Chicago and New York City
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Get ready for your trip to Chicago, where you can marvel at the stunning architecture of the Willis Tower and the historic charm of Navy Pier, all while savoring deep-dish pizza and strolling along the scenic Lake Michigan waterfront. The city's rich cultural scene, from the Art Institute to the jazz clubs of Lincoln Park, provides a dynamic backdrop. Transitioning to New York City, the energy shifts to a frenetic pace, where iconic landmarks like Times Square, Central Park, and the Statue of Liberty dominate the skyline. Here, the diverse culinary landscape and Broadway shows offer endless entertainment options. Each city has its own unique rhythm and charm, making the journey between them an exhilarating blend of Midwestern warmth and East Coast bustle.
15 - 20 October
- Chicago, IL | 5 nights | Fairmont Chicago Millennium Park
20 - 28 October
- New York, NY | 8 nights | The Times Square EDITION
In October, Chicago experiences a crisp and often unpredictable transition from fall to winter. Average daytime temperatures typically range from the mid-40s to mid-60s Fahrenheit (around 7-18°C). Early in the month, you might enjoy mild weather with plenty of sunshine, but as the month progresses, temperatures can drop and rainy days become more common. By late October, you might even see the first hints of frost. It's a good idea to bring layers and a warm jacket to stay comfortable while exploring the city’s parks and outdoor attractions. The fall foliage along the lakefront and in Chicago's many parks adds a colorful touch to the cityscape.
In October, New York City enjoys a pleasant autumn climate with moderate temperatures and crisp air. Daytime highs typically range from the mid-50s to mid-60s Fahrenheit (around 12-19°C), while nighttime temperatures can drop to the 40s Fahrenheit (4-9°C). The weather is generally sunny and dry, but occasional rain showers can occur. The fall foliage in Central Park and throughout the city provides a stunning backdrop of vibrant colors. It’s a great time to explore outdoor attractions and enjoy the city’s parks, with a comfortable coolness that’s perfect for walking and sightseeing.
These guidelines are for reference only. Scenset holds no responsibility for travel restrictions. Travelers are responsible for ensuring the right documentation to travel.
Welcome to Chicago! Once you land, you will have transportation from the airport to a hotel.
Why we love it for you The Fairmont Chicago Millennium Park is a luxurious oasis in the heart of downtown Chicago, offering an elegant retreat with unparalleled access to the city's vibrant attractions. Situated just steps from Millennium Park, the hotel boasts sophisticated rooms with stunning views of the city skyline or Lake Michigan. Guests can indulge in upscale dining, relax at the stylish lounge, or rejuvenate at the modern fitness center. With its prime location, the Fairmont provides convenient access to cultural landmarks like the Art Institute of Chicago and the historic Chicago Theater, making it an ideal base for exploring the best of the Windy City.
Fairmont Chicago at Millennium Park
- Fairmont King
- King Sized Bed
- Full En Suite Bathroom
Once you've settled in to your accommodation, get ready for an afternoon food tour and full dinner experience.
Experience a half-day tour that will allow you to take full advantage of Chicago’s fantastic food scenset. You’ll taste all of the must-eat dishes, as well as having time to try an iconic deep-dish pizza, get behind the scenes at a local coffee roastery, and try some tasty desserts at a chocolate factory. This tour will give you a chance to truly craft your perfect Chicago tasting menu, from beginning to end.
Good morning and get ready for a full day of being a true tourist. You will start your day off on a Chicago River Electric Boat tour.
These little picnic boats are our most popular model and offer a super smooth, quiet ride. At 18 feet in length, these boats sit up to 8 people and have a fully covered seating area with optional clear window flaps.
Once you finish up your tour, grab a bite to eat at one of these iconic restaurants.
Lou Malnati’s: A staple of Chicago’s deep-dish pizza scenset, Lou Malnati’s serves up rich, cheesy pizzas with a buttery crust and abundant toppings, making it a popular choice for a hearty lunch.
Portillo’s: An iconic Chicago chain known for its classic Italian beef sandwiches, Chicago-style hot dogs, and rich chocolate cake. Portillo’s offers a quintessential taste of Chicago's fast-casual dining scenset.
After lunch, experience breathtaking city views from the top of Willis Tower.
Ascend to the Skydeck on the 103rd floor and step out onto The Ledge, a glass-floored observation area that offers a thrilling, unobstructed view of the city's skyline and beyond. From this vantage point, you can see up to four states on a clear day, making it an unparalleled spot for panoramic photos and awe-inspiring vistas. The experience combines cutting-edge architecture with an exhilarating perspective, encapsulating the grandeur of Chicago from above.
The rest of the evening has been left for you to relax and explore at your own pace.
Fairmont Chicago at Millennium Park
- Fairmont King
- King Sized Bed
- Full En Suite Bathroom
Start your morning off at your own pace. Grab a bite to eat or take a walk around downtown before your Chicago Architecture by Train Experience.
The Allis: Located in the nearby Soho House, The Allis offers a chic atmosphere with a menu featuring fresh pastries, hearty breakfasts, and specialty coffee. It’s a stylish spot for a relaxing morning meal.
Wildberry Pancakes and Cafe: A short walk from the Fairmont, Wildberry is renowned for its extensive pancake and waffle menu, along with delicious omelets and hearty breakfast plates. It’s a favorite for a classic, satisfying breakfast.
The Gage: Situated across from Millennium Park, The Gage provides a hearty breakfast menu with options ranging from traditional eggs benedict to flavorful breakfast sandwiches. It’s a cozy spot with a robust menu.
After lunch, explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop.
The city's first elevated train started making trips in 1892. Now considered one of Chicago’s most defining features, the "L" offers incredible views of downtown. By being more than 20 feet off the ground, you'll see architectural details that are missed by most pedestrians at street level. This is our most comprehensive tour in the Loop, passing hundreds of buildings and highlighting ones of architectural significance.
In the evening, escape into Chicago's underworld on a crime and mob tour with stops on and off the climate-controlled bus.
Walking tour paths explore historic crime scenes with great photo opportunities. True crime stories about Chicago gangsters, The Untouchables, The Chicago Mob, Prohibition, and more. Visit historic landmark buildings: Biograph Theater, Holy Name Cathedral, Cook County Criminal Courthouse, Harry Caray’s Italian Steakhouse, etc. Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational, entertaining and cultural attraction is a unique and fun thing to do in Chicago.
Fairmont Chicago at Millennium Park
- Fairmont King
- King Sized Bed
- Full En Suite Bathroom
Today you will get to visit one of Major League Baseball's most historic ballparks, Wrigley Field.
A tour of Wrigley Field, one of Major League Baseball’s most historic ballparks, offers a fascinating glimpse into the rich history and unique charm of Chicago’s beloved stadium. Established in 1914, Wrigley Field is renowned for its iconic ivy-covered outfield walls and charming manual scoreboard. On the tour, you'll explore areas usually reserved for players and staff, including the dugouts, press box, and the private suites. You'll also get to learn about the park's storied past, including its role in baseball history and memorable moments that have taken place there. The tour provides insights into the stadium’s architecture, the renovation efforts over the years, and behind-the-scenes anecdotes, making it an essential experience for baseball fans and history enthusiasts alike.
After visiting Wrigley Field, grab a bite to eat before taking a Chicago Movie and TV Tour!
A Chicago movie tour offers a fascinating exploration of the city’s prominent role in film history and its iconic locations featured on the big screen. On this tour, you’ll visit famous sites such as the historic Chicago Theater, which has appeared in numerous films, and the legendary Union Station, known for its appearances in classics like "The Untouchables." You'll also see locations from "Ferris Bueller's Day Off," including the Art Institute of Chicago, where the famous "Ruben’s Stupid Art" scene was filmed. The tour often includes stops at neighborhoods featured in movies like "The Blues Brothers" and "Chicago," providing insights into how these locations have been transformed on film. With a knowledgeable guide sharing behind-the-scenes stories and filming trivia, a Chicago movie tour offers a unique way to see the city and its cinematic landmarks.
Fairmont Chicago at Millennium Park
- Fairmont King
- King Sized Bed
- Full En Suite Bathroom
Today is completely up to you! Whether you decide to take another tour or shop till you drop, the world is your oyster.
Take an Architectural River Cruise: Chicago’s architecture is world-renowned, and a river cruise is one of the best ways to appreciate the city’s stunning skyscrapers and historic buildings. You'll learn about the city's architectural history from knowledgeable guides.
Walk Down the Magnificent Mile: This upscale section of Michigan Avenue is lined with shopping, dining, and entertainment options. It’s also a great place to admire some of Chicago’s historic and modern architecture.
Visit the Shedd Aquarium: Located on the Museum Campus, the Shedd Aquarium features a wide range of aquatic life from around the world, including a fantastic collection of marine mammals, fish, and reptiles
Once you've had a full day of fun, spend your last night enjoying a nice meal from one of Chicago's best restaurants.
Alinea: Alinea is a Michelin-starred restaurant known for its avant-garde cuisine and innovative dining experience. A chef's restaurant in Lincoln Park offers a multi-sensory tasting menu that's both artistic and memorable.
The Girl & The Goat: Located in the West Loop, this popular spot by a chef is renowned for its creative small plates and lively atmosphere. The menu features a mix of global flavors with a focus on bold, inventive dishes.
Smyth: Smyth offers an intimate, farm-to-table dining experience with a focus on locally sourced ingredients. Their multi-course tasting menu is a culinary journey through the Midwest.
Bavette's Bar & Boeuf: Bavette's combines a classic steakhouse vibe with French flair. Known for its juicy steaks and rich sides, it's perfect for a special night out.
Fairmont Chicago at Millennium Park
- Fairmont King
- King Sized Bed
- Full En Suite Bathroom
Today you will begin the second leg of your trip to New York City! There will be a private transfer from the Fairmont Chicago to the airport. Once you land in NYC, you will have a private transfer take you to your accommodation at the Times Square EDITION.
Why We Love It For You? The hotel, located in the heart of New York City's Times Square, is a luxury hotel known for its modern design, upscale amenities, and prime location. You should expect a variety of room types, all featuring sleek, contemporary decor, floor-to-ceiling windows, and luxurious bedding. Some rooms offer stunning views of Times Square. The hotel is ideal for travelers looking for a luxurious stay in one of New York City's most iconic locations.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Once you've settled in, take the rest of the evening to explore Times Square and Broadway!
Times Square, often referred to as "The Crossroads of the World," is one of the most iconic and vibrant areas in New York City. Located at the intersection of Broadway and Seventh Avenue, it’s a bustling commercial and entertainment hub that draws millions of visitors each year.
Shop at the Flagship Stores: Times Square is home to some of the largest and most unique flagship stores, including the M&M's World, Hershey’s Chocolate World, and the massive Disney Store.
Dine at Iconic Restaurants: There are plenty of dining options, from quick bites to themed restaurants like Planet Hollywood and Hard Rock Café. For a unique experience, try dining at The View, a revolving restaurant with panoramic views of the city.
Explore Madame Tussauds New York: This famous wax museum features incredibly lifelike wax figures of celebrities, historical figures, and pop culture icons. It’s a fun spot for photos and interactive exhibits.
During your first full day in NYC, you will be experiencing NYC as a tourist!
Start your morning off walking the High Line, an elevated park that stretches over 1.45 miles through Manhattan's West Side.
Feel free to stop along the way if anything catches your eye! Once you've walked far enough on the High Line, head to the 9/11 Memorial & Oculus World Trade Center.
The 9/11 Memorial consists of two massive reflecting pools set within the footprints of the original Twin Towers. Each pool features the largest man-made waterfalls in North America, with the names of the nearly 3,000 victims inscribed around the edges. The serene atmosphere is designed for reflection and remembrance.
Adjacent to the memorial, the museum offers exhibits on the events of 9/11, the history of the World Trade Center, and personal stories from that day. It’s a deeply moving experience with artifacts, photos, and multimedia displays.
You can also stop by the One World Observatory, located at the top of One World Trade Center. It offers breathtaking views and a comprehensive experience of New York City from its tallest building.
Spend the rest of your afternoon exploring NYC and all its quirks. Grab a bite to eat at one of the many restaurants New York City has to offer.
According the New York Times, these are the top 100 restaurants of 2024 and we wanted to share it with you.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Start your morning off by grabbing a famous NYC bagel before going on to see one of America's most famous monuments.
Ess-a-Bagel: Ess-a-Bagel is a New York City institution known for its oversized, chewy bagels and a wide variety of cream cheese spreads. It's about a 15-minute walk from Times Square and well worth the trip for an authentic NYC bagel experience.
Bagel & Schmear: Known for its delicious bagels and wide selection of schmears, this spot offers a great variety of flavors and a cozy atmosphere.
Brooklyn Bagel & Coffee Company: Famous for its freshly baked bagels and a variety of creative toppings, this place provides a genuine bagel experience close to Times Square.
Then head on over to Battery Park in Manhattan and get ready to see the Statue of Liberty.
The tour typically begins with a ferry ride from either Battery Park in Manhattan. The boat trip provides fantastic views of the New York Harbor and the Manhattan skyline. Upon arrival at Liberty Island, you'll get up close to the Statue of Liberty, a symbol of freedom and democracy. The statue stands 305 feet tall from the base to the tip of the torch, and you’ll have time to admire its grandeur and take photos. Some tours come with a guide who provides historical context and interesting anecdotes about the statue and its significance. This can enhance the experience by offering deeper insights.
After you've seen Lady Liberty in all her glory, hopefully you've built up an appetite for the DUMBO food tour and walk across the infamous Brooklyn Bridge.
Ready your appetite and dig into New York City’s coolest borough, Brooklyn! Led by a local guide, this walking tour will introduce you to the diverse culinary delights of the DUMBO and Brooklyn Heights neighborhoods. You'll savor the delicious flavors of authentic New York City pizza and other local favorites while learning about the history of the restaurants and their owners. Along the way, you'll also see iconic landmarks like the Brooklyn Bridge, all while getting a taste of the vibrant culture of Brooklyn.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Today you will experience a captivating journey through the wonders of the natural world. Visiting the American museum of Natural History will surely show you exhibits you will be thinking about for the rest of your life.
The museum's vast and diverse exhibits showcase everything from towering dinosaur skeletons and immersive dioramas of African wildlife to the fascinating mysteries of outer space and the intricate details of human cultures. Highlights include the impressive Hayden Planetarium and the spectacular Rose Center for Earth and Space. With its engaging displays and educational programs, the museum offers a deep dive into the natural sciences and is a must-visit destination for anyone curious about the world around us.
Spend the rest of your afternoon visiting sights in a similar area or shopping in a trendy neighbourhood.
Trump Tower in New York City is a prominent skyscraper located on Fifth Avenue, known for its distinctive design and luxurious features. Rising 58 stories, it boasts a sleek, reflective facade and a lavish marble atrium that sets the tone for its high-end retail spaces and upscale offices. As a high-profile landmark, it has been a symbol of opulence and a center of business and media attention. The tower also houses a number of exclusive residences, offering stunning views of Central Park and the city skyline.
Shopping in SoHo is a vibrant and eclectic experience, offering a blend of high-end boutiques, trendy designer stores, and unique independent shops. This fashionable Manhattan neighborhood is renowned for its stylish streets lined with chic storefronts and historic cast-iron buildings. Whether you're hunting for the latest in fashion, discovering emerging designers, or exploring quirky, one-of-a-kind shops, SoHo provides a dynamic shopping environment. The area also features charming cafes and art galleries, making it a perfect spot for a leisurely shopping spree paired with cultural exploration.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Start your day off in the Lower East Side for a private food experience.
Explore what was once a neighborhood rich in ethnic diversity and culture, previously occupied largely by immigrant and working-class families. Learn about the history of the tenement buildings. The neighborhood is best known for its history as a center of Jewish culture. View historic synagogues and sample delicacies from kosher-style delis and bakeries.
After you've had your food fix, spend the rest of your afternoon at your own pace. Explore the different neighborhoods that NYC has to offer.
Upper East Side
Upper West Side
Harlem
Chelsea
Greenwich Village
SoHo
Tribeca
Lower East Side
East Village
Financial District
Battery Park City
Head over to Chelsea Piers to end the night on a world-class premier dinner cruise.
A world-class city deserves a world-class harbor cruise that offers unparalleled service, dining, and entertainment. Come aboard a yacht for a New York Premier Dinner Cruise and be treated to a delectable prix fixe menu, and jaw-dropping, panoramic views of New York City’s skyline. You’ll see iconic landmarks up close, such as the Statue of Liberty, Empire State Building, Brooklyn Bridge, and One World Trade Center. As you marvel at Manhattan from the Hudson and East Rivers, enjoy tasty cocktails and the sweet sounds of a superb vocalist and acoustic band. This one-of-a-kind experience on our Premier cruise is as exhilarating as it is memorable.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Good Morning! What you do with your day is completely up to you. There is so much to explore in New York City and having a full day to see one of the greatest places on earth.
Central Park is an iconic urban oasis nestled in the heart of Manhattan, offering a lush retreat from the bustling city. Spanning 843 acres, it features a diverse landscape of rolling meadows, serene lakes, and wooded areas, providing a perfect setting for outdoor activities and relaxation. Visitors can enjoy a leisurely stroll along the picturesque paths, take a rowboat out on the Central Park Lake, or explore landmarks like Bethesda Terrace, the Bow Bridge, and the Central Park Zoo. With its beautiful gardens, expansive lawns, and cultural events, Central Park serves as a vibrant hub for recreation, tranquility, and community life amidst the city’s energy.
The Museum of Modern Art (MoMA) in New York City is a premier destination for contemporary and modern art enthusiasts. Renowned for its extensive and influential collection, MoMA showcases masterpieces by some of the most celebrated artists of the 20th and 21st centuries, including works by Van Gogh, Picasso, Warhol, and Matisse. The museum’s diverse exhibits span painting, sculpture, photography, film, and design, offering a dynamic and thought-provoking experience. MoMA’s striking architecture and innovative exhibitions make it a hub for artistic exploration and cultural dialogue, reflecting the ever-evolving landscape of modern art.
Chinatown in New York City is a vibrant and bustling neighborhood known for its rich cultural heritage and lively atmosphere. Located in Lower Manhattan, this area is one of the largest and oldest Chinese enclaves in the city. Visitors can immerse themselves in a sensory experience as they stroll through streets lined with colorful shops, authentic eateries, and traditional markets. The neighborhood offers a taste of Chinese culture through its diverse range of restaurants serving everything from dim sum to Peking duck, and its array of herbal medicine shops and bakeries. Chinatown also features cultural landmarks and festivals, such as the annual Lunar New Year Parade, making it a dynamic and integral part of New York City’s multicultural fabric.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Start your morning off by grabbing a bite to eat before heading off to Madison Square Garden for a tour of the famous arena.
Madison Square Garden, often referred to as "The Garden," is one of New York City's most iconic sports and entertainment arenas. Located in the heart of Manhattan, this legendary venue has hosted countless memorable events since its opening, including major concerts, sports games, and special performances. Home to the New York Knicks (NBA) and New York Rangers (NHL), it’s a hub for passionate fans and a centerpiece of the city’s sporting culture. Beyond sports, Madison Square Garden has seen performances from some of the biggest names in music, making it a dream stage for artists. With its rich history and central location, "The Garden" remains a symbol of New York's vibrant and diverse entertainment scene.
Once you've finished your tour, start heading over to the Yankee Stadium where you will have a tour of the ballpark before watching a World Series Yankee's Game.
Yankee Stadium, located in the Bronx, is a hallowed ground for baseball fans and a symbol of New York City’s sports legacy. As the home of the New York Yankees, one of Major League Baseball’s most storied franchises, the stadium is steeped in history and tradition. The current stadium, opened in 2009, preserves the grandeur of the original while offering modern amenities and state-of-the-art facilities. Fans flock to Yankee Stadium not only to watch thrilling baseball games but also to experience the electric atmosphere that comes with rooting for the 27-time World Series champions. Beyond baseball, the stadium hosts concerts, soccer matches, and other major events, making it a versatile and iconic venue in the heart of the Bronx.
Grab a hotdog and some peanuts and enjoy the American dream!
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Today is the big day, Broadway! You'll start the day off at your own pace, explore the last few areas you've missed before getting ready for a backstage tour of the Broadway Theater.
A Broadway behind-the-scenes tour offers an exclusive glimpse into the magic that happens offstage in New York City's famed Theater District. This immersive experience takes you beyond the dazzling performances and into the inner workings of Broadway, where you'll explore iconic theaters and learn about their rich histories. Guided by theater insiders, the tour reveals fascinating details about set design, costume creation, and the complex technical operations that bring productions to life. You might walk through backstage areas, see rehearsal spaces, and even visit dressing rooms where actors prepare for their roles. Along the way, you'll hear captivating stories about famous shows, legendary performers, and the everyday challenges and triumphs of working on Broadway. It's a unique opportunity to appreciate the artistry, dedication, and teamwork that make Broadway the pinnacle of live theater.
Wicked Wicked is a wildly popular Broadway musical that reimagines the story of the witches from The Wizard of Oz, exploring their untold backstories and complex friendship. With its captivating music, stunning visuals, and powerful performances, Wicked has become a beloved theatrical experience that continues to enchant audiences worldwide.
The Lion King The Lion King is a visually stunning Broadway musical that brings Disney's beloved animated film to life with breathtaking puppetry, vibrant costumes, and unforgettable music by Elton John and Tim Rice. Set against the backdrop of the African savanna, the show’s powerful storytelling and iconic songs, like "Circle of Life," have made it a timeless favorite among audiences of all ages.
Hamilton Hamilton is a groundbreaking Broadway musical that tells the story of American Founding Father Alexander Hamilton through a dynamic blend of hip-hop, R&B, and traditional musical theater. With its innovative score, diverse cast, and powerful exploration of history, Hamilton has redefined the genre and become a cultural phenomenon.
Chicago Chicago is a long-running Broadway musical that dazzles audiences with its sultry jazz music, sharp choreography, and darkly comedic take on crime and celebrity in the 1920s. Known for iconic songs like "All That Jazz" and its stylish, minimalist staging, Chicago remains a timeless tale of ambition, corruption, and showbiz.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
During your last full day you will spend the day exploring the Hudson Valley. Get ready to enjoy picturesque landscapes that showcase the natural beauty and rich history of the region.
The journey typically begins with a comfortable bus or train ride from the heart of Manhattan, allowing you to relax and take in views of the cityscape as it transitions to the scenic landscapes of the Hudson Valley. As you leave the city behind, the bustling streets give way to rolling hills, lush forests, and the serene Hudson River.
Upon arrival in the Hudson Valley, the tour often includes stops at historic estates, where you can explore beautifully preserved grounds and learn about the area's rich history. Many tours also feature visits to charming small towns, known for their local art galleries, unique shops, and farm-to-table dining experiences. Depending on the season, you might also enjoy activities like apple picking, wine tasting at local vineyards, or hiking in the scenic trails of the Catskills.
Throughout the tour, knowledgeable guides provide insights into the history, culture, and natural beauty of the region, making the experience both educational and enjoyable. After a day of exploration, the tour concludes with a return trip to Times Square, where the lights and energy of the city welcome you back from your serene Hudson Valley adventure.
Times Square EDITION
- City View King
- View of lively Times Square
- King Sized Bed
Unfortunately, all good things must come to an end...
Thank you for travelling with us. We hope you had a fantastic trip and we wish you a safe flight home!
While on the trip, you can access your support team if any need arises to make your trip as smooth as possible. We are here to support you.
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