Experience the ultimate ladies-only getaway in Chicago!
Join like-minded female travelers as we board the Amtrak train for a long-weekend getaway in Chicago.
Enjoy a stress-free adventure filled with shopping, iconic dining, and memory-making attractions.
Our journey begins as we make our way to Chicago
Today begins bright and early as we head to the Newton Train Station to board our morning Amtrak departure. Get ready for a stress-free and scenic journey into the heart of the Midwest!
Traveling by Amtrak offers a refreshing alternative to air or car travel. With wide, reclining seats, generous legroom, and panoramic windows, you’ll be able to stretch out, relax, and truly enjoy the ride. Roam the train at your leisure, settle in with a good book, or simply gaze out as the scenery transforms from rural landscapes to city skylines. There’s no need to worry about traffic, long airport lines, or cramped seating—just sit back and savor the journey.
Midday, we’ll gather in the Traditional Dining Car to enjoy a delicious two-course lunch service—just one of the many unique experiences onboard. Our train adventure concludes today as we arrive at Chicago’s historic Union Station, ready to begin the next chapter of our city getaway.
Stay in the heart of Chicago at a stunning hotel near the Magnificent Mile, where luxury and convenience meet. Just steps from world-class shopping, iconic landmarks, and vibrant dining, these hotels offer stylish accommodations with breathtaking city or lake views. Enjoy spacious rooms, modern amenities, rooftop lounges, on-site dining, and wellness facilities. Whether you're unwinding after a day of sightseeing or gearing up for a night on the town, the Magnificent Mile area puts you at the center of it all. It’s the perfect home base for exploring Chicago in comfort and style.
A visit to Chicago’s iconic Navy Pier offers the perfect blend of lakeside beauty, entertainment, and cultural experiences. Stretching into Lake Michigan, this vibrant destination features stunning skyline views, and lively public art. We plan to ride the famous Centennial Wheel—offering panoramic rides over the water. Optional activities include a stroll through beautiful gardens, browse unique shops, or catch a live performance at the Chicago Shakespeare Theater. Whether you're watching boats glide by or simply soaking up the atmosphere, Navy Pier delivers something for everyone. It’s an ideal stop for travelers who want to unwind, explore, and experience a true Chicago favorite in one scenic, walkable spot.
As the sun sets, we'll head to a nearby pizzeria for a true taste of Chicago—deep-dish style! A Chicago-style pizza dinner is a true deep-dish delight! Picture a golden, buttery crust baked in a deep pan, piled high with layers of gooey mozzarella, rich tomato sauce, and your favorite toppings. Served hot and hearty, each slice is a satisfying meal on its own. The atmosphere at a classic pizzeria is warm and welcoming—perfect for relaxing with fellow travelers after a day of sightseeing. Pair your pizza with a crisp salad, a local brew, or a classic soda for the full Chicago experience. It’s more than just dinner—it’s a delicious taste of the city’s proud culinary tradition.
Get to know Windy City!
The Shedd Aquarium in Chicago is a National Historic Landmark and one of the world's leading aquariums, featuring over 1,500 species of marine life. We will explore immersive exhibits like the Caribbean Reef, Wild Reef, and the Abbott Oceanarium, where beluga whales and dolphins delight. Hands-on experiences like stingray feedings and sea star touch tanks bring learning to life. Special animal encounters and behind-the-scenes tours offer unique, up-close experiences. With interactive exhibits, 4-D shows, and lakeside dining at the Bubble Net food court, Shedd offers a fun, educational day for all.
The Adler Planetarium offers an unforgettable experience for anyone seeking inspiration, discovery, and connection. As the first planetarium in the Western Hemisphere, it has been a Chicago lakeside icon since 1930. Explore the mysteries of the cosmos through award-winning Sky Shows in the dome theaters and uncover the universe’s secrets through immersive exhibits. Visit the historic Atwood Sphere for a glimpse of Chicago’s 1913 night sky, or peer into the universe through the Doane Observatory’s powerful telescope. Whether you're a lifelong stargazer or simply curious about the cosmos, the Adler blends science, history, and imagination to spark wonder at any age.
After a day of museum touring, enjoy a well-deserved free evening! Take time to unwind or discover the city at your own pace. Stroll along the Magnificent Mile for world-class shopping, enjoy a leisurely dinner at one of Chicago’s acclaimed restaurants, or catch live music at a cozy jazz lounge. Prefer to relax? Take in stunning skyline views with a walk along the Riverwalk or unwind at your hotel. Whether you’re up for adventure or ready to rest, this free night is yours to enjoy however you choose.
Immersion Day!!
A visit to the Field Museum in Chicago is a journey through time, nature, and cultures of the world—perfect for the curious. Explore ancient civilizations, marvel at towering totem poles, and meet SUE, the world’s most complete Tyrannosaurus rex. Discover rare gems, fossils, and mummies, or dive into science in the DNA Discovery Center. Wander through the expansive halls at your own pace or join a docent tour. With engaging exhibits, thought-provoking collections, and stunning architecture, the Field Museum offers an enriching and inspiring experience many different interests.
Chicago’s Willis Tower (formerly Sears Tower) offers sky-high thrills and unforgettable city views. Ride the elevator 103 floors up to the Skydeck, where panoramic sights stretch across four states on a clear day. Step onto The Ledge—glass boxes extending outside the building—for a heart-pounding, photo-worthy moment suspended above the city streets. Along the way, interactive exhibits showcase Chicago’s history, architecture, and iconic skyline. Willis Tower delivers a perfect blend of awe, excitement, and perspective from one of the tallest buildings in the Western Hemisphere.
After soaking in the sunset from one of the world’s tallest buildings, the night is yours to enjoy at your own pace! Dive into the energy of the city—browse the shops along the Magnificent Mile, indulge in a delicious dinner at a local hotspot, or settle in for relaxing at a local speakeasy. Want something even quieter? Have dinner delivered to the hotel and simply relax and recharge. Whether you're up for exploring or winding down, this evening is yours to savor.
I'll share a list of nearby recommendations to help inspire your plans!
Last, but not least. You're going to enjoy iconic sights of the city.
A brief stop in Grant and Millennium Park is the perfect way to experience some of Chicago’s most iconic sights. Stroll through beautifully landscaped gardens, admire public art, and snap a photo with the world-famous Cloud Gate—lovingly known as "The Bean." Enjoy the tranquil atmosphere of Crown Fountain and the architectural beauty of the Jay Pritzker Pavilion. Just steps away, Grant Park offers wide green spaces, views of the lakefront, and Buckingham Fountain, one of the largest in the world. It’s a refreshing, scenic break in the heart of the city.
An architecture tour on the Chicago River is a relaxing and inspiring way to explore the city’s world-renowned skyline. Guided by an expert, this one-hour cruise offers stunning views of architectural landmarks like the Willis Tower, Wrigley Building, Tribune Tower, and Aqua Tower. Learn fascinating stories behind Chicago’s rise from the Great Fire, the invention of balloon-frame construction, and the bold visions of legendary architects. From the water, you'll see the city's most iconic buildings in a whole new light, covering all three branches of the river with unbeatable photo opportunities. It’s a must for visitors!
A lunch stop at Portillo’s is a must for anyone craving a true taste of Chicago. Portillo’s combines a nostalgic, 1950s-themed atmosphere with fast-casual convenience. Everyone enjoys the fun retro décor, quick service, and hearty comfort food that hits the spot after a day of sightseeing. Whether you're diving into a loaded hot dog “dragged through the garden” or savoring a slice of their famous chocolate cake, Portillo’s delivers classic Chicago flavor with a side of local charm. It’s casual, delicious, and distinctly Windy City.
After our delicious lunch we will depart for Union Station and settle in onboard the Amtrak train to make our way back to Newton Station.
Enjoy your dinner in the dining car and discuss the wonderful time you had exploring Chicagoland.
We plan to arrive back in the early morning hours of Day 5.
Solo traveler, Private King Room $2950 pp.
2 Travelers, King Room, shared bed $1800 pp.
2 Travelers, Private Queen Bed in a shared two-bed room $1825 pp.
3 Travelers, 2 Queen Room, $1475 pp.
4 Travelers, 2 Queen Room, $1280 pp.
And much much more!!
Ideal For:
Adventurous ladies looking to connect with like-minded companions in a fun, supportive group setting
Young ladies ages 13+ are welcome! Minors under 18 must travel and room with a parent or legal guardian
Travelers who enjoy intimate group experiences—this tour is limited to a small group size of no more than 20, for a more personalized and connected vibe
Guests with moderate physical ability—lots of walking is planned. Mobility devices are welcome, but travelers must be able to manage independently.
Those open to the charm and ease of a more relaxed transit pace of train travel
Best for travelers who crave a short, high-energy getaway packed with culture, sightseeing, shopping, and culinary delights
Perfect for those who appreciate a thoughtfully planned itinerary with a balance of group fun and personal exploration time.
Not Recommended For:
Guests who prefer minimal walking—while there are no strenuous activities, the trip includes plenty of walking and time on your feet
Those who may have difficulty lifting or managing their own luggage
Children under age 13
Furry friends—pets are not allowed (service animals are welcome, in accordance with applicable law)
Travelers who need help managing mobility devices or wheelchairs—while activities and the train are accessible, participants must be able to handle mobility needs on their own
Anyone who requires medical support, medication, or equipment that can’t be managed independently
Group Travel Terms and Conditions:
Rates & Availability: All rates and availability are subject to change until payment is received and confirmation is . Prices are not guaranteed until full deposit is processed and booking is confirmed in writing.
Deposit: A refundable deposit (see terms below) of 50% per traveler is required at the time of reservation to secure space on the tour.
Final Payment: The remaining balance is due no later than 30 days prior to departure. Reservations made within 30 days of departure require full payment at the time of booking.
Late Payments: Failure to remit payment by the due date may result in cancellation of the reservation and forfeiture of deposit.
Confirmation: Booking is considered confirmed only upon receipt of the deposit and written confirmation from Here I Go Travel Co.
One guest 21+ years is required in each hotel room.
Cancellation Policy:
Cancellations made 60+ days before departure may receive a refund (excluding above cancellation fee), subject to supplier policies.
Cancellations 30–59 days before departure may receive a refund up to a 50% (excluding above cancellation fee), subject to supplier policies.
Cancellations less than 30 days before departure are generally non-refundable.
No-shows are non-refundable.
If the tour is canceled by Here I Go Travel Co. due to unforeseen circumstances or lack of minimum participants, a full refund will be issued.
Travel insurance is strongly recommended to protect your investment from circumstances beyond your control. Policy details and exceptions vary depending on the trip. A policy quote will be provided to each traveler.