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USA Road Trip from Chicago to the Wilds of Montana

Chicago, Glacier National Park, Livingston & Big Sky

Best time to travel
Apr – Nov
Ideal length
12 nights
Perfect for
From (incl flights)
€3,999 pp

At a glance

  • International flights from Dublin to Chicago and home from Montana.
  • 9 days' pre-arranged car rental as well as all domestic flights.
  • 12 nights’ luxury accommodation in Chicago, Glacier National Park, Livingston and Big Sky, Montana.
  • Admire Chicago’s dynamic architecture on a privately guided walking tour.
  • Explore Montana’s scenic landscapes with an expedition up Lone Mountain, adventures in Glacier National Park and ranch activities in Big Sky, Montana.
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The United States of America’s epic and varied nature has long been responsible for the nicknames of metropolises and states. The Windy City will blow you away with its high-flying architecture and emblematic dishes. Whimsical public art, steely skyscrapers and a superb range of global eateries stud the streets of Chicago. Further west, the Great Plains meet the Rockies in Big Sky Country. Montana’s landscapes are defined by the sculpted peaks of Glacier National Park and vast wildernesses. On this suggested itinerary, discover the urban delights of Illinois’ capital and road trip through the picturesque scenery of Montana.

View all of our luxury holidays to the USA.

Trip Overview

Depart from Dublin to Chicago.

Upon arrival, be privately transferred to your luxury hotel in the heart of the Windy City. Enjoy a three night stay here, getting to know the capital of the Prairie State.

Privately tour the iconic buildings of the Windy City.

Discuss with your expert guide which route you would like to take whether it be past historic skyscrapers, Art Deco downtown, sculptures in the Loop or the secrets of Millennium Park. We’ll also reserve tables at our favourite eateries so that you can sample Chicago classics.

Board your flight to Montana.

Upon arrival, collect your rental car and drive to your luxury accommodation in scenic Glacier National Park for a three night stay. The park’s pristine forests, alpine meadows, rugged mountains and spectacular lakes are ripe for exploring.

Glacier National Park
Drive to historic Livingston.

Spend two nights in this town located on the banks of the mighty Yellowstone River. The town is rich in history, harkening back to the glory days of rail and some of the Old West’s most iconic figures including Calamity Jane. Just a short way south, Yellowstone National Park is a must-see during your stay.

Head west to Big Sky.

Spend four nights here at a charming ranch, immersing yourself in activities in the rugged scenery including horseback riding. With a guide to teach you about the area’s flora, fauna and history, ride a suspended tram to the peak of Lone Mountain. At 11,166 feet up, enjoy spectacular highland views.

Big Sky Colours of Montana
Drive to the airport for your flight home.

Drop off your rental car and board your flight home. Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

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Where to rest your head

Looking for the best accommodation? We've got the contacts

The Gwen

The Gwen, A Luxury Collection Hotel

Reflecting the glamour of 1930s Chicago, the Gwen provides the perfect setting to enjoy the Windy City. Named after Chicago-born sculptor Gwen Lux, the hotel’s shared spaces feature Art Deco adornments.

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Lake McDonald Lodge

Lake McDonald Lodge

Built in 1913, the historic Lake McDonald Lodge sits on the picturesque eastern shore of Glacier National Park’s biggest lake. This classic Swiss chalet style lodge offers rustic rooms with modest amenities.

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The Murray

The Murray

An ode to the Old West, the Murray is a historic landmark hotel in downtown Livingston. It was originally built in 1904 to accommodate railroad travellers.

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Mountain Sky Ranch

Mountain Sky Ranch

Enjoy rustic elegance across the 10,000 acres of rugged countryside at the Mountain Sky Ranch. Originally a cattle ranch, Mountain Sky converted to a lodge in 1929 and offers adventures in the Paradise Valley.

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What people are saying

We just wanted to say a big thank you to you and your team for organising our fabulous trip to Florence. The hotel was superb and in a brilliant location. Our tour guide was excellent – the wealth of information and knowledge he had was wonderful. The transport to and from the airport was always on time.  We loved every minute of it!


Lisa & family – Florence, 2022


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