Chicago: The Greastest City I Know

Matt M


Signature Room at the 95th

Grab a fantastic buffet brunch and look out upon the expansive city. Look south for skyscrapers and city splendor, or look north to see the beautiful shoreline all the way to Wisconsin lined with parks, harbors, and residences.

The Magnificent Mile

Walk the magnificent mile to shop at the best stores, stop at fabulous coffee shops, or head north towards the lakefront for a nice walk to get you started after a fantastic breakfast.

navy pier

Head over to Navy Pier and ride the famous Ferris Wheel, signifying its unveiling in the World Fair in Chicago. Plenty of food and sights to been seen both on the wheel and the pier!

Seadog Speedboat Rides

From Navy Pier, take the Seadog (or other competitor's) trip along the lakeshore. Another fantastic alternative is to take the architecture tour through the Chicago River which shows off Chicago's diverse array of styles and buildings. Highly recommended.

Castaways Bar & Grill

Head north to Old Town and North Beach! At North Beach there is a great restaurant/bar in the shape of a boat were you can get some sun, people watch, and enjoy an appetizer or drink.

Lakefront Trail

Take a walk up the lakefront trail and enjoy! The entire Chicago shoreline is lined with the trail, which provides get views of the city, harbors, grounds.

Lincoln Park Zoo

After heading North about a mile, you'll be close to the best, free city Zoo in the country: the Lincoln Park Zoo! Check out your favorite animal and enjoy!

wrigley field

Head up to the hustling and bustling Wrigleyville area and watch a game! This will truly indoctrinate you into Chicago life!

gilt bar

After the game, get cleaned up and head out to Gilt Bar for a fantastic, intimate dinner! The food is great, and the cocktails even better. A great place to begin the night!

Rock Bottom Restaurant & Brewery

A great place to grab some craft beer or other drinks to conclude your fabulous day in Chicago!

I would stay at: The Westin Michigan Avenue Chicago

A relatively affordable location for prime real estate along the Magnificent Mile!