Chat with us, powered by LiveChat Escorted Tours to America for Solo Travellers | Chicago, USA

What you can expect

Centrally Located Hotel

Centrally Located Hotel

Three-star Voco Chicago Downtown - Riverwalk

Guided City Tour

Guided City Tour

Learn about the city & get your bearings

Go City All-Inclusive Pass

Go City All-Inclusive Pass

Access to 37 attractions and 1 day Hop On - Hop Off Bus included!

Day at Leisure

Day at Leisure

Time to explore more or just enjoy the hotel facilities

About this trip...

Experience the very best of the Windy City with this exciting 3-night Solos Holidays city break, combining guided sightseeing with plenty of time to explore at your own pace. Discover Chicago's iconic landmarks and vibrant neighbourhoods on a guided city tour, then admire the city's spectacular skyline and world-famous architecture from the water on a relaxing architectural river tour. Your 2-day Go City All-Inclusive Pass gives you the freedom to choose from a wide range of attractions and experiences, while a 1-day hop-on hop-off bus tour makes it easy to see even more of the city. With additional free time built into the itinerary, you can shop, dine, visit your must-see attractions or simply soak up the atmosphere of this unforgettable American city.
 
Fancy visiting Toronto too? Speak to our team about adding our Toronto & Niagara Falls City Break to this trip.
Activity Level: Activity Level Rating
What's this?

What's included?

  • Return flights and airport transfers
  • Checked Baggage
  • Airport taxes & charges
  • Double/twin room for sole use
  • Solos Board : Breakfast Daily, + 2 dinners
  • Welcome drink & information meeting
  • Half-day guided city tour
  • Architectural River Cruise
  • 2 day Go City All-Inclusive Pass
  • 1 day Big Bus Hop On - Hop Off Ticket
  • Free Solos App with all your travel documents
  • Dedicated Whatsapp group for your trip
  • Accompanying Solos Tour Leader
  • Fully Financially Protected

What's Extra

  • Insurance click here
  • US ESTA required - currently USD21

Itinerary

  • Arrive Chicago
  • City Tour & River Cruise
  • Hop On - Hop Off Bus and explore!
  • Day at Leisure
  • Depart Chicago

What you'll be doing

Day One: Arrive Chicago

Day One: Arrive Chicago

Welcome to Chicago! On arrival, we transfer to our hotel where we have time to unpack, relax and freshen up before meeting the group for a welcome drink and dinner.
 
  • Dinner included
Day Two: Guided City Tour + Architectural River Tour

Day Two: Guided City Tour + Architectural River Tour

After breakfast, we meet our guide for a fascinating city tour of Chicago, the famous 'Windy City', situated on the shores of Lake Michigan.

We explore the city centre, known as 'The Loop', and discover some of Chicago's most famous landmarks, including the bustling business district, the iconic Sears Tower, the historic Board of Trade, Navy Pier and one of the city's most recognisable landmarks, the Chicago Water Tower. 
We'll also see the John Hancock Building, the exclusive Gold Coast neighbourhood and Lake Shore Drive, before continuing through Lincoln Park to the University of Chicago and the impressive Fountain of Time.
 
There is plenty more to discover along the way, with a stop at the Shedd Aquarium offering wonderful views across Lake Michigan towards Chicago's spectacular skyline.
 
We end our tour at the Chicago River, where we board an architectural river cruise. Sit back and relax as we admire some of the Windy City's most iconic buildings and views from the water, including the magnificent Wrigley Building and John Hancock Building.
 
Disembarking at Michigan Avenue, it is just a short walk back to our hotel, or you may wish to take a leisurely stroll to Pioneer Court, a historic landmark in the heart of the city.
 
This evening, dinner is at leisure.
 
  • Breakfast included
Day Three: Chicago your way - Hop on Hop Off Bus

Day Three: Chicago your way - Hop on Hop Off Bus

Chicago... Your way!

 
Today is yours to experience Chicago exactly as you choose. With your All-Inclusive Go City Pass and 1-day hop-on hop-off sightseeing bus ticket, you have the freedom to explore the Windy City at your own pace, discovering the sights and experiences that capture your imagination.

Simply hop on and off the sightseeing bus as you travel between Chicago's iconic neighbourhoods and landmarks, making it easy to see more of this vibrant city in a single day.
 
With 37 attractions included, there is plenty to choose from. Rise above the city at the Skydeck Chicago, take in spectacular panoramic views from 360 Chicago, uncover fascinating stories at the Field Museum, or immerse yourself in the world of modern and contemporary art at the Museum of Contemporary Art. And that's just the beginning!
 
Whether you want to admire the skyline from above, delve into Chicago's fascinating history and culture, or simply soak up the atmosphere, today is all about discovering Chicago your way - and ticking more unforgettable experiences off your bucket list.
 
This evening, we meet for a farewell dinner and to share tales of our time in this wonderful city.
 
  • Breakfast & dinner included
Day Four: Depart Chicago

Day Four: Depart Chicago

After a leisurely breakfast, why not enjoy a stroll on the Chicago Riverwalk, a scenic 1.25 mile waterfront path through the heart of the city? Just a short stroll from the hotel, it's the perfect opportunity to enjoy one last taste of Chicago, soak up the vibrant atmosphere and admire the city's impressive architecture from the riverside.

Alternatively, you may prefer to relax and make the most of the hotel's facilities before we transfer to the airport for our flight home, bringing our unforgettable Chicago adventure to a close.

  • Breakfast included
Day Five: Arrive UK

Day Five: Arrive UK

Welcome Home! On arrival, we clear immigration, collect our luggage and say our goodbyes with memories to last a lifetime!

Accommodation

Voco Chicago Downtown - Riverwalk

Nestled on the banks of the Chicago River, the three star Voco Chicago Downtown - Riverwalk hotel offers style, comfort and relaxation, with stunning views of the city's skyline and easy access to all that this amazing city has to offer.
Facilities include
To match the excellent location, the property offers facilities such as WiFi, bar, restaurant, 24hr market with snacks, coffee and more, indoor swimming pool, gym and filtered water stations.
Room includes
The stylish and modern rooms feature WiFi, air conditioning, safe, TV, coffee maker, hair dryer and private ensuite bathroom.

Dates & Prices

Departure Return Nights Price from Other Info Regional flights
21 Jun 2027 24 Jun 2027 3
£3669
  Please call for regional flights

Essential Information

Go City App
Prior to departure, it is recommended to download the Go City App where you will find all the information you need to start planning your sightseeing using the hop-on hop-off bus to get around the city.
 
The app includes entry information, opening hours and a handy map.
 
To download for Android devices, go to Go City: Travel Plan & Tickets - Apps on Google Play
 
To download for Apple devices, go to ‎Go City -Travel Plan & Tickets App - App Store
Currency
US Dollars $
Passport, Visa & Entry Requirements

Passport Validity

To enter the US, your passport must be valid for the length of your planned stay.

Visa Requirements

To enter or transit through the US, you must have either an Electronic System for Travel Authorisation (ESTA) visa waiver or a visa.

You can Apply for an ESTA visa waiver through US Customs and Border Protection.

You cannot apply for an ESTAvisa waiver if you have:
  • been arrested (even if the arrest did not result in a criminal conviction)
  • a criminal record
  • been refused admission into, or have been deported from the US
  • previously overstayed under an ESTA visa waiver
You cannot normally apply for an ESTA visa waiver if you were in the following countries on or after March 2011: Iran, Iraq, Libya, North Korea, Somalia, Sudan, Syria or Yemen. You cannot apply for an ESTA visa waiver if you travelled to or were in Cuba on or after 12 January 2021. If you are not eligible for an ESTA, you must instead apply for a US visa. More information can be found here
Health Requirements
Compulsory vaccinations: None.
 
All clients are responsible for acquainting themselves with up to date health information of the countries being visited and where necessary take the required precautions. We recommend that you check with your doctor prior to departure as this information can change. Please remember to pack any prescribed medication, as they can often be expensive and may not be readily available.
 
You can also visit the travel health website for more information; Travel Health USA
WhatsApp Group
WhatsApp Group: Shortly before your holiday, you will be invited to join an optional WhatsApp group to connect with your fellow travellers and your Tour Leader.
Booking Information
It is important to consider whether this holiday is suitable for your level of fitness, mobility, and any medical conditions. We are committed to making reasonable adjustments wherever possible. Please tell us about any disability, medical condition, or additional requirements before booking so we can assess whether we can safely and appropriately accommodate your needs. If you are unsure whether this holiday is suitable for you, please contact us before booking. We will be happy to discuss the holiday requirements and your individual circumstances.
Airport Transfers
The transfer time from Chicago O'Hare International Airport to the hotel is approximately 35 minutes depending on traffic.
Gratuities
We suggest a Group Collection to cover transfer drivers, and hotel staff of $40.00 per person. Your Tour Leader will collect this on your behalf and distribute it accordingly, thus relieving you of the burden of who, when and how much to tip. The tipping of housekeeping will be left to your individual discretion (a small amount left in your room on departure should cover this and would be much appreciated). As is customary, ‘the hat’ will be passed around for the driver and guide on all optional excursions. For any meals that are not included in your itinerary, or taxi fares, your Tour Leader can advise of an appropriate % to add on. If you choose to have ski lessons, you may also like to thank your ski instructor at the end of the week with a token of appreciation.

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Rated as Excellent (4.8/5) by our customers

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First Class

I’d highly recommend Solos to people looking to travel on their own with a group of like minded people.
-David F

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Fabulous experience

Solos are extremely organised and provide fantastic holidays for people on their own. The tour leaders are of a very high standard and are extremely caring with the guests.
-Carole

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Don't Delay any Longer!

This was my first Solos holiday and it hugely exceeded my expectations. Lovely, lovely people made the holiday so special.....it will stay with me for always
-L Heaton

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Well worth going

I’ve recently returned from my first Solos holiday and had a fantastic time. I can honestly say that I enjoyed every minute, and the memories will last a lifetime.
-Patricia B

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