15 days in Midwest & Montana Itinerary

15 days in Midwest & Montana Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
1
Chicago
— 3 nights
2
Billings
— 1 night
3
West Yellowstone
— 1 night
4
Bozeman
— 2 nights
5
Kansas City
— 1 night
6
Branson
— 2 nights
7
Saint Louis
— 3 nights
8
Cleveland
— 1 night

S M T W T F S
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22

3
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, engage your brain at Museum of Science and Industry, learn about wildlife with up-close encounters at Lincoln Park Zoo, and admire nature's wide array of creatures at Shedd Aquarium.

To see traveler tips, ratings, photos, and tourist information, go to the Chicago day trip site.

Hartford to Chicago is an approximately 5-hour flight. You can also drive; or take a bus. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. May in Chicago sees daily highs of 71°F and lows of 52°F at night. Finish up your sightseeing early on the 11th (Tue) so you can travel to Billings.

Things to do in Chicago

Parks · Museums · Zoos & Aquariums · Shopping
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

1
night
Billings

Billings ©
Billings is the largest city in the state of Montana, and is the principal city of the Billings Metropolitan Area with a population of 166,855.Billings is located in the south-eastern portion of the state and is the seat of Yellowstone County, which had a 2015 population of 157,048. Start off your visit on the 12th (Wed): take in nature's colorful creations at DanWalt Gardens, then stop by Scheels, then test your problem-solving skills at The Grand Escape Room, and finally indulge your thirst for a good beer at Angry Hank's Microbrewery.

To see photos, other places to visit, where to stay, and tourist information, refer to the Billings day trip planner.

Traveling by flight from Chicago to Billings takes 5.5 hours. Alternatively, you can drive; or take a bus. You'll gain 1 hour traveling from Chicago to Billings due to the time zone difference. Plan for a bit cooler nights when traveling from Chicago in May since evenings lows in Billings dip to 45°F. Finish up your sightseeing early on the 12th (Wed) so you can go by car to West Yellowstone.

Things to do in Billings

Breweries & Distilleries · Parks · Fun & Games · Shopping
Highlights from your plan
The Grand Escape Room ©
The Grand Escape Room
Angry Hank's Microbrewery ©
Angry Hank's Microbrewery
DanWalt Gardens ©
DanWalt Gardens

1
night
West Yellowstone

West Yellowstone ©
The town of West Yellowstone has served as a gateway to Yellowstone National Park since the early 1900s.
Kick off your visit on the 13th (Thu): see what you can catch with a fishing tour, then find something for the whole family at Yellowstone Big Gun Fun, and then identify plant and animal life at Grizzly and Wolf Discovery Center.

To see more things to do, reviews, maps, and other tourist information, you can read our West Yellowstone tour itinerary maker website.

You can drive from Billings to West Yellowstone in 4.5 hours. Other options are to fly; or take a bus. Prepare for slightly colder weather when traveling from Billings in May: high temperatures in West Yellowstone hover around 57°F and lows are around 31°F. Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Bozeman.

Things to do in West Yellowstone

Wildlife · Outdoors · Parks · Tours
Highlights from your plan
Yellowstone Big Gun Fun ©
Yellowstone Big Gun Fun
Grizzly and Wolf Discovery Center ©
Grizzly and Wolf Discovery Center
Fishing Charters & Tours

2
nights
Bozeman

Bozeman ©
Bozeman is a city in and the county seat of Gallatin County, Montana, United States, in the southwestern part of the state. Kick off your visit on the 14th (Fri): stroll around Sacajawea Park and then get interesting insight from Yellowstone Guidelines. Keep things going the next day: cast your line with a fishing tour and then see the interesting displays at American Computer & Robotics Museum.

For other places to visit, traveler tips, ratings, and more tourist information, refer to the Bozeman road trip planning website.

Drive from West Yellowstone to Bozeman in 2 hours. Alternatively, you can take a bus. Expect somewhat warmer temperatures when traveling from West Yellowstone in May; daily highs in Bozeman reach 65°F and lows reach 37°F. On the 15th (Sat), wrap the sightseeing up by early afternoon so you can travel to Kansas City.

Things to do in Bozeman

Wildlife · Outdoors · Tours · Parks

Side Trip

Highlights from your plan
Yellowstone Guidelines ©
Yellowstone Guidelines
American Computer & Robotics Museum ©
American Computer & Robotics Museum
Fishing Charters & Tours

1
night
Kansas City

Kansas City ©

City of Fountains

The largest municipality in Missouri, Kansas City has an impressive array of world-class museums, shopping areas, and great places to eat, all of which attract tourism to the area.
On the 16th (Sun), get engrossed in the history at National WWI Museum and Memorial, steep yourself in history at Bingham Waggoner Mansion & Estate, and then get engrossed in the history at Harry S. Truman Library and Museum.

To see ratings, maps, traveler tips, and tourist information, read our Kansas City tour itinerary builder site.

Traveling by flight from Bozeman to Kansas City takes 7.5 hours. Alternatively, you can drive; or do a combination of bus, car, taxi, shuttle, and train. You'll lose 1 hour traveling from Bozeman to Kansas City due to the time zone difference. Traveling from Bozeman in May, things will get a bit warmer in Kansas City: highs are around 76°F and lows about 57°F. Cap off your sightseeing on the 16th (Sun) early enough to go by car to Branson.

Things to do in Kansas City

Museums · Historic Sites

Side Trip

Highlights from your plan
Bingham Waggoner Mansion & Estate ©
Bingham Waggoner Mansion & Estate
National WWI Museum and Memorial ©
National WWI Museum and Memorial
Harry S. Truman Library and Museum ©
Harry S. Truman Library and Museum

2
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.
On the 17th (Mon), cool off at Silver Dollar City. Keep things going the next day: get engrossed in the history at Titanic Museum, contemplate the waterfront views at Table Rock Lake, and then take in nature's colorful creations at College of the Ozarks.

To see other places to visit, photos, ratings, and other tourist information, read our Branson road trip tool.

You can drive from Kansas City to Branson in 4 hours. Alternatively, you can take a bus; or fly. Expect a daytime high around 75°F in May, and nighttime lows around 55°F. Finish up your sightseeing early on the 18th (Tue) so you can go by car to Saint Louis.

Things to do in Branson

Theme Parks · Parks · Nature · Museums

Side Trip

Highlights from your plan
College of the Ozarks ©
College of the Ozarks
Silver Dollar City ©
Silver Dollar City
Table Rock Lake ©
Table Rock Lake

3
nights
Saint Louis

Saint Louis ©

Gateway to the West

Test the local claim that Saint Louis is second only to Washington, D.C.
Saint Louis is known for museums, zoos & aquariums, and parks. Your plan includes some of its best attractions: enjoy breathtaking views from The Gateway Arch, examine the collection at City Museum, experience rural life at Grant’s Farm, and take in the architecture and atmosphere at Cathedral Basilica of Saint Louis.

To find more things to do, maps, and more tourist information, you can read our Saint Louis road trip planning tool.

Getting from Branson to Saint Louis by car takes about 4.5 hours. Other options: do a combination of car and flight; or do a combination of taxi and bus. In May, daytime highs in Saint Louis are 77°F, while nighttime lows are 57°F. Finish your sightseeing early on the 21st (Fri) so you can travel to Cleveland.

Things to do in Saint Louis

Parks · Zoos & Aquariums · Museums · Historic Sites
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis
The Gateway Arch ©
The Gateway Arch
Saint Louis Zoo ©
Saint Louis Zoo

1
night
Cleveland

Cleveland ©

Forest City

A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
Kick off your visit on the 22nd (Sat): explore the world behind art at The Cleveland Museum of Art, then see the interesting displays at Rock & Roll Hall of Fame, and then browse the eclectic array of goods at West Side Market.

Before you visit Cleveland, use our trip planner to discover what you can do and see there.

Fly from Saint Louis to Cleveland in 4 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Saint Louis to Cleveland. While traveling from Saint Louis, expect slightly colder days and about the same nights in Cleveland, ranging from highs of 69°F to lows of 54°F. Cap off your sightseeing on the 22nd (Sat) early enough to travel back home.

Things to do in Cleveland

Highlights from your plan
The Cleveland Museum of Art ©
The Cleveland Museum of Art
Rock & Roll Hall of Fame ©
Rock & Roll Hall of Fame
West Side Market ©
West Side Market

Similar plans

28 days in Montana BY A USER FROM UNITED KINGDOM July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems Preferences: July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 31 days in United States BY A USER FROM UNITED KINGDOM July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems Preferences: July, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 34 days in United States BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 16 days in Montana & Connecticut BY A USER FROM UNITED STATES October, outdoors, relaxing, historic sites, wildlife, hidden gems Preferences: October, outdoors, relaxing, historic sites, wildlife Attraction style: Hidden gems Pace: Medium 60 days in United States BY A USER FROM UNITED STATES August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 60 days in United States BY A USER FROM UNITED STATES August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: August, kids, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 17 days in Montana BY A USER FROM UNITED STATES September, outdoors, romantic, fast-paced, hidden gems Preferences: September, outdoors, romantic Attraction style: Hidden gems Pace: Fast-paced 13 days in Montana BY A USER FROM UNITED STATES June, kids, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular sights Preferences: June, kids, culture, outdoors, relaxing, beaches, historic sites, wildlife Attraction style: Popular sights Pace: Medium 54 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, hidden gems Preferences: September, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Hidden gems Pace: Medium 47 days in United States BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife, hidden gems Preferences: September, culture, outdoors, relaxing, beaches, historic sites, museums, wildlife Attraction style: Hidden gems Pace: Medium 60 days in United States BY A USER FROM UNITED STATES August, kids, culture, outdoors, relaxing, historic sites, museums, wildlife, popular & hidden gems Preferences: August, kids, culture, outdoors, relaxing, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 43 days in Montana & Wyoming BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, historic sites, museums, wildlife, popular & hidden gems Preferences: May, culture, outdoors, relaxing, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans