Best Spring Weekend Trips from Chicago

A flamingo paddle boat on the water in Saugatuck, Michigan, highlighting vacation rental experiences and travel activities

There’s something about spring in the Midwest that just feels hopeful. The snow melts, patios reopen, trees start to bloom, and suddenly everyone in Chicago is itching for a weekend out of the city. If you’re searching for the best spring weekend trips from Chicago, you don’t have to go far. Within just a few […]

Fall in Galena, Illinois: Things to Do, Where to Stay, and Travel Guide 

Exterior of American Popcorn Co on Main Street Galena Illinois, featuring the storefront and signage

If you’re searching for the best things to do in Galena IL in fall, just know this — autumn is when this town truly shows off. Rolling hills explode into shades of red, orange, and gold. Main Street feels like a movie set dressed for sweater weather. Crisp air drifts through historic brick-lined sidewalks, and […]

Summer in Galena, Illinois: Things to Do, Where to Stay, and Travel Guide 

Sunset over Main Street in Galena, Illinois, highlighting historic architecture and charming Midwest travel experiences

Planning a Midwest summer getaway? If you’re searching for the best things to do in Galena IL in summer, picture this: a Hallmark movie town tucked into rolling green hills, where brick-lined Main Street feels timeless and every storefront looks like it belongs in a postcard. Galena has that rare kind of charm that works […]

The Ultimate Spring & Summer Madison, Wisconsin Guide

Person standing in a hallway inside the Wisconsin State Capitol building in Madison, Wisconsin

Madison in Spring and Summer: Where to Start If you’re searching for the best things to do in Madison, Wisconsin in spring and summer, this is a good place to begin. Madison shifts completely once the weather warms up. Patios reopen along State Street. The lakes start filling with paddle boards and sailboats. Capitol Square […]

Spring in Galena, Illinois: Things to Do, Where to Stay, and Travel Guide 

The beekeepers and owners of DryCreek Beekeeping in Galena, Illinois, standing together and showcasing local honey production and travel experiences

If you’re searching for the best things to do in Galena IL in spring, this is your sign to go. Spring in Galena feels like the town is waking up again. Storefronts open their doors. The hills shift from muted winter tones to bright green. Waterfalls flow a little stronger after seasonal rain, and Main […]

Trying Outdoor Curling at Fox & Turtle in Itasca, IL

Curling stones sitting on the ice at Fox & Turtle in Itasca, Illinois, highlighting Midwest sports and travel experiences

Big thank you to Meet Chicago Northwest for partnering with me on this post! Tap the story below to see the full experience, including videos! Monetizing my travel social media content helps support even more blog adventures! Are you a DMO looking for top-notch Chicago & Midwest content? Reach out at HELLO@HOWWESEEIT.COM Outdoor curling at […]

Cozy Igloo Experience at Eagle Ridge Resort in Galena, Illinois (Winter Guide)

Igloo dining experience at Eagle Ridge Resort in Galena Illinois during winter

At Eagle Ridge Resort in Galena, IL, a delightful winter dining experience awaits those who crave something truly special. The resort offers an enchanting outdoor igloo restaurant experience, combining the charm of nature with the comforts of modern dining. As the trend of outdoor igloo dining grows in popularity, Eagle Ridge has perfectly captured the […]

Winter in Galena, Illinois: Things to Do, Where to Stay, and Travel Guide

Sunset over Main Street in Galena, Illinois, highlighting historic architecture and charming Midwest travel experiences

Planning a Midwest winter escape? Winter in Galena, IL feels like stepping into a Hallmark winter movie town. Just a few hours from Chicago, this historic river town transforms into one of the most charming cold-weather destinations in the region. Whether you’re planning a romantic weekend, a girls getaway, a Chicago day trip, or a […]