Best of Chicago: Skydeck, Architecture River Cruise and Loop Walking Tour in Chicago, IL

Get ready to discover the storied architecture of Chicago. You'll take the first elevator ride of the morning up to Skydeck at Willis Tower to see the city from a birds-eye prime vantage spot. Journey back to street level for an immersive tour of the Loop, guiding you from the iconic 'L' train circling downtown Chicago to the city's impressive Art Deco architecture. This insider's look will supply you with the history to truly appreciate these colossal structures. A 90-minute river cruise awaits at the end of the tour, taking you from the Chicago River to Lake Michigan.

The Loop is where Chicago's history and bustling present truly intersect. Boasting some of the city's most impressive buildings, The Loop may be a business district, but it's much more than that—including the birthplace of the world's first skyscraper. Begin your tour at the base of the Monadnock Building, where your expert local guide will be waiting to take you on a journey through the city's most storied structures.

Take the first elevator of the day up 103 floors to the Skydeck at Willis Tower. Take advantage of the observational decks to get the best possible view of the city from above.

Back on ground level, it's time to traverse Chicago's Financial District alongside your local guide and see the city's Art Deco architecture will be laid out before – or rather, above – you! Pass the magnificent Board of Trade Building and take in the statue of Ceres, the Ancient Greek goddess of the harvest, looming over the skyline three stories high.

Next, walk through the Rookery's awe-inspiring lobby, designed by Frank Lloyd Wright. Only an expert can point out many elements here, including the secret glass mosaics adorning the lobbies. You'll listen to the history of the cast of characters that brought Chicago to worldwide fame, admire one of the world's most historically significant doors and get a view of the largest Tiffany glass dome in the world.

Millennium Park is the next stop, where the iconic Cloud Gate can be found. After getting a picture in front of 'The Bean,' it's time to walk up Michigan Avenue for more architectural stories and history.

The day's last stop is Chicago's iconic Riverwalk for a 90-minute architecture cruise, passing down the Chicago River and Lake Michigan. Enjoy the snacks and refreshments available to purchase on board, and take in the day's discoveries from the water.