14 days in Chicago, Orlando & Houston Itinerary

14 days in Chicago, Orlando & Houston Itinerary

Created using Inspirock United States visit planner

Plan created by another user. Make it yours
1
Chicago
— 1 night
2
Orlando
— 8 nights
3
Houston
— 4 nights

S M T W T F S
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24

1
night
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 6th (Tue), explore the world behind art at The Art Institute of Chicago, tour the pleasant surroundings at Millennium Park, then observe the fascinating underwater world at Shedd Aquarium, and finally enjoy breathtaking views from Skydeck Chicago - Willis Tower. Keep things going the next day: engage your brain at Museum of Science and Industry and then stop by The Magnificent Mile.

To see photos, traveler tips, where to stay, and other tourist information, read Chicago road trip tool.

Dubuque to Chicago is an approximately 3.5-hour flight. You can also fly; or drive; or take a bus. In April, plan for daily highs up to 59°F, and evening lows to 40°F. Cap off your sightseeing on the 7th (Wed) early enough to travel to Orlando.

Things to do in Chicago

Museums · Parks · Childrens Museums · Neighborhoods
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Shedd Aquarium ©
Shedd Aquarium

8
nights
Orlando

Orlando ©

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Take a break from Orlando with a short trip to Boat Tours & Water Sports in Saint Cloud, about 38 minutes away. Have a day of magic on the 8th (Thu) at Walt Disney World Resort. Pack the 10th (Sat) with family-friendly diversions at Universal Orlando Resort. There's still lots to do: find something for the whole family at Universal's Islands of Adventure, walk around B-52 Memorial Park, admire the natural beauty at Harry P. Leu Gardens, and make an unforgettable trip to Disney's Typhoon Lagoon Water Park.

To find more things to do, where to stay, photos, and tourist information, use the Orlando holiday maker.

Getting from Chicago to Orlando by flight takes about 5.5 hours. Other options: drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Plan for much hotter temperatures traveling from Chicago in April, with highs in Orlando at 84°F and lows at 65°F. Finish up your sightseeing early on the 15th (Thu) so you can travel to Houston.

Things to do in Orlando

Theme Parks · Parks · Outdoors · Beaches

Side Trips

Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

4
nights
Houston

Houston ©

Bayou City

Although urban sprawl remains synonymous with Houston, most of the city's tourist attractions lie within the relatively small downtown area, surrounded by diverse neighborhoods housing the nation's biggest African-American, Asian-American, and Latino communities.
Get out of town with these interesting Houston side-trips: College Station (Bonfire Memorial & George Bush Presidential Library and Museum), The Seawall (in Galveston) and St. Anthony Catholic Church (in Bryan). The adventure continues: stroll the grounds of Glenwood Cemetery, admire the striking features of The Heights Theater, admire the sheer force of Water Wall, and get curious at The Houston Museum of Natural Science.

For ratings, traveler tips, reviews, and other tourist information, you can read our Houston trip planner.

You can fly from Orlando to Houston in 5.5 hours. Other options are to drive; or take a bus. You'll gain 1 hour traveling from Orlando to Houston due to the time zone difference. Traveling from Orlando in April, expect nights in Houston to be about the same, around 62°F, while days are a bit cooler, around 79°F. Finish your sightseeing early on the 19th (Mon) so you can travel back home.

Things to do in Houston

Museums · Historic Sites · Parks · Zoos & Aquariums

Side Trips

Highlights from your plan
Space Center Houston ©
Space Center Houston
Glenwood Cemetery ©
Glenwood Cemetery
George Bush Presidential Library and Museum ©

Similar plans

17 days in United States BY A USER FROM UNITED KINGDOM October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, hidden gems Preferences: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Hidden gems Pace: Medium 25 days in Orlando BY A USER FROM KUWAIT January, teens, kids, culture, outdoors, relaxing, beaches, museums, shopping, wildlife, popular & hidden gems Preferences: January, teens, kids, culture, outdoors, relaxing, beaches, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 22 days in Illinois BY A USER FROM UNITED STATES June, teens, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife, fast-paced, hidden gems Preferences: June, teens, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife Attraction style: Hidden gems Pace: Fast-paced 48 days in United States BY A USER FROM UNITED KINGDOM September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 17 days in United States BY A USER FROM BRAZIL April, culture, outdoors, relaxing, romantic, historic sites, wildlife, slow & easy, popular sights Preferences: April, culture, outdoors, relaxing, romantic, historic sites, wildlife Attraction style: Popular sights Pace: Slow & easy 31 days in United States BY A USER FROM IRELAND August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 18 days in United States BY A USER FROM BRAZIL April, culture, outdoors, relaxing, romantic, historic sites, slow & easy, popular sights Preferences: April, culture, outdoors, relaxing, romantic, historic sites Attraction style: Popular sights Pace: Slow & easy 60 days in United States BY A USER FROM ISRAEL May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, slow & easy, popular & hidden gems Preferences: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 8 days in Orlando BY A USER FROM UNITED STATES October, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: October, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 16 days in New York City & Orlando BY A USER FROM BRAZIL July, teens, kids, culture, historic sites, museums, shopping, popular sights Preferences: July, teens, kids, culture, historic sites, museums, shopping Attraction style: Popular sights Pace: Medium 15 days in Orlando BY A USER FROM UNITED KINGDOM April, teens, beaches, shopping, wildlife, popular & hidden gems Preferences: April, teens, beaches, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans