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![3-Day Road Trip from Big Sky to Chicago](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018ff34d-9b97-7c57-93c4-a9b9e9912b8e/location918.jpg)
3-Day Road Trip from Big Sky to Chicago Itinerary
Last updated: 2024 Jun 14Exploring Big Sky's Natural Wonders
Morning
Start your day with a hearty breakfast at Café 191 in Big Sky. Following breakfast, embark on the From Bozeman Exclusive Yellowstone Tour (2 Days 1 Night). This tour will take you through some of the most breathtaking landscapes and geothermal features of Yellowstone National Park. You'll have the opportunity to see geysers, hot springs, and possibly even some wildlife. The tour is guided, ensuring you get the most out of your visit.
Afternoon
Continue your exploration of Yellowstone with the tour. In the afternoon, you'll visit iconic spots like Old Faithful and the Grand Prismatic Spring. These natural wonders are must-sees for any visitor to Yellowstone. Lunch will be provided as part of the tour, allowing you to focus on taking in the stunning scenery without worrying about finding a place to eat.
Evening
Return to Big Sky in the evening and enjoy a relaxing dinner at Horn & Cantle. This restaurant offers a cozy atmosphere and delicious local cuisine, perfect for unwinding after a day of adventure. If you're up for it, take a stroll around Big Sky's charming town center before heading back to your accommodation.
Bedtime
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![Visit From Bozeman Exclusive Yellowstone Tour (2 Days 1 Night) in Big Sky](https://cdn.getyourguide.com/img/tour/eac43413356bff7f73f0599c653cea8637c1c11749962adaca373e6ed72c6037.jpg/21.jpg)
From Bozeman Exclusive Yellowstone Tour (2 Days 1 Night)
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![Visit From Bozeman Exclusive Yellowstone Tour (2 Days 1 Night) in Big Sky](https://cdn.getyourguide.com/img/tour/eac43413356bff7f73f0599c653cea8637c1c11749962adaca373e6ed72c6037.jpg/21.jpg)
From Bozeman Exclusive Yellowstone Tour (2 Days 1 Night)
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Journey Through Medora's Western Charm
Morning
Depart from Big Sky early in the morning and drive towards Medora, North Dakota. The drive will take approximately 6-7 hours, so make sure to have some snacks and drinks for the road. Upon arrival in Medora, start your day with brunch at The Farmhouse Café, known for its hearty meals and friendly service.
Afternoon
After brunch, explore Theodore Roosevelt National Park. Spend your afternoon hiking or driving through this beautiful park that offers stunning views of badlands terrain and abundant wildlife. Make sure to visit Painted Canyon Overlook for some incredible photo opportunities.
Evening
In the evening, experience Medora's western charm by attending the famous Medora Musical at Medora Musical. Beforehand, enjoy dinner at Pitchfork Steak Fondue, where you can savor steaks cooked on pitchforks over an open flame while enjoying panoramic views of the Badlands.
Bedtime
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Discovering Chicago's Iconic Landmarks
Morning
Leave Medora early in the morning for a long drive to Chicago (approximately 12 hours). Upon arrival in Chicago, start with brunch at The Bongo Room, known for its creative breakfast dishes and vibrant atmosphere.
Afternoon
Spend your afternoon exploring some of Chicago's iconic landmarks starting with Millennium Park, where you can see Cloud Gate (The Bean) and Crown Fountain. Next, head over to The Magnificent Mile for some shopping or simply enjoy walking along this famous stretch.
Evening
In the evening visit House of Blues for dinner while enjoying live music performances that showcase both local talent as well as renowned artists from around world.
Bedtime
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![Visit Millennium Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
4.69Millennium Park
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![Visit Millennium Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
Millennium Park
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![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
4.65The Magnificent Mile
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![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
The Magnificent Mile
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![Visit House of Blues in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/77/d4.jpg)
5.00House of Blues
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![Visit House of Blues in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/77/d4.jpg)
House of Blues
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