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Depart 10 May 2025

Return 17 May 2025

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Chicago Reviews 458

Chicago Offers 10

Chicago Hotels 54

USA Fly-Drives 32

Chicago Offers 10

Chicago Hotels 54

Chicago Fly-Drives 3

What 458 of our customers thought of Chicago...

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Thanks to Claire and her team for another well organised fly/drive trip.

Aimee Mearkle Visited Chicago | Posted on 09 Mar

Exceptional service in arranging our recent flights to Chicago.

Anthony Gold Visited Chicago | Posted on 16 Jan | Stayed at ibis Styles London Heathrow Airport

Molly Smith was super helpful and followed up on my various questions. Slightly disappointed with Aer Lingus - the screens didn’t work in our seats

Victoria Partington Visited Chicago | Posted on 29 Dec

As always absolutely brilliant service!

Becky Herbert Visited Chicago | Posted on 21 Nov

We had a great holiday and very grateful for all the help received from Bella

Emma Hughes Visited Chicago | Posted on 12 Nov | Stayed at Hotel Felix

Claire and her team were, as always, efficient and helpful.

Aimee Mearkle Visited Chicago | Posted on 29 Oct

Ryan was a superstar! Thank you.

Karim Davezac Visited Chicago | Posted on 24 Oct

Jenson Palmer is excellent

Sue Green Visited Chicago | Posted on 11 Oct

Probably change the Arizona hotel from this road trip.

David Norbury Visited Chicago | Posted on 10 Oct | Stayed at Ambassador Chicago

As always, Amelia provided her excellent expertise resulting in a really enjoyable trip.

Christopher Hawkes Visited Chicago | Posted on 09 Oct | Stayed at Millennium Knickerbocker Chicago

Great professional service

Ann Wragg Visited Chicago | Posted on 07 Oct

Brilliant support all round and knowing you are there to help should it be necessary ensures peace of mind.

Jenny Badger Visited Chicago | Posted on 06 Oct

No issues at all. Very happy with the service

Jatinder Paul Visited Chicago | Posted on 20 Sep

Excellent service as always

Nicholas Ridgeon Visited Chicago | Posted on 20 Sep

Leaving UK, no problem. Leaving USA, disaster.

John Hatfield Visited Chicago | Posted on 17 Sep

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!

Alicia Felce Visited Chicago | Posted on 02 Sep

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

Alison Mcausland Visited Chicago | Posted on 29 Aug | Stayed at InterContinental Chicago Magnificent Mile

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

Julia Morjaria Visited Chicago | Posted on 17 Aug

A huge thank you to Kitty. Everything worked brilliantly.

Pamela Robertson Visited Chicago | Posted on 12 Aug | Stayed at Hilton Chicago/Oak Brook Suites

Dealt with Joe Orton many times, never failed us.

David Gibson Visited Chicago | Posted on 10 Aug

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

Verna Brandford Visited Chicago | Posted on 05 Aug

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

Neil Binder Visited Chicago | Posted on 30 Jul | Stayed at Ambassador Chicago

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

David Radford Visited Chicago | Posted on 24 Jul | Stayed at Warwick Allerton Chicago

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

Dominik Hughes Visited Chicago | Posted on 21 Jul | Stayed at Hilton Garden Inn New York/Tribeca

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

Ros Howell Visited Chicago | Posted on 20 Jul

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

Pauline Ollive Visited Chicago | Posted on 16 Jul

Kept informed when flights changed and alternatives.

Mervyn Stradling Visited Chicago | Posted on 03 Jul

Many thanks to Christian for getting good deals for us

Martin Ebsworth Visited Chicago | Posted on 02 Jul | Stayed at Millennium Knickerbocker Chicago

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

Anne-Marie Shawe Visited Chicago | Posted on 13 Jun

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

Rowland Webb Visited Chicago | Posted on 04 Jun

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Staying in Chicago? Did you know you get better
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Illinois Iconic Route 66 - Fly Drive

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8 nts / 9 days from £1,279pp

3 nights from £985pp

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The Millennium Knickerbocker 4*

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Chicago Reviews 458

Chicago Offers 10

Chicago Hotels 54

USA Fly-Drives 32

WHY 98% OF CUSTOMERS SAY THEY’D BOOK WITH US AGAIN
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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.

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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

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Luxury For Less

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.

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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.

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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.

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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.