Planning a visit to Chicago for the first time is exciting, overwhelming, fun, and challenging, all in one. How do you decide what’s best to see, eat, and do in this historic, lakefront city when you’ve never been here before? With a never-ending list of places to go and sights to see, building the ideal itinerary takes a lot of research. That’s where we come in.

Chicago Charter Bus Company offers group travelers a unique and personalized way to see the city for the first time. With a private charter bus rental, you can travel to Chicago’s biggest attractions and must-see spots according to your schedule—and if it’s your first time in the city, you’ll want to be efficient and comfortable so you can see and enjoy as much as possible. Once you build an itinerary that fits your idea of the perfect first visit to Chicago, call 312-667-0906 to get a free, personalized quote for your private, premium bus rental.

The Chicago First-Timer’s Bucket List:

Looking for a place to kick-start your ideal Chicago itinerary? Here’s seven of the top things to do, dining to enjoy, and places to visit that are perfect for a first-timer’s bucket list:

1. Enjoy a boat cruise on the Chicago River

If you’ve never been to Chicago, the first thing to do is take a tour of the city with a professional tour guide. You’ll see all of the city’s most famous landmarks paired with stories of history, art and culture in Chicago that you can use to shape the rest of your visit. And what’s the most unique way to see Chicago? A Chicago River boat cruise!

Most cruises launch from the historic Navy Pier, where you can choose from a variety of tour types to fit your fancy. History buffs will love an architecture-focused river tour of the city’s landmarks, while foodies will want to opt for a multi-hour leisurely lunch or dinner cruise. Enjoy your ride while seeing the best of the city and building excitement and anticipation for your first trip to Chicago.

Chicago Architecture Foundation Center River Cruise

Address: Chicago’s First Lady Cruises, 112 E Wacker Dr, Chicago, IL 60601

Phone: 847-358-1330

Odyssey Lake Michigan Dinner Cruise

Address: 600 E. Grand Avenue, Chicago, IL 60611

Phone: 312-321-1241

2. Take a photo by “The Bean” at Millennium Park

Chicago has many beautiful parks to visit, but if you can only visit one, make it Millennium Park. It’s home to Cloud Gate (aka “The Bean”), one of the most famous outdoor art sculptures in Chicago, and the perfect place to take a group photo or selfie. While you’re there, explore award-winning Lurie Garden—known as a marvel of botanical landscaping—and visit the Maggie Daley Park, where kids and adults alike can enjoy a rock-climbing wall, an 18-hole mini golf course, and the Skating Ribbon: an in-line skating/walking path in summer, and an ice-skating path in winter.

Millennium Park

Address: 201 E Randolph St, Chicago, IL 60602

Phone: 312-742-1168

People cutting a slice of Chicago deep dish pizza

3. Eat deep dish pizza at the original Pizzeria Uno

Long before UNO Pizzeria & Grill expanded across the country to give deep-dish pizza to Americans near and far, it was dishing out slices to Chicagoans in downtown. Founded in 1943 by Ike Sewell, Pizzeria Uno is home to Chicago’s original deep dish pizza. Sewell invented the unique slice when he thought to combine larger portions of classic Italian ingredients into a dish for a heartier, saucier, meatier bite. Today, it’s known as a Chicago classic, and a must-try when you’re in the city.

Reserve a table or host a private party to enjoy a variety of original Chicago-style deep dish pizzas, like the famous “Numero Uno,” a mix of sausage, pepperoni, onions, peppers, mushrooms, and Uno’s famous tomato sauce. Fun fact: as Pizzeria Uno grew, and Sewell wanted to expand, he opened Pizzeria Due across the street in the first level of a Victorian mansion. This spot is a historic location for a group dinner, kitchen tour, or a cooking class (and is especially popular for a school field trip or company outing).

Pizzeria Uno

Address: 29 E Ohio St, Chicago, IL 60611

Phone: 312-321-1000

Pizzeria Due

Address: 619 North Wabash Ave, Chicago, IL 60611

Phone: 312-943-2400

4. See a Chicago Cubs game at Wrigley Field

No trip to Chicago is complete without a trip to Wrigley Field for a Chicago Cubs baseball game. You can book single-game tickets or reserve a Cub Suite for your group to watch the game in style. You can also reserve a private rooftop that overlooks Wrigley Field from a bird’s eye view—the perfect option for a corporate event or sports fan party. Your reservation can include all-inclusive food and drinks, meeting spaces (both indoors and out), and alternative cover options for unpredictable Chicago weather.

Additionally, Wrigley Field is one of the most historic places in Chicago, built in 1914 and the second-oldest ballpark in major league baseball behind Fenway Park in Boston.

If you can’t make it to a game, schedule a tour and get a behind-the-scenes look into this 100+ year-old ballpark.

Wrigley Field

Address: 1060 W Addison St, Chicago, IL 60613

Phone: 773-404-2827

Two people looking down at their feet and Chicago streets from the Skydeck at Willis Tower

5. Take in the city skyline views from the Skydeck at Willis Tower

The Chicago Skydeck at Willis Tower is one of the quintessential stops for a first visit to the city. Opened in 1974, the Skydeck invites visitors to stand on The Ledge: an observation deck with a glass floor 1,353-feet above Chicago. It’s the perfect spot to snap a commemorative photo of your trip to the Windy City, and the best time to go is at sunrise or sunset. If you’re traveling with a group, you can also rent event space at The Ledge or the 99th floor of Willis Tower for an unforgettable first visit to Chicago.

Skydeck Chicago

Address: Willis Tower, 233 S Wacker Dr, Chicago, IL 60606

Phone: 312-875-9447

6. Visit Goose Island craft brewery

Chicago is known as the craft brewery capital of the country, and for good reason. There are more than 165 breweries in Chicago—the most breweries of any city in the United States—and Goose Island Beer Company is Chicago’s most famous. You’ll want to head to the Brewhouse on Clybourn Ave (just a few blocks from its namesake island) to tour the brewing facility and reserve a table for lunch, dinner, or brunch.

If you’re traveling with a large group of folks, consider renting event space at the Goose Island Barrel House. Goose Island ages its renowned Bourbon County Brand Stout here, and oak barrels line the walls of the massive rustic-industrial event space. It’s a great place to host a party or wedding reception for any beer lovers coming to Chicago.

Goose Island Brewhouse

Address: 1800 N Clybourn Ave, Chicago, IL 60614

Phone: 312-915-0071

Goose Island Barrel House

Address: 603 N Sacramento Blvd, Chicago, IL 60612

Audience laughing at comedy club

7. See a show at The Second City

This world premier comedy club, theatre, and improv school is a legendary spot to visit for a Chicago first-timer. With famous comedians like Bill Murray, Amy Poehler, and Steve Carrell getting their start here, you could very well be watching the next SNL head-liner or comedy A-lister at an improv or sketch comedy show. Get your visitors tickets to one of a variety of rotating funny shows, or plan a special event with venue and dining options on-site. No matter how you enjoy your Second City experience, you’re sure to be walking away with lots of laughs and a great story from your visit to this comedy mecca.

The Second City

Address: 230 W North Ave, Chicago, IL 60614

Phone: 312-337-3992

Explore Chicago with a Private Charter Bus Rental

The easiest way to hit everything on your Chicago beginner’s bucket list is with a private, premium charter bus rental. You can craft your own itinerary—from Millennium Park to Pizzeria Uno to Wrigley Field—and operate exclusively on your time. No waiting for rideshares or public transit, just riding from one Chicago hotspot to the next in comfort and style. Call Chicago Charter Bus Company at 312-667-0906 to tell us about your trip to Chicago and reserve your charter bus rental.