9 days in Chicago & Islamorada Itinerary

9 days in Chicago & Islamorada Itinerary

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9 days in Chicago & Islamorada Itinerary

Start: Chicago
1
Chicago
— 5 nights
Fly + shuttle:  7​h 30​min
2
Islamorada
— 2 nights
shuttle + Fly:  7​h 30​min
End: Chicago

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Magnificent Mile and Millennium Park. Explore hidden gems such as Grand Mere State Park and Silver Beach County Park. Explore the numerous day-trip ideas around Chicago: Jasper-Pulaski Fish and Wildlife Area (in Medaryville), University of Notre Dame (in South Bend) and Sarett Nature Center (in Benton Harbor). There's much more to do: explore the world behind art at The Art Institute of Chicago, do a tasting at Lemon Creek Winery, hike along Cowles Bog, and admire the majestic nature at Starved Rock State Park.

For other places to visit, photos, reviews, and tourist information, use the Chicago trip itinerary tool .

In July in Chicago, expect temperatures between 83°F during the day and 67°F at night. Wrap up your sightseeing on the 28th (Sun) early enough to travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Utica, University of Notre Dame, Silver Beach County Park, Lemon Creek Winery, Jasper-Pulaski Fish and Wildlife Area
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Silver Beach County Park ©
Silver Beach County Park
The Art Institute of Chicago ©
The Art Institute of Chicago

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 29th (Mon), see the vivid underwater world at Sombrero Reef and then take a memorable tour with Captain Hook's Marina & Dive Center. On the 30th (Tue), you'll have a packed day of sightseeing: view the masterpieces at Old Road Gallery, explore the gorgeous colors at Spiegel Grove, then tour the water at your own pace with A1A Watersports, and finally sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room.

To see reviews, where to stay, photos, and other tourist information, you can read our Islamorada tour itinerary planner.

You can do a combination of flight and shuttle from Chicago to Islamorada in 7.5 hours. Alternatively, you can do a combination of flight and bus; or drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Expect somewhat warmer temperatures when traveling from Chicago in July; daily highs in Islamorada reach 92°F and lows reach 81°F. Wrap up your sightseeing by early afternoon on the 31st (Wed) to allow enough time to travel back home.

Things to do in Islamorada

Wildlife Parks Transportation

Side Trips

Key Largo, Marathon
Highlights from your plan
Sombrero Reef ©
Sombrero Reef
Spiegel Grove ©
Spiegel Grove
Molasses Reef ©
Molasses Reef

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