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Eastern USA

Cities and mountains of North East USA

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Chicago City Centre

Group Size: Max 25

Trip code: CTEU

Duration: 7 days

7 day group experience
Chicago to New York
Twin-share accommodation

Keep it East side with this banging tour of Northeastern USA. From Chicago’s soaring skyscrapers and deep-dish pizzas, NYC’s incomparable razzamatazz, and Boston’s Freedom Trail, sport stadiums and Ivy League Universitiestothe stunning mountain landscapes and luminous night skies of the Catskills, it’s wall-to-wall American wonders. With tons of included activities from tours of Chicago’s historic and sporting highlights and a visit to Boston’s illustrious Harvard University to lip-smacking pizza dinners and laid-back market dining, this trip’s one delicious slice of American pie! 

Trip highlights

  • Get schooled with a student-led tour of Harvard, Boston
  • Explore Chicago’s biggest and boldest bits on a tour of its highlights from Guaranteed Rate Stadium to Lake Michigan
  • Get a taste of America’s finest culinary offerings with deep-dish pizza in Chicago and dinner at Boston’s iconic Time Out Market
  • Hike into the mountains before toasting s'mores under a canopy of stars in the Catskills
  • Finish up your tour in the one-and-only Big Apple
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What's included
  • 6 nights accommodation
  • 6 breakfasts, 1 lunch and 4 dinners
  • Internal flight from Chicago to New York
  • On trip transport
  • Trip leader and driver 
  • See Soldier Field home to "The Bears" American Football
  • See Guaranteed Rate Stadium, home to the Chicago White Sox baseball club
  • See Lake Michigan, Buckingham Fountain, the Navy Pier & Chicago River
  • See the Hancock Building, Willis Tower & the Magnificent Mile
  • Go local at a pizza dinner in Chicago
  • Time Out Market Dinner in Boston
  • Harvard tour
  • 24 hour emergency support
What's not included
  • International flights
  • Optional activities
  • Some meals and drinks 
  • Airport transfers
  • Visas
  • Insurance
Further trip information

Day 1: Chicago. Welcome to the Windy City! Start with a guided tour of some of the biggest and boldest highlights, including Soldier Field, Guaranteed Rate Stadium, Lake Michigan, Buckingham Fountain and more – phew! Go local this evening with a mouth-watering pizza dinner.

Day 2: Chicago. Chicago’s your oyster today. Join our optional ‘bike and roll’ tour, book our fascinating architectural cruise, or get a bird’s eye view of the city streets from the Observation Deck. Check out Chicago’s incredible international food scene tonight with a few brewskis.

Day 3: Catskill Mountains (via NYC). Hop on a flight to NYC today, from where we’ll take a private coach into the mountains. Check into our accommodation and feel the peace of your beautiful natural setting wash over you. You’ll sleep like a baby tonight after all that fresh mountain air!

Day 4: Catskill Mountains. You’ve got a full day in your gorgeous mountain setting to hike, swim, hire a bike or just sit back and soak up the beauty of your surroundings. Tonight, get together round a fire to toast some s'mores under a canopy of stars – life doesn’t get any better than this.

Day 5: Catskill Mountains to Boston. ‘Beantown’ is on the menu today. This forward-thinking city is packed to the rafters with art, history, sports, great food, and beautiful public parks. We’ll get the measure of its culinary chops with an included dinner at the iconic Time Out Market – yum!

Day 6: Boston. Start the day at the legendary Harvard University with a student-led tour, then the rest of the day is yours. Join our optional Freedom Trail walk, take a stroll through the Emerald Necklace and tuck into some of the city’s famous seafood – amazing!

Day 7: Boston to NYC and trip end. The time has come to say your goodbyes and either head home or continue your travels. There’s a complimentary transfer to NYC if you’re headed in that direction, with a drop at the Moxy Times Square. See you next time!

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Booking options

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Online booking is unavailable for this trip

Online booking isn't currently available but if you'd like to enquire please use the form below. Alternatively if you'd like to discuss alternate trips or if you have any other questions please don't hesitate to contact us.
Call us on: 01892 527392
Email us at: [email protected]
Arrival information

Your trip starts in Chicago on day 1. As there are planned activities for day 1, we recommend you arrive into Chicago at least 1 day in advance of your trip. If you need help arranging pre-tour accommodation please let us know.

Your trip ends in Boston on day 7, however we include a transfer to New York City where you will be dropped near Times Square. If you want to take some independent travel time in NYC, let us know and we can recommend some accommodation options.

Airport transfers are not included, and you will need to meet your group at the starting hotel on day 1. Once your trip is confirmed, we will advise on the best way to get from the airport to the starting hotel.

Accommodation & meals


6 nights of accommodation are included in this trip. You’ll be staying in twin-share rooms. If you’re travelling with a partner or friend, let us know so we can place you together.


6 breakfasts, 1 lunch and 4 dinners are included. You’ll need to source the rest of your meals yourself. This gives you maximum flexibility to eat where and when you like. 

Minimum age & eligibility

You’ll need to be a minimum of 18 years old to participate in this trip. This trip is designed for 18-35 year olds.

British passport holders can enter the USA for up to 90 days without a visa. You’ll need to apply online for an Electronic System for Travel Authorisation (ESTA) though. Your passport should be valid for the proposed duration of your stay.

If you’re under 21, you won’t be able to enter bars, clubs or other establishments where alcohol is served. It’s recommended that even if you are over 21, you always carry a valid form of ID.

Please note, this trip requires you to show evidence that you have been fully vaccinated against covid-19 (final dose administered a minimum of 14 days prior to the start of the trip).

Please note: Visa, passport and entry restrictions can be subject to change. Always check foreign travel advice before your trip. 

Covid safety

This trip is designed with your safety and wellbeing in mind. As a result of Covid-19, many of our suppliers and partners around the world are introducing new policies and procedures surrounding health and safety in response to the Coronavirus outbreak. As the state of travel is evolving these new safety measures will adapt over time, and will be different for each trip. Here are some of the changes you may see on your trip:

Arrival safety meetings
Most trips have an arrival meeting on the first day where the guide or local team will run through the trip, the safety protocols, and to answer any questions you may have. Now more than ever it is important you arrive in time for these meetings.

Proof of vaccination or negative covid test
For the safety of all travellers, at the start of some trips you may be required to show evidence that you are fully vaccinated (14 days after your second dose) and/or show evidence of a negative PCR test taken within 72 hours of the tour start date in order to join the programme.

Updated hygiene and safety procedures
Our suppliers and partners have health and safety procedures in place on all of our trips. These protocols will be updated and adapted as a response to the Coronavirus outbreak, dependent on local restrictions and laws.

Transport and accommodation choices
Our suppliers and partners choose the accommodation and transport on our trips very carefully, and you may see a change to what would normally be used as a response to the outbreak. This may involve such changes as enhanced use of private transport or quieter accommodation.

Trained and knowledgeable staff
Our staff in the UK are trained to help you with your trip before you depart and answer any questions you may have. In addition, the local team and guides on our trips are there to help with any health and safety concerns and to ensure our trips run safely and smoothly.

Reduced group sizes
Some trips will run with reduced group sizes to start with. You may find that trips are more intimate and chilled, whilst still being packed with fun and adventure.

Your guide or the local team will be on hand to help you seek medical attention should you require it during your trip. As medical facilities and standards can vary around the world, you should ensure you have adequate travel insurance in place before you depart to cover you for any medical emergencies.

24/7 emergency support
We operate an emergency phone line for our travellers abroad. This is operated by a UK based member of staff 24/7 if you have a genuine emergency or urgent matter that you need attending.

It is important that you take measures to make travelling safer for yourself and others around you. Ensure you frequently wash your hands, cover your face when you sneeze and cough, bring and use your own hand sanitiser and facial coverings/masks, and enable social distancing where necessary. You should also ensure you listen to the instructions and guidance of the local team at all times, and follow all local laws and restrictions.