15 days in Midwest & Portland Itinerary

15 days in Midwest & Portland Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
1
Branson
— 3 nights
2
Chicago
— 2 nights
3
Mackinac Island
— 1 night
4
Munising
— 2 nights
5
Custer
— 2 nights
6
Portland
— 3 nights

S M T W T F S
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3
nights
Branson

Branson ©

Live Entertainment Capital of the World

Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Step out of the city life by going to Dogwood Canyon Nature Park and Shepherd of the Hills Fish Hatchery. Explore hidden gems such as Table Rock Lake and Fishing Charters & Tours. There's much more to do: whizz through the canopy at some of the top local zipline courses and adventure parks, do a tasting at Stone Hill Winery, take some stellar pictures from 165 Scenic Overlook, and look for all kinds of wild species at National Tiger Sanctuary.

Use Inspirock's suggestions to plan your Branson trip and find the best activities and attractions for your vacation.

Portland to Branson is an approximately 9.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 2 hours traveling from Portland to Branson. Traveling from Portland in June, expect Branson to be somewhat warmer, temps between 84°F and 65°F. Cap off your sightseeing on the 4th (Thu) early enough to travel to Chicago.

Things to do in Branson

Parks · Wildlife · Nature · Tours

Side Trips

Highlights from your trip

2
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 5th (Fri), engage your brain at Museum of Science and Industry, then contemplate the waterfront views at Lake Michigan, and then admire the masterpieces at The Art Institute of Chicago. On the 6th (Sat), you'll have a packed day of sightseeing: get a new perspective on nature at Field Museum, then stroll around Millennium Park, and then get a taste of the local shopping with The Magnificent Mile.

For more things to do, reviews, and tourist information, go to the Chicago day trip app.

Traveling by flight from Branson to Chicago takes 4.5 hours. Alternatively, you can drive; or do a combination of taxi, bus, and train. June in Chicago sees daily highs of 81°F and lows of 63°F at night. Wrap up your sightseeing on the 6th (Sat) early enough to travel to Mackinac Island.

Things to do in Chicago

Museums · Childrens Museums · Parks · Neighborhoods

Side Trip

Highlights from your trip
©
Neighborhood
The Magnificent Mile
4.4
©
Natural History Museum
Field Museum
4.5

1
night
Mackinac Island

Mackinac Island ©
Mackinac Island is a city in Mackinac County in the U.S. Start off your visit on the 7th (Sun): brush up on your military savvy at Fort Mackinac and then admire the majestic nature at Mackinac Island State Park. Get ready for a full day of sightseeing on the next day: steep yourself in history at Fort Holmes, then take a tour by water with Boat Tours & Water Sports, then identify plant and animal life at The Original Mackinac Island Butterfly House & Insect World, and finally take in the architecture and atmosphere at St Anne's Catholic Church.

To find traveler tips, other places to visit, and other tourist information, refer to the Mackinac Island online trip itinerary planner.

Traveling by combination of flight and ferry from Chicago to Mackinac Island takes 7.5 hours. Alternatively, you can do a combination of train, bus, and ferry; or do a combination of bus and ferry. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Plan for slightly colder temperatures traveling from Chicago in June, with highs in Mackinac Island at 67°F and lows at 51°F. Finish up your sightseeing early on the 8th (Mon) so you can travel to Munising.

Things to do in Mackinac Island

Parks · Historic Sites · Tours · Nature
Highlights from your trip

2
nights
Munising

Munising ©
Munising is a city on the southern shore of Lake Superior on the Upper Peninsula of the U.S. Start off your visit on the 9th (Tue): admire the sheer force of Munising Falls and then explore the striking landscape of Pictured Rocks National Lakeshore. On the next day, admire the sheer force of Wagner Falls, then explore the striking landscape at Miners Castle Rock, and then take in the dramatic scenery at Miners Falls.

Discover how to plan a Munising trip in just a few steps with Inspirock's itinerary builder.

Traveling by combination of ferry, bus, and car from Mackinac Island to Munising takes 7 hours. Alternatively, you can do a combination of ferry, bus, and taxi. In June, plan for daily highs up to 68°F, and evening lows to 49°F. Finish your sightseeing early on the 10th (Wed) so you can travel to Custer.

Things to do in Munising

Parks · Nature · Wildlife
Highlights from your trip
©
Must see
Munising Falls
4.7
©
Must see
Miners Falls
4.8

2
nights
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Start off your visit on the 11th (Thu): contemplate the waterfront views at Sylvan Lake, then take in the dramatic natural features at Needles Eye Tunnel, and then take a peaceful walk through Black Hills National Forest. Get ready for a full day of sightseeing on the 12th (Fri): pause for some photo ops at Mount Rushmore National Memorial, then hike along Presidential Trail, and then explore and take pictures at Iron Mountain Road.

To see reviews, where to stay, more things to do, and more tourist information, you can read our Custer road trip app.

Traveling by flight from Munising to Custer takes 8 hours. Alternatively, you can drive; or do a combination of car, bus, and taxi. The time zone difference when traveling from Munising to Custer is minus 2 hours. In June, daily temperatures in Custer can reach 73°F, while at night they dip to 48°F. Cap off your sightseeing on the 12th (Fri) early enough to travel to Portland.

Things to do in Custer

Parks · Nature · Outdoors · Trails

Side Trip

Highlights from your trip
©
Must see
Sylvan Lake
4.8

3
nights
Portland

Portland ©

City of Roses

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Visiting The Grotto - National Sanctuary of Our Sorrowful Mother and Mount Hood will get you outdoors. Satisfy your inner culture vulture at Western Antique Aeroplane & Automobile Museum and The Depot Rail Museum. Change things up with these side-trips from Portland: Mount St. Helens National Volcanic Monument (in Amboy), Oneonta Gorge (in Cascade Locks) and Latourell Falls (in Corbett). Next up on the itinerary: hike along Horsetail Falls- Columbia River Gorge, take a peaceful walk through Camassia Natural Area, and explore the landscape on two wheels at Willamette River Trail.

Start your trip to Portland by creating a personalized itinerary on Inspirock.

Getting from Custer to Portland by flight takes about 8 hours. Other options: drive; or do a combination of taxi, bus, and train. The time zone difference moving from Mountain Standard Time to Pacific Standard Time is minus 1 hour. Expect somewhat warmer evenings in Portland when traveling from Custer in June, with lows around 56°F. Finish up your sightseeing early on the 15th (Mon) so you can travel back home.

Things to do in Portland

Parks · Nature · Outdoors · Trails

Side Trips

Highlights from your trip
©
Must see
Mount Hood
4.7
©
Must see
Oneonta Gorge
4.7