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

Walks LLC55 W Jackson BlvdChicago, IL 60604
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Explore the best of Chicago's architecture scene! This guided tour begins with a bird’s-eye view from the Skydeck at Willis Tower, then back to street level with a walking tour of the Loop, and finishes with a relaxing architecture river cruise. An expert local guide provides an insider’s look at legendary skyscrapers, Art Deco architecture and hidden gems.

up to 5.5 hrs 1 or more people

Good To Know

  • Discover the best of Chicago's Art Deco architecture and modern cityscapes on this guided Chicago architecture tour.
  • Get an up-close look at the largest Tiffany glass dome in the world, and one of Frank Lloyd Wright's first masterpieces.
  • Begins with the first elevator of the day up to the Chicago Skydeck at Willis Tower, and finishes with a 90-minute architecture river cruise.
  • Tour duration is approximately 5 hours and 30 minutes.
  • Arrive 15 minutes prior to the start of the tour.
  • Arrive early to be assured of nearby parking.
  • Wear comfortable shoes and weather-appropriate clothing.
  • Bring sunscreen, hat or umbrella, and a camera.


from Best of Chicago: Skydeck, Architecture River Cruise and Loop Walking Tour
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.
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Best of Chicago: Skydeck, Architecture River Cruise and Loop Walking Tour is located at Walks LLC55 W Jackson BlvdChicago, IL 60604
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Frequently Asked Questions about Best of Chicago: Skydeck, Architecture River Cruise and Loop Walking Tour

Where is the meeting point?

The departure point is at 53 W Jackson Blvd, Chicago, or as confirmed in your confirmation email. The tour meeting time is 15 minutes prior to the tour start time. The tour guides will hold a sign with the Walks logo and “MEET HERE” on it.

How long is this tour?

Approximately 5 hours and 30 minutes.

What if I'm late?

If you are running late, it's best to contact the tour operator at the phone number on your e-ticket so they can reach out to your guide.This is not always possible for all tours - their guides are with other clients and are already into the tour (they ask them not to use their phones during their tour). But in some cases, few-minute delays can be remedied. Most times, guides leave the meeting point within 5 minutes of the tour start time

What is included in this tour?

This tour includes tickets to the first entry at the Willis Tower Skydeck, a 90-minute river cruise, an expertly guided walking tour, and a local English-speaking guide.

What landmarks will we be visiting?

You will see the Monadnock Building, the Chicago Board of Trade with Ceres Statue, the Federal Reserve, the Rookery Building, the Marquette Building, the Inland Steel Palmer House, the Carson Pirie Scott Building, the Marshall Field Building, and the Chicago Cultural Center.

Is transportation included?

Transportation is not included in this tour.

Is parking provided?

No, but multiple parking garages and street parking are available near the departure point. The departure point is also near public transportation.

Are there any age/physical/health/etc. Restrictions for this tour/attraction/activity?

There aren't any age restrictions for this tour. True to their name, most tours involve walking for at least half, if not most of the time. Except for a few of their daytrips, driving tours, or boat excursions, you can expect to walk a fair amount. Guests should be able to walk at a moderate pace without difficulty.

Is the tour wheelchair accessible?


Can I bring my camera?

Yes! There are a lot of photo opportunities on this tour.

What should I bring?

You may bring water, a hat, sunglasses, parasol, and/or sunscreen, a coat, umbrella, or outer layers for the cooler months), and a photo ID for some of the stop oversights.

What should I wear?

Guests must wear attire appropriate for the day's weather forecast and comfortable walking shoes, so it's easy to navigate along uneven surfaces, dirt paths, cobblestone, etc. Due to the religious nature of holy sites such as churches and catacombs, all individuals, regardless of gender and age, must cover their shoulders and knees. During warmer seasons, you can bring extra covering (scarves, sweaters, sarongs, etc.) to put on just before entering.

What is the protocol for when it rains?

The tours run rain or shine, and their guides are great at navigating various weather conditions to ensure you're as comfortable as possible. They will find shade where they can, overhangs to pause under - stuff like that. On rare occasions, if the weather is particularly dramatic, some sites may close (e.g., the Colosseum may close in case of flooding). If time allows and they have a prior warning, they will contact you as soon as they find out.

Should I bring the confirmation email?

A physical or digital copy of this confirmation email is not required to join your tour. Your guide (or tour coordinator) will have your name in their database, so as long as you know the name on the booking, you're set!

How many people are on a tour?

The tour is ideal for small groups and has a maximum of 20 participants or less.