Chicago in 2 Days: A Beginner's Guide to the Windy City

Planning to travel to Chicago for the first time? 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. Book a Chicago bus to explore the best of this city with ease!

Book with us for an easy and stress-free experience on your next trip.

Your Chicago Trip

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!

Chicago skyline in the evening

Where to Stay:

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

Raffaello Hotel

Phone: (312) 943-5000

Address: 201 E Delaware Place, Chicago, IL 60611

How to Get Around:

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.

Where to Go:

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:

Day 1


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.


Millennium Park

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.

The Chicago skyline from Millennium Park

Day 2


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.


Navy Pier

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!

What to Eat:

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:

A Chicago deep-dish pizza with one slice being lifted up by a pizza cutter.

Pequod’s Pizza

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.

Book A Charter Bus for Your Chicago Trip

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!