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USA (Boston, New York City, Chicago) 7-Day Trip Itinerary

USA (Boston, New York City, Chicago) Trip - Apr 27 to May 3

Apr 27 - May 3

Embark on a captivating 7-day urban exploration across Boston, New York, and Chicago, starting April 27th from London. This moderate-budget journey focuses on cultural sites, museums, local markets, and photography, with ample time for relaxing cafes. Conclude your adventure on May 3rd, departing Chicago by train for Denver, having savored the unique charm of each iconic city.

USA (Boston, New York City, Chicago) view
1

Arrival in Boston & Waterfront Stroll

Monday, April 27
1.1
Afternoon

Arrive in Boston

Arrive at Boston Logan International Airport (BOS) from London.

Transfer to your hotel, check-in, and settle in after your international flight.

Consider pre-booking an airport transfer or using a ride-share service to your hotel.

Boston Logan International Airport (BOS), Boston

From BOS, take a taxi, ride-share, or the Silver Line bus to downtown Boston.

1.2
17:00

Boston's Waterfront

Enjoy a leisurely walk along Boston's scenic waterfront, taking in the harbor views and fresh sea air.

A perfect way to unwind after your journey. There are many restaurants along the waterfront for dinner.

1.3
19:00

Dinner in Seaport District

Enjoy a welcoming dinner in Boston's bustling Seaport District, known for its diverse culinary scene.

Many restaurants offer fresh seafood. Consider Legal Sea Foods or similar for a classic Boston experience.

2

Boston History & Travel to NYC

Tuesday, April 28
2.1
09:30
USD 99 for 3 people

New England Aquarium

Meet amazing sea creatures and learn about marine conservation at this global center for ocean exploration.

A great place for all ages. Pre-book tickets to save time. Rated 4/5 on TripAdvisor.

2.2
12:00

Lunch near Faneuil Hall

Grab a quick and casual lunch near the historic Faneuil Hall Marketplace, offering a variety of food options.

Perfect for a quick bite before heading to the train station.

2.3
14:00

Train to New York City

Take a high-speed train from Boston's South Station to New York Penn Station, enjoying the scenic journey through the Northeast Corridor.

Book Amtrak tickets in advance for better rates and to secure your seats. Aim for an afternoon departure to maximize time in Boston.

Boston South Station to New York Penn Station

Amtrak's Acela Express is faster but more expensive; Northeast Regional is a good alternative.

2.4
19:00

Arrive in NYC & Dinner

Arrive at Penn Station, transfer to your hotel in Manhattan, check-in, and then enjoy dinner in your chosen neighborhood.

Public transport (subway) is the most efficient way to get around NYC. Many restaurants are open late.

3

Iconic NYC Landmarks & Immersive Art

Wednesday, April 29
3.1
09:30

New York Public Library

Visit the monumental main branch of the New York Public Library, known for its stunning architecture and the majestic Rose Main Reading Room.

Free to enter and explore. Take a break from the city's hustle and bustle. Rated 4.6/5 on TripAdvisor.

3.2
11:00

Grand Central Terminal

Marvel at the Beaux-Arts architecture and iconic main concourse of one of the world's most beautiful train stations.

Don't miss the celestial ceiling and the Whispering Gallery.

3.3
12:30

Lunch in Midtown

Find a quick lunch spot in Midtown Manhattan before your afternoon activities.

3.4
14:00
USD 126-150 for 3 people

Color Factory New York

Embark on a bright and colorful journey through 12+ immersive art installations, celebrating the joy of color. Voted #1 Immersive Art Experience in America by USA Today.

A fun and interactive experience for photos. Book tickets in advance as it can sell out. Rated 4/5 on TripAdvisor.

3.5
17:00

Times Square & Dinner

Experience the dazzling lights and energy of Times Square.

Enjoy dinner at one of the many restaurants in the area.

It's best experienced as the sun sets and the billboards come to life.

4

Travel to Chicago & Millennium Park

Thursday, April 30
4.1
Morning

Flight to Chicago

Take an early morning flight from New York City (LGA or EWR) to Chicago (ORD or MDW).

Book flights in advance for best prices. Budget airlines often fly this route.

4.2
Afternoon

Arrive in Chicago & Hotel Check-in

Arrive at Chicago O'Hare International Airport (ORD) or Midway International Airport (MDW).

Transfer to your hotel and check-in.

Chicago

From O'Hare, the Blue Line CTA train goes directly downtown. From Midway, the Orange Line CTA train is direct.

4.3
16:00

Millennium Park Exploration

Explore the iconic Millennium Park, home to famous public art and architecture.

Highlights include Cloud Gate ('The Bean'), Jay Pritzker Pavilion, and Crown Fountain. Rated 4.8/5 on Google.

4.4
18:00

Cloud Gate & Pritzker Pavilion

Visit 'The Bean' for unique reflections and photograph the stunning architecture of the Jay Pritzker Pavilion.

4.5
19:30

Dinner in Downtown Chicago

Enjoy dinner in the vibrant downtown area, with many culinary options to choose from.

5

Chicago Art & Architecture

Friday, May 1
5.1
10:00
USD 84-105 for 3 people

The Art Institute of Chicago

Immerse yourselves in art at one of the oldest and largest art museums in the United States, featuring renowned collections.

Home to iconic works like 'American Gothic' and 'A Sunday on La Grande Jatte'. Rated 4.8/5 on Google. Book tickets online.

5.2
13:00

Lunch in The Loop

Grab lunch in Chicago's central business district, The Loop, with many eateries nearby.

5.3
14:30

Chicago Architecture Center

Learn about Chicago's world-renowned architecture through interactive exhibits and models.

Consider joining one of their famous architecture boat tours if time permits on Day 6. Rated 4.7/5 on Google.

5.4
16:30

Chicago Cultural Center

Visit this stunning landmark building, home to the world's largest Tiffany stained-glass dome.

Free admission.

A beautiful and often overlooked gem. Check for free events or exhibits. Rated 4.7/5 on Google.

5.5
19:00

Deep Dish Pizza Dinner

Indulge in Chicago's iconic deep-dish pizza for dinner, a must-try culinary experience.

Be prepared for a hearty meal! Expect a wait at popular spots, especially on a Friday evening.

6

Chicago: Architecture, Art & Millennium Park

Saturday, May 2
6.1
09:00 - 11:30
USD 0 for 3 people

Explore Millennium Park

Discover Chicago's famous Millennium Park.

Take photos at Cloud Gate (The Bean), stroll through Lurie Garden, and admire the Jay Pritzker Pavilion.

Cloud Gate is less crowded in the morning. Wear comfortable shoes for walking.

6.2
11:45 - 14:45
USD 75 for 3 people

The Art Institute of Chicago

Immerse yourselves in world-class art at The Art Institute of Chicago, home to a vast collection spanning centuries and cultures, including famous Impressionist and Post-Impressionist works.

Book tickets online in advance to secure your entry time and save time.

6.3
15:00 - 16:00

Lunch in The Loop

Enjoy a casual lunch at one of the many eateries in Chicago's vibrant Loop district, near the Art Institute.

Plenty of options from quick bites to sit-down restaurants.

6.4
16:15 - 18:15
USD 60 for 3 people

Chicago Architecture Center

Learn about Chicago's world-renowned architectural heritage through engaging exhibits and models at the Chicago Architecture Center.

Consider their popular river cruise for stunning views (book far in advance if interested, not included in this time estimate).

6.5
19:30 - 21:00

Dinner in River North

Dine in the trendy River North neighborhood, known for its diverse culinary scene and vibrant evening atmosphere.

Advance reservations are recommended for popular restaurants on a Saturday night.

7

Chicago Morning & Train to Denver

Sunday, May 3
7.1
09:30 - 11:30
USD 0 for 3 people

Chicago Cultural Center Visit

Explore the stunning Chicago Cultural Center, an architectural gem with free art exhibits and the world's largest Tiffany stained-glass dome.

It's a beautiful, free, and inspiring start to your day.

Check for any special events or free performances taking place on Sundays.

7.2
11:45 - 12:45

Brunch/Lunch Before Departure

Enjoy a final Chicago meal with brunch or lunch near the Loop before heading to the train station.

Look for cafes or diners that offer quick service.

7.3
13:00 - 13:30

Travel to Union Station

Make your way to Chicago Union Station, allowing ample time for traffic and navigating the station.

Consider a taxi or ride-share for convenience with luggage.

Chicago Union Station

Depending on your accommodation, public transport (CTA) is an option, but a taxi/rideshare is recommended with luggage for ease.

7.4
14:00

Train to Denver

Board your train for a scenic journey from Chicago to Denver, marking the next leg of your American adventure.

Ensure you have your tickets and any necessary provisions for the long train ride. The train offers dining car services.

This 7-day itinerary for USA (Boston, New York City, Chicago) can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.