
Best of Chicago: First Elevator at Skydeck, River Cruise, & Inside the Loop Tour
Best of Chicago: First Elevator at Skydeck, River Cruise, & Inside the Loop 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.
Book This ExperienceA glimpse of the journey









Your Itinerary
A curated journey through the experience
Monadnock Building
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.
Skydeck Chicago - Willis Tower
At Willis Tower, take the first elevator of the day up 103 floors to the Skydeck. Take advantage of the observational decks to get the best possible view of the city from above.
45 minutesChicago Board of Trade Building
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, Ancient Greek goddess of the harvest, looming over the skyline three stories high.
10 minutesThe Rookery Building
Walk through the awe-inspiring lobby designed by Frank Lloyd Wright at the Rookery. Many elements here only an expert can point out, including the secret glass mosaics adorning the lobbies. You’ll listen to the history of the cast of characters that brought Chicago to world-wide fame, admire one of the world’s most historically significant doors and get a view of the largest Tiffany glass dome in the world.
15 minutesMillennium Park
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.
30 minutesChicago Riverwalk
The last stop of the day 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.
1 hour 30 minutesIncluded
- Expertly guided walking tour with Local Guide
- River Cruise
- Tickets to first entry at the Willis Tower Sky Deck
- Entry/Admission - Chicago Riverwalk
- Entry/Admission - Skydeck Chicago - Willis Tower
Not Included
- Hotel pickup and drop-off
- Gratuities
Good to Know
- Not wheelchair accessible
- Near public transportation
- We are unable to accommodate guests with mobility limitations, wheelchairs, or strollers on this tour.
- PLEASE NOTE: Walks complies with all local government regulations. You may need to wear a mask or provide proof of vaccination to enter certain venues. Please refer to Chicago government guidelines for the most up to date information
- Most travelers can participate
- Face masks required for travelers in public areas
- Face masks required for guides in public areas
- Hand sanitizer available to travelers and staff
- Social distancing enforced throughout experience
- This tour/activity will have a maximum of 20 travelers
- Confirmation will be received at time of booking
Tickets & Cancellation
You can present either a paper or an electronic voucher for this activity.
For a full refund, cancel at least 24 hours in advance of the start time of the experience.