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Ultimate Yellowstone and Cowboy Country Adventure

Chicago, Jackson Hole, Yellowstone & The Ranch at Rock Creek

There's nowhere quite like Yellowstone with its dramatic scenery and wildlife - this itinerary allows you to see it all. Don your cowboy hat and experience the Rockies, enjoying the active adventures to be had in Wyoming and Montana in true western style.

At a Glance

  • You'll visit some of the most photographed sites in the USA

  • Get a city fix with a stop over in Chicago on the way out to the Rockies or on your return

  • Private guide to take you off-the-beaten track wildlife watching in Yellowstone National Park

  • All activities and meals are included on the safari and on the ranch

  • Experience fly fishing and horse-riding at its best in Montana country

Adventure, Couples, Family, Riding

Insider's View

Swing by the lobby in the Peninsula on Friday and Saturday night for their gourmet chocolate buffet! A hit with kids, big and small!

Anna Bleasdale

Insider's View

The safari can be condensed to a 2-night, 3-day experience if preferred - it just means more time on the road!

Maudie Tomlinson

Insider's View

Sit comfortable on a saddle in the Silver Dollar Saloon at the ranch and ask Ned to make you a house cocktail!

Maudie Tomlinson

We design each itinerary around you, so this suggested itinerary is a starting point that we can tweak or transform into something completely bespoke to you. Call us on 858 523 9000 to start planning your vacation.


This itinerary is suitable for both couples and families looking to embrace the Wild West in Jackson Hole, experience the best of Yellowstone National Park's wildlife and iconic scenery, and don their cowboy hat in style at The Ranch at Rock Creek.

Begin your vacation in Chicago; known as the Windy City, Chicago will blow you away with its stratospheric architecture, incredible gastronomy and fascinating history from politics to gangster tales. Grab a Segway down at Navy Pier and take a tour of Chicago’s past, followed by a walk around the famous Millennium Park. Home to some of the most iconic architecture in the states, a stay here warrants a trip up to the famous Willis tower, or for a drink with a view, head up to the 95th floor of the Hancock building - the sixth tallest building in the US - to the signature lounge. We recommend a two-night stay at Peninsula Chicago, with an ideal location on Michigan Avenue from which to explore.

Next you’ll fly onto Jackson Hole, a charming Rocky Mountain western town and the gateway to the popular Grand Teton and Yellowstone National Parks. We suggest three nights here to make the most of the activities on offer, including rafting on Snake River, hiking and biking in the Tetons, and you wouldn’t want to miss the rodeo every Wednesday and Saturday in the summer. In the evening, explore the boutique shops, followed by dinner at one of the fantastic restaurants serving elk and bison burgers. Finish the night listening to bands playing everything from country to rock at the Silver Dollar bar, the most vibrant family restaurant in town. By the end of the night you'll be ready to jump into bed and what better hotel than the delightful Rusty Parrot Lodge. This intimate hotel has large rooms, most with fireplaces creating a cosy retreat on a chilly evening. It's also home to the only Four-Diamond restaurant in Jackson - Wild Sage.

Next begin a four-day adventure exploring Grand Teton and Yellowstone with an experienced naturalist guide. Here you’ll delve deeper into the parks and spend time viewing elk, bison, moose, bears, foxes and see wild horses run. One of the highlights is the Lamar Valley where you'll see if you can spot a handsome grizzly bear or elusive wolves. It’s not all about wildlife however, as Yellowstone is famed for its geysers and active geothermal activity - there’s a reason it’s such a photographed area. You will see famous sights including Mammoth Hot Springs and Old Faithful – a geyser that shoots hot water into the air up to 140ft every hour or so. With guides that specialize in wildlife, geology, photography and ex-park rangers that are fantastic with children, we will ensure that your guide is matched to your requirements to make your trip one to remember.

To finish, your guide will drop you off at one of the most exclusive ranches in the USA - The Ranch at Rock Creek. Continuously awarded for impeccable service and one-of-a-kind facilities, you’ll be able to go at you own speed here. Fill your days with the vast array of activities on offer including shooting, horse riding, fly fishing, mountain biking, archery and paint-balling. If you would prefer to relax, then while away your day swinging in a riverside hammock or soothe those aching muscles at The Granite Spa. In the evening you’ll be wowed by pre-dinner cocktails and the five course tasting menu serving the best of Montana fare with locally sourced ingredients and the best quality wines.

What really sets this ranch apart is the level of entertainment that is sure to fill your days and entertains adults and children alike. The Silver Dollar Saloon houses a billiard room and bowling alley and, for those tired and seeking solace after a day's adventure in beautiful Montana, snuggle up in the cinema room with your choice of film and a hot chocolate. By the end of this trip you'll have a yearning to continue the good life of the well-heeled cowboy!





Fly to Chicago
2 nights

Midwest, United States of America

Peninsula Hotel Chicago
Fly Chicago to Jackson Hole 3-hours
3 nights

Jackson Hole, Grand Teton National Park, Wyoming

Rusty Parrot Lodge and Spa
3 nights

Grand Tetons, Yellowstone, Cody

Yellowstone and Grand Teton Wildlife Discovery
5 nights

Philipsburg, Montana, United States of America

The Ranch at Rock Creek
Fly Missoula to Denver 2-hours
1 night Fly Denver to Home

Location & Directions

Chicago, Jackson Hole, Yellowstone & The Ranch at Rock Creek

Jackson Hole Valley is formed by the Teton Range to the western and the Gros Ventre Range to the east, with Grand Teton National Park occupying the whole north-western side of the valley. The southern entrance to Yellowstone is located 60-miles north of Jackson Hole town, widely held to be the first national park in the world, this expansive 3,500 square mile park also extends into Montana and Idaho.

When to go

Chicago is a fantastic destination most of the year around as there’s always lots of things going on in the city. Summers are hot and humid, with daily averages of 24 degrees, and winters can be very cold, which makes spring and autumn for most the best time to go.

Jackson Hole has five distinct seasons: summer (usually June to August), fall (September through October), off-season (November), winter (December through March) and off-season (April and May). Combining Jackson with Yellowstone in the spring and autumn is ideal for viewing wildlife, although the summer can be a wonderful time for those seeking that warmer weather.

Spring and Fall in Montana allow for mild days and cool nights, whilst the summers offer hot days and warm evenings. Peak time at the ranch is June through to end of August but fall is a stunning time to visit when foliage turns the Montana mountains russet and gold. Winter is marked by crisp days and cold evenings, with snowfall creating a winter wonderland.

Best time to Visit

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We design each itinerary around you, so this suggested itinerary is a starting point that we can tweak or transform into something completely bespoke to you. Call us on 858 523 9000 to start planning your vacation.

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