5-Day Chicago Adventure

Day 1 You'll See: 

Day 2 You'll See:

Day 3 You'll See:

Day 4 You'll See:

Day 5 You’ll See:


Steve’s Segway Tours - What better way to start your big Chicago adventure than with a tour of some of the cities finest sights, streets, and side attractions? That’s exactly what you’ll get with Steve’s Segway Tours, a really exciting way to see the city! Operating in downtown Chicago, Museum Campus, and most major park areas, these tours are conducted on Segway i2s, each individual in your group riding his/her own Segway during the tour. If you haven't ridden on a Segway before, don’t worry, you’ll get a quick rundown on how the machines work, basically just moving in any direction you lean while on the move. The tour will be led by an experienced city guide who will relay tons of great city knowledge on history, local legends, and popular architecture, as well as entertain the group with interesting stories and jokes.

Art Institute of Chicago - Next stop, the Art Institute of Chicago, the highly regarded fine art museum created in 1879. This world-renown Chicago classic is known for ‘embracing the individual experience of art’, and also for allowing it’s over 1.5 million annual guests each to experience their own personal ‘Ferris Bueller moment’. This institution strives to collect, observe, and interpret works of art and encourages personal appreciation of said art. The Art Institute is located just one block away from Lake Michigan, anchoring down the east side of downtown with its massive 8 building, 1 million square foot complex. Once here your group will have the dizzying task of deciding which of the 300,000 permanent pieces within the 11 different departments you’d like to see. Find ancient treasures from across the globe to modern works from Dali, Picasso, and Matisse!

Skydeck Willis - The view of Chicago from the top of a skyscraper, or what feels like the top of the world, is completely unbeatable, possibly even more so at night! Willis Tower, the premier corporate office building in the city of Chicago, will allow you to see such a view tonight, the building itself truly an essential and iconic Chicago skyline member. This tower is actually known as the tallest in the entire Western Hemisphere, holding over 4.5 million square feet of space, 103 floors, and 1,353 feet in height not counting spires. Previously known as Sears Tower, this attraction will allow you to experience a truly immersive city viewing experience, holding what they like to call The Ledge, the onsite fully enclosed glass box that retracts into the building. The box is 4.3 feet out of the Skydeck, giving you never before seen views of the city as you learn tons of interesting information about the structure and history of this influential Windy City building.



Lincoln Park Zoo - Take a walk on the wild side today as you and your travel group head over to the Lincoln Park Zoo, the ‘wildest spot in Chicago’! This 365-day a year free attraction has seen millions of guests annually since it’s opening, the zoo dedicated to connecting people with nature and advancing the highest quality of animal care. Located in a verdant park just North of Chicago you will find this ‘world of wildlife in a shadow of skyscrapers’, allowing you as a guest to hear a big cat’s roar echo off of nearby buildings, or see a monkey climb a tree with skyscrapers as his looming backdrop. Head to the tropical rainforest while here, the dry thorn forest, or the savannah, each really great options to learn something and be entertained all at the same time. Be sure to check for daily special events or festivals, and head over to Patio at Cafe Brauer for a delicious lunch if you get hungry!

Federal Reserve Visitor Center - Perhaps one of the most nationally influential attractions in Chicago is the Federal Reserve, the Money Museum that teaches guests a lot about our nation’s financial woes and wants, the history of money as we know it, and so much more American money-related issues. This is the spot where you can create coins, see rare bills such as the ten thousand dollar bill, learn details on the counterfeiting business today, and see where the old money goes to die. You can even stand and pose by a cube of a million bucks, probably the closest you may get to this amount of money in quite some time! There are onsite scavenger hunts, documentaries, and other fun activities, you’ll even get a souvenir bag of authentic shredded green before you go! Money talks, so get ready for a lot of conversation with this stop!

Magnificent Mile - After seeing all that money now is your chance to burn through some of yours at one of the most vibrant and successful commercials, residential, cultural, and tourist areas in the world, the 1 full square mile of downtown Chicago shopping and dining known as the Magnificent Mile. This 13-block stretch of the shopping paradise is located along North Michigan Avenue and will allow your group to shop, stroll, and sightseeing all at once, a truly essential Chicago experience you won’t want to miss out on. As one of the greatest avenues of the world, this is the best spot to shop over 460 stores, eat at your choice of over 75 restaurants, and even stay or tour any of the 60 hotels! See the historic water tower, DuSable Bridge, and Wrigley building as you figure out for yourselves exactly why the Magnificent Mile is one of the top 10 districts in hospitality, dining, and retail in the world!


360 Chicago (Hancock Observatory) - Welcome to the John Hancock Observatory Tower, sometimes otherwise known as 360 Chicago. 360 Chicago is actually an attraction inside Hancock Tower, a quite popular attraction that allows guests to see the Magnificent Mile, Lake Michigan, downtown, and, on clear days, four different neighboring states, all from their 1,000-foot sightseeing perch. While you are catching these amazing morning views of the city and its surroundings you will be taking in a lot of information from the surrounding plaques and exhibits, plus you will have the chance to be a daredevil and view the panorama from TILT, the outwardly tilting box that takes you 30 degrees from the building into a vertigo-tripping ‘free-fall’ view of the street below. This is truly a great sight to see, as well as the greatest way to really see the sights!

Grant Park - Get ready for a midday adventure at Grant Park, the gorgeous green space of 319 acres often tenderly referred to by locals as ‘Chicago’s Front Yard.’ This pretty patch of land was set aside in 1836 as a public ground ‘to be clear and free of structures’ and serves as such still today, a separate park area focusing on the gorgeous lakefront and typical Chicago storied architecture/skyline views. Located within the Central Business District in the Loop community, this park includes such prominent landmarks to explore as Millennium Park, Buckingham Fountain, the Art Institute, and Museum Campus, which of the latter you will visit next. While here be sure to find out all about the park’s namesake, US President Ulysses S Grant! Oh, and you'll probably want to check out Buckingham Fountain, or the Clarence Buckingham Memorial more officially, before you go, putting on a display every 20 minutes to show off its gorgeous rococo wedding cake style figure and function!

Field Museum - Next stop, Field Museum, where you and your group will encounter countless equally entertaining and educational exhibits sure to spark your wide range of interests. Within the walls of this massive, both literally and reputation-wise, museum you will see such exhibits as Haitian Voodoo, Titans of the Ice Age, Bat Caves of Kenya, and even the largest Tyrannosaurus Rex ever discovered, Sue! Descend into an ancient Egyptian tomb or shrink down to microscopic size in Bug World, the options for fun and learning something new are almost endless here. Believe it or not, this museum spans over 4.6 billion years of ‘life’ history under one, quite clearly massive, roof. Get ready to be enlightened, entertained, and inspired all at once! There are eating/snacking opportunities within the museum, as well as a gift shop. (Be sure to learn all about the man-eating lions of Tsavo before you go, too!)

Shedd Aquarium - End your day with a visit to the Shedd Aquarium, a true Windy City treasure that doubles as the world’s largest indoor aquarium, as well. Inside you will see such things as the Caribbean Coral Reef, chock-full of nurse sharks, barracudas, hawksbill sea turtles, and other ravenous residents, or the Oceanarium, a place where you will see eager dolphins doing various tricks and shows. There is so much more to see in here, so much, in fact, you may want to be sure you have solid 2-3 hours to spend exploring. Head over to the Wild Reef-Sharks at Shedd exhibit before you go to get up close and personal with sharks, or to the Jellies exhibit to get a privileged peek into the mysterious world of these fragile predators. If an aquarium isn’t really your thing you can easily replace this attraction with the next door Adler Planetarium, the best place to really see the stars in Chi-Town.


Museum of Science and Industry - Welcome to the highly popular Chicago Museum of Science and Industry, one of the absolute largest science museums in the entire world, and certainly the largest in the western hemisphere. Home to over 35,000 artifacts and 400,000 square feet of hands-on exhibits, this museum was created and designed to spark scientific inquiry and creativity, having done just that for over 180 million guests since opening in 1933. Explore such popular exhibits and attractions as Science Storms, You!, and the U-505 Submarine, the latter being the only remaining German U-Boat in the U.S. Science truly comes alive here, especially if you make your way to the 5-story domed Omnimax Theater, Brain Food Court, or Shop Earth Gift Shop. This is one seriously fun scientific adventure, just be sure to wear comfortable walking shoes if you want to experience it all!

Navy Pier -
No Windy City adventure would be complete without a stop by historic Navy Pier, Chicago's lakefront playground and the Midwest's premier leisure destination, featuring 50 acres of parks, promenades, gardens, shops, eateries, and attractions. Take a spin on a 15-story tall iconic Ferris wheel or run amuck on three floors of interactive fun at Chicago Children's Museum, you can even hop aboard a cruise or speed boat departing from Navy Pier's South Dock and browse Family Pavilion’s exciting retail shops for that perfect Chi-Town souvenir. Summertime on the Pier brings spectacular twice-weekly fireworks shows perfectly synchronized to music on Lake Michigan; basically, Navy Pier has it all, in a classic carnival atmosphere!

Shoreline Sightseeing Tours - Step right outside the Navy Pier and right onto a boat, as the Chicago Shoreline Company is going to take you on a refreshing, relaxing, and really scenic Shoreline Sightseeing Tour next! The tours offered by this cruising company are truly interesting and full of vibrant city sights, the options including such themes as architecture, lake, and even fireworks tours. During the night Architecture River Tour you will see several iconic locations such as the Tribune Tower, Wrigley Building, Trump Tower, and Marina City, all even more spectacular by moonlight. Any tour choice you make you won’t be disappointed with, each and every one of them providing really quality information and entertainment. You may want to bring layers for the cruise and you definitely will want to bring a camera to capture the journey!


Chicago Botanic Gardens - Welcome to the Chicago Botanic Gardens, one of the world's’ great living museums and conservation science centers. This garden center is actually comprised of 26 different gardens and 4 natural areas uniquely situated on 385 acres, on and around 9 islands and 6 miles of lake shoreline. While here your group can tour the grounds, stroll through the themed gardens such as the Japanese garden or English Walled Garden, hike the many different nature trails, check out the Lenhardt Library, or see for yourselves the special species collections, including things such as oaks, willows, or ginkgos!

Wrigley Field -  This stop depends on how much time you have left and what kind of games are happening in the city during this particular day, the ideal choice is a live game at Wrigley Field or Soldier Field. As you probably already know, Chicagoans are passionate people and they surely love their sports. Wrigley Field is the centerpiece of this love with the fighting Chicago Cubs. Built in 1914, this historic field has been encouraging a love of America's favorite pastime for over 100 years. Come by for a game or just a tour of the historic ballpark and learn about the famous players over the years, and the same can be done at the Bears’ home in the Soldier Field!

Millennium Park  - End your amazing Chicago adventure here at the phenomenal 24-5 acre public space known as Millennium Park. Situated atop a parking garage on the world-renowned Loop District is Chicago's definitive modern showplace – a favorite destination and gathering spot for Chicagoans and visitors, alike. Stunning architecture, breathtaking landscape design, fantastic concerts and more share the spotlight in this park in the heart of the Windy City. While here you will see such iconic features as the Jay Pritzker Pavilion, an outdoor bandshell used for many festivals, concerts, and public events, Cloud Gate (The Bean), the massive and really Chicago iconic reflective sculpture, and Lurie Gardens, the green garden space in the midst of the concrete jungle of Chicago! This is the perfect spot to see before heading back home!