Planning to travel to Chicago? With jazz music, great sports, plenty of unique architecture to admire, and all the Chicago-style pizza and hot dogs you can eat, Chicago is a great destination for groups of all types.
Whether you’re traveling with a small group of friends or an entire department from work, Total Charters makes it easy to book the perfect transportation arrangements. We charter buses of all sizes and types and work with groups from across the nation to help make their Chicago trips unforgettable.
If you’ve never been to the city before, planning an itinerary can be a bit overwhelming; so, we’ve put together some sample itineraries based on Chicago trips we’ve booked before. Don’t miss these must-see stops on your first trip to the Windy City!
The Peninsula Chicago
Phone: (312) 337-2888
Address: 108 E Superior Street, Chicago, IL 60611
Four Seasons Hotel Chicago
Phone: (312) 280-8800
Address: 120 E Delaware Place, Chicago, IL 60611
Inn of Chicago
Phone: (312) 787-3100
Address: 162 E Ohio Street, Chicago, IL 60611
Phone: (312) 943-5000
Address: 201 E Delaware Place, Chicago, IL 60611
While public transportation and rideshare apps are available for your use, a private bus rental offers you the opportunity to completely customize your transportation experience while keeping your group together on one vehicle. Choose where you’d like to go, when you’d like to get there, and how long you’d like to stick around before moving on to your next stop. You’ll be in control through your entire Chicago trip.
As a first-timer, you can’t miss these classic tourist stops that make Chicago unique. Whether you’re traveling with family & friends or with your school group, these attractions are sure to make your trip unforgettable. Below is a recommended itinerary for Chicago newcomers, based on trips we’ve helped to book in the past:
The Art Institute of Chicago
Phone: (312) 443-3600
Address: 111 South Michigan Avenue, Chicago, Illinois 60603
As one of the country’s oldest and largest art museums, the Art Institute of Chicago is a must-see for all first-timers. Home to priceless works of art such as A Sunday on La Grande Jatte and Picasso’s The Old Guitarist, this 139-year-old museum is sure to wow visitors of all ages.
Phone: (312) 742-1168
Address: 201 E Randolph Street, Chicago, IL 60602
Home to one of Chicago’s most iconic landmarks, Millennium Park is perfect for an afternoon stroll with your traveling group. Spend the afternoon enjoying the sunshine, and make sure you get a picture by the famous Cloud Gate before you leave!
A show with the Lookingglass Theatre Company
Phone: (312) 337-0665
Address: 821 N Michigan Avenue, Chicago, IL 60611
Founded in 1988, this company produces theatrical works focusing on new and cutting-edge techniques in the world of theatre. They also participate in theatre education for both students and teachers from their permanent home at the Water Tower Water Works on Chicago’s Magnificent Mile.
Museum of Science and Industry Chicago
Phone: (773) 684-1414
Address: 5700 S Lake Shore Drive, Chicago, IL 60637
With a WWII German submarine, the command module of Apollo 8, plus over 2,000 other unique exhibits, the Museum of Science and Industry is sure to wow visitors of all ages. As the largest science museum in the country, it’s also one of the city’s most popular attractions.
SkyDeck Chicago at Willis Tower
Phone: (312) 875-9696
Address: 233 S Wacker Drive, Chicago, IL 60606
Sitting on Willis Tower’s 103rd floor, SkyDeck Chicago boasts the highest public viewing area in the country, offering views up to 50 miles away and into 4 separate states on a clear day. As it’s located in one of Chicago’s most recognizable landmarks, the SkyDeck is a must-see for all new tourists.
Phone: (312) 595-7437
Address: 600 E Grand Avenue, Chicago, IL 60611
Finish off your weekend with a trip to Chicago’s iconic Navy Pier, home to over 50 acres of parks, gardens, shops, restaurants, and more. The lights and water views make for breathtaking scenery as you close out your trip with a bang!
Between stops, there are endless restaurant options to choose from. For an unforgettable introduction to Chicago’s food scene, we recommend working the following into your itinerary:
Phone: (773) 327-1512
Address: 2207 N Clybourn Avenue, Chicago, IL 60614
Though it’s often debated who truly serves the best Chicago-style pizza, Pequod’s is no doubt a local favorite, known for its delicious caramelized crust topped with a ring of mozzarella cheese.
Byron’s Hot Dogs
Phone: (773) 271-0900
Address: 1701 W. Lawrence Avenue, Chicago, IL 60640
For a true Chicago-style hot dog, Byron’s is a local favorite. Stop by for a proper introduction to some of the best hot dogs the city has to offer, making it the perfect stop for the Chicago newcomer.
Phone: (773) 654-1460
Address: 3500 N Elston Avenue, Chicago, IL 60618
Parachute is not only one of the best restaurants in Chicago; it’s ranked as one of the best in the nation. The unique blend of Korean and American cuisine plus the “mom-and-pop” feel make it one of the most popular restaurants in the city.
As the #1 bus rental service in the Midwest, Total Charters is your top choice for all of your Chicago travel. No matter what brings you into the city, we’ll make sure you always ride in style. Let us bring you in from anywhere in the Midwest, including cities such as Detroit, St. Louis, Louisville, and more.
We’ll help you find the perfect bus rental for your group’s individual needs. Once you’ve figured out where you’re going, call Total Charters at 312-766-2242 to schedule your trip’s transportation. We can’t wait to help you plan your trip!