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Depart 12 September 2024

Return 19 September 2024

Economy

Business

Chicago Offers 8

Chicago Hotels 55

Chicago Fly-Drives 1

What 443 of our customers thought of Chicago...

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Cody was great helping me to make alternative arrangements when my flight was delayed by 6 hours, which was really important for this trip. Many thanks!

Fantastic location of hotel for what we wanted to visit in Chicago.

Good service, quick response to requests for prices and flight options.

A huge thank you to Kitty. Everything worked brilliantly.

Dealt with Joe Orton many times, never failed us.

Speed with which calls were answered and with which queries were dealt with was exemplary.

The hire car we were given (Dodge Charger) was much less sophisticated than the car I drive in England (Kia Niro).

Everything as promised. My third trip with them and exceptionally happy with the service

Great service and app. Everything worked well with my trip and I will be using you again.

Everything exactly as expected from Ellis and DialAFlight as always. Very happy customer

Always helpful, and caring. Would definitely recommend, they take the effort out of booking so a big thank you

Kept informed when flights changed and alternatives.

Many thanks to Christian for getting good deals for us

Everything worked out well. I'll definitely use DialAFlight again

Friendly staff and competitive prices, will be back for my next trip

Staff always there to help. Will be back next year for another trip. Thank you to all the staff at DialAflight.

Jude was excellent .

Well co-ordinated arrangements with good reminders when deadlines or events were approaching.

As always a flawless experience with Ellis

I have used DialAFlight for 6 years for my flights to visit my family in Chicago. They have always been very friendly and helpful.

I need to make regular trips to the States to see my elderly mother. Claire and her team at DialAFlight were, as always, friendly, efficient and helpful in finding me the best price and suitable dates and times. I needed a car for my last trip and they arranged a fly drive package which was very reasonable.

Lee Coughtrey who I always deal with, gives me excellent service,

I believe I have sorted out the problem with the car hire and tolls, which may be of use to others.

Great help and support from Saf to plan and book our trip. Easy to contact when we had queries or needed help - a great trip spending 3 weeks driving Route 66.

Everything perfect, service outstanding above and beyond, would not use anyone else

Thank you very much for all your help - brilliant service

Curtis provided an outstanding service and support.

Philippa was very helpful and considerate in dealing with all aspects of our journey...will always use DialAFlight for long haul holidays. Great job

Alan White is brilliant. One of my internal USA flights kept changing departure time which had an impact on my longhaul flight back. Of course Alan sorted it all out.

Very pleasant people to deal with and helpful.

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Staying in Chicago? Did you know you get better
value by booking flights and hotels together?

Cruise Route 66 - Fly Drive

Save £100pp

15 nts / 16 days from £2,035pp

3 nights from £1,125pp

Includes flights

The Millennium Knickerbocker 4*

Further details

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Chicago Reviews 443

USA Fly-Drives 32

Chicago Offers 8

Chicago Hotels 55

WHY 98% OF CUSTOMERS SAY THEY’D BOOK WITH US AGAIN
Based on reviews on Trustpilot

020·7962·9933

Calls answered LIVE in FIVE seconds

Good old fashioned customer service
Best value for money
Your travel plans automatically updated on the DAF app
24/7 emergency helpline
Triple protection for clients. ABTA, ATOL, Trust Account
Insider knowledge. Access to fares you'll never see
Any Air Miles automatically added
Your bookings help thousands of children learn to read

Car Rental

Would you like to rent a car for a day or two, or are you planning an adventurous one or two week driving holiday? Perhaps you wish to hire a campervan to tour around in for a month?

We have a selection of vehicles to suit every need, from economy 2 door cars to seven seaters, compact campervans and cool convertibles.

SEE ALL CAR RENTAL PRICES

For more inspiration, read what travel writers have to say...

Singing the blues in Chicago!

The Windy City is unbeatable for music, art and glitz, says Mark Porter

Not quite what you're looking for?
We can easily customise an offer to suit your exact requirements

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Other services which make a trip special

Corporate Travel

How we can help your Business

Good old fashioned service and VALUE for money

Clients range from TV companies to Space agencies, investment banks to firms recruiting nurses, doctors and teachers around the world. One saves tigers, elephants and and orang-utans, another clears landmines around the world.

But they all have one thing in common. They love the unique DialAFlight approach. Read more here

98% would book again with DialAFlight
based on reviews on Trustpilot

Amazing Business Class Fares

Save on First & Business Class

Save on First & Business Class Fares

Let us extend the personalised service of your booking into your holiday with great prices on business class flights ready to add a touch of class to your trip.

Take the stress out of travelling with a host of wonderful perks on offer from priority check-in and premium lounge access to chauffeur service and fine in-flight dining, plus the supreme comfort of a fully-reclining seat.

Call us to see how much you could save on Business Class flights.

020·7962·9933

Call us to book

Airport lounges

Relax in comfort before you fly

Beat the airport chaos. Swap the crowds for a luxury lounge

Airport Lounges from £25

Once you’re through security leave the crowds, kids and chaos behind you with a visit to one of our comfortable airport lounges.

All offer complimentary food, drinks, wifi and newspapers with some also including Fastrack through security. Prices from £25.

020·7962·9933

See more

Meet and greet

We'll arrange to meet you on arrival

Avoid the stress with our Meet & Greet service

Use our speedy private transfer service to avoid the stress of finding your way out of the airport terminal and looking for a taxi or bus on arrival.

With our meet and greet service, our driver will meet you in the arrivals hall. They will monitor flight arrival times giving you peace of mind that someone will be waiting for you with a name board even if your flight is late.

They will then assist you with your luggage and organise a private transfer directly to your hotel - there’s no waiting around for other passengers for shared transfers!

So no queues, no delays and less stress.

020·7962·9933

Call us to book

Travel Vouchers

Gift of Travel

What could be better than giving someone the Gift of Travel?

Starting at just £50, with no maximum value, DialAFlght's 'Gift of Travel' vouchers make the perfect present for any occasion or celebration.

And it couldn't be simpler to organise, just contact one of our travel experts today and they will organise a personalised travel voucher to be sent out.