Yellowstone holiday with Chicago city break

Tailor-made holidays
Duration (in days): 12

From: UK – Chicago

To: Jackson Hole - UK



Inc. International flights (per person, based on 2 sharing) 
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Explore the USA on this Yellowstone holiday. Start in Chicago, where you can wander along the canals, watch a baseball game at Wrigley Field or simply indulge with the signature deep-dish pizza. After a few days exploring you’ll fly to Montana, for a glamping adventure in Yellowstone National Park. Hike past bubbling geysers, swim in pristine lakes and look for wildlife on the vast grasslands. Finish your trip in Grand Teton National Park, watching the sunset behind the mountains.

This itinerary can be tailored to suit your requirements; please contact one of our consultants to start planning your dream trip.

This holiday includes

  • International flights
  • All transfers
  • All accommodation in the USA  
  • Excursions as mentioned in the itinerary
  • Meals as mentioned in the itinerary        


You’ll remember…

  • Catch a baseball game at Wrigley Field
  • Enjoy views over the city from the Skydeck of Willis Tower
  • Try a slice of famous Chicago deep dish pizza
  • Explore Yellowstone National Park where Old Faithful geyser erupts  
  • Photograph Grand Teton National Park’s stunning vistas            



Itinerary in brief:

  • 3 nights Chicago
  • 4 nights Yellowstone National Park
  • 3 nights Grand Teton National Park

Day 1: London to Chicago

Depart the UK from your chosen airport. You’ll arrive in Chicago later the same day, making your own way to your hotel and checking in for three nights.

Included: International flights, 4* hotel

Days 2 & 3: Chicago

Two days is enough time to enjoy the highlights of Chicago. Start with a trip to the Cloud Gate, more popularly known as “The Bean” where you can snap a photo in its distorted reflection, before heading to Intelligentsia Coffee for a latte. We’ve included the Chicago City Pass so you can use it to explore two of America’s best museums. The Art Institute of Chicago holds paintings by Picasso and O’Keefe, as well as the famous American gothic portrait by Grant Wood, while at the Field Museum you can visit Sue, the most complete T-Rex skeleton ever found.

Enjoy a slice of Chicago deep dish pizza at Giordano’s before a night of comedy at Second City, where many famous comedians made their debuts. Don’t leave before heading to the top of the Willis Tower SkyDeck, where you can stand in a glass box high and admire endless views of the city and Lake Michigan below.

Included: 4* hotel

Day 4: Fly to Bozeman

Enjoy a final breakfast in the Windy City, before making your own way to the airport in time for your flight to Bozeman in Montana. On arrival, you’ll pick up your hire car and drive to your accommodation, just north of Yellowstone National Park.

Included: Flights, Glamping accommodation, car hire   

Days 5 - 7: Yellowstone National Park

Two days of exploration will barely scratch the surface of Yellowstone, so get stuck in and see as much as you can! Highlights include Old Faithful, a geyser that erupts with convenient regularity and the Grand Prismatic Spring, a rainbow coloured hot spring that steams in the cool mountain air. You could hike to the edge of Yellowstone Falls and then relax in the Boiling River, one of the only hot springs that you can bathe in.

Next, why not rent a kayak and venture out onto the deep blue waters of Mount Yellowstone before heading to the lush green and yellow grasslands of Hayden Valley at dusk, one of the best places and times to see wildlife like elk, bears, bison and coyotes. There are endless beautiful sights and activities here, with hundreds of bubbling mud pools and scenic vistas to get swept up in.

Included: Car hire, glamping accommodation  

Day 8: Drive to Grand Teton National Park

This morning you’ll drive a couple of hours south to Grand Teton National Park, the often-overlooked neighbour of Yellowstone. On arrival, you’ll check into your hotel for three nights and head out to the park to start exploring.

Included: Car hire, dinner, 4* lodge

Days 9 - 10: Grand Teton National Park  

For the best views, head into the park for sunrise and watch the pink sunshine light up the mountains behind the Moulton Barn. As the most famous view in Grand Teton, of a rugged barn surrounded by peaks, it’s the perfect start to your time here. Spend the day kayaking along the Snake River, hiking to Oxbow Bend to see Mount Moran reflected in the water and watching moose wading upstream. A day here will go very quickly so make the most of it!           

Included: Car hire, breakfast, dinner, 4* lodge   

Day 11: Depart USA

Finish your time in the USA with a final hike, before driving back to the airport in time to drop off your car and catch your flight back home.

Included: Breakfast, car hire, international flights          

Day 12: Arrive UK


The Rocky Mountains have long snowy winters and short balmy summers, so travelling between June and September is ideal but will be very busy. The shoulder seasons of spring and autumn are often lovely times to visit, but the weather can be less predictable, and wildlife is often harder to spot compared to mid-summer.

This itinerary is purely a suggestion and can be tailor-made to your requirements, so please contact us with your dates and requests, and we’ll put together a bespoke quotation for you.           

What's included: 

  • International flights
  • Return airport transfers
  • Accommodation as mentioned in the itinerary   
  • Meals as mentioned in the itinerary
  • Excursions as mentioned in the itinerary

Not included: 

  • Any meals not mentioned
  • Personal expenses
  • Tips & gratuities
  • Fuel      
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