contact details, organized and easily accessible. Consider creating a shared digital document or group chat to keep everyone informed and updated throughout the planning process.

9. Safety Precautions: Prioritize safety during your trip by researching any potential risks or hazards at your destination and taking necessary precautions. Share emergency contact information and establish a plan for staying in touch and looking out for each other during the trip.

10. Have Fun!: Once you've completed the planning process, relax and enjoy your girls' trip to the fullest. Embrace new experiences, savor quality time with your friends, and create unforgettable memories together. Don't forget to capture photos and souvenirs to commemorate your adventure!

Chicago Girls Trip Itineraries

Why visit Chicago on your next girls trip?

Chicago offers a plethora of attractions and activities that make it an excellent destination for a girls' trip. Here are several reasons why:

1. Cultural Diversity: Chicago is a melting pot of cultures, offering a rich tapestry of experiences from diverse neighborhoods like Chinatown, Pilsen, and Little Italy. Exploring these areas can be both enlightening and entertaining.

2. Shopping: The Magnificent Mile is a shopper's paradise, featuring upscale boutiques, department stores, and designer labels. Additionally, neighborhoods like Wicker Park and Bucktown offer unique shops and vintage finds.

3. Cuisine: Chicago is renowned for its food scene, from deep-dish pizza to gourmet dining. The city boasts numerous Michelin-starred restaurants, ethnic eateries, and trendy brunch spots. Food tours and cooking classes can also be a fun activity for a girls' trip.

4. Arts and Culture: Chicago is home to world-class museums like the Art Institute of Chicago, the Museum of Contemporary Art, and the Field Museum. The city also hosts numerous theaters, galleries, and live music venues, offering a vibrant arts and culture scene.

5. Architecture: Chicago is famous for its stunning architecture, with iconic landmarks like the Willis Tower (formerly known as the Sears Tower), the John Hancock Center, and the historic Wrigley Building. Architectural boat tours along the Chicago River provide an excellent way to admire the city's skyline.

6. Outdoor Spaces: Millennium Park, with its iconic Cloud Gate sculpture (affectionately known as "The Bean"), is a must-visit destination for tourists. The city also offers beautiful lakefront parks, beaches, and outdoor activities like kayaking and biking along Lake Michigan.

7. Nightlife: From rooftop bars with stunning views to trendy clubs and speakeasies, Chicago offers a vibrant nightlife scene. Whether you're looking to dance the night away or enjoy craft cocktails with friends, there's something for everyone.

8. Relaxation: If relaxation is on the agenda, Chicago has plenty of spas and wellness centers where you can indulge in massages, facials, and other pampering treatments.

9. Events and Festivals: Chicago hosts numerous events and festivals throughout the year, celebrating everything from food and music to culture and art. Planning your trip around one of these events can add an extra layer of excitement to your girls' getaway.

10. Accessibility: Chicago is easily accessible by plane, train, or car, making it a convenient destination for travelers from all over the country. Once you're in the city, the efficient public transportation system makes it easy to get around and explore everything Chicago has to offer.

Chicago Girls Trip Itineraries

Chicago Girls Trip Itineraries:

1 - A Chicago Bachelorette Party itinerary -

• Thursday:

  • Check into AirBnB, we stayed at the ALOHA | Tropical Penthouse

  • Hang out at the AirBnb and a game of Chopped

• Friday:

  • Brunch at the AirBnb

  • Lunch in a cabana at Shore Club and hang out on the beach

  • Group photoshoot

  • Dinner at Paradise Park Pizza

  • Bar Hop

• Saturday:

  • Brunch at the AirBnb

  • Bungee or other unique fitness class (the place we went to has since closed)

  • Afternoon snack at JoJo’s Shake Bar

  • Drag Show

  • Evening Fireworks Architecture Cruise

Chicago Girls Trip Itineraries

2 - A College Sorority Chicago Reunion Itinerary -

• Thursday:

  • Check into Airbnb, we stayed at Stylish 2-Level Designer Home by DePaul

  • Order Deep Dish pizza from Lou Malnati’s

• Friday:

  • Breakfast at Cafe Deko

  • Cubs Game

  • Afternoon drinks at Alma at Hotel Zachary

  • Dinner at Adalina Italian Cuisine

• Saturday:

  • Coffee at Printer’s Row Coffee Co.

  • Permanent Bracelet Appointment at Alexandra Marks

  • Brunch at Lyra

  • Color Factory

  • Shop and Walk Mag Mile, take a Water Taxi

  • Dinner at the Airbnb

• Sunday:

  • Head home

Chicago Girls Trip Itineraries

3 - A 20th High School Reunion Chicago Itinerary -

• Thursday:

  • Check into Airbnb, we stayed at Large 3BR/2BA Wicker Park Apt +Free Garage Parking

  • Order Deep Dish pizza from Pequad’s

  • Private karaoke room at King Karaoke to sing favorite songs from high school

• Friday:

  • Breakfast at West Town Bakery

  • Chat and catch up at the AirBnb

  • Lunch at Portillo’s

  • Architecture Boat Tour

  • Dinner at Ramen-San

  • Cocktails and Dancing at Good Night John Boy

• Saturday:

  • Brunch at RJ Grunt’s

  • Explore the city

  • Baking Class at Bettie’s Chicago

  • Come home and freshen up

  • Dinner at Beatnik West Town

• Sunday:

  • Head home